CHI Cubs

Early club history

1876–1902: A National League

The Cubs began playing in 1870 as the Chicago White Stockings, joining the National League (NL) in 1876 as a charter member. Owner William Hulbert signed multiple star players, such as pitcher Albert Spalding and infielders Ross Barnes, Deacon White, and Adrian "Cap" Anson, to join the team prior to the NL's first season. The White Stockings played their home games at West Side Grounds and quickly established themselves as one of the new league's top teams. Spalding won forty-seven games and Barnes led the league in hitting at .429 as Chicago won the first-ever National League pennant, which at the time was the game's top prize.

After back-to-back pennants in 1880 and 1881, Hulbert died, and Spalding, who had retired to start Spalding sporting goods, assumed ownership of the club. The White Stockings, with Anson acting as player-manager, captured their third consecutive pennant in 1882, and Anson established himself as the game's first true superstar. In 1885 and 1886, after winning NL pennants, the White Stockings met the champions of the short-lived American Association in that era's version of a World Series. Both seasons resulted in matchups with the St. Louis Brown Stockings, with the clubs tying in 1885 and with St. Louis winning in 1886. This was the genesis of what would eventually become one of the greatest rivalries in sports. In all, the Anson-led Chicago Base Ball Club won six National League pennants between 1876 and 1886. As a result, Chicago's club nickname transitioned, and by 1890 they had become known as the Chicago Colts, or sometimes "Anson's Colts", referring to Cap's influence within the club. Anson was the first player in history credited with collecting 3,000 career hits. After a disappointing record of 59–73 and a ninth-place finish in 1897, Anson was released by the club as both a player and manager. Due to Anson's absence from the club after 22 years, local newspaper reporters started to refer to the Colts as the "Orphans".

After the 1900 season, the American Base-Ball League formed as a rival professional league, and incidentally the club's old White Stockings nickname (eventually shortened to White Sox) would be adopted by a new American League neighbor to the south.

1902–1920: A Cubs dynasty

In 1902, Spalding, who by this time had revamped the roster to boast what would soon be one of the best teams of the early century, sold the club to Jim Hart. The franchise was nicknamed the Cubs by the Chicago Daily News in 1902, although not officially becoming the Chicago Cubs until the 1907 season. During this period, which has become known as baseball's dead-ball era, Cub infielders Joe Tinker, Johnny Evers, and Frank Chance were made famous as a double-play combination by Franklin P. Adams' poem "Baseball's Sad Lexicon". The poem first appeared in the July 18, 1910 edition of the New York Evening Mail. Mordecai "Three-Finger" Brown, Jack Taylor, Ed Reulbach, Jack Pfiester, and Orval Overall were several key pitchers for the Cubs during this time period. With Chance acting as player-manager from 1905 to 1912, the Cubs won four pennants and two World Series titles over a five-year span. Although they fell to the "Hitless Wonders" White Sox in the 1906 World Series, the Cubs recorded a record 116 victories and the best winning percentage (.763) in Major League history. With mostly the same roster, Chicago won back-to-back World Series championships in 1907 and 1908, becoming the first Major League club to play three times in the Fall Classic and the first to win it twice. However, the Cubs would not win another World Series until 2016; this remains the longest championship drought in North American professional sports.

The next season, veteran catcher Johnny Kling left the team to become a professional pocket billiards player. Some historians think Kling's absence was significant enough to prevent the Cubs from also winning a third straight title in 1909, as they finished 6 games out of first place. When Kling returned the next year, the Cubs won the pennant again, but lost to the Philadelphia Athletics in the 1910 World Series.

In 1914, advertising executive Albert Lasker obtained a large block of the club's shares and before the 1916 season assumed majority ownership of the franchise. Lasker brought in a wealthy partner, Charles Weeghman, the proprietor of a popular chain of lunch counters who had previously owned the Chicago Whales of the short-lived Federal League. As principal owners, the pair moved the club from the West Side Grounds to the much newer Weeghman Park, which had been constructed for the Whales only two years earlier, where they remain to this day. The Cubs responded by winning a pennant in the war-shortened season of 1918, where they played a part in another team's curse: the Boston Red Sox defeated Grover Cleveland Alexander's Cubs four games to two in the 1918 World Series, Boston's last Series championship until 2004.

Beginning in 1916, Bill Wrigley of chewing-gum fame acquired an increasing quantity of stock in the Cubs. By 1921 he was the majority owner, maintaining that status into the 1930s.

Meanwhile, the year 1919 saw the start of the tenure of Bill Veeck, Sr. as team president. Veeck would hold that post throughout the 1920s and into the 30s. The management team of Wrigley and Veeck came to be known as the "double-Bills".

The Wrigley years (1921–1945)

1929–1938: Every three years

Near the end of the first decade of the double-Bills' guidance, the Cubs won the NL Pennant in 1929 and then achieved the unusual feat of winning a pennant every three years, following up the 1929 flag with league titles in 1932, 1935, and 1938. Unfortunately, their success did not extend to the Fall Classic, as they fell to their AL rivals each time. The '32 series against the Yankees featured Babe Ruth's "called shot" at Wrigley Field in game three. There were some historic moments for the Cubs as well; In 1930, Hack Wilson, one of the top home run hitters in the game, had one of the most impressive seasons in MLB history, hitting 56 home runs and establishing the current runs-batted-in record of 191. That 1930 club, which boasted six eventual hall of fame members (Wilson, Gabby Hartnett, Rogers Hornsby, George "High Pockets" Kelly, Kiki Cuyler and manager Joe McCarthy) established the current team batting average record of .309. In 1935 the Cubs claimed the pennant in thrilling fashion, winning a record 21 games in a row in September. The '38 club saw Dizzy Dean lead the team's pitching staff and provided a historic moment when they won a crucial late-season game at Wrigley Field over the Pittsburgh Pirates with a walk-off home run by Gabby Hartnett, which became known in baseball lore as "The Homer in the Gloamin'".

After the "Double-Bills" (Wrigley and Veeck) died in 1932 and 1933 respectively, P.K. Wrigley, son of Bill Wrigley, took over as majority owner. He was unable to extend his father's baseball success beyond 1938, and the Cubs slipped into years of mediocrity, although the Wrigley family would retain control of the team until 1981.

1945: "The Curse of the Billy Goat"

The Cubs enjoyed one more pennant at the close of World War II, finishing 98–56. Due to the wartime travel restrictions, the first three games of the 1945 World Series were played in Detroit, where the Cubs won two games, including a one-hitter by Claude Passeau, and the final four were played at Wrigley. The Cubs lost the series, and did not return until the 2016 World Series. After losing the 1945 World Series to the Detroit Tigers, the Cubs finished with a respectable 82–71 record in the following year, but this was only good enough for third place.

In the following two decades, the Cubs played mostly forgettable baseball, finishing among the worst teams in the National League on an almost annual basis. From 1947 to 1966, they only notched one winning season. Longtime infielder-manager Phil Cavarretta, who had been a key player during the 1945 season, was fired during spring training in 1954 after admitting the team was unlikely to finish above fifth place. Although shortstop Ernie Banks would become one of the star players in the league during the next decade, finding help for him proved a difficult task, as quality players such as Hank Sauer were few and far between. This, combined with poor ownership decisions such as the College of Coaches, and the ill-fated trade of future Hall of Fame member Lou Brock to the Cardinals for pitcher Ernie Broglio (who won only seven games over the next three seasons), hampered on-field performance.

1969: Fall of '69

The late-1960s brought hope of a renaissance, with third baseman Ron Santo, pitcher Ferguson Jenkins, and outfielder Billy Williams joining Banks. After losing a dismal 103 games in 1966, the Cubs brought home consecutive winning records in '67 and '68, marking the first time a Cub team had accomplished that feat in over two decades.

In 1969 the Cubs, managed by Leo Durocher, built a substantial lead in the newly created National League Eastern Division by mid-August. Ken Holtzman pitched a no-hitter on August 19, and the division lead grew to 8 1⁄2 games over the St. Louis Cardinals and by 9 1⁄2 games over the New York Mets. After the game of September 2, the Cubs record was 84–52 with the Mets in second place at 77–55. But then a losing streak began just as a Mets winning streak was beginning. The Cubs lost the final game of a series at Cincinnati, then came home to play the resurgent Pittsburgh Pirates (who would finish in third place). After losing the first two games by scores of 9–2 and 13–4, the Cubs led going into the ninth inning. A win would be a positive springboard since the Cubs were to play a crucial series with the Mets the next day. But Willie Stargell drilled a two-out, two-strike pitch from the Cubs' ace reliever, Phil Regan, onto Sheffield Avenue to tie the score in the top of the ninth. The Cubs would lose 7–5 in extra innings.[6] Burdened by a four-game losing streak, the Cubs traveled to Shea Stadium for a short two-game set. The Mets won both games, and the Cubs left New York with a record of 84–58 just 1⁄2 game in front. More of the same followed in Philadelphia, as a 99 loss Phillies team nonetheless defeated the Cubs twice, to extend Chicago's losing streak to eight games. In a key play in the second game, on September 11, Cubs starter Dick Selma threw a surprise pickoff attempt to third baseman Ron Santo, who was nowhere near the bag or the ball. Selma's throwing error opened the gates to a Phillies rally. After that second Philly loss, the Cubs were 84–60 and the Mets had pulled ahead at 85–57. The Mets would not look back. The Cubs' eight-game losing streak finally ended the next day in St. Louis, but the Mets were in the midst of a ten-game winning streak, and the Cubs, wilting from team fatigue, generally deteriorated in all phases of the game.[1] The Mets (who had lost a record 120 games 7 years earlier), would go on to win the World Series. The Cubs, despite a respectable 92–70 record, would be remembered for having lost a remarkable 17½ games in the standings to the Mets in the last quarter of the season.

1977–1979: June Swoon

Following the 1969 season, the club posted winning records for the next few seasons, but no playoff action. After the core players of those teams started to move on, the 70s got worse for the team, and they became known as "the Loveable Losers". In 1977, the team found some life, but ultimately experienced one of its biggest collapses. The Cubs hit a high-water mark on June 28 at 47–22, boasting an 8+1⁄2 game NL East lead, as they were led by Bobby Murcer (27 HR/89 RBI), and Rick Reuschel (20–10). However, the Philadelphia Phillies cut the lead to two by the All-star break, as the Cubs sat 19 games over .500, but they swooned late in the season, going 20–40 after July 31. The Cubs finished in fourth place at 81–81, while Philadelphia surged, finishing with 101 wins. The following two seasons also saw the Cubs get off to a fast start, as the team rallied to over 10 games above .500 well into both seasons, only to again wear down and play poorly later on, and ultimately settling back to mediocrity. This trait became known as the "June Swoon". Again, the Cubs' unusually high number of day games is often pointed to as one reason for the team's inconsistent late-season play.

Wrigley died in 1977. The Wrigley family sold the team to the Chicago Tribune in 1981, ending a 65-year family relationship with the Cubs.

Tribune Company years (1981–2008)

1984: Heartbreak

After over a dozen more subpar seasons, in 1981 the Cubs hired GM Dallas Green from Philadelphia to turn around the franchise. Green had managed the 1980 Phillies to the World Series title. One of his early GM moves brought in a young Phillies minor-league 3rd baseman named Ryne Sandberg, along with Larry Bowa for Iván DeJesús. The 1983 Cubs had finished 71–91 under Lee Elia, who was fired before the season ended by Green. Green continued the culture of change and overhauled the Cubs roster, front-office and coaching staff prior to 1984. Jim Frey was hired to manage the 1984 Cubs, with Don Zimmer coaching 3rd base and Billy Connors serving as pitching coach.

Green shored up the 1984 roster with a series of transactions. In December 1983 Scott Sanderson was acquired from Montreal in a three-team deal with San Diego for Carmelo Martínez. Pinch hitter Richie Hebner (.333 BA in 1984) was signed as a free-agent. In spring training, moves continued: LF Gary Matthews and CF Bobby Dernier came from Philadelphia on March 26, for Bill Campbell and a minor leaguer. Reliever Tim Stoddard (10–6 3.82, 7 saves) was acquired the same day for a minor leaguer; veteran pitcher Ferguson Jenkins was released.

The team's commitment to contend was complete when Green made a midseason deal on June 15 to shore up the starting rotation due to injuries to Rick Reuschel (5–5) and Sanderson. The deal brought 1979 NL Rookie of the Year pitcher Rick Sutcliffe from the Cleveland Indians. Joe Carter (who was with the Triple-A Iowa Cubs at the time) and right fielder Mel Hall were sent to Cleveland for Sutcliffe and back-up catcher Ron Hassey (.333 with Cubs in 1984). Sutcliffe (5–5 with the Indians) immediately joined Sanderson (8–5 3.14), Eckersley (10–8 3.03), Steve Trout (13–7 3.41) and Dick Ruthven (6–10 5.04) in the starting rotation. Sutcliffe proceeded to go 16–1 for Cubs and capture the Cy Young Award.

The Cubs 1984 starting lineup was very strong. It consisted of LF Matthews (.291 14–82 101 runs 17 SB), C Jody Davis (.256 19–94), RF Keith Moreland (.279 16–80), SS Larry Bowa (.223 10 SB), 1B Leon "Bull" Durham (.279 23–96 16SB), CF Dernier (.278 45 SB), 3B Ron Cey (.240 25–97), Closer Lee Smith (9–7 3.65 33 saves) and 1984 NL MVP Ryne Sandberg (.314 19–84 114 runs, 19 triples, 32 SB).

Reserve players Hebner, Thad Bosley, Henry Cotto, Hassey and Dave Owen produced exciting moments. The bullpen depth of Rich Bordi, George Frazier, Warren Brusstar and Dickie Noles did their job in getting the game to Smith or Stoddard.

At the top of the order, Dernier and Sandberg were exciting, aptly coined "the Daily Double" by Harry Caray. With strong defense – Dernier CF and Sandberg 2B, won the NL Gold Glove- solid pitching and clutch hitting, the Cubs were a well-balanced team. Following the "Daily Double", Matthews, Durham, Cey, Moreland and Davis gave the Cubs an order with no gaps to pitch around. Sutcliffe anchored a strong top-to-bottom rotation, and Smith was one of the top closers in the game.

The shift in the Cubs' fortunes was characterized June 23 on the "NBC Saturday Game of the Week" contest against the St. Louis Cardinals; it has since been dubbed simply "The Sandberg Game". With the nation watching and Wrigley Field packed, Sandberg emerged as a superstar with not one, but two game-tying home runs against Cardinals closer Bruce Sutter. With his shots in the 9th and 10th innings, Wrigley Field erupted and Sandberg set the stage for a comeback win that cemented the Cubs as the team to beat in the East. No one would catch them.

In early August the Cubs swept the Mets in a 4-game home series that further distanced them from the pack. An infamous Keith Moreland-Ed Lynch fight erupted after Lynch hit Moreland with a pitch, perhaps forgetting Moreland was once a linebacker at the University of Texas. It was the second game of a doubleheader and the Cubs had won the first game in part due to a three-run home run by Moreland. After the bench-clearing fight, the Cubs won the second game, and the sweep put the Cubs at 68–45.

In 1984, each league had two divisions, East and West. The divisional winners met in a best-of-5 series to advance to the World Series, in a "2–3" format, first two games were played at the home of the team who did not have home-field advantage. Then the last three games were played at the home of the team, with home-field advantage. Thus the first two games were played at Wrigley Field and the next three at the home of their opponents, San Diego. A common and unfounded myth is that since Wrigley Field did not have lights at that time the National League decided to give the home field advantage to the winner of the NL West. In fact, home-field advantage had rotated between the winners of the East and West since 1969 when the league expanded. In even-numbered years, the NL West had home-field advantage. In odd-numbered years, the NL East had home-field advantage. Since the NL East winners had had home-field advantage in 1983, the NL West winners were entitled to it.

The confusion may stem from the fact that Major League Baseball did decide that, should the Cubs make it to the World Series, the American League winner would have home-field advantage. At the time home field advantage was rotated between each league. Odd-numbered years the AL had home-field advantage. Even-numbered years the NL had home-field advantage. In the 1982 World Series the St. Louis Cardinals of the NL had home-field advantage. In the 1983 World Series the Baltimore Orioles of the AL had home-field advantage.

In the NLCS, the Cubs easily won the first two games at Wrigley Field against the San Diego Padres. The Padres were the winners of the Western Division with Steve Garvey, Tony Gwynn, Eric Show, Goose Gossage and Alan Wiggins. With wins of 13–0 and 4–2, the Cubs needed to win only one game of the next three in San Diego to make it to the World Series. After being beaten in Game 3 7–1, the Cubs lost Game 4 when Smith, with the game tied 5–5, allowed a game-winning home run to Garvey in the bottom of the ninth inning. In Game 5 the Cubs took a 3–0 lead into the 6th inning, and a 3–2 lead into the seventh with Sutcliffe (who won the Cy Young Award that year) still on the mound. Then, Leon Durham had a sharp grounder go under his glove. This critical error helped the Padres win the game 6–3, with a 4-run 7th inning and keep Chicago out of the 1984 World Series against the Detroit Tigers. The loss ended a spectacular season for the Cubs, one that brought alive a slumbering franchise and made the Cubs relevant for a whole new generation of Cubs fans.

The Padres would be defeated in 5 games by Sparky Anderson's Tigers in the World Series.

The 1985 season brought high hopes. The club started out well, going 35–19 through mid-June, but injuries to Sutcliffe and others in the pitching staff contributed to a 13-game losing streak that pushed the Cubs out of contention.

1989: NL East division championship

In 1989, the first full season with night baseball at Wrigley Field, Don Zimmer's Cubs were led by a core group of veterans in Ryne Sandberg, Rick Sutcliffe and Andre Dawson, who were boosted by a crop of youngsters such as Mark Grace, Shawon Dunston, Greg Maddux, Rookie of the Year Jerome Walton, and Rookie of the Year Runner-Up Dwight Smith. The Cubs won the NL East once again that season winning 93 games. This time the Cubs met the San Francisco Giants in the NLCS. After splitting the first two games at home, the Cubs headed to the Bay Area, where despite holding a lead at some point in each of the next three games, bullpen meltdowns and managerial blunders ultimately led to three straight losses. The Cubs could not overcome the efforts of Will Clark, whose home run off Maddux, just after a managerial visit to the mound, led Maddux to think Clark knew what pitch was coming. Afterward, Maddux would speak into his glove during any mound conversation, beginning what is a norm today. Mark Grace was 11–17 in the series with 8 RBI. Eventually, the Giants lost to the "Bash Brothers" and the Oakland A's in the famous "Earthquake Series".

1998: Wild card race and home run chase

The 1998 season began on a somber note with the death of broadcaster Harry Caray. After the retirement of Sandberg and the trade of Dunston, the Cubs had holes to fill, and the signing of Henry Rodríguez to bat cleanup provided protection for Sammy Sosa in the lineup, as Rodriguez slugged 31 round-trippers in his first season in Chicago. Kevin Tapani led the club with a career-high 19 wins while Rod Beck anchored a strong bullpen and Mark Grace turned in one of his best seasons. The Cubs were swamped by media attention in 1998, and the team's two biggest headliners were Sosa and rookie flamethrower Kerry Wood. Wood's signature performance was one-hitting the Houston Astros, a game in which he tied the major league record of 20 strikeouts in nine innings. His torrid strikeout numbers earned Wood the nickname "Kid K", and ultimately earned him the 1998 NL Rookie of the Year award. Sosa caught fire in June, hitting a major league record 20 home runs in the month, and his home run race with Cardinal's slugger Mark McGwire transformed the pair into international superstars in a matter of weeks. McGwire finished the season with a new major league record of 70 home runs, but Sosa's .308 average and 66 homers earned him the National League MVP Award. After a down-to-the-wire Wild Card chase with the San Francisco Giants, Chicago and San Francisco ended the regular season tied, and thus squared off in a one-game playoff at Wrigley Field. Third baseman Gary Gaetti hit the eventual game-winning homer in the playoff game. The win propelled the Cubs into the postseason for the first time since 1989 with a 90–73 regular-season record. Unfortunately, the bats went cold in October, as manager Jim Riggleman's club batted. 183 and scored only four runs en route to being swept by Atlanta in the National League Division Series. The home run chase between Sosa, McGwire and Ken Griffey, Jr. helped professional baseball to bring in a new crop of fans as well as bringing back some fans who had been disillusioned by the 1994 strike. The Cubs retained many players who experienced career years in 1998, but, after a fast start in 1999, they collapsed again (starting with being swept at the hands of the cross-town White Sox in mid-June) and finished in the bottom of the division for the next two seasons.

2001: Playoff push

Despite losing fan favorite Grace to free agency and the lack of production from newcomer Todd Hundley, skipper Don Baylor's Cubs put together a good season in 2001. The season started with Mack Newton being brought in to preach "positive thinking". One of the biggest stories of the season transpired as the club made a midseason deal for Fred McGriff, which was drawn out for nearly a month as McGriff debated waiving his no-trade clause. The Cubs led the wild card race by 2.5 games in early September, but crumbled when Preston Wilson hit a three-run walk-off homer off of closer Tom "Flash" Gordon, which halted the team's momentum. The team was unable to make another serious charge, and finished at 88–74, five games behind both Houston and St. Louis, who tied for first. Sosa had perhaps his finest season and Jon Lieber led the staff with a 20-win season.

2003: Five more outs

The Cubs had high expectations in 2002, but the squad played poorly. On July 5, 2002, the Cubs promoted assistant general manager and player personnel director Jim Hendry to the General Manager position. The club responded by hiring Dusty Baker and by making some major moves in 2003. Most notably, they traded with the Pittsburgh Pirates for outfielder Kenny Lofton and third baseman Aramis Ramírez, and rode dominant pitching, led by Kerry Wood and Mark Prior, as the Cubs led the division down the stretch.

Chicago halted St. Louis' run to the playoffs by taking four of five games from the Cardinals at Wrigley Field in early September, after which they won their first division title in 14 years. They then went on to defeat the Atlanta Braves in a dramatic five-game Division Series, the franchise's first postseason series win since beating the Detroit Tigers in the 1908 World Series.

After losing an extra-inning game in Game 1, the Cubs rallied and took a three-games-to-one lead over the Wild Card Florida Marlins in the National League Championship Series. Florida shut the Cubs out in Game 5, but the Cubs returned home to Wrigley Field with young pitcher Mark Prior to lead the Cubs in Game 6 as they took a 3–0 lead into the 8th inning. It was at this point when a now-infamous incident took place. Several spectators attempted to catch a foul ball off the bat of Luis Castillo. A Chicago Cubs fan by the name of Steve Bartman, of Northbrook, Illinois, reached for the ball and deflected it away from the glove of Moisés Alou for the second out of the eighth inning. Alou reacted angrily toward the stands and after the game stated that he would have caught the ball. Alou at one point recanted, saying he would not have been able to make the play, but later said this was just an attempt to make Bartman feel better and believing the whole incident should be forgotten. Interference was not called on the play, as the ball was ruled to be on the spectator side of the wall. Castillo was eventually walked by Prior. Two batters later, and to the chagrin of the packed stadium, Cubs shortstop Alex Gonzalez misplayed an inning-ending double play, loading the bases. The error would lead to eight Florida runs and a Marlin victory. Despite sending Kerry Wood to the mound and holding a lead twice, the Cubs ultimately dropped Game 7, and failed to reach the World Series.

The "Steve Bartman incident" was seen as the "first domino" in the turning point of the era, and the Cubs did not win a playoff game for the next eleven seasons.

2004–2006

In 2004, the Cubs were a consensus pick by most media outlets to win the World Series. The offseason acquisition of Derek Lee (who was acquired in a trade with Florida for Hee-seop Choi) and the return of Greg Maddux only bolstered these expectations. Despite a mid-season deal for Nomar Garciaparra, misfortune struck the Cubs again. They led the Wild Card by 1.5 games over San Francisco and Houston on September 25. On that day, both teams lost, giving the Cubs a chance at increasing the lead to 2.5 games with only eight games remaining in the season, but reliever LaTroy Hawkins blew a save to the Mets, and the Cubs lost the game in extra innings. The defeat seemingly deflated the team, as they proceeded to drop six of their last eight games as the Astros won the Wild Card.

Despite the fact that the Cubs had won 89 games, this fallout was decidedly unlovable, as the Cubs traded superstar Sammy Sosa after he had left the season's final game after the first pitch, which resulted in a fine (Sosa later stated that he had gotten permission from Baker to leave early, but he regretted doing so). Already a controversial figure in the clubhouse after his corked-bat incident, Sosa's actions alienated much of his once strong fan base as well as the few teammates still on good terms with him, to the point where his boombox was reportedly smashed after he left to signify the end of an era. The disappointing season also saw fans start to become frustrated with the constant injuries to ace pitchers Mark Prior and Kerry Wood. Additionally, the 2004 season led to the departure of popular commentator Steve Stone, who had become increasingly critical of management during broadcasts and was verbally attacked by reliever Kent Mercker. Things were no better in 2005, despite a career year from first baseman Derrek Lee and the emergence of closer Ryan Dempster. The club struggled and suffered more key injuries, only managing to win 79 games after being picked by many to be a serious contender for the NL pennant. In 2006, the bottom fell out as the Cubs finished 66–96, last in the NL Central.

2007–2008: Back to back division titles

After finishing last in the NL Central with 66 wins in 2006, the Cubs re-tooled and went from "worst to first" in 2007. In the offseason they signed Alfonso Soriano to a contract at eight years for $136 million, and replaced manager Dusty Baker with fiery veteran manager Lou Piniella. After a rough start, which included a brawl between Michael Barrett and Carlos Zambrano, the Cubs overcame the Milwaukee Brewers, who had led the division for most of the season. The Cubs traded Barrett to the Padres, and later acquired catcher Jason Kendall from Oakland. Kendall was highly successful with his management of the pitching rotation and helped at the plate as well. By September, Geovany Soto became the full-time starter behind the plate, replacing the veteran Kendall. Winning streaks in June and July, coupled with a pair of dramatic, late-inning wins against the Reds, led to the Cubs ultimately clinching the NL Central with a record of 85–77. They met Arizona in the NLDS, but controversy followed as Piniella, in a move that has since come under scrutiny, pulled Carlos Zambrano after the sixth inning of a pitcher's duel with D-Backs ace Brandon Webb, to "....save Zambrano for (a potential) Game 4." The Cubs, however, were unable to come through, losing the first game and eventually stranding over 30 baserunners in a three-game Arizona sweep.

The Tribune company, in financial distress, was acquired by real-estate mogul Sam Zell in December 2007. This acquisition included the Cubs. However, Zell did not take an active part in running the baseball franchise, instead concentrating on putting together a deal to sell it.

The Cubs successfully defended their National League Central title in 2008, going to the postseason in consecutive years for the first time since 1906–08. The offseason was dominated by three months of unsuccessful trade talks with the Orioles involving 2B Brian Roberts, as well as the signing of Chunichi Dragons star Kosuke Fukudome. The team recorded their 10,000th win in April, while establishing an early division lead. Reed Johnson and Jim Edmonds were added early on and Rich Harden was acquired from the Oakland Athletics in early July. The Cubs headed into the All-Star break with the NL's best record, and tied the league record with eight representatives to the All-Star game, including catcher Geovany Soto, who was named Rookie of the Year. The Cubs took control of the division by sweeping a four-game series in Milwaukee. On September 14, in a game moved to Miller Park due to Hurricane Ike, Zambrano pitched a no-hitter against the Astros, and six days later the team clinched by beating St. Louis at Wrigley. The club ended the season with a 97–64 record and met Los Angeles in the NLDS. The heavily favored Cubs took an early lead in Game 1, but James Loney's grand slam off Ryan Dempster changed the series' momentum. Chicago committed numerous critical errors and were outscored 20–6 in a Dodger sweep, which provided yet another sudden ending.

The Ricketts era (2009–present)

The Ricketts family acquired a majority interest in the Cubs in 2009, ending the Tribune years. Apparently handcuffed by the Tribune's bankruptcy and the sale of the club to the Ricketts siblings, led by chairman Thomas S. Ricketts, the Cubs' quest for a NL Central three-peat started with notice that there would be less invested into contracts than in previous years. Chicago engaged St. Louis in a see-saw battle for first place into August 2009, but the Cardinals played to a torrid 20–6 pace that month, designating their rivals to battle in the Wild Card race, from which they were eliminated in the season's final week. The Cubs were plagued by injuries in 2009, and were only able to field their Opening Day starting lineup three times the entire season. Third baseman Aramis Ramírez injured his throwing shoulder in an early May game against the Milwaukee Brewers, sidelining him until early July and forcing journeyman players like Mike Fontenot and Aaron Miles into more prominent roles. Additionally, key players like Derrek Lee (who still managed to hit .306 with 35 home runs and 111 RBI that season), Alfonso Soriano, and Geovany Soto also nursed nagging injuries. The Cubs posted a winning record (83–78) for the third consecutive season, the first time the club had done so since 1972, and a new era of ownership under the Ricketts family was approved by MLB owners in early October.

2010–2014: The decline and rebuild

Rookie Starlin Castro debuted in early May (2010) as the starting shortstop. The club played poorly in the early season, finding themselves 10 games under .500 at the end of June. In addition, long-time ace Carlos Zambrano was pulled from a game against the White Sox on June 25 after a tirade and shoving match with Derrek Lee, and was suspended indefinitely by Jim Hendry, who called the conduct "unacceptable". On August 22, Lou Piniella, who had already announced his retirement at the end of the season, announced that he would leave the Cubs prematurely to take care of his sick mother. Mike Quade took over as the interim manager for the final 37 games of the year. Despite being well out of playoff contention the Cubs went 24–13 under Quade, the best record in baseball during that 37 game stretch, earning Quade the manager position going forward on October 19.

On December 3, 2010, Cubs broadcaster and former third baseman, Ron Santo, died due to complications from bladder cancer and diabetes. He spent 13 seasons as a player with the Cubs, and at the time of his death was regarded as one of the greatest players not in the Hall of Fame. He was posthumously elected to the Major League Baseball Hall of Fame in 2012.

Despite trading for pitcher Matt Garza and signing free-agent slugger Carlos Peña, the Cubs finished the 2011 season 20 games under .500 with a record of 71–91. Weeks after the season came to an end, the club was rejuvenated in the form of a new philosophy, as new owner Tom Ricketts signed Theo Epstein away from the Boston Red Sox, naming him club President and giving him a five-year contract worth over $18 million, and subsequently discharged manager Mike Quade. Epstein, a proponent of sabremetrics and one of the architects of the 2004 and 2007 World Series championships in Boston, brought along Jed Hoyer from the Padres to fill the role of GM and hired Dale Sveum as manager. Although the team had a dismal 2012 season, losing 101 games (the worst record since 1966), it was largely expected. The youth movement ushered in by Epstein and Hoyer began as longtime fan favorite Kerry Wood retired in May, followed by Ryan Dempster and Geovany Soto being traded to Texas at the All-Star break for a group of minor league prospects headlined by Christian Villanueva, but also included little thought of Kyle Hendricks. The development of Castro, Anthony Rizzo, Darwin Barney, Brett Jackson and pitcher Jeff Samardzija, as well as the replenishing of the minor-league system with prospects such as Javier Baez, Albert Almora, and Jorge Soler became the primary focus of the season, a philosophy which the new management said would carry over at least through the 2013 season.

The 2013 season resulted in much as the same the year before. Shortly before the trade deadline, the Cubs traded Matt Garza to the Texas Rangers for Mike Olt, Carl Edwards Jr, Neil Ramirez, and Justin Grimm. Three days later, the Cubs sent Alfonso Soriano to the New York Yankees for minor leaguer Corey Black. The mid season fire sale led to another last place finish in the NL Central, finishing with a record of 66–96. Although there was a five-game improvement in the record from the year before, Anthony Rizzo and Starlin Castro seemed to take steps backward in their development. On September 30, 2013, Theo Epstein made the decision to fire manager Dale Sveum after just two seasons at the helm of the Cubs. The regression of several young players was thought to be the main focus point, as the front office said Sveum would not be judged based on wins and losses. In two seasons as skipper, Sveum finished with a record of 127–197.

The 2013 season was also notable as the Cubs drafted future Rookie of the Year and MVP Kris Bryant with the second overall selection.

On November 7, 2013, the Cubs hired San Diego Padres bench coach Rick Renteria to be the 53rd manager in team history. The Cubs finished the 2014 season in last place with a 73–89 record in Rentería's first and only season as manager. Despite the poor record, the Cubs improved in many areas during 2014, including rebound years by Anthony Rizzo and Starlin Castro, ending the season with a winning record at home for the first time since 2009, and compiling a 33–34 record after the All-Star Break. However, following unexpected availability of Joe Maddon when he exercised a clause that triggered on October 14 with the departure of General Manager Andrew Friedman to the Los Angeles Dodgers, the Cubs relieved Rentería of his managerial duties on October 31, 2014. During the season, the Cubs drafted Kyle Schwarber with the fourth overall selection.

Hall of Famer Ernie Banks died of a heart attack on January 23, 2015, shortly before his 84th birthday. The 2015 uniform carried a commemorative #14 patch on both its home and away jerseys in his honor.

2015–2019: Championship run

On November 2, 2014, the Cubs announced that Joe Maddon had signed a five-year contract to be the 54th manager in team history. On December 10, 2014, Maddon announced that the team had signed free agent Jon Lester to a six-year, $155 million contract. Many other trades and acquisitions occurred during the off season. The opening day lineup for the Cubs contained five new players including center fielder Dexter Fowler. Rookies Kris Bryant and Addison Russell were in the starting lineup by mid-April, and rookie Kyle Schwarber was added in mid-June. On August 30, Jake Arrieta threw a no hitter against the Los Angeles Dodgers. The Cubs finished the 2015 season in third place in the NL Central, with a record of 97–65, the third best record in the majors and earned a wild card berth. On October 7, in the 2015 National League Wild Card Game, Arrieta pitched a complete game shutout and the Cubs defeated the Pittsburgh Pirates 4–0.

The Cubs defeated the Cardinals in the NLDS three-games-to-one, qualifying for a return to the NLCS for the first time in 12 years, where they faced the New York Mets. This was the first time in franchise history that the Cubs had clinched a playoff series at Wrigley Field. However, they were swept in four games by the Mets and were unable to make it to their first World Series since 1945.

Before the season, in an effort to shore up their lineup, free agents Ben Zobrist, Jason Heyward and John Lackey were signed. To make room for the Zobrist signing, Starlin Castro was traded to the Yankees for Adam Warren and Brendan Ryan, the latter of whom was released a week later. Also during the middle of the season, the Cubs traded their top prospect Gleyber Torres for Aroldis Chapman.

In a season that included a no-hitter on April 21 by Jake Arrieta, the Cubs finished with the best record in Major League Baseball and won their first National League Central title since the 2008 season, winning by 17.5 games. The team also reached the 100-win mark for the first time since 1935 and won 103 total games, the most wins for the franchise since 1910. The Cubs defeated the San Francisco Giants in the National League Division Series and returned to the National League Championship Series for the second year in a row, where they defeated the Los Angeles Dodgers in six games. This was their first NLCS win since the series was created in 1969. The win earned the Cubs their first World Series appearance since 1945 and a chance for their first World Series win since 1908. Coming back from a three-games-to-one deficit, the Cubs defeated the Cleveland Indians in seven games in the 2016 World Series, They were the first team to come back from a three-games-to-one deficit since the Kansas City Royals in 1985. On November 4, the city of Chicago held a victory parade and rally for the Cubs that began at Wrigley Field, headed down Lake Shore Drive, and ended in Grant Park. The city estimated that over five million people attended the parade and rally, which made it one of the largest recorded gatherings in history.

In an attempt to be the first team to repeat as World Series champions since the Yankees in 1998, 1999, and 2000, the Cubs struggled for most of the first half of the 2017 season, never moving more than four games over .500 and finishing the first half two games under .500. On July 15, the Cubs fell to a season-high 5.5 games out of first in the NL Central. The Cubs struggled mainly due to their pitching as Jake Arrieta and Jon Lester struggled and no starting pitcher managed to win more than 14 games (four pitchers won 15 games or more for the Cubs in 2016). The Cub offense also struggled as Kyle Schwarber batted near .200 for most of the first half and was even sent to the minors. However, the Cubs recovered in the second half of the season to finish 22 games over .500 and win the NL Central by six games over the Milwaukee Brewers. The Cubs pulled out a five-game NLDS series win over the Washington Nationals to advance to the NLCS for the third consecutive year. For the second consecutive year, they faced the Dodgers. This time, however, the Dodgers defeated the Cubs in five games. In May 2017, the Cubs and the Rickets family formed Marquee Sports & Entertainment as a central sales and marketing company for the various Rickets family sports and entertainment assets: the Cubs, Wrigley Rooftops and Hickory Street Capital.

Prior to the 2018 season, the Cubs made several key free agent signings to bolster their pitching staff. The team signed starting pitcher Yu Darvish to a six-year, $126 million contract and veteran closer Brandon Morrow to two-year, $21-million contract, in addition to Tyler Chatwood and Steve Cishek. However, the Cubs struggled to stay healthy throughout the season. Anthony Rizzo missed much of April due to a back injury, and Bryant missed almost a month due to shoulder injury. However, Darvish, who only started eight games in 2018, was lost for the season due to elbow and triceps injuries. Morrow also faced two injuries before the team ruled him out for the season in September. The team maintained first place in their division for much of the season. The injury-depleted team only went 16–11 during September, which allowed the Milwaukee Brewers, to finish with the same record. The Brewers defeated the Cubs in a tie-breaker game to win the Central Division and secure the top-seed in the National League. The Cubs subsequently lost to the Colorado Rockies in the 2018 National League Wild Card Game for their earliest playoff exit in three seasons.

The Cubs' roster remained largely intact going into the 2019 season. The team led the Central Division by a half-game over the Brewers at the All-Star Break. However, the team's control over the division once again dissipated going into final months of the season. The Cubs lost several key players to injuries, including Javier Báez, Anthony Rizzo, and Kris Bryant during this stretch. The team's postseason chances were compromised after suffering a nine-game losing streak in late September. The Cubs were eliminated from playoff contention on September 25, marking the first time the team had failed to qualify for the playoffs since 2014. The Cubs announced they would not renew manager Joe Maddon's contract at the end of the season.

2020–present: Post-Maddon years

On October 24, 2019, the Cubs hired David Ross as their new manager. Ross led the Cubs to a 34–26 record during the 2020 season, which was condensed due to the COVID-19 pandemic. Starting pitcher Yu Darvish rebounded with an 8–3 record and 2.01 ERA, while also finishing as the runner-up for the NL Cy Young Award. The Cubs finished first in the NL Central, but were swept by the Miami Marlins in the Wild Card round.

Following the 2020 season, the Cubs' president, Theo Epstein, resigned from his position on November 17, 2020. He was succeeded Jed Hoyer, who previously served as the team's general manager since 2011. However, it was announced that Hoyer would also remain as general manager until the team could conduct a proper search for a replacement. Prior to the 2021 season, the Cubs announced they would not re-sign Jon Lester, Kyle Schwarber, or Albert Almora. In addition, the team then traded Darvish and Victor Caratini to the San Diego Padres in exchange for prospects. After suffering an 11-game losing streak in late June and early July 2021 that put the Cubs out of the pennant race, they traded Javier Báez, Kris Bryant, and Anthony Rizzo and other pieces at the trade deadline. This left Willson Contreras, Jason Heyward, and Kyle Hendricks as the only remaining players from the World Series team.

On October 15, 2021, the Cubs hired Cleveland assistant general manager Carter Hawkins as the new general manager.