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The Chicago Cubs’ Path Back to MLB’s Contenders Club

The Cubs used a series of shrew moves to build a stacked offense and increase payroll, finally resinserting themselves into the World Series conversation.

The Chicago Cubs haven’t reached the postseason since 2020 and haven’t won a playoff game since 2017, an unacceptable run of futility for one of Major League Baseball‘s flagship franchises. But a series of key managerial decisions over the last four years has finally brought the Cubbies to the top of the National League Central and back in the sport’s club of contenders, where they belong.

Heading into Monday’s games, Chicago leads MLB in runs scored, hits, and stolen bases, is second in OPS, third in batting average, and sixth in home runs. The Cubs‘ offense has propelled them to the best run differential in the NL, giving them the second-best World Series odds, according to Baseball-Reference. And they’re accomplishing all this while playing baseball’s toughest schedule over the season’s first month, playing all 27 games to date against teams who have a .500 or better record.

The seeds of this prolific offense were first planted in 2021 when they traded two-time All-Star shortstop Javier Báez to the New York Mets for outfielder Pete Crow-Armstrong, their first-round pick in 2020. PCA has since blossomed into one of the game’s brightest stars, leading MLB in stolen bases, second in defensive WAR, and third in overall WAR as an intriguing early-season MVP candidate at 23 years old.

Crow-Armstrong joined their already entrenched homegrown players Ian Happ and Nico Hoerner, who are now veteran lineup mainstays. Less than eight months after acquiring PCA, Chicago signed Japanese outfielder Seiya Suzuki to a five-year, $85 million contract, though the Cubs finished with another losing season in 2022 with the 14th-highest payroll for the second straight year.

After finishing 74-88 in 2022, three key moves showed that longtime lead executive Jed Hoyer was ready to ramp up and put a product on the field ready to win. Chicago signed All-Star shortstop Dansby Swanson to a seven-year, $177 million contract and inked veteran starting pitcher Jameson Taillon to a four-year, $68 million deal. And on the same day they fired longtime manager and 2016 championship hero David Ross, they poached manager Craig Counsell from the rival Milwaukee Brewers on an MLB-record five-year, $40 million contract.

Although the Cubs fell a game short of the postseason in 2023, Jan. 11, 2024, proved to be a pivotal day for the organization. They not only signed Japanese lefty ace Shota Imanaga to a four-year, $58 million contract — before he became an All-Star with a 15-3 record in 2024 — but also acquired first baseman Michael Busch in a four-player afterthought of a trade with the Dodgers. Busch hit 21 homers last year and has emerged as one of the team’s top hitters.

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While Chicago finished with the same 83-79 record in 2024 as it did in 2023, again missing the playoffs, Hoyer brought the payroll into the top 10, and the mix of youth and veterans was ready to make another leap. After trading star outfielder Cody Bellinger to free up salary space, the Cubs acquired All-Star outfielder Kyle Tucker from Houston, dealt for All-Star closer Ryan Pressly in a separate trade with the Astros, and made a pair of shrewd signings for veteran pitchers Matthew Boyd and Colin Rea to bolster their staff.

With St. Louis in a rebuild of its own and Cincinnati, Milwaukee, and Pittsburgh in the bottom third in MLB payroll, Chicago’s back among the top five spenders as it believes it has the roster in place geared toward sustained success, though Tucker will be a free agent after the season who will likely command baseball’s next contract worth at least $300-400 million.

Stocked with seven of MLB.com’s top 100 minor league prospects, the Cubs can either bring their young talent aboard or trade them to acquire pitchers to boost a staff that’s clearly their weak point right now. They’re 20th in ERA, in the bottom 10 in strikeout rate, and in the bottom half in home run rate. Its pitching is the likely reason why, despite the Cubs’ early-season success, their World Series odds at FanDuel SportsBook are +2100, just the ninth-most likely team to win it all behind teams currently with worse records than them.

But for the first time in nearly a decade, the Cubs’ famed Wrigley Field faithful expect a winner on a daily basis with a young, exciting offense poised to make a postseason run and finally rejoin MLB’s contenders club for the foreseeable future.

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Shlomo Sprung

Shlomo Sprung is a Senior Staff Writer at Boardroom. He has more than a decade of experience in journalism, with past work appearing in Forbes, MLB.com, Awful Announcing, and The Sporting News. He graduated from the Columbia University Graduate School of Journalism in 2011, and his Twitter and Spotify addictions are well under control. Just ask him.

About The Author
Shlomo Sprung
Shlomo Sprung
Shlomo Sprung is a Senior Staff Writer at Boardroom. He has more than a decade of experience in journalism, with past work appearing in Forbes, MLB.com, Awful Announcing, and The Sporting News. He graduated from the Columbia University Graduate School of Journalism in 2011, and his Twitter and Spotify addictions are well under control. Just ask him.