The Chicago Cubs remain one of the most profitable franchises in the MLB. Yet, owner Tom Ricketts ostensibly keeps the profits for himself rather than investing the money into one of the most storied organizations in American sports.
Chicago brought in the third-highest revenue in the league last year, Patrick Mooney and Ken Rosenthal of The Athletic ($) note. Meanwhile, Ricketts fell well short of his expectations of spending around the $241 million luxury tax threshold for 2025, boasting a sub-$200 million total payroll.
Mooney/Rosenthal quoted a source stating that Cubs president of baseball operations Jed Hoyer has been tasked with constructing a playoff contender while wearing ' handcuffs.' Unfortunately, Ricketts' conservative approach has cost Chicago dearly, preventing them from closing deals with impactful players on multiple occasions.
Over the past two offseasons, we've seen the Cubs stay engaged in free agency, positioning themselves for chances to sign high-end talent. Nonetheless, Ricketts' frugality has gotten in the way of Hoyer's plans, specifically involving the three names mentioned below.
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3 franchise-altering stars the Cubs could've added if owner Tom Ricketts' stinginess didn't get in the way
3. Cubs had an opportunity to land Alex Bregman before he joined the Red Sox
Per Mooney/Rosenthal, Hoyer "was authorized" to present Bregman and super agent Scott Boras a four-year deal worth $115 million. The only problem is that the offer fell significantly short of the Houston Astros, Detroit Tigers and Boston Red Sox's bids.
Houston and Detroit exceeded $150 million across six years before Bregman opted for a shorter deal with Boston at a considerably higher average annual value. Whether you agree with the decision, it's paid early dividends thus far -- he's wasted no time getting situated in Beantown.
Bregman's batting .314/.351/.486 with one home run and four RBIs. His .837 OPS is outstanding, especially compared to the league-average rate of .692. The two-time All-Star is also a versatile, Gold Glove-caliber defender who can play multiple positions at a high level and is a respected clubhouse leader. He has the skill set to solve many issues for the Cubs, though Rickett wasn't willing to pony up.
2. Jack Flaherty would've bolstered an already-solid Cubs rotation
A three-headed top-of-the-rotation monster with Flaherty one-time All-Stars, Justin Steele and Shota Imanaga sounds lethal. Plus, in this hypothetical scenario, veteran right-hander Jameson Taillon gives them one of the better No. 4 options in baseball.
Chicago's starters rank fifth in the National League in Wins Above Average (WAA) thus far in 2025. However, the Cubs left meat on the bone, considering they were in the mix for Flaherty's services this offseason.
Instead, Flaherty ultimately chose a second stint with the Tigers, who re-routed him to the Los Angeles Dodgers ahead of last year's trade deadline. But after contributing to an NL pennant and World Series run, he returns to the Motor City.
Flaherty went 13-7 in 2024 with a 3.17 ERA, 1.068 WHIP and 194 strikeouts across 28 starts and 162 innings of work last season. His arm might've been a swing factor in this year's NL Central race.
1. In an alternate universe, Matt Chapman transforms the Cubs into a force to be reckoned with
Chapman revealed that the Cubs had "'a lot of interest" in poaching him from the San Francisco Giants last winter (h/t Mooney/Rosenthal). Nonetheless, Chicago wanted him on their terms: A one-year deal.
Despite wanting Chapman and having a need at the hot corner, the Cubs "kept [him] on their radar." They "never made a formal offer due to budgetary constraints."
Eventually, Chapman agreed to a three-year, $54 million pact to stay in the Bay Area before severely outperforming his salary and renegotiating a new deal. His efforts earned him a whopping six-year, $151 million contract extension with the Giants last September. Conversely, the Cubs changed third basemen like socks.
Chicago started six and eight players at the third base in 2023 and 2024, respectively. And now, they're throwing their top prospect, rookie Matt Shaw, into the fire to be a long-term solution. He has the pedigree and talent to do it. But the No. 13 pick in the 2023 draft could've been treated as a luxury more than a necessity or a potential bargaining chip.
Chapman's 7.1 Wins Above Replacement (WAR) and 5.0 WAA were seventh in the majors in 2024. He posted a .247/.328/.463 slash line with a .790 OPS, 27 home runs and 78 RBIs. Like Bregman, his status as a Gold Glove fielder and reliable middle-of-the-lineup hitter is highly valuable. The Giants star finished 11th in NL MVP voting, highlighting the level of talent Chicago whiffed on.
Moreover, Chapman also displayed a newfound aggression on the basepaths last season, racking up a career-best 15 steals. As he continues rounding into one of baseball's most complete third basemen, all the Cubs can do is fantasize about what could've been.