The Chicago Cubs’ pursuit of star outfielder Kyle Tucker has become one of the most closely watched storylines of the 2025 MLB season. With Tucker’s contract situation looming and his value skyrocketing, MLB insider and New York Post reporter Jon Heyman has pinpointed an important factor that could determine whether the Cubs land a long-term extension with their new franchise cornerstone, despite the franchise’s $3.15 billion valuation and historically conservative spending habits.
Chicago Cubs Have the Star, but Will They Pay the Price?
Since coming to the Cubs from the Houston Astros via a blockbuster offseason trade, Kyle Tucker has been everything Chicago hoped for and more. He’s off to a phenomenal start, hitting .300/.409/.600 (batting average/on-base percentage/slugging percentage) with seven home runs, eight stolen bases and 25 RBIs across 28 games.
Tucker has quickly become the heart of the Cubs’ lineup. His historic production—setting MLB records for hits, runs and RBIs in his first 19 games with the team—has only increased pressure on the front office to secure his future in Chicago.
According to MLB insider Jon Heyman, the single biggest factor in the Cubs’ pursuit of Tucker is their willingness (or lack thereof) to match the precedent set by Vladimir Guerrero Jr.’s massive 14-year, $500 million contract with the Toronto Blue Jays. Heyman reported that the Cubs and Tucker’s representatives at Excel Sports Management are expected to begin extension talks this summer.
Heyman also points out that Pete Alonso will likely aim for the same $35.7 million average annual salary that Guerrero secured. Still, it seems more likely the Cubs would be willing to offer Tucker the full 14-year, $500 million deal. A source told Heyman the Guerrero contract is a reasonable comparison for what Tucker should expect.
The Guerrero deal is widely seen as the benchmark. Tucker—despite being slightly older—could command a similar or even larger contract given his all-around value and the assets the Cubs surrendered to acquire him.
While the Cubs are one of MLB’s most valuable franchises, with Forbes valuing them at over $3.15 billion, their recent track record in free agency has been cautious. The front office has often acted more like a “biggest small-market team” than a financial powerhouse.
Their most recent big deals—Jason Heyward and Dansby Swanson — were significant but still dwarfed by what Tucker will likely command.
The question isn’t whether the Cubs can afford Tucker, but whether ownership is willing to break precedent and commit to a deal in the $450–$500 million range. Insiders note that failing to retain Tucker after trading top prospects for him would be a major blow to the team’s credibility and its fan base.
Unlike many stars who prefer to test the open market, there’s optimism that Tucker could sign an extension during the season. The Cubs’ strong relationship with Excel Sports Management — Tucker’s agency — could help facilitate talks, and Tucker’s immediate impact in Chicago may make him more open to staying put.
Still, some believe Tucker’s best move would be to wait for free agency to maximize his value, especially since he’s now positioned to be the top player available after Guerrero re-signed.
Tucker is in his eighth season in the majors with 132 home runs and a career .276 batting average. He’s a Gold Glove winner, a Silver Slugger and a three-time All-Star.
Negotiations are expected to heat up this summer, with the Cubs aiming to lock up Tucker before he reaches free agency. The outcome will hinge on whether the franchise is ready to make a historic financial commitment and set a new standard for spending in Chicago.
The critical factor in the Cubs’ pursuit of Kyle Tucker isn’t just their financial capacity — it’s their willingness to match or exceed the $500 million mega-deal set by Guerrero.
If they do, Tucker could become the face of the franchise for the next decade. If not, the Cubs risk losing their new superstar to the open market—and fans will be left questioning the ambition of a $3.15 billion franchise.