The Chicago Cubs aren’t strangers to big swings—and even bigger regrets. As Kyle Tucker continues to rake and charm the Windy City, the front office finds itself staring down a familiar dilemma: spend like a contender or hedge like a historian. Just because Jason Heyward’s contract gave the Ricketts family financial whiplash doesn’t mean Tucker should inherit the cold feet that came with it.

Now with Kyle Tucker a big name and teams eyeing him, the Cubs will either have to pay him big bucks or watch him bash homers for another team. The ball is now in Chicago’s court. But according to David Samson, the Cubs might not go for him with one thing in mind.

In his recent episode, David Samson talked to Boog Sciambi about the Kyle Tucker situation in Chicago. He said, “Kyle Tucker, one of those trades that works for both teams, but you’re valuing Kyle Tucker in the Soto range… you’re saying $500 million…” 

Sciambi replied, “I’m saying that he’s very similar to the level of player that Juan Soto is. He’s two years older so that changes the contract changes. What I am saying is that he is absolutely a superior player to Vladimir Guerrero and he got $500 million. Between 760 and 500, if I’m Kyle Tucker, somewhere in there. They did the Jason Hayward deal, and that did not work out, and that was in the prime… I wouldn’t say that they’ve shown an inclination towards dipping into those giant contracts. Well, what we’re saying is when they do, it often doesn’t work out.”

The Cubs’ front office still carries the scars of the Jason Heyward contract. Signed for eight years and $184 million, Heyward never delivered the expected offensive production. While his defense remained elite, his bat disappeared in Chicago’s lineup. That deal became a cautionary tale and reshaped how the Cubs approached long-term spending.

Kyle Tucker offers a different profile—one built on both consistency and completeness. Through July 4, Tucker is batting .287 with 17 home runs and 52 RBIs. He also owns a .921 OPS and remains a defensive asset in right field. His balanced production on both ends makes him rare in today’s game.

Unlike Heyward, Tucker is in his prime and trending upward statistically. He’s a four-time All-Star and just earned his first starting nod. His value lies in power, plate discipline, and defensive versatility. For a franchise seeking stability and stardom, Tucker’s profile matches the investment.

The Cubs have seen what happens when big contracts backfire—but they’ve also seen what happens when stars walk. If Chicago wants to play scared, they can keep drafting “the next Kyle Tucker” instead of paying the one they have. At some point, you stop flinching and swing with purpose. Tucker isn’t a gamble; he’s the kind of bet contenders make. And Wrigley deserves a star worth the spotlight.

If the Cubs don’t act, they might lose more than just Tucker

The Chicago Cubs have mastered the art of hesitation, just not the kind that wins championships. As front offices crunch numbers and clutch pearls over Kyle Tucker’s potential price tag, the clock keeps ticking. This isn’t just about one superstar; it’s about a ripple effect that could drown a quarter of the roster. Blink too long, and Tucker won’t be the only one packing his bags out of Wrigley.

The Chicago Cubs aren’t just staring at Kyle Tucker’s price tag—they’re staring at a purge. Ian Happ, Seiya Suzuki, Nico Hoerner, Jameson Taillon, and Matt Boyd are all 2026-27 free agents. That group, alongside Tucker, makes up 37% of the team’s current fWAR contribution. Losing multiple core contributors isn’t a rebuild—it’s a full-blown identity crisis in pinstripes.

Kyle Tucker’s potential $500–$600 million contract could reshape Chicago’s budget like Wrigley renovations on steroids. He’s elite, no doubt—but elite doesn’t win alone, and payrolls don’t stretch forever. Committing that much to one star may leave the Cubs unable to retain foundational pieces. Suddenly, keeping Tucker means losing the glue guys who built the boat he’s steering.

Tucker’s bat is electric, but it’s the synergy that’s kept the Cubs competitive this season. Hoerner’s grit, Happ’s leadership, and Suzuki’s consistent bat all balance the star power. fWAR isn’t just a stat—it’s the heartbeat of a functioning roster. Without the ensemble, Tucker’s talent might sparkle, but the team could still sink.

And here lies the paradox: spend big to look like contenders, or act scared and rebuild by accident. The Cubs can’t window-dress ambition while watching half the core exit stage left. If Tucker’s the crown jewel, don’t pawn the rest of the treasure. Chicago has a choice—build a powerhouse or preserve payroll spreadsheets. Because hesitation might save money, but it sure doesn’t sell tickets in October.