Money doesn’t win rings—just ask the Angels. While Shohei Ohtani and Mike Trout collected generational paychecks, October baseball never showed up in Anaheim. Now the Chicago Cubs find themselves flirting with a Kyle Tucker megadeal, chasing star power over sustainable depth. The warning signs aren’t subtle, and the blueprint for buyer’s remorse is already written in red and white on the West Coast.

As time passes, Kyle Tucker’s market price is going upwards only, and things are starting to get hot for the Chicago Cubs. With the contract ending after this season, Kyle Tucker will walk into free agency, and the Cubs have 2 choices: pay big now or pay bigger later. But ex-MLB executive, David Samson, explains why the Cubs should keep this as the last resort, and he gave the Angels as an Example.

In his recent YouTube video, David Samson talked about Kyle Tucker and his contract situation. He said, “The question is, what do the Cubs do as a team… he’s not giving you a hometown discount… If you get him signed before free agency, it’ll be an overpay… if you’re the Cubs, you just gotta be careful… one person does not make a World Series. Look at Shohei and Mike Trout in Anaheim, where they never even won a playoff game.”

Kyle Tucker has been everything the Cubs hoped for and more in his 2025 campaign. Slashing .282/.384/.887 with 17 home runs, 56 RBIs, and 22 stolen bases, he’s a five-tool presence who doesn’t flinch under pressure. He’s played in 94 of 95 games, made his fourth straight All-Star appearance, and quietly fueled Chicago’s charge to first place. Whether boosting Pete Crow-Armstrong’s confidence or stabilizing the lineup, Tucker’s impact ripples well beyond the box score.

Yet despite the on-field brilliance, a $500+ million contract could steer the Chicago Cubs into dangerous waters. Juan Soto’s $765 million megadeal and Vladimir Guerrero Jr.’s $500 million extension reset the market’s ceiling. But Tucker, for all his poise, is nearing 29 and may already be at his athletic peak. One contract that large could handcuff roster flexibility and put future postseason depth at risk.

Look no further than Anaheim, where Shohei Ohtani and Mike Trout became stars without October validation. Despite generational talent, the Angels never won a single playoff game with both under contract. Superstar contracts drain ecosystems—they elevate ceilings but strip away support systems essential for winning. If the Cubs overcommit, Tucker’s prime could echo through a hollowed-out clubhouse, not a championship parade.

So here’s the billion-dollar question—can the Cubs afford Kyle Tucker without bankrupting their future? His bat may anchor the lineup, but his price tag could sink the ship. Paying for greatness is one thing; paying for isolation in October is another. The Cubs must decide if they’re building a contender or funding a one-man show. History, after all, doesn’t hang banners for cautionary tales.

Forget the Cubs, Kyle Tucker might be heading to Florida.

Superteams are built with checkbooks, but dynasties? Those need vision—and maybe a little restraint. While the Cubs marvel at Kyle Tucker’s bat and consider backing up a Brink’s truck for it, another possibility is quietly brewing down south. Tucker has thrived in Chicago, but with free agency looming and dollar signs dancing, the Windy City might find itself bidding against palm trees, tax breaks, and a Tampa twist.

MLB insider Ken Rosenthal recently floated what he called a “wild and crazy” idea involving Kyle Tucker. The Chicago Cubs outfielder, acquired from the Astros last offseason, is due for a mega-deal. While the Cubs have benefited from his production, no extension has materialized with free agency approaching. Rosenthal suggested Tucker could land with the Rays, calling the possibility “not as preposterous as it sounds.”

The Tampa Bay Rays, often financially cautious, may have a rare opportunity to spend big this offseason. Rosenthal speculated, “Depending upon how much Zalupski is willing to spend… Kyle Tucker.” Jacksonville developer Patrick Zalupski is expected to be confirmed as the team’s new owner soon. With Wander Franco’s contract potentially off the books, payroll flexibility could become a key asset.

For Tucker, a move to Tampa would represent both a homecoming and a clean contractual slate. He hails from Tampa and played high school ball at Plant High School. The Rays, long reliant on internal development, could gain an elite hitter entering his prime. If the Cubs balk at a $500 million price tag, the Rays might surprisingly take the plunge.

Baseball rarely hands out fairy tales, but sometimes, the luxury tax writes the plot twist. If the Rays suddenly find themselves with a wallet and a will, Tucker’s Florida return could flip the script. The Cubs may keep counting WAR, but Tampa might be counting on fate. Hometown stories sell tickets. And if Zalupski wants to make a splash, Tucker could be his billion-dollar cannonball.