Let's face it: The Chicago Cubs will have to spend a lot of money to retain Kyle Tucker past this winter. He has no reason to extend in season, knowing how much more players have made in free agency. Vlad Guerrero Jr. is the rare exception — a superstar who didn't go to free agency but still got a deal he was happy with. We'll never know if he could have gotten more. Still, Juan Soto — rumored to be around $500 million but landed $750 million in free agency — is one example of bidding wars adding hundreds of millions of dollars to a contract.
Therefore, it wouldn't make much financial sense for Tucker to extend, and he may be willing to come back to Chicago if the money is there. That money, however, will need to be nearly triple what the Cubs and the Ricketts family have ever paid for a player. For a big market team that has shown reluctance to go over the luxury tax, why should Cubs fans now believe there's any hope that ownership will hand Tucker a blank check this winter?
Calling the Ricketts family cheap is the typical response among the fan base when they see that the Cubs not only don't go over the luxury tax, especially when they are worth $380 million more as a franchise from a season ago, according to Forbes, but also that they are still $25 million under the luxury tax to begin the season. It's tough to argue against, but considering that all of this could be mitigated if they now spend to land the correct player, let's continue.
Losing Cody Bellinger as a salary dump without immediately reallocating those funds supported this theory. However, there are key elements in this debate regarding Tucker that Cubs fans should remember.
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1. If they're willing to go over for Bregman, they should do the same for Tucker
Before Alex Bregman signed a $120 million deal with the Boston Red Sox for three years, he almost landed in Chicago on a deal that would have taken the Cubs over the luxury tax in 2025. Ricketts made it known that this was a unique circumstance in an attempt to better the team, and not something the Cubs would do for just anyone.
At age 27, Tucker is at least twice the player Bregman is, and if the front office is willing to do what they need to do to "make the team better," they need to keep the same energy regarding Tucker this winter.
If the Cubs landed Bregman, they would go over the luxury tax for the second season, meaning 30 percent penalties on all dollars over the $241 million tax threshold for 2025. Another thing to keep in mind, per MLB.com: A team that exceeded the CBT threshold in the preceding season will lose its second- and fifth-highest selections in the following year’s draft, as well as $1 million from its international bonus pool for the upcoming signing period. Given that the Cubs value the draft and their international monies, there's much more at play than just a financial penalty for going over.
That is why not going all out for Bregman, a player attached to a qualifying offer, costing the team even further draft pick compensation, did not make the most sense for the future. Not when the team can reset itself this season to avoid consecutive years (more significant fines) of going over.
Leaving as much as they did on the table wasn't cheap, but it could help the Cubs in the long run if they decide to make a run at Tucker based on construct structure, other variables, etc. Resetting now means they can go over next year, and then they will quickly have another reset for 2027.
2. The Cubs have massive money freed up after the 2026 season
Looking at potential free agents on the Cubs, Ian Happ, Seiya Suzuki, Jameson Taillon, Nico Hoerner, Justin Turner and Colin Rea are a group that collectively are set to hit UFA, combining for over $75 million in payroll. Resetting their luxury tax now means the team will likely have to go over in 2026 again if they land Tucker, but they can get right back under after next season.
For that to work, the Cubs need to see team-friendly contract players and prospects, such as Pete-Crow Armstrong, Matt Shaw, Michael Busch, Miguel Amaya, etc., work out at the highest level. If the Cubs spend as much as they will need to on Tucker, they must have multiple players on incredibly cheap contracts to justify the high team-record AAV he will receive. Thankfully, the Cubs have one of the deepest farm systems in baseball, and that hope is a real possibility.
Be thankful the Cubs didn't land Bregman. It would almost guarantee they don't land Tucker because that would require Ricketts to go to levels we know he is uncomfortable with. However, there are multiple ways to make a long-term Tucker contract make sense financially, even without repeatedly going over the luxury tax. The last thing we should do is assume the Cubs have nothing up their sleeves.