After three seasons with a superstar as the face of the franchise leading the winter, no. Aaron Judge, Shohei Ohtani or Juan Soto V 2025–26 free agent class. But there's another player whose potential availability could shake up the upcoming offseason: Pull Skubal.
Why not Detroit Tigers perhaps moving his ace on the heels of his second straight American League Cy Young Award and the team's second straight postseason appearance?
Simply put, because keeping Skubal in Detroit is about to get very expensive. The 28-year-old left-hander will enter the final year of his contract in 2026 before he is scheduled to become a free agent after the season. If it hits the market next winter, Skubal has a chance to surpass Los Angeles Dodgers ace Yoshinobu Yamamoto a record $325 million contract, and he could even become baseball's first $400 million pitcher.
With Tigers president of baseball operations Scott Harris facing a decision that will shape the future of the franchise and impact all of MLB, we spoke with 11 industry insiders about what Detroit is doing. must make this offseason broken down into three main options.
1. Trade Skubal this winter
This was the least popular option among our group, and one of the competing executives explained why.
“The whole reason you're doing all this is to start the season with a potential opponent who has an ace. You can't throw it away before the season starts. How long will it take to be here again?”
Some panelists hemmed and hawed about how much the team would have to overpay to get Detroit to consider a trade, believing that an offer involving a young starting pitcher with cutting-edge potential would be enough to start internal negotiations – but no one could bring themselves to logically advocate a trade unless something completely illogical was proposed. And these kinds of deals increasingly don't happen in modern baseball.
If the Tigers were to trade Skubal for anything less than a stunning return, it would likely mean their competitive window would be tightened – and it would be difficult to call Detroit a contender without Skubal next season. Giving up a player of his caliber will call into question whether they will find themselves in this situation again when other star players become free agents, branding the Tigers as a small-market team, at least in mentality. It's much easier to move some, but not all, of their chips into the middle of the upcoming season and see what they can do with Skubal leading the way. Who knows when the next opportunity will arise?
When I asked these sources what the Tigers should do, they seemed unsure of Detroit's view of the situation but were leaning towards the Tigers continuing Skubal into next season. Still, Harris likes to know what the market will bear, so speculation that Skubal is willing to make the right deal – or at least in the sense that Detroit will listen before hanging up – is likely to continue.
2. Keep Skubal, but trade him at the deadline if the season doesn't go as planned.
If things don't go well in the first half of the 2026 season, everyone in our group agreed it was the right move. Defining what “moving sideways” means in the expanded playoffs is difficult, but the battle for a wild card spot near the trade deadline was where the gray area began for our panelists.
“You cannot under any circumstances keep Skubal at the trade deadline and miss the playoffs. It would be a disaster,” one agent said.
The amount would still be huge for a rental deal – the back-of-the-envelope math suggests two top-100 prospects later, or one elite young player, to put it bluntly – but also because the offers would have to clear the bar of Detroit receiving a compensatory pick right after the first round to even be considered, since that's what the Tigers would get if Skubal were to become a free agent (under the current free agent system).
Another rival executive has a valid theory about Harris' focus: “He's looking at 2027 and 2028 as the best years of his career.” If things go well in 2026, the window will expand to include him. Top prospects Kevin McGonigle and Max Clarke, No. 2 and No. 6 prospects in sports could become key players as early as the second half of 2026, so it makes sense to aim for things to really pick up in 2027.
Opinions are on whether Skubal will get more this winter or at the deadline because it's hard to predict how desperate a contender is. could hypothetically be at the deadline compared to what this team would offer to get Skubal's entire season plus a first-round pick when he leaves. It's safe to assume that by the deadline, the return will likely be a little less.
3. Keep Skubal no matter what, try to extend him and take a draft pick if he leaves.
This would be a bold move in the era of the asset-based approach that many teams now take. If Skubal were to become a free agent, the compensation would likely be a draft pick in the 30s next summer – and that's it. This type of selection is valued at approximately $8-10 million in added value, depending on your source.
There's even more value for Detroit, but it's hard to quantify. The Tigers will get another title shot against the reigning back-to-back AL Cy Young winner and more time to convince him to stay in Detroit. Perhaps this combination could work wonders and both sides could get a deal done before he hits free agency. Skubal has said he wants to stay in Detroit, so that can't be ruled out. Another rival executive believes Harris is focused on how to get there. “[Harris] will never believe that he cannot sign Skubal.”
That being said, Skubal, who is represented by Scott Boras, makes it unlikely that he will sign a deal without at least testing the market, as Boras typically advises clients to hit the free agent market.
However, there is another variable that is unique to the timing of Skubal's free agency: an expected labor fight next winter, with the current CBA set to expire on December 1, 2026. It's unlikely that Boras would want Skubal on the market due to the work stoppage that could lead to him potentially signing right before spring training after some teams spent their available money, and with the economics of the game potentially changing in ways that would hurt Skubal's market. One source said complications with the CBA increase the likelihood of Skubal signing an extension before free agency from 0% to 10%.
The last time a shutdown loomed over free agency, we saw a trade frenzy in late November before the December 1st lockout. A similar faster free-agent process that ends with Skubal's signing on Thanksgiving would give Detroit a slight advantage, given familiarity and an exclusive negotiating window before free agency, over a protracted winter bidding war.
The contract marks to be surpassed are Yamamoto's $325 million guarantee, the most for pitchers, and Max Fried's $218 million guarantee, the best of all-time for a left-hander. Both of these contracts were awarded to agencies, not Boras Corp., and setting precedents goes a long way toward helping top agencies market themselves to potential nine-figure clients.
It's also worth noting that Skubal underwent Tommy John surgery in college and flexor tendon surgery in 2022, which are factors to consider when planning a long-term deal as a free agent.
Can Harris and the Tigers win a straight bidding war with a precedent-setting guarantee? No, but if they can offer a shorter AAV record deal with a waiver, they will at least have a path, albeit a narrow one, to keeping their bargaining chip.
The real problem for Detroit is their payroll. They finished last season with a payroll of $155 million, more than $90 million below the first CBT tax threshold. If Skubal gets an AAV of $30 million or even $40 million, can the Tigers really justify handing over a quarter of their salary to one player? Will Harris do it, or will signing Skubal be part of a larger move to the kind of salary that could justify putting Skubal there when the Tigers see their peak window of competitiveness? If McGonigle and Clark emerge at the end of 2026 and look like future stars, it won't translate into higher payrolls, but it could make the Tigers more competitive in the future, and it could also help their long-term relationship with Skubal.
That logic—if things go well in 2026, the Tigers will compete and retain Skubal through the season—also explains why another executive was mulling over Detroit's options if it traded Skubal at the deadline. “You can still trade [Skubal] and then sign him back long-term, but I can't imagine a series of events where that would actually happen.”
There is also tea leaf reading for this winter. Several sources have mentioned that Detroit is targeting pitching depth early in free agency. Is this compensation for a potential Skubal trade? Deal now or on time? Or simply to add depth to the title fight, as all competing teams need? Or create leverage/depth so they have maximum options for all of 2026? You can see what you want to see when it comes to the Rorschach test that is the winter team building mystery.
