Detroit – Tarik Skubal is a Tiger, at least for now. He’s not likely to be a Tiger come 2027. Heck, he might not even be a Tiger on Opening Day 2026.
But maybe, just maybe, it doesn’t have to be that way.
By most accounts, there are two options for the Tigers when it comes to their back-to-back American League Cy Young winner: Trade him this winter and get whatever you can for him – one major-league-ready player and two top-100 prospects? – or keep him, go all-in for 2026 and try to win one World Series before the very real Skubal window shuts.
Nobody seems to think the Tigers – or 24 other major-league teams –are going to pony up the long-term freight that’s being floated, somewhere in the 10-year, $400 million range. Those megadeals in baseball almost never work out on the back end, and they’re especially risky for pitchers, particularly ones with past arm ailments.
Maybe, though, there’s another option, one that’s not being talked much about – but one that could make sense for both parties: The Tigers should offer Skubal a multi-year but shorter-term contract with an overinflated annual average salary. They can afford that, and it’d still make Skubal the highest-paid pitcher in the game, which, let’s be honest, is the paramount priority for his super-agent, Scott Boras. Such a scenario would provide both sides with future flexibility.
The Tigers would get to keep the stud they drafted, developed and watched turn into the best pitcher on the planet for at least a few more years, and Skubal still would get one more bite at the big free-agent apple at a young-enough age.
“Our point of view is we always listen,” Boras, between lame, preplanned puns, said during the GM meetings last week in Las Vegas. “We’re prepared to listen to about anything that Chris (Ilitch) or really Scott (Harris) has to say.”
Well, this proposal would qualify under the anything umbrella. So, let’s see.
This proposal would signal the Tigers are serious, but not reckless.
Bregman as baseline
So, what would such an offer look like? I’ve thought a lot about this in recent weeks, and I tried to find a recent comparison – one obviously one was Alex Bregman’s three-year, $120 million deal with the Boston Red Sox last winter. Bregman took the short-term deal over the six-year deal, worth more than $170 million, that the Tigers reportedly offered. Any Skubal offer has to exceed what Bregman got in Boston. Skubal’s younger (he turns 29 on Thursday; Bregman was about to turn 31 when he signed) and, even as a pitcher, the more valuable player.
Perhaps a more fair comparison to the Skubal situation is the three-year, $126 million extension the Philadelphia Phillies gave ace Zack Wheeler before the 2024 season, when he was 33. Wheeler’s player-value metrics compare better to Skubal’s, but the age gap is even greater.
Any offer from the Tigers to Skubal’s camp must start with the following baseline: It has to be serious enough to be taken seriously by an agent in Boras who much prefers taking clients to free agency over signing early. That means there can be no angling for a hometown discount on the Tigers’ part. Make it hard for Skubal and Boras to say no, understanding that, yes, Skubal is the boss, but you don’t hire Boras without acknowledging the goal is max money.
And, so, I’d start in the three-year, $150 million range, and be willing to stretch the dollars to $180 million. That seems eye-popping, even crazy pants, at first glance, but it’s really not for a Tigers team with lots of payroll wiggle room.
The Tigers’ 2026 payroll currently projects allocations in the $120 million to $130 million range, and that includes predicted arbitration figures. With $50 million to $60 million a year for Skubal, minus his arbitration projections, that would push Detroit’s payroll to the $150 million to $170 million range, which would still leave Ilitch, team CEO and chairman, and Harris, team president, ample money to spend on free agents (yes, even Bregman or Bo Bichette) to surround Skubal and appeal to his desire to get a ring in Detroit, all still without having to carry a top-10 payroll.
More: Ready, set, shop! Tony Paul’s top 50 MLB free agents, with predictions
Nobody’s saying the Tigers have to or should spend like Chris’ father, Mike, did all those years, as he fruitlessly chased that World Series ring. From 2011-17, the Tigers carried a top-five payroll. They spent nearly a billion dollars on players during that span. The Tigers of Mike Ilitch acted like they were the New York Yankees. Well, they aren’t the Yankees, or the Los Angeles Dodgers, or the New York Mets. Then again, they’re also not the Arizona Diamondbacks.
They can afford such a Skubal salary for three years, without disrupting that apple cart ― they currently have just two player contracts that go beyond 2026, Javy Báez through 2027 and Colt Keith through at least 2029.
A three-year Skubal deal would run at a time when most of the Tigers’ supposed core is young and relatively cheap. This deal would get the Tigers to the point where they have to start making some decisions on whether to give long-term, big-money contracts to Riley Greene, Spencer Torkelson, Kerry Carpenter, Parker Meadows, Troy Melton, etc. A decision will have to be made sooner on Casey Mize, who’s a free agent next winter.
Perhaps, then, at that point, the Tigers will have to split with Skubal, but at least you’ve given yourself three more chances at the franchise’s first World Series title since 1984, without handcuffing the club’s finances for a decade with a player who, in all likelihood, won’t be living up to a 10-year deal on the back end. (We all saw what Miguel Cabrera became.) Also worth noting, I’d assume, the Tigers would have an easier time insuring a shorter-term contract at Skubal’s current age, than a long-term deal that could expire after Skubal turns 40.
Meanwhile, for Skubal, such a deal has potentially great benefits, too.
For starters, he’d get a significant raise over what he’s projected to get in arbitration for 2026. He’s due to get somewhere up to $20 million; this theoretical Tigers deal could pay him more than two or three times that. Such a deal also would give him his generational wealth as well as protection from any serious injury in 2026, before the lefty hits the free-agent market next winter.
Looming lockout
Speaking of next winter, there’s a very real possibility that will be a lockout, as owners make their latest push for a salary cap ― the budget-less Dodgers just won a second straight World Series ― which the union, one of the strongest on planet Earth, will never agree to. Skubal could be left in limbo, scrambling to sign somewhere once a new CBA is signed. He’d surely still get paid, but any lockout could bleed into spring training, or even into the regular season. A Tigers extension would give him peace of mind (no small thing) at a time of great uncertainty in the game.
Skubal, notably, also is a member of the MLB Players Association’s executive subcommittee. All players take their responsibility to look out for players who come after them very seriously when it comes to getting the best contract possible. But union reps take that stance to the next level. This proposal doesn’t hinder Skubal’s efforts. This would make Skubal the highest-paid pitcher in the game (by average annual value), and one of the top-paid players in the game.
After this three-year proposal expires, Skubal then would become a free agent at age 32. Assuming he stays healthy and dominant (would you bet against that?), he’d be in line for another big-buck bonanza. Gerrit Cole got $324 million at age 29; Corbin Burnes got $210 million at 30; Max Scherzer got $210 million at 30, and that was a decade ago. In the end, this scenario, between two deals, could end up paying Skubal significantly more than $400 million.
It’d take some creativity and a good-faith attempt by the Tigers to keep him beyond 2026 ― but, and this is important, no opt-out, a la Bregman and Boston; you’re either all in or you’re not ― and one more bet on himself from Skubal.
“I’ve given everything I have to this organization,” Skubal, who won pitching’s Triple Crown in 2024 and was even better in 2025, said after becoming the American League’s first repeat Cy Young winner since the turn of the century.
“I want to be a Tiger for a very long time.”
How about, not that long?
But not that short, either.