What would it take to lock up Tarik Skubal, Gunnar Henderson and more? MLB Extension Week

On Tuesday, I looked at possible extensions for players set to hit free agency at the end of the 2025 season.

To be honest, thats the easy one during Extension Week.

Heres the harder one, looking at players multiple years away from free agency, from a reigning Cy Young award winner two years from a big payday to a superstar rookie with five years of team control remaining.

Advertisement This exercise is tougher because Im estimating what players may make in arbitration (again via comparisons to similar players) and because the risk/reward balance is huge here.

Bet big on the right player, and you lock in savings for a decade.

Do so on the wrong player, and it can handcuff you for years.

Of note, for a lot of the comps Im looking less at the headline value of an extension and more at how it valued a players free-agent years.

That again requires extrapolating and estimating arbitration salaries, so its not set in stone.

Today Im looking at: Tarik Skubal (28) Controlled through 2026 Heres what I wrote last spring when suggesting that a projected extension made a lot more sense for the Tigers than it did for Skubal: A whole lot of people inside the sport expect a major breakout from Skubal this year, which would change the landscape for his earnings significantly.

The landscape has changed significantly.

Skubal put together a full season of outstanding performance, running away with the AL Cy Young Award unanimously.

The average annual values (in todays money) for deGrom ($29 million) and Hernandez ($37.5 million) create reasonable bookends for Skubal.

Lets go with five free-agent years at about $35 million apiece, taking Skubal through his age-34 season in Detroit.

Hes making just over $10 million this year and, with a solid year, could make about $16 million in 2026 (which would establish a new record in arbitration for a non-Super Two pitcher).

Add it all together and we reach the $200 million mark.

2024 extension projection: Five years, $70 million 2025 Salary: $10.15 million 2025 extension projection: Seven years, $200 million Garrett Crochet (26) Controlled through 2026 While I didnt project an extension for Crochet last spring you know, back before hed ever started a major-league game I did take a crack at it in July, landing on five years and $110 million .

While Crochets employer has changed, not much else about his trajectory has.

On the one hand, Crochets potential earnings are held down by his scant track record when he first entered arbitration ahead of last season: Hell probably earn about $15 million over three seasons in arbitration, whereas similarly talented pitchers can get that in the final year alone.

On the other hand, Crochet is set to hit free agency ahead of his age-28 season (and with a birthday in late June, hell be a young 28 that season.) So an extension would cover more of his prime years than for the typical pitcher who hits free agency at 30.

The comparison I made in the summer to Spencer Strider still holds.

Like Strider, Crochet has one really good season on his ledger.

Strider was under control for five more seasons, and his six-year deal with Atlanta valued one free-agent year at about $38 million (or two years at $55 million, if a club option is exercised as Atlanta would assuredly hope).

Crochets relative youth could mean that the Red Sox are comfortable buying out four or even five free-agent years at a price in that range.

For now, Ill stick with what I said last summer: an extension that values three free-agent years at $32 million apiece and ends up at five years and $110 million.

2024 extension projection: N/A 2025 Salary: $3.8 million 2025 extension projection: Five years, $110 million Logan Gilbert (28) Controlled through 2027 As a Super Two, Gilbert should make about $35 million over his remaining three years under team control with Seattle.

Now Gilbert, unlike Crochet, isnt slated to hit free agency until after his age-30 season three years older than the left-hander.

So a deal here might only buy out two to three free-agent years.

Gilberts best comp is Blake Snell ahead of Snells extended free agency in 2023-2024.

Of course, Gilbert doesnt have Snells Cy Young pedigree, so lets tick that AAV down to $30 million even, for three seasons.

2024 extension projection: Seven years, $115 million 2025 Salary: $7.625 million 2025 extension projection: Six years, $126 million William Contreras (27) Controlled through 2027 Another outstanding season for Contreras in Milwaukee means hes actually making the most of the three very good catchers hitting arbitration for the first time, ahead of Adley Rutschman and Cal Raleigh.

Contreras should reach about $30 million over his three years of arbitration.

The two recent extensions for catchers with multiple years of team control left were for Sean Murphy (2023) and Will Smith (2024).

Murphys bought out three years of free agency for $54 million, while Smiths was a remarkable eight years for about $102 million (accounting for deferrals).

Smiths an excellent comp, but his contract, with its record length to limit the average annual value, is tough to extrapolate from.

So lets add in a few free-agent catchers to see how the market has valued them.

Theres a pretty set level at about $23 million per season in todays money.

Adding three seasons at that level for Contreras to what he should earn in arbitration gets him to $99 million.

And who can resist rounding up? 2024 extension projection: Six years, $70 million 2025 Salary: $6 million 2025 extension projection: Six years, $100 million Adley Rutschman (27) Controlled through 2027 Last spring, I estimated $36 million for Rutschmans three years in arbitration and a $30 million annual salary beyond that in line with Buster Poseys 2013 extension with the Giants in todays money.

Posey in his third season won a second World Series and an MVP with around 10 wins above replacement.

Rutschman...did not.

A relatively down season for Rutschman means hes into a different stratum of comps with guys like Contreras and Smith and Murphy, rather than with Posey or Joe Mauer.

Instead of $36 million in arbitration, hes likelier to come in around $28 million now given his starting point.

And instead of a $30 million salary per free-agent year, he should be right with Contreras at $23 million.

Perhaps Rutschmans pedigree as a No.

1 overall pick adds a little to that, so lets go with buying out four free-agent years at $24 million apiece.

2024 extension projection: Eight years, $134 million 2025 Salary: $5.5 million 2025 extension projection: Seven years, $123 million Gunnar Henderson (24) Controlled through 2028 Hendersons phenomenal 2024 doesnt just put him in the same class as Fernando Tatis Jr.

and Bobby Witt Jr.

when they signed their huge extensions.

It actually places him above both those players.

The extensions for Witt and Tatis valued their free-agent years at around $35 million per season.

Henderson can go higher than that, closer in fact to Francisco Lindors extension with the Mets ($41 million per season in todays money).

And its not crazy to think Henderson could make more in three years of arbitration than Mookie Betts record $57.5 million.

Advertisement So lets estimate Hendersons arb earnings at $55 million and buy out eight free-agent years at $40 million each.

2024 extension projection: 12 years, $274 million 2025 Salary: Pre-arbitration 2025 extension projection: 12 years, $375 million George Kirby (27) Controlled through 2028 Having entered arbitration early as a Super Two player, Kirby could make more than $40 million before he even hits free agency.

(David Price holds the record for a starter at just under $45 million.) Like Gilbert, Kirby isnt going to be a free agent until after his age-30 season.

But his work to this point compares well with one of the best free-agent deals in recent memory.

Valuing two of Kirbys free-agent years at $30 million per season leads to a six-year deal.

Hes essentially stayed the course from where he was last spring.

2024 extension projection: Seven years, $100 million 2025 Salary: $4.3 million 2025 extension projection: Six years, $100 million Elly De La Cruz (23) Controlled through 2029 De La Cruz is not far behind Henderson when it comes to production early in his career.

(Henderson finished eighth in the MVP balloting in his second season in 2023, same as De La Cruz in his second season last year.) The first question here is when De La Cruz will first be eligible for arbitration.

Right now, he has one year and 118 days of service time; adding another full year to that would have qualified him for Super Two status (and early arbitration) in three of the last six seasons.

There is precedent for pre-arbitration extensions that offer different salaries based on whether the player eventually earns Super Two status.

(Jose Quintana and Madison Bumgarners early-career extensions are two such examples.) Lets estimate De La Cruzs arbitration earnings at around $50 million about the same as Lindors.

If De La Cruz qualifies as a Super Two player, his salary for 2026 can jump by about $5 million.

Again, Tatis and Witt work as comps.

Buying out eight free-agent years at $35 million apiece gets us to 12 years and $330 million.

Again, if De La Cruz qualifies for early arbitration, the deal would add $5 million in guarantees.

2024 extension projection: N/A 2025 Salary: Pre-arbitration 2025 extension projection: 12 years, $330 million Jackson Merrill (22) Controlled through 2029 Sometimes the comparisons make themselves.

Rodriguezs deal, as you may know, is complex.

Ive spent far too much time in the years since it was signed looking at it on Cots Baseball Contracts and scribbling out some math in a notebook.

At its basic level, Rodriguezs deal guaranteed him $209.3 million over 12 years in a worst-case scenario, essentially buying out seven free-agent years for $155 million or so.

But the likelier end point is a deal of 15-plus years worth in excess of $400 million, or buying out 10 free-agent years at close to $350 million.

So lets find the middle ground for Merrill, for simplicitys sake.

Advertisement For players who have one superstar season, I like to estimate about $50 million in arbitration.

The Padres have tended to emphasize the long in long-term deals.

They signed Tatis to 14 years, Manny Machado to a pair of 10-year deals, Xander Bogaerts for 11 years and even Yu Darvish through his age-42 season.

So lets imagine San Diego buying out 10 of Merrills free-agent years, taking him through his age-36 season, at $32.5 million per year.

2024 extension projection: N/A 2025 Salary: Pre-arbitration 2025 extension projection: 15 years, $375 million (Illustration: Demetrius Robinson / The Athletic ; Photos: Jason Miller, Greg Fiume / Getty Images).

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