What Does an Extension for Zack Wheeler Look Like?

The five-year, $118 million deal Zack Wheeler signed with the Phillies following the 2019 season will undoubtedly go down as one of the greatest free agent contracts in franchise history.

That same winter, Gerrit Cole signed with the Yankees for nine years and $324 million. Stephen Strasburg signed with the Nationals for seven years and $245 million. Wheeler’s salary is a pittance in comparison.

Since first suiting up for Philadelphia in 2020, the 6-foot-4 right-hander has made 101 starts with a 3.06 ERA and 2.90 FIP. He ranks eighth among all pitchers in strikeouts, sixth in wins, and fourth in innings pitched and quality starts.

As if all that weren’t enough, Wheeler has been worth 19.3 fWAR and 19.6 bWAR across the past four seasons; no other pitcher has topped 18.0 on either leaderboard, and no other pitcher has topped 16.0 on both. His impressive combination of consistency and durability puts the 33-year-old in a class of his own.

Moreover, if you add in Wheeler’s postseason performance, his numbers only look better. In 11 playoff appearances, he has pitched 63.1 innings with a 2.42 ERA, bringing his overall ERA in that time down to an even 3.00. Suffice it to say, Philadelphia wouldn’t have made two consecutive NLCS appearances without him.

In short, Zack Wheeler could stay in the clubhouse baking cookies for all of next season and he’d still have been worth every penny of his $118 million deal. He’s one of the best pitchers in baseball, yet he’s making a No. 2/3 starter’s salary.

Early in the offseason, Phillies president of baseball operations Dave Dombrowski mentioned a couple of tasks on his to-do list. Re-signing Aaron Nola, a free agent, was one of them. Discussing an extension with Zack Wheeler, set to reach free agency following the 2024 season, was another.

After coming to terms with Nola, Dombrowski doubled down on his interest in Wheeler, telling reporters, “We know we’d like to keep him in the organization for a lengthy period.” However, he also qualified the statement, adding, “But it’s not always easy. So it’s something that I’m sure we’ll pursue at some point. But I’m not sure, at this point, how important it is for them at this time.”

Presumably, “them” refers to Wheeler and his agent, who might be hesitant to sign an extension. It’s hard to blame them if that is indeed the case. With another successful season in 2024, Wheeler could be in for a windfall in free agency.

Still, one has to presume that if the money is right, the Phillies could change Wheeler’s mind. An extension would give the veteran some added security in case he struggles next season, and he wouldn’t have to deal with the ever-increasing pressure of his walk year every time he took the mound.

As for the Phillies, it’s not hard to see what they’d get out of an extension with one of the best pitchers in baseball.

A couple of days ago, I wrote about how the Phillies could use an extension to bring down the annual average value of Bryce Harper’s mega-deal for luxury tax purposes. Needless to say, that’s not going to happen here. Wheeler’s $23.6 million AAV is far too low for a pitcher of his caliber, and the only way the Phillies could get that number any lower would be if they extended him into his forties.

Instead, the incentive for the Phillies to extend Wheeler now is to take advantage of the exclusive negotiating window this offseason provides. Wheeler can’t negotiate with other teams until November 2024, when he officially becomes a free agent. Presumably, the Phillies are done making big moves this winter, so they have nothing but time over the next few months.

Can they get a deal done?

How Much Money Are We Talking Here?

There aren’t any perfect comps for a Zack Wheeler extension – I told you he was in a class of his own, didn’t I?

Starters of his caliber are few and far between, to begin with, and it’s even less common to see a pitcher at the top of his game as he enters his mid-thirties. Still, here are some of the best comparisons we have:

Hyun Jin Ryu’s deal is a good jumping off point, but he hadn’t proven himself nearly as consistent and reliable as Wheeler when he signed a four-year, $80 million pact with the Blue Jays. Meanwhile, Yu Darvish was already a couple of years older than Wheeler when he signed his six-year, $108 million extension with the Padres, and he had not had quite as much recent success.

Max Scherzer and Justin Verlander were also older than Wheeler when they signed their massive deals with the Mets, but these are a couple of future Hall of Famers we’re talking about. As good as he is, Wheeler won’t command a record-breaking annual salary quite like Scherzer or Verlander.

Finally, there’s Jacob deGrom. The former Mets ace was entering his age-35 season when he signed a five-year, $185 million deal with the Rangers – that’s the same age Wheeler will be if he enters free agency next winter. However, deGrom is simply unparalleled. When he’s on the field, he’s the best pitcher in baseball. Texas paid for his upside, a kind of upside that even Wheeler doesn’t possess.

With all this in mind, I think a reasonable starting point for a Wheeler extension is a number somewhere in between Darvish’s and deGrom’s.

The midpoint of their annual salaries is $27.5 million, which seems like a fair number for Wheeler on a five-year deal. That would add up to $137.5 million from 2025-’29, his age-35 to 39 seasons. He could surely command a higher AAV on a shorter contract, but a slightly longer deal will net him a higher guarantee.

Only one pitcher age 33 or older, deGrom, has ever signed for more guaranteed money. Only three, deGrom, Scherzer, and Verlander, have ever signed for a higher average annual salary.

Thus, Wheeler gets a guarantee commensurate with his talent and track record, and the Phillies get to keep their ace in town until the tail-end of his career.

There’s no doubt that such a move is risky for Philadelphia. The injury bug can strike at any time, and it only becomes a bigger threat as pitchers get older. That said, a deal like this could also prove to be another bargain.

Will Zack Wheeler be “worth” $27.5 million per year when he’s 39? Probably not. But if the Phillies sign him to a five-year deal, they’ll be hoping he’ll be worth far more than $27.5 million per year in the first few seasons of the deal.

According to the dollars/WAR estimates at FanGraphs, Wheeler has been “worth” an average of $46.2 million per year over the last three seasons. Those estimates are hardly an exact science, but still, that’s nearly $20 million more per year than the AAV I’m suggesting. If Wheeler keeps pitching like Wheeler for the next few years, the Phillies won’t have any qualms about paying him $27.5 million a year through his age-39 season.

In other words, a risk of this degree is one the Phillies must be willing to take. Wheeler isn’t going to forgo free agency for anything less – and honestly, $137.5 million still might not be enough. Simply put, if the Phillies want one of the best pitchers in the game to spend the rest of his career in red pinstripes, this is the kind of offer they’re going to have to make.

So, I repeat: Can they get it done?