It was imperative the Phils’ ace and postseason legend stick around for a while.
When former general manager Matt Klentak entered the 2019 off-season, he knew the Phillies needed a running buddy for Aaron Nola.
To that point, the Phils had tried to fill out the Nola-headed starting rotation with the likes of Vincent Velasquez, Jake Arrieta, and Nick Pivetta. None delivered. It was clear the team needed to go out and sign a marquee free agent or trade for one in the worst way, and Klentak had options.
He could have signed Gerrit Cole, who starred for the Houston Astros and is still perhaps the best pitcher in the American League, now with the New York Yankees. He signed a nine-year, $324 million contract. He could have signed Stephen Strasburg, fresh off a World Series title with the Washington Nationals. Instead, Strasburg re-signed with the Nats, a seven-year, $245 million nightmare of a deal thanks to a thoracic outlet injury that has limited the right-hander to eight starts since signing that deal, essentially ending his career. He could have gone with veteran left-hander Madison Bumgarner, who inked a deal with the Diamondbacks for five years and $85 million. It was clear almost right away he had used all his bullets during the Giants postseason runs.
Instead, Klentak signed Wheeler, who had proven to be an ace-level starter to that point, to ace-level money, five years and $118 million. Four years later, it’s clear Klentak and the Phillies got it right.
On Monday, team president Dave Dombrowski doubled down on that commitment, inking Wheeler to a three-year, $126 million contract extension that begins in 2025, one that will pay him a record $42 million a season, the most per-year dollars for any player extension in MLB history. It is the third-highest average annual value for a pitcher in big league history, one that will keep him in a Phils uniform through the 2027 season, when he will be 37.
We discussed the extension at length on the most recent edition of Hittin’ Season, obviously.
The original Wheeler contract is one of the best free agent bargains in baseball history, and the extension is certainly a lot of money that will affect the team’s luxury tax penalties starting next season. But at just three years, it keeps the team from having to pay a pitcher in his age 38-39 season upwards of $35 million a season. The shorter-term deal assures a better chance the Phillies will not be throwing good money after bad.
It is true the Phils are somewhat paying for past performance. But that past performance is something else.
- In four seasons with the Phillies, Wheeler has started 101 games. He is 43-25 with a 3.06 ERA (it was 3.77 with Mets).
- He has two top-10 Cy Young finishes (2021, ‘23), including being runner-up in 2021 when he led the league in strikeouts (247).
- Over the last three seasons, he has been worth 7.5, 5.0 and 4.3 Wins Above Replacement (WAR), the most of any pitcher in baseball since he became a Phillie.
- In the playoffs, he has 10 starts and one relief appearance and is 4-3 with a 2.42 ERA. He has the lowest combined walks and hits allowed per inning (WHIP) in postseason history with a minimum of 40 innings.
After signing Aaron Nola to a seven year contract at the start of the off-season, the Phillies have spent more than $300 million on Wheeler and Nola, guaranteeing their two top pitchers will front their rotation for next four years.
That’s not good news for teams who play the Phils in October.
There are risks to signing pitchers in their mid-30s to long-term contracts, and we’ve seen fantastic arms like Roy Halladay and Cliff Lee lose their stuff pretty quickly over the last few years. The Phils have also committed around $228 million to just nine players in 2025, so folks who are worried the roster may get too expensive for them to keep enough good players around the superstars have some legitimacy. No one wants to see a return to the 2012-15 Phillies, an era of aging stars desperately trying for one last shot at a title.
However, it’s fair to note that in the two years after the 2008 title, the Phils signed many of their players to big extensions, and got three more cracks at a title to show for it. That’s what they’re attempting to do now.
There’s a chance this could all go bad, but there was no way the Phillies could let Wheeler leave after next season. He would have been the most sought after free agent to hit the market and almost certainly would have landed a bigger deal than the one he just signed to stay in Philadelphia.
During his press conference yesterday, Wheeler said he didn’t want to be anywhere else.
It’s pretty safe to say the Phillies and the fanbase feel the same way.
