Has Bryce Harper proven Dave Dombrowski wrong enough to earn his Phillies extension?

Credit where credit is due: Bryce Harper talked a big game this offseason, and he's backed up every bit of it. After a tough 2025 season in which his own team president, Dave Dombrowski, questioned whether he was still the star his pedigree suggested, his future with the Philadelphia Phillies became a matter of some consternation. Right now, though, he's one of the only things going right for a team still mired below .500, with a .938 OPS that's behind only Kyle Schwarber among Philly batters. He's got four homers in the month of May already, seemingly resolved to put a struggling team on his back.

All of which is great for Phillies fans, and a tremendous story for baseball at large; the sport is better when Harper is mashing. And, sure, it does make Dombrowski look even sillier than he already did. But if Harper and his agent, Scott Boras, think that this changes anything when it comes to their demands for a contract extension, the team needs to hold a firm line.

Phillies should stiff-arm Bryce Harper extension despite his hot start

Harper has been a god-send, yes, and it's clear he's still one of the best all-around hitters in the game. But, in the words of Don Draper, that's what the money is for — and Harper is still being paid quite a bit of it, and will be for five more seasons after this one, at which point he'll be 38 years old (going on 39).

What is the motivation for the Phillies to give in here, exactly? While Harper's been great this season, it's also clear that he's not the player he was when he first came to the team, with his bat speed and contact metrics all slowly but steadily trending in the wrong direction. He's also bringing very little value as a defender or a base-runner at this point in his career.

All of that matters, because paying him right now would be about what he's going to be moving forward, not what he is right now.

History suggests another Bryce Harper extension would be a disaster

But we don't need to leave this in the realm of hypotheticals. While there is no exact parallel to the Phillies' current situation with Harper, there are a couple that come close — and neither of them bode well for paying him significant money past his 40th birthday.

The first is Alex Rodriguez, who more than earned the 10-year, $252 million contract he originally signed with the Rangers. But with the threat of opting out on the table after another MVP season in 2007, Scott Boras convinced Brian Cashman to hand him a fresh deal worth $275 million over 10 years. Needless to say, that one didn't go nearly as well as the first: Rodriguez had a handful more All-Star-caliber years left in him, but he fell off a cliff in his late 30s and the contract became an albatross for its final few years.

We're seeing a similar story play out in San Diego, where the Padres are already regretting the 11-year, $350 million contract extension they gave Manny Machado back in 2023. Machado is now set to be under contract until he's 41, a terrifying thought given that his bat already seems to be in decline. But really, we shouldn't be surprised: While most big free agent deals overpay on the back end in order to secure a star in his prime, these second extensions are paying only for the back end, all risk with very little possibility of reward. Even if Harper is still capable of big-time production at the plate, Father Time comes for us all, and the Phillies will almost certainly regret being talked into giving Boras what he wants — especially if they need to rebuild after a lost 2026 campaign.

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