Determining whether Padres' Manny Machado actually has the worst contract in MLB

Let’s be honest about something immediately: if we were having this conversation at the start of the 2026 season, Manny Machado might not have even been the first Padres contract dragged into this room. That honor probably would have gone to Xander Bogaerts.

Bogaerts signed an 11-year, $280 million deal with the San Diego Padres in December 2022, and almost from the moment the ink dried, the deal hasn’t aged well. The Padres went from celebrating another star addition to trying to explain why one of the biggest contracts in franchise history suddenly felt more like a payroll anchor than adding a championship piece.

Still, Machado’s deal is a problem. But within his own clubhouse, he hasn’t always been the most obvious place to start.

Why Manny Machado’s Padres deal is complicated, not automatically the worst

“Worst contract in baseball” is a heavy label and a tricky conversation. It’s not just about who is slumping right now nor is it just about who makes the most money. It’s a combination of age, production, availability, future money, positional value and whether the team has any realistic path out of that commitment.

And when we frame it that way, Machado doesn’t quite win the nightmare contest yet.

Lucky for him, we guess? For a while, this argument couldn’t even get off the ground as long as Anthony Rendon was still haunting the Los Angeles Angels’ payroll. Rendon’s deal became the gold standard for free-agent regret. He was barely available, rarely productive, and somehow remained one of the most expensive reminders in baseball that guaranteed contracts can turn into financial cement blocks.

The Angels finally worked out a restructuring and buyout arrangement with Rendon, but let’s call that what it was. Rendon pulled off an all-time. He got his money. The Angels ate the pain. And he played his own role in ruining a team that had Mike Trout and Shohei Ohtani on it. Just…wow.

Machado also dodges the top spot because Kris Bryant still exists in Colorado. Bryant signed a seven-year, $182 million deal with the Rockies, and it has been brutal from almost every angle. He hasn’t played even half a season since joining Colorado in 2022, has dealt with chronic back issues, and has produced like a player nowhere near the version the Rockies thought they were buying.

That is what a true worst-contract case looks like. Big money. Little availability. No real path to surplus value. 

So no, Machado probably does not have the worst contract in MLB today. But that’s not the same thing as saying the Padres should feel good about it.

Machado’s 11-year, $350 million extension runs through 2033. There are no opt-outs. And there is a full no-trade clause. The deal is not just long. It’s recklessly backloaded. He’s making $21 million in 2026, but the real pain comes later, when the contract jumps to $40 million annually for his age-34 through age-40 seasons.

Machado is 33 years old, and if this version is a blip, that would be great news. Every great player gets a grace period. And he’s earned that. How quickly we lose sight of the fact that he was an All-Star in 2025, picked up MVP votes, won another Silver Slugger and played 159 games. 

He has been one of the most important players in Padres history. But we also do not need to do the thing where we treat yesterday’s résumé like it’s a fix for today. 

Machado is slashing .169/.254/.342 with 11 home runs, 32 RBI and a 67 OPS+ so far this season. It’s not a slow start anymore because we are in June.

One fact about his deal is that it doesn't have to be the worst contract in baseball to be one of the most concerning contracts in baseball.

The Padres are paying him like a franchise pillar. If he is still that guy, then this debate fades. But if he isn’t, the Padres have a real future problem on their hands.

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