Let’s Sign Some Contracts! 2026 Edition

If there’s something even more satisfying than spending your hard-earned money, it’s spending someone else’s money that you didn’t earn. When we’re talking baseball, unless you’re an extremely high-net-worth individual who can casually spend hundreds of millions of dollars — if this describes you, call me and we can totally hang out or something — you only have the option to spend other people’s cash. I mean, I haven’t technically asked American Express to up my credit limit to $300 million, but I’m guessing the answer would be no. Every year around this time, I make a whole piece out of it, naming seven players I think teams should attempt to sign to long-term contracts now, rather than waiting until later. There are some additional complications, of course, with a lockout likely coming after this season, but teams and players could be willing to act with more urgency to sign contracts now before all the uncertainty ahead of them.

I’ve (hopefully) chosen seven players whose possible extensions would benefit both the player and the team, as all good contracts ought to do. I’ve included the up-to-date ZiPS projections for each player, as well as the contract that ZiPS thinks each player should get, though that doesn’t necessarily mean I think the player will end up with that figure or even sign an extension.

Elly De La Cruz, Cincinnati Reds: Eight years, $280 million

It would not be crazy for the Reds to spend a ton of money on a big extension for their most valuable player. They did it with Joey Votto a long time ago, and that turned out to be one of the few big deals for a first baseman that actually worked out for the team that signed it. Cincinnati tried to do this with De La Cruz before last season, but it’s something worth trying again. While De La Cruz is a year closer to free agency, set for after the 2029 season, there’s also some additional risk on his side, as last year was a bit of a down year for him, at least relative to his breakout 2024 campaign. If De La Cruz doesn’t want to sign an extension, he certainly doesn’t have to do it, but this might be Cincinnati’s last, best chance to keep him through his prime years.

James Wood, Washington Nationals: Nine years, $235 million

Not a lot has gone Washington’s way lately, but Wood is for real, and a classic middle-of-the-order thumper at a time when it doesn’t look like many will be available in free agency anytime soon. The Nats have been burned in the past when it comes to attempting to extend their best hitters into their free agency years, even though they’ve been serious about it, but trying to make a deal earlier in a player’s career is better if the team wants to avoid a repeat of seeing Bryce Harper and Juan Soto playing for divisional rivals. ZiPS projects Wood to finish top 10 in career home runs among all players currently active.

Hunter Brown, Houston Astros: Seven years, $191 million

OK, this extension recommendation is a repeat from last year, but I, again, feel strongly that the Astros ought to lock up Hunter Brown as soon as possible. The difference is this contract projection is double the one from a year ago! Brown is as good a bet as any to be in the Cy Young race, and it’s not like the Astros can’t afford it. Now will they? Houston always seems to be willing to move on from its best starting pitchers, but it’d be nice for the team to make an exception. In projected five-year WAR, ZiPS has Brown fifth in the majors among pitchers, behind Paul Skenes, Tarik Skubal, Garrett Crochet, and Logan Webb. Three of these guys won’t be available on the open market anytime soon, and the fourth (Skubal) will cost a helluva lot more than $191 million. This extension is priced to start in 2027.

Riley Greene, Detroit Tigers: Six years, $175 million

The effect of the lack of impact bats hitting free agency can be seen in the contracts for Vladimir Guerrero Jr. and Kyle Tucker, which are massive numbers for hitters who aren’t Soto or Shohei Ohtani. Now, Greene isn’t quite in the class of Tucker or Vladito, but there aren’t a lot of even Greene-level outfielders likely to hit free agency in the next few years. With it looking increasingly unlikely that the Tigers will retain Skubal’s services past the end of 2026, it would be nice to lock up another big, if lesser, part of the team’s foundation.

Konnor Griffin, Pittsburgh Pirates: Eight years, $142 million

If the projections — and the scouts — are right, signing Konnor Griffin to an extension is going to get really expensive very quickly. I think the Pirates have more of a chance of signing Griffin past his cost-controlled years than they do with Skenes, and having Griffin locked up will make a potential Skenes trade in the future less painful for Pittsburgh fans. Getting Griffin signed now also gives the Pirates the biggest incentive not to play service-time games with him (and possibly net that extra draft pick). That’s pretty important; ZiPS may be skeptical about the Pirates, but this team does have a path to the postseason in 2026. That path is most likely if Griffin breaks out and plays 150 or so games in the majors.

Jesús Luzardo, Philadelphia Phillies: Five years, $91 million

I know about Luzardo’s injury history, of course, but I think ZiPS is selling him incredibly low here. I certainly don’t envision $91 million getting the job done, but I’d be willing, in Philadelphia’s position, to go far higher. The Phillies are basically designed to win over the next few years, and Luzardo’s pending free agency is a pretty big concern. As good as Philadelphia’s rotation looks to be this year, Ranger Suarez has shipped up to Boston, and your pants would instantly burst into flames if you claimed that Zack Wheeler and Aaron Nola were as good of bets as they appeared to be a year ago. The Phillies already have club options that could keep Cristopher Sánchez around through the 2030 season, and ensuring they have another strong starter under contract ought to be a priority.

Kyle Bradish, Baltimore Orioles: Five years, $61 million

Bradish is a really hard player to value, which is why I think that it’s in the interest of both him and the Orioles to split the difference here. There’s a real chance that Bradish has a full, healthy 2026 season and emerges as a legitimate ace. Do you know the last time the Orioles had a pitcher with four WAR in a season? Not since 2007, when Erik Bedard pulled off the feat. (Corbin Burnes finished with 3.9 WAR in 2024.) But at the same time, Bradish is also a pitcher who has basically lost two seasons to injury, and there’s a real risk he never repeats his 2023 performance. So an extension here (starting in 2027) would give the Orioles a chance at having a long-term ace without paying market value for one, while giving Bradish a hedge that still amounts to generational wealth.