MLB Extension Week Tiers: Which deals should get done and which should wait?

Over the first three days of Extension Week, I try to be as objective as possible: Here’s what history says about how this player should be valued.

Today? Today I get to opine on which projected extensions I’d like to see come to pass, which make more sense for one side and which don’t make sense for either. The context for every contract matters: Smaller-market teams rely more on capitalizing on extensions, but they’re also less equipped to handle one if it goes poorly.

So how do the 16 players I examined in-depth fit? Which extensions make the most sense?

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Tier 1: Get this deal done now

You want to take the temperature of Pirates fans right now? You could do worse than checking out the comments on this week’s Skenes piece, where many have — justifiably — chortled at the idea of Pittsburgh signing this magnitude of a contract. Guaranteeing Skenes would be in black and yellow for a decade-plus would energize a fan base that’s had little to root for in years. And for Skenes, this deal guarantees him more money through his first 10 seasons than Gerrit Cole made. And remember it also gives him the chance to more than double that by the end of it.

Crochet has expressed an interest in an extension since last summer, and the Red Sox didn’t trade the kind of prospect package they sent to the White Sox for Crochet just to watch him walk away in two years. Crochet can anchor the starting staff as Boston opens a new competitive window.

A nine-figure deal would set a new record for a starter with Kirby’s service time — a very nice outcome for a pitcher who won’t hit free agency until he’s in his 30s. The Mariners should be looking to extend either Kirby or Logan Gilbert.

The Reds’ last competitive window closed in part because they chose the wrong starting pitcher (Homer Bailey) to extend. This time around, they can keep that window open for longer by making sure De La Cruz is in Cincinnati for as long as possible. It’s not cheap, of course, but it’s unlikely to get cheaper anytime soon.

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Tier 2: Makes more sense for the team

A full, healthy season from Tucker would push this number even higher. The Cubs presumably didn’t trade for Tucker just to watch him walk in free agency, and this kind of agreement would change the narrative around Chicago’s ownership.

In general, you don’t like to sign a long-term deal off of your worst season. Rutschman’s talented enough to believe 2024 was a blip, and a season more in line with his prior production would push him above $150 million.

It’s hard to imagine another player catching Juan Soto in terms of total value in a contract. But Henderson might be the active player with the best chance of approaching Soto’s $51 million average annual value. Another MVP-caliber season from the shortstop, and this price will go up yet again.

It’s never comfortable for a pitcher to turn down this kind of money, especially one that’s missed time with injuries the way Skubal has. But he’s been so good when he’s pitched the last couple seasons that Skubal could be, without doubt, the sport’s best starter by the end of this season.

I set Contreras’ price in line with what other catchers have made in free agency. But that market could be reset with J.T. Realmuto scheduled to be a free agent this winter (and if Rutschman or Seattle’s Cal Raleigh sign long-term extensions).

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Tier 3: Makes more sense for the player

If the Astros are going to make a significant commitment in the starting rotation, they should probably prioritize the younger Hunter Brown.

This comes down to Arizona’s comfort in paying two top-of-the-rotation starters at the top of the market. Even another strong season probably doesn’t push Gallen’s potential earnings that much beyond this point.

This is an awful lot of money to guarantee off a single season, and San Diego’s financial uncertainty only exacerbates the risk. The Padres aren’t in the same spot they were when they agreed to a similar deal with Fernando Tatis Jr.

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Tier 4: Better for both sides to wait

There’s a reason these two sides have reached this kind of stalemate. Another five- or six-win season from Guerrero could push him over $500 million. Another losing season in Toronto could make the Jays decide it’s time to try with a different core.

Given that this deal values Williams very close to the top of the closer market, the Yankees can afford to wait to see how the right-hander fits in New York and how healthy he is coming off last season.

Again, the Padres’ uncertain finances — there’s a reason Cease is still the subject of spring trade rumors again — makes them less likely to pursue this kind of long-term deal. And a year away from free agency, Cease could enter the open market as the best pitcher available.

I’ve prioritized Kirby over Gilbert — he’s younger and farther from free agency, and thus cheaper — but this wouldn’t be a bad fallback option for Seattle.

(Top photo: Photo by G Fiume / Getty Images)

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