Grading the risk factor for large MLB free agent contracts handed out this winter

The MLB offseason hasn't moved as quickly as MLB fans might like, but that does not mean big moves haven't taken place. We've seen six players sign deals worth $75 million or more, and several others who remain on the market are near locks to pass that threshold.

While it's obviously encouraging to see teams spend money in an effort to get better, any deal worth $75+ million includes some level of risk. Some of the biggest deals, though, involve more risk than others. Were free agents like Pete Alonso, Tatsuya Imai and Dylan Cease worth the gamble?

INF/OF Kazuma Okamoto

Contract: Four years, $60 million
Team: Toronto Blue Jays

The Toronto Blue Jays handed out the largest guarantee to an international free agent this offseason by giving Kazuma Okamoto a four-year deal worth $60 million. Okamoto might not have the ceiling guys like Munetaka Murakami and Tatsuya Imai have, but his floor is substantially higher than that duo's, which led to him getting the contract he did.

Okamoto's defense might not be great away from first base, but his contact-oriented style at the plate fits perfectly with how the Blue Jays play. There's always some risk with guys making the move to MLB, but Okamoto is as safe as they come with international prospects.

Grading the risk: 4/10

RHP Devin Williams

Contract: Three years, $51 million with $15 million deferred
Team: New York Mets

The second-largest contract handed out to a reliever this offseason was the three-year, $51 million pact that the New York Mets gave to Devin Williams, who is coming off a season that saw him post a 4.79 ERA in 67 appearances with the New York Yankees. What this contract proves is that teams don't view ERA as a tell-all statistic.

Despite the high ERA, Williams' peripherals indicate he was unlucky in 2025, and he finished strongly down the stretch of the regular season and in the postseason. Williams should be fully adjusted to pitching in New York after a rough start to his 2025 season, and there's every reason to believe he'll bounce back. However, betting on someone to bounce back is inherently taking on some risk. The contract isn't bad, especially with nearly a third of it deferred, but the Mets are taking a risk, even if it's a calculated one, by signing Williams to close games for them.

Grading the risk: 6.5/10

DH Kyle Schwarber

Contract: Five years, $150 million
Team: Philadelphia Phillies

On the surface, handing out a five-year, $150 million deal to a 32-year-old who is exclusively a DH at this stage of his career and happens to strike out a lot while not running well sounds like a bad idea. While it could absolutely age poorly, not only did the Philadelphia Phillies have to do whatever it took to keep him in town, but I don't think this deal will age as poorly as some might think.

Will Schwarber have a better year than the MVP runner-up campaign he had in 2025? Probably not. Does that mean he won't be a superstar at the dish? Schwarber is only getting better as he ages, and there's no reason to believe, when looking at the data, that he can't hit 40 or 50 home runs annually for the next couple of years while reaching base at a 36 percent clip like he's been doing. The end of the contract probably won't be pretty, but the Phillies are hoping he'll perform at an elite level for the first two or three years of the deal while they're in a contending window. I think they'll get what they paid for, but based on what we've seen from players of his archetype, there's certainly some risk.

Grading the risk: 5/10

RHP Tatsuya Imai

Contract: Three years, $54 million (max $63 million with incentives) with opt-outs after 2026 and 2027 seasons
Team: Houston Astros

Tatsuya Imai was projected to get closer to $200 million than $100 million entering the offseason, so it's definitely surprising to see that he had to settle for a three-year, $54 million deal that maxes out at $63 million. For a cash-strapped Houston Astros team that needed starting pitching, this contract is a huge win for them, especially since the risk isn't as great as initially perceived.

As mentioned above, there's always some risk when it comes to signing players who haven't played in MLB before, but there's a big difference between a 6+ year deal worth nine figures and, at most, a three-year, $63 million pact. If Imai pitches well, he'll opt out of his contract and test free agency, ensuring the risk was worthwhile for Houston. If Imai doesn't pitch well, a three-year, $54 million deal is rather cheap for a 27-year-old starting pitcher with tremendous upside. Imai is the one taking a risk, as pitching poorly will ensure he'll never cash in on the massive deal he hoped. The Astros will either get one or two really strong years of a starter they desperately need or overpay by a smidge for an underwhelming starter.

Grading the risk: 3/10

RHP Dylan Cease

Contract: Seven years, $210 million with $64 million deferred
Team: Toronto Blue Jays

Not even a month after falling short in the World Series, the Blue Jays signed Dylan Cease to a seven-year, $210 million deal, one of the largest deals a starting pitcher has received. To say this deal raised some eyebrows would be an understatement. While he has obviously been elite in the past, Cease was coming off a 4.55 ERA season and has posted an ERA above 4.50 in two of his last three seasons. It goes without saying that Cease pitching to a 4.50 ERA over the course of his seven-year deal would be disappointing.

It's clear that the Jays are paying for two things: upside and durability. While he pitched poorly in 2025 and 2023, Cease finished in the top four of Cy Young balloting in 2022 and 2024. It wouldn't be surprising to see him get back to a Cy Young level. Additionally, Cease has made 32+ starts, thrown 160+ innings, and struck out 200+ batters in each of the last five seasons. The production might be a mixed bag, but he's as good a bet as any to take the ball every fifth day.

The big question I have is, will this continue into his 30s? If so, the deal probably won't be a major overpay even if he doesn't get back to his Cy Young form, considering how valuable innings eaters are nowadays. I'm not sure it will, though, so pairing that with his inconsistency on the bump makes the deal risky. It could pay off, and I'm not saying it wasn't a wise move for the Jays to make as they attempt to win the World Series, but if Cease continues to be a 4.50 ERA guy and can't make 30+ starts consistently, yikes.

Grading the risk: 7/10

1B Josh Naylor

Contract: Five years, $92.5 million
Team: Seattle Mariners

Fresh off a crushing defeat in Game 7 of the ALCS, the Seattle Mariners re-signed Josh Naylor on a five-year, $92.5 million deal. Handing a five-year deal to a first baseman might not be a thing that has aged well in the past, but there are a couple of reasons to like this deal from Seattle's perspective.

First, Naylor is only 28 years old, so it's not as if this deal, which doesn't even pay him an average of $20 million annually, will keep him locked in through his late 30s. Second, Naylor isn't a prototypical first baseman. His game isn't built on power; instead, he's known for making consistent contact while being rock-solid defensively at first base. He's a lot more athletic than most might think. Naylor had arguably his most well-rounded season in 2025, and should continue to be an outstanding player for a majority of the deal, even if his play begins to tail off around year four or five of the deal.