Scott Boras finishes offseason to forget with Jordan Montgomery’s 1-year deal

For Scott Boras, the offseason is finally over. It wasn’t a good time.

The 2023-24 MLB offseason will be remembered by many as the winter in which Shohei Ohtani signed his record-shattering, 10-year, $700 million contract. Or for the Los Angeles Dodgers’ overall $1 billion offensive on the free market. Or for the New York Yankees landing Juan Soto in a blockbuster trade with the San Diego Padres.

It was a lively offseason, but the storyline that took the longest to develop was that of Boras and his big four free agents. Boras entered the winter counting half of Yahoo Sports’ top 10 free agents as clients: reigning Cy Young winner Blake Snell; former MVP Cody Bellinger; playoff hero Jordan Montgomery; defensive ace Matt Chapman; and Korean import Jung Hoo Lee.

Lee quickly signed a $113 million deal with the San Francisco Giants, and that was absolutely a win for Boras. However, the four other players were expected to sign deals bigger than that.

None of them did.

Instead, all four of them took their free agencies into late February or March, then signed shorter-term deals with opt-outs that give them the ability to retest the market next offseason if they perform as well as last year. Montgomery was the last to sign, agreeing to a one-year, $25 million deal with the Arizona Diamondbacks on Tuesday. Suffice to say, that was not Boras’ plan.

The guaranteed money doled out to the top 10 free agents shows how badly this went (Boras clients in bold):

1. Shohei Ohtani: 10 years, $700 million

2. Yoshinobu Yamamoto: 12 years, $325 million

3. Aaron Nola: seven years, $172 million

4. Blake Snell: two years, $62 million

5. Cody Bellinger: three years, $80 million

6. Jordan Montgomery: one year, $25 million

7. Sonny Gray: three years, $75 million

8. Matt Chapman: three years, $54 million

9. Josh Hader: five years, $95 million

10. Jung Hoo Lee: six years, $113 million

Boras is well known for his strategy of prioritizing free agency over extensions and his willingness to wait out teams for the biggest deals for his clients. It’s a strategy that has worked very well in the past, with some hiccups here and there.

This winter was definitely bigger than a hiccup. Let’s go through each of the big four, what they were expected to get, what they turned down and why teams might’ve been apprehensive to back up the Brink’s truck.

Blake Snell

Median Fangraphs crowdsource projection: five years, $125 million
Reported asking price: $270 million
Reality: two years, $62 million (with an opt-out)

Snell won the NL Cy Young award last season, one of 22 pitchers in the history of baseball to win the award multiple times, and ended up getting less than half of what his former teammate Tyler Glasnow got from the Los Angeles Dodgers (a five-year, $135 million extension).

It’s hard to see Snell improving on a Cy Young season, which makes the short, prove-it deal especially awkward.

If you’re wondering why so many teams were hesitant to bring in Snell, it probably starts with his age. At 31, Snell is old for an elite, first-time free agent. He has also been volatile for a supposedly elite pitcher, in both health and performance. His two Cy Young wins happen to be the only seasons in his career in which he threw more than 130 innings.

His 2023 also included some peripheral red flags, most notably a career-worst 13.3% walk rate. Add all that together, and you can see why some teams were apprehensive to bet Snell would be worth elite pitcher money at age 35.

Even with all that, though, Snell was reportedly offered a six-year, $150 million deal from the New York Yankees at one point this offseason. Boras would probably prefer he forget that.

Cody Bellinger

Fangraphs projection: six years, $144 million
Reported asking price: $200 million+
Reality: three years, $80 million (with two opt-outs)

Bellinger really was excellent in 2023, parlaying a change in scenery from the Dodgers to Chicago Cubs into one of the best offensive seasons of his career. A strong defensive center fielder who can hit 307/.356/.525, as Bellinger did last year, would be one of the best players in baseball and absolutely worth a nine-figure deal.

But teams were skeptical that’s what Bellinger was. It’s hard to forget what a mess he was in his later years with the Dodgers, which was at least partially attributable to a shoulder injury sustained via a hard high-five in the 2020 NLCS (yes, really).

Bellinger was in dire enough straits that the Dodgers non-tendered him rather than pay him an arbitration salary of around $18 million, and he ended up with the Cubs on a one-year, $17.5 million deal. It’s tough to go from being a one-year guy to being a nine-figure guy, especially when you’re a hard swinger with an injury history.

That said, Bellinger is probably the best bet of all these guys to get a big deal if he has a great 2024.

Jordan Montgomery

Fangraphs projection: five years, $105 million
Reported asking price: $170 million
Reality: one year, $25 million (with a vesting option for a second year)

Unlike the other deals, Montgomery has to actually do some work to reach free agency after this season. He reportedly can opt out only if he makes at least 10 starts in 2024.

Go back five months, tell anyone that Montgomery would be in this position and enjoy the laughs. Montgomery spent most of his career as a solid-to-good pitcher for the Yankees and St. Louis Cardinals, then found another level after he was traded to the Texas Rangers at last year’s deadline.

The southpaw finished the season with a 2.79 ERA for the Rangers, then was the rock in the team’s rotation, with a 2.90 ERA in 31 innings across six appearances (five starts). It was widely assumed that some team would see Montgomery’s playoff performance and think he could do that for them, but apparently no one bit.

One year, $25 million is the kind of deal that makes you wonder why every other contending team didn’t make an offer. Now, Montgomery will switch sides from the 2023 World Series and hope he can make those teams regret it.

Matt Chapman

Fangraphs projection: five years, $80 million
Reported asking price: $150 million
Reality: three years, $54 million (with two opt-outs)

Chapman was reportedly offered a $125 million contract from the Toronto Blue Jays last year and a 10-year, $150 million contract from the Oakland Athletics in 2019. He seemed headed for a superstar contract as an elite fielder at third base and decent hitter at the plate, but his strikeout-heavy approach at the plate might’ve scared teams off this winter.

It’s hard to justify spending the kind of money Chapman wanted when he has shown himself to have a clear ceiling at the plate, especially when he’s a third baseman and not, say, a middle infielder. Chapman’s former teammate Marcus Semien hit a career. .256/.324/.444 and got $175 million. Chapman hit a career .240/.329/.461 and got $54 million. Defensive position matters.

Chapman’s offensive numbers also likely won’t benefit from the move to the Giants’ Oracle Park, a notoriously pitcher-friendly park that reportedly scared off another Boras client, J.D. Martinez, from signing with the team.

There’s nothing wrong with a player’s defensive abilities outpacing his offense. That player just needs to be prepared for players in the opposite position to get paid more.