Scott Boras ends the season to forget with Jordan Montgomery’s one-year contract

By | March 27, 2024

The offseason is finally over for Scott Boras. It wasn’t a good time.

The 2023-2024 MLB offseason will be remembered by many as the winter in which Shohei Ohtani signed his record-breaking 10-year, $700 million contract. Or for the Los Angeles Dodgers’ total $1 billion splash on the open 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 with 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 definitely a win for Boras. However, the other four players were expected to sign bigger deals.

None of them did.

Instead, all four took their free agency into late February or March, then signed shorter-term deals with opt-outs that gave them the opportunity to test the market again next season 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 it to say, that wasn’t Boras’ plan.

The guaranteed money handed out to the top 10 free agents shows just 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

MLB's top 10 free agents have finally signed.

MLB’s top 10 free agents, half of whom are Scott Boras clients, have all finally signed. (Taylar Sievert/Yahoo Sports)

Boras is 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 is 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 was expected of them, what they rejected, and why teams might have been afraid to back 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, ultimately receiving 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 improve in a Cy Young season, which makes the short, prove-it deal particularly difficult.

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

His 2023 also had some peripheral red flags, most notably a career-worst 13.3% walk rate. Put all that together and you can see why some teams were afraid to bet on Snell being worth the elite pitchers’ money at age 35.

But despite all that, Snell was reportedly offered a six-year, $150 million contract by the New York Yankees at some point this offseason. Boras would probably prefer he forgot about that.

Cody Bellinger

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

Bellinger was truly outstanding in 2023, parlaying a change of 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, like Bellinger did last year, would be one of the best players in baseball and definitely worth a nine-figure deal.

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

Bellinger was in so much trouble that the Dodgers non-tendered him in lieu of paying him an arbitration salary of about $18 million, and he ended up with the Cubs on a one-year, $17.5 million deal. It’s hard to go from a one-year-old to a nine-figure guy, especially if you’re a hard swinger with an injury history.

That said, Bellinger is probably the best choice 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 actually has to do some work after this season to reach free agency. He Reportedly can only opt out if he makes at least ten starts in 2024.

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

The southpaw finished the season with a 2.79 ERA for the Rangers and was the rock of the team’s rotation afterward, posting a 2.90 ERA in 31 innings across six appearances (five starts). It was widely believed that a team would see Montgomery’s playoff performance and think he could do that for them, but apparently not.

One year, $25 million is the kind of deal that makes you wonder why every other competing team didn’t make an offer. Now Montgomery will switch sides in the 2023 World Series and he hopes 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 appeared headed for a superstar contract as an elite fielder at third base and a good hitter at third base. at the plate, but his strikeout-heavy approach at the plate may have deterred teams this winter.

It’s hard to spend the kind of money Chapman wanted to spend when he’s shown he has a clear ceiling, especially if he’s a third baseman and not, say, a middle infielder. Chapman’s former teammate Marcus Semien made a career. .256/.324/.444 and was paid $175 million. Chapman had a career .240/.329/.461 and was paid $54 million. Defensive position is important.

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

There is nothing wrong with a player’s defensive skills being greater than his offensive prowess. That player just needs to be prepared for players in the opposite position to be paid more.

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