Jordan Montgomery contract delivers fatal blow to Dodgers enemy Scott Boras

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The "Boras Five" — Blake Snell, Cody Bellinger, Matt Chapman, JD Martinez, and Jordan Montgomery, five of this offseason's most in-demand free agents, joined together by shared agent Scott Boras — stay losing. All five took months to finally be re-employed, thanks to the losing strategy of playing chicken with teams. They were all angling for long-term, lucrative deals, but the first four all had to settle for 1-3 year contracts at incredibly team-friendly prices when front offices refused to budge.

None of these five have a guaranteed year of employment beyond the 2024 season.

Jordan Montgomery, the last to come off the board on Tuesday night, is no exception. After an incredible postseason run with the World Series-winning Rangers, Montgomery's stock had never been higher going into free agency. He was connected to the Rangers, Red Sox, Yankees, and Mets to varying degrees since November, but an unexpected winner and Dodgers rival swept in and came out on top — the Arizona Diamondbacks.

Just a few days ago, Joel Sherman of The New York Post reported Montgomery had taken his asking price down from "Aaron Nola range to Tyler Glasnow range," meaning fewer years but a higher AAV. As it turns out, he didn't get either.

Jeff Passan first reported that Montgomery would be headed to the Diamondbacks, and then came in with the contract details — one year, $25 million, with a vesting option for a second season. Montgomery is the last of the big-name free agents, not only of Boras' clients but of free agents league-wide, and the resulting contract was (sort of unsurprisingly at this point) a dud. If we needed any more proof about the ineffectiveness of Boras' strategy, we got it on Tuesday night.

Jordan Montgomery's contract with Dodgers rival proves that Scott Boras' strategy isn't working

The vesting option in Montgomery's contract is a little confusing, but it basically means that he'll have a player option for 2025 in escalating value depending on the amount of starts he makes this year. If he makes 10 starts, he'll be eligible for $20 million next year; 18 starts, $22.5 million; 23 starts, $25 million. Montgomery clearly wanted to sign with a real contender, and given the fact that he faced the Diamondbacks in the World Series last year, it makes sense why he would choose them over the Red Sox or Mets. If Arizona fails to repeat their successes, he can easily opt out at the end of the season.

However, a one-year contract is never ideal, and the fact that Montgomery, Snell, Bellinger, Chapman, and Martinez all had to settle for them (in different ways) is a very bad look for Boras. It leaves all four open to hitting the free agent market again at the end of this season, and lays out a clear strategy for teams to net talented players on team-friendly contracts if Boras tries this again next year. It leaves more high-profile clients who will be free agents — Juan Soto, Corbin Burnes, and Alex Bregman — after this season vulnerable to this kind of outcome as well, though we'd venture to say Soto will probably be excluded because of his unique situation.

The Dodgers don't like to deal with Boras in part because he's known to be intransigent, but with the collective wins for the Diamondbacks, Giants, Mets, and Cubs this year on the Boras Five's contracts, maybe they should get in on the waiting game next year and get stars on the cheap.