In his just over two years' tenure as the CBO of the Boston Red Sox, Craig Breslow has signed four players to pre-arbitration contracts. It started just months in, with Ceddanne Rafaela and Brayan Bello signing in March and April of 2024, respectively. Then in 2025, he added Kristian Campbell and Roman Anthony to the growing list. He was also able to get Garrett Crochet to sign a long-term deal before he reached free agency in 2025.
Getting players to sign long-term contracts before they reach free agency has become a popular trend in MLB over the last decade. The Braves are the poster child for it, with seven players on their current roster signed to a long-term extension that happened before free agency. Breslow is seemingly following their model.
Of course, any long-term contract comes with risks, especially when they are pre-arbitration. Guaranteeing a player money while they are still developing is a big gamble. If they don't pan out, that's a lot of money tied up in a negative asset. If the player reaches their upside, though, the team is likely paying well below market value for their services.
With the sheer amount of players on long-term contracts around the league, signed in both before free agency or in free agency, Bleacher Report decided to take a look around the league and project the players who won't be worth the money they are making in two years' time.
The Wicked Pitcher of the AL East
— MLB (@MLB) November 13, 2025
Garrett Crochet dazzled in his first season with Boston 🐷 pic.twitter.com/Yh6RgNYyku
Boston fans can't see Bleacher Report's prediction for 2 Red Sox players coming true
While no Red Sox player was listed in the top nine, two did make the list of 15 honorable mentions: Garrett Crochet and Roman Anthony. Both players will have over $110 million left on their contracts in 2028, with Anthony being under contract until at least 2033 and Crochet 2030 (that would require him opting out of $30 million for 2031, though).
This is just plain wrong. In less than half a season in 2025, Anthony was worth 3.1 bWAR, the eighth most valuable player on the Red Sox. If he had played 150 games at the same pace, it would have been 6.5, making him the most valuable player. Anthony is also only 21 years old; he'll be 23 going on 24 in 2028, not even in his prime. He has insane potential, and he showed it. There's no way the contract isn't worth it.
Crochet is just 26, he'll be 28 going on 29 in 2028. He just showed that he is a Cy Young-caliber pitcher, getting first-place votes alongside Tarik Skubal. The lefty will be in the midst of his prime. The only way this contract looks bad is if he gets repeatedly injured, and even then, there are clauses in his contract that can void his opt-out and give a very friendly team option for 2032 if he injures his throwing arm.
The other problem with the list is that Bleacher Report did it based on just cash numbers, not luxury tax numbers. For the life of Anthony's contract, he is going to count against the luxury tax for $16.25 million a year. If he is a 3-WAR player every year, that is still worth the money, even if he is making over $100 million.
Long-term extensions are a risk, especially so when they are signed early in a player's career. Some players in Boston may not live up to the weight of their extension, but Anthony and Crochet? No way.
