The Red Sox Bet Big on Roman Anthony — and MLB's Favorite Contract Cheat Code
Pre-arbitration extensions used to be the secret to front-office success. Now they're riskier, and more expensive, than ever. (Just don't tell Boston that.)
Fewer than 50 games into Roman Anthony’s big-league career, the Boston Red Sox had seen enough. On Wednesday, they signed Anthony, who went into the 2025 season as Baseball Prospectus’ No. 1 ranked prospect,1 to an 8-year, $130 million contract extension that will keep the 21-year-old outfielder at Fenway Park through at least the 2033 season.2
In exchange for owning years of his free-agency eligibility down the line, the deal buys out Anthony’s 2026 and 2027 pre-arbitration seasons, in addition to the arbitration years he would have had in 2028, 2029 and 2030.3 This makes him part of the growing lineage of recent players whose arbitration and pre-arb years were bought up by a team early with a long contract extension. In Anthony’s case, his 8-year deal is tied for the sixth-longest of any pre-arbitration extension since 2011, per Spotrac, and the total value of $130 million — which equates to a projected 73.2 percent of the average team’s payroll next season,4 — is the ninth-largest relative to the league in that span:
