Time to rewind to spring training — a time when teams size up their rosters and management think a few steps ahead. As per Tyler Milliken and Alex Speier, there were three distinctive extension offers made to the fastest-rising young star of MLB, Roman Anthony, at that period. The idea? Lock in potential early and ignore a payday down the line. However, things did not quite go that way.
“There had been a considerable gap in talks between the sides in spring training,” Speier said. “Though the distance had narrowed… the conversations had never gotten close enough to a deal to produce true back-and-forth about a framework,” he added.
That statement speaks volumes. It was not a matter of neglect — it was a matter of misreading the moment. The Red Sox were well aware of the value of Roman Anthony in question, yet failed to push hard enough to get it done when the cost was still manageable. At the time, this move could have looked cautious. Now, with the star finalizing an 8-year, $130 million deal — that might go up to $230M- the Red Sox’s restraint looks more like a misstep.
Now, it is time to talk numbers. This rising star, Roman Anthony, has been a sensation in his first 46 big league games. In those games, Anthony slashed .283/.400/.428 with elite poise at the plate. The star’s rise was not exactly a surprise. Ranked No. 1 overall by Baseball America and MLB Pipeline before being called up, Roman Anthony had already gone viral with a 497-foot grand slam and owned Triple-A with a .288 average, 10 home runs, and 29 RBIs in 58 games. What is happening now? This was always in the cards.
Not only Alex Speier, but former MLB GM Jim Bowden also highlighted his discomfort with the deal. Speaking on Foul Territory TV, the former GM compared Anthony’s deal to Ronald Acuña Jr.’s early deal, highlighting that the young outfielder could have undersold his future worth.
However, not every risk is a red flag. From the Red Sox’s standpoint, this deal is an investment not just in a star, but in stability. At 21, Anthony has a .392 OBP and is showing plate discipline beyond his seasons. The team is in wild-card position, riding a hot streak, and Anthony’s availability has been vital to that momentum. Add in the star’s pairing with top stars like Marcelo Mayer and Kristian Campbell, and you have the blueprint of a powerful dynasty brewing.
The Red Sox made 3 extension offers to Roman Anthony during spring training, per @alexspeier.
“There had been a considerable gap in talks between the sides in spring training. Though the distance had narrowed throughout three separate offers by the Sox, the conversations… pic.twitter.com/xqOyUkYUEJ
— Tyler Milliken (@tylermilliken_) August 7, 2025
While the Red Sox made a vital financial commitment to Roman Anthony to secure their long-term offensive future, the team’s strategy at the 2025 trade deadline told a more intricate story—one filled with ambition, however, ultimately, missed scope.
Trade deadline aggression without reward
Despite criticism of playing it safe, the Red Sox president, Sam Kennedy, insists that the management was anything but passive at the time of the 2025 trade deadline. As per Kennedy, Chief Baseball Officer Craig Breslow was “all-in,” providing “everybody and everything” in the farm system to land a controllable starter. Yet, no elite deals materialized. The team pushed hard for pitchers like the Twins’ Joe Ryan; however, other teams simply would not budge. Kennedy framed the failed pursuits as a matter of circumstance instead of hesitation, emphasizing a win-now mentality that did not translate into outcomes.
Credits: MLB.com
The Red Sox’s delay in locking down Roman Anthony at a lower cost could prove costly if the star’s trajectory continues upward. With long-period financial flexibility now effected, the team’s management will need to be sharper moving forward.
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