The Red Sox made their pitch, but Max Fried is heading to the Bronx. After speculation, the star left-hander inked a massive $218 million deal with the Yankees. Leaves Boston fans wondering what went wrong. Alex Cora recently addressed this. He confirmed that Fried seriously considered the Red Sox but ultimately chose New York. Boston’s pursuit of Fried wasn’t just wishful thinking—they met with him, discussed their plans, and even pitched him on their improving defense. But in the end, it wasn’t enough. So, what went into Fried’s decision, and why is he donning pinstripes instead of a Red Sox uniform?

The Red Sox were firmly in the mix for Max Fried, and the interest was mutual. Fried confirmed he met with Boston’s coaching staff and front office. He described them as “really nice, great people” and stated that he “definitely considered” signing. That alone shows that Boston was a legitimate contender, not just a team making an obligatory free agency call. With their need for an ace, the Red Sox positioned themselves as a powerful suitor. Offered a competitive environment and a team looking to turn the corner. “They were interested and I met with the coaching staff and front office. Nice, great people, and I considered them,” Fried said.

One of the major selling points Boston emphasized was its defense. Alex Cora later revealed that Fried specifically mentioned defense when discussing the team. This played a role in their pitch. “He knew what he was talking about because he mentioned our defense. It is a guy who they’re going to put the ball in play so you’re going to have to play defense behind him. We told him we’re going to be better defensively,” Cora explained. The Red Sox were trying to address a past weakness. He signaled their commitment to building a more balanced team.

So why did Max Fried ultimately choose the Yankees? The answer lies in a combination of factors—contract security, championship aspirations, and team fit. The Yankees’ offer of $218 million over seven years provided long-term financial stability. Making it one of the largest contracts ever given to a starting pitcher in franchise history. Financial security aside, the Yankees’ status as a perennial World Series contender made them an appealing destination. Fried himself admitted, “It was just more of a gut feeling. I felt like this was the right place for me.” That instinct was backed by the Yankees’ recent roster moves, which signaled an aggressive push to win now.

Beyond the financial and competitive aspects, New York’s defensive setup could have played a vital role in Max Fried’s decision. The Yankees’ infield defense, anchored by Gold Glove finalist Anthony Volpe and a revamped roster. Stood out as a strong support system for a groundball-heavy pitcher like Fried. Last season, the Yankees ranked sixth in defensive runs saved among AL teams. A key metric that reflects their capability to turn batted balls into outs. With solid defensive backing and a championship-ready roster, the Yankees presented an environment that fit Fried’s pitching style and long-period aspirations. This makes a clear choice for Boston.

The Red Sox’s struggles in landing elite arms

The Red Sox’s failure to sign Max Fried is another chapter in their struggle to land elite pitching. For over a decade, Boston has missed out on top arms, including Yoshinobu Yamamoto, who inked a $325 million deal with the Dodgers, and Zack Wheeler, who found a home in Philadelphia. While their rivals invest in frontline starters, the Red Sox have settled for mid-tier options, hoping to build a rotation through depth rather than dominance.

That strategy has yet to yield results. In 2024, Boston finished with an 81-81 record, and their pitching woes were a glaring issue. The team ranked 18th in starter ERA (4.37) and struggled with durability, cycling through 12 different starters over the course of the season. Lucas Giolito, one of their biggest offseason signings, didn’t even throw a pitch in 2024 due to elbow surgery. Now, heading into 2025, he’s already set to open the season on the injured list with a hamstring strain.

To address their rotation concerns, Boston acquired left-hander Garrett Crochet from the White Sox. An All-Star in 2024, Crochet logged 209 strikeouts with a 3.58 ERA, but his 6-12 record reflects how inconsistent run support and bullpen stability were for him. Meanwhile, the Red Sox also took a gamble on Walker Buehler, signing him to a one-year, $21.05 million deal. Buehler has a postseason pedigree, but after missing all of 2023 recovering from Tommy John surgery, he made only 10 starts in 2024, posting a 4.11 ERA.

Injuries continue to be a major concern. Brayan Bello is dealing with shoulder discomfort, and Kutter Crawford is recovering from a knee issue, further thinning an already fragile rotation. The Red Sox may have no choice but to rely on Richard Fitts, Quinn Priester, or Cooper Criswell—none of whom have proven themselves as reliable MLB starters.

With the Yankees and Orioles making effective moves, Boston’s cautious approach to pitching acquisitions could once again leave them on the outside looking in. If they do not get the necessary production from their rotation, another season of mediocrity could be looming. Max Fried choosing the Yankees highlights Boston’s pitching struggles. Without an ace, they need to either adjust their approach or risk another disappointing season. Will they finally break the trend next offseason? Is this their new normal?