Jon Heyman of the New York Post has reported that the New York Yankees “like” free agent right-hander Lucas Giolito, a 31-year-old veteran who spent last season with the Boston Red Sox. While Giolito may not headline this winter’s pitching class, his connection to new Yankees ace Max Fried makes the interest especially intriguing. The two aren’t just peers—they’re old friends who anchored one of the most legendary high school rotations in baseball history.
Harvard-Westlake Reunion in the Bronx?
Giolito and Fried’s friendship dates back more than a decade, to their days at Harvard-Westlake School in Studio City, California, where they shared a rotation alongside Detroit Tigers‘ starter Jack Flaherty. Under the guidance of coach Ethan Katz—who would later become an MLB pitching coach—the trio developed into elite arms, bonding through competition, adversity, and mutual respect.
“There is a special bond,” Katz told The Athletic in 2020. “Everywhere I coach, everyone asks me questions about them.”
That bond never faded. Giolito even attended Katz’s wedding, and Fried has long credited Katz for “opening my eyes to preparation and what it takes” to succeed as a professional pitcher. Both players endured Tommy John surgery early in their careers, leaned on each other through their recovery years, and eventually fulfilled the promise they showed as teenagers—Fried becoming a Cy Young winner, and Giolito throwing a no-hitter for the White Sox in 2020.
Now, more than ten years later, a reunion in pinstripes could bring their journey full circle.
According to Heyman, the Yankees are monitoring Giolito’s market closely after Boston declined to extend him a $22 million qualifying offer. That decision means New York wouldn’t need to forfeit draft-pick compensation to sign him—an important factor for a team already balancing luxury-tax considerations after adding Fried.
Giolito’s Market and the Yankees’ Rotation Needs
Giolito posted a 3.41 ERA with 121 strikeouts in 145 innings for Boston in 2025, stabilizing a middle-of-the-rotation that desperately needed consistency. His underlying numbers—including a 4.17 FIP and 1.18 WHIP—suggest he’s more of a reliable No. 3 or No. 4 starter than a frontline ace. But his mix of durability, competitiveness, and command fits perfectly with what the Yankees need behind Fried, Carlos Rodón, and Luis Gil.
The right-hander’s arsenal remains largely intact from his White Sox days: a four-seam fastball he throws nearly 50% of the time, a fading changeup, and a biting slider. Though the fastball has lost a tick of velocity since his 2024 elbow surgery, his vertical movement and sequencing continue to generate weak contact.
For the Yankees, Giolito represents a rare blend of affordability and familiarity. Spotrac projects his market value at roughly three years, $61 million, while MLB Trade Rumors predicts a shorter two-year, $32 million deal. Either price could be reasonable for a franchise seeking a mid-rotation stabilizer who already shares chemistry with their new ace.
Signing Giolito wouldn’t just make baseball sense—it would make narrative sense. Reuniting with Fried would rekindle one of the sport’s most remarkable prep baseball stories, one that began on the sun-soaked fields of Southern California and could now continue under the lights of Yankee Stadium.
After years of facing each other from opposite dugouts, Fried and Giolito could finally share the same mound again—only this time, chasing a World Series title together.
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