“I Wanted to Stay With the Yankees, But It Never Happened”: Former Yankees Pitching Prospect "International League Pitcher of the Week" Opens Up After Landing With Padres
New York, New York – November 27, 2025
When Sean Boyle officially moved on from the New York Yankees this offseason, it marked more than just a routine minor-league departure. For Boyle, it was the closing of a chapter he had hoped—quietly but sincerely—would last longer.
In a recent conversation with people close to the situation, the former Yankees pitching prospect revealed that his preference entering free agency was clear: remain in the organization that drafted and developed him, even if his role was strictly depth.
“I wanted to stay with the Yankees,” Boyle said. “That was always the goal. I wasn’t asking for guarantees. I just wanted the chance to keep proving myself. But there really wasn’t much interest in continuing it.”
Boyle’s journey with New York dates back to the 25th round of the 2018 MLB Draft. A steady climber through the system, he began to gain legitimate traction in 2022, emerging as a viable upper-level depth arm. Then came the setback that altered everything — a torn UCL that required Tommy John surgery in 2023.
The injury stalled his momentum, but Boyle fought his way back. In 2025, he spent the entire season at Triple-A, logging heavy innings and taking on one of the largest workloads in the system. While his numbers — a 9–9 record with a 4.61 ERA — weren’t eye-popping, he provided reliability, durability, and experience in a rotation often defined by turnover.
Still, when the offseason arrived, the Yankees chose not to bring him back.
Instead, Boyle signed a minor-league free agent deal with the San Diego Padres, a move that offers him a fresh opportunity — and perhaps a clearer path — heading into Spring Training. At 29 years old, time is no longer a luxury, but Boyle remains confident that he still has something to offer.
“I don’t regret my time with the Yankees at all,” he said. “They gave me my start. But as a player, you always wonder — what if I’d stayed healthy? What if I’d gotten one more look?”
For New York, the decision reflects a broader organizational reality. With the Yankees aggressively seeking pitching help at the major-league level, depth arms like Boyle often become casualties of roster churn. For Boyle, it’s another reminder of baseball’s unforgiving nature — where perseverance doesn’t always guarantee opportunity.
Now with San Diego, he turns the page.
In a sport driven by projections, health, and timing, Sean Boyle’s story underscores a familiar truth: sometimes, departures aren’t about performance or money — but about a window that quietly closes before you realize it ever existed.
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