Yankees Considering Risky Trade for Injury-Prone Flamethrower

The New York Yankees enter the offseason facing significant uncertainty in their bullpen, with closer David Bednar and several other key relievers set to reach free agency.

While much of the league has focused on the San Diego Padres’ higher-profile arms, the Yankees have quietly maintained interest in a different option from the same organization: 27-year-old right-hander Jeremiah Estrada.

According to Joel Sherman of the New York Post, New York has long monitored Estrada, leaving the door open for a potential trade this winter.

Estrada remains under club control through 2029, which would give the Yankees a multi-year late-inning piece rather than a short-term rental.

That combination of remaining control and age makes him an attractive target on paper, particularly as the Padres prepare to lose free agent Adrian Morejon and continue to field interest in star reliever Mason Miller.

San Diego is under no immediate pressure to move Estrada, and any deal would likely require a meaningful return.

There are clear reasons for caution. Estrada’s four-seam fastball velocity dropped from an average of 97.9 mph in 2025 to 95.9 mph in 2026.

He also dealt with elbow, knee, and shoulder issues during the season, with the shoulder problem sidelining him for the playoffs.

In 33 appearances, he posted a 3.48 ERA while striking out roughly 11 batters per nine innings—solid numbers, but a step back from the previous year, when he recorded a 3.45 ERA and 108 strikeouts across 73 innings.

That earlier campaign included 12 home runs allowed, though he surrendered only two long balls in limited 2026 work.

The Padres’ willingness to trade Estrada may hinge on the severity of those injury concerns and the quality of offers they receive. For the Yankees, the appeal lies in adding a controllable high-velocity arm without committing long-term free-agent dollars, especially if they cannot retain Bednar, Paul Blackburn, or Ryan Yarbrough.

Even if some of those pitchers return, New York may still seek additional bullpen depth after heavy workloads for Blackburn and Brent Headrick last season.

The organization has prospect capital available and could include a player such as outfielder Jasson Dominguez in discussions if the price is right.

Any pursuit of Estrada would carry risk. The velocity decline and recent injuries raise questions about whether his peak stuff will return, and the cost in talent could be substantial given his years of control.

At the same time, if San Diego is open to moving him at a reasonable price, the Yankees may view him as a worthwhile gamble to stabilize a bullpen that is about to lose several important pieces. The coming weeks should reveal how aggressively New York pursues the idea.