Mitch Keller has emerged as one of the most sought-after pitchers at this year’s trade deadline, boasting a 3.69 ERA, 1.20 WHIP, and 100 strikeouts in 127 innings. His strong performance — including 15 quality starts — places him among the top arms available, making him a crucial figure for teams looking to bolster their rotations. Keller’s value is heightened by his team control through the 2028 season, setting him apart from other trade candidates.

As the trade deadline approaches, the Chicago Cubs lead the charge to acquire Keller, followed closely by contenders such as the New York Yankees, Boston Red Sox, Toronto Blue Jays, New York Mets, Houston Astros, and San Francisco Giants. Pirates general manager Ben Cherington is expected to carefully navigate negotiations, aiming to secure top prospects while also addressing salary concerns that remain a priority for owner Bob Nutting.

Top Prospects the Pirates Should Seek in Mitch Keller Trade Negotiations

Owen Caissie: Chicago Cubs’ Rising Outfielder

Owen Caissie, a 23-year-old Canadian outfielder, is the Cubs’ top prospect and ranks 36th overall in baseball, according to MLB.com. Currently in his second full season with Triple-A Iowa, Caissie continues to impress with his bat. He produced a .278/.375/.472 slash line with 19 home runs and 29 doubles in 127 games last year, and has matched his batting average with power gains in 2025. So far this season, in just 81 games, he has raised his slugging percentage to .563, hammering 20 home runs and adding 24 doubles and 46 RBIs.

Caissie’s main weaknesses are his difficulty handling fastballs and a high strikeout rate. He recorded 164 strikeouts in 120 games at Double-A in 2023, followed by 156 strikeouts in 127 games last year at Triple-A and 105 this season so far. Despite these challenges, his raw left-handed power has excellent potential, especially in a hitter-friendly ballpark like PNC Park.

Rafael Flores: Yankees’ Promising Catcher and First Baseman

Rafael Flores, 24, signed with the Yankees as an undrafted free agent in July 2022 and has quickly risen through their minor league ranks. He began 2024 in High-A Hudson Valley before earning a promotion to Double-A Somerset, where he amassed a .287/.346/.496 slash line with 15 home runs, 23 doubles, and 56 RBIs in 87 games. This strong showing earned him a promotion to Triple-A in 2025.

Flores is noted for delivering above-average power, aided by his 6-foot-4 frame, although his defensive skills behind the plate are still developing. While not ranked in MLB’s top 100 prospects, he ranks seventh within the Yankees system and presents a solid potential return for the Pirates, who have a history of developing strong defensive catchers.

Jhostynxon Garcia: Young Outfield Talent from the Red Sox

Venezuelan-born Jhostynxon Garcia was signed by the Boston Red Sox as a 16-year-old in July 2019 and debuted professionally in 2021 in the Dominican Summer League. After early struggles, he broke out in 2024 while playing across three minor league levels, ascending from Low-A Salem to Triple-A Worcester. The 22-year-old currently boasts a .291/.364/.524 slash line with 11 home runs, seven doubles, and 31 RBIs in 48 Triple-A games.

Garcia fills an important need as a corner outfielder and is on track to reach the majors by mid-2026, with a possible call-up as soon as late 2025. His combination of power and progress through the system makes him a key prospect for the Pirates to target if they acquire Keller.

Additional Notable Prospects from Other Contending Teams

Several other prospects could be part of the return package, depending on which team lands Keller. The New York Mets might part with their fourth-ranked prospect, outfielder Carson Benge, who has notably impacted the minor leagues this season. The 22-year-old is excelling with a .315/.428/.508 slash line between High-A Brooklyn and Double-A Binghamton, along with nine home runs, 22 doubles, and 18 stolen bases over 81 games.

San Francisco’s potential offer could include Bo Davidson, their fifth-best prospect. The 23-year-old outfielder signed as an undrafted free agent in 2023 and has quickly advanced to Double-A. Davidson carries a projectable 50-grade power and fielding ability, paired with 55-grade hitting and arm strength, and 60-grade speed. His .304/.402/.498 slash line, 11 home runs, and 57 RBIs across 78 games this season reflect his rapid ascent.

Meanwhile, the Toronto Blue Jays and Houston Astros present fewer enticing prospects. Toronto might include eighth-ranked prospect Yohendrick Pinango, a 23-year-old infielder who has split much of 2025 between Triple-A Buffalo and lower levels. Houston’s system remains less robust; their third-ranked prospect, pitcher Walker Janek, though highly regarded, remains in High-A and is not yet close to major league readiness.

Why Mitch Keller’s Trade Deadline Market Matters

Mitch Keller is a rare asset in the trade market due to his combination of strong, consistent pitching and extended team control through 2028, offering long-term value to any acquiring club. His ability to produce quality starts and strikeouts positions him alongside elite pitchers like Zack Wheeler, Bryan Woo, Logan Webb, and Framber Valdez, further increasing demand.

For the Pittsburgh Pirates, this scenario creates an urgent opportunity to strengthen their farm system with top-tier prospects. How Ben Cherington handles these negotiations will deeply influence the franchise’s future trajectory, especially with owner Bob Nutting’s focus on reducing payroll. The right deal could bring several impact prospects ready to contribute within the next few seasons, shaping the Pirates’ competitive outlook.