Failed Ben Cherington trade feels even worse after Pirates target's playoff heroics

Ben Cherington took over as the Pittsburgh Pirates’ general manager during the 2019-2020 offseason, and fans still aren’t happy about the decision nearly six years later, especially given how poorly his trades have gone. Many of Cherington’s boldest trades haven’t worked out, and his strategies have led to a team that averaged fewer runs per game than they did about 100 years ago during the Deadball Era.

However, the focus and anger this week is centered specifically around one trade that fell through at the last minute, and Pittsburgh's goal-line fumble looks even worse as the target in question thrives. Let this be a reminder that thePirates tried to acquire Toronto Blue Jays two-time All-Star Alejandro Kirk for starting pitcher Joe Musgrove at the 2020 trade deadline.

It’s not as if Kirk was a small player to ask for at the time. During 2019, Kirk established himself as one of the best pure hitters in the minor leagues. He hit .299/.403/.465 with a 152 wRC+. Kirk hit for a respectable amount of power, with a .174 isolated slugging percentage and seven home runs over 372 plate appearances between A-Ball and High-A. But the best part of his game was his plate discipline. Kirk struck out just 10.5% of the time, with an outstanding 15.5% walk rate. Only two minor league batters in 2019 had a BB:K ratio over 1.25 and a wRC+ over 150: Kirk and baseball’s number one prospect (prior to his off-field actions), Wander Franco.

Kirk completely skipped Double-A and Triple-A before making his debut in the major leagues. He only appeared in nine games with 25 plate appearances, but racked up nine hits, with two doubles and a home run. All of this was enough for Baseball America to rank him as the 70th-best prospect in baseball. Although Kirk then missed part of 2021 due to a hip flexor injury, he took off in 2022 and has not looked back since. 

Pirates missing out on Alejandro Kirk feels even worse now after MLB Postseason heroics.

Kirk is hitting .269/.346/.392 over his last four MLB seasons. He has continued to keep his strikeout rate low, at 11.5%, and draws walks at a healthy 10.5% clip. While his .122 isolated slugging percentage is below average, Kirk has still gone yard at least a dozen times two times over his last four campaigns, including 15 in 506 plate appearances in 2025. Overall, he has a quality .324 wOBA, .343 xwOBA, and 110 wRC+. 

The one detriment to Kirk's game at the time was his poor defense behind the dish. Both MLB Pipeline and Baseball America only projected him as a 45-grade defender. However, he has since developed into one of baseball’s best defenders. Since 2022, Kirk has +48 defensive runs saved and +38.2 framing runs. The only other backstop with more DRS is San Francisco Giants catcher Patrick Bailey. Kirk also has the fifth most framing runs, and is an elite blocker, with +50 blocking runs above average, which leads all catchers since 2022. Even Kirk’s poptime has gotten better, from 1.99 seconds in 2022 to 1.95 seconds in 2025.

Pirates backstops have struggled badly since 2022. They’re only batting a collective .210/.286/.319, with a .271 group wOBA and 68 wRC+. They rank last in slugging percentage and among the bottom five teams in batting average, OPS, wOBA, and wRC+. Their defense has been solid behind the plate, with +13 DRS and +33 framing runs —the third most in MLB over the last four seasons —but that 68 wRC+ is not fun to look at, to say the least. Like many MLB teams, the Pirates have turned catcher into a defense-only position - but the Blue Jays sure haven't.

The Pirates ended up getting five players back for Joe Musgrove when they ultimately pulled the trigger on a deal. Of those five, only one has panned out: David Bednar, who was traded during this year’s trade deadline to the New York Yankees for another catching prospect, Rafael Flores. They also got Endy Rodriguez in the Musgrove trade. The switch-hitter showed a ton of promise throughout the minor leagues and entered 2023 as a consensus top 100 prospect. Rodriguez made his MLB debut that season, and while he struggled, his 204 plate appearances weren't enough to fundamentally judge him on. However, since that season, Rodriguez has constantly battled injuries, from Tommy John surgery that eliminated him from 2024 to undergoing ulnar nerve transposition surgery that kept him out for all but 18 games in 2025.

What makes this all sting even more is Kirk has been a hero for the Blue Jays in October. He has 15 hits in 60 Postseason plate appearances. Of those 15 hits, seven have gone for extra bases. Five are home runs, and two are doubles. He has 32 total bases, a total which is only surpassed by teammate Vladimir Guerrero Jr. and LA Dodgers superstar Shohei Ohtani in October's action.

Sure, hindsight is 20/20, and while you couldn’t have predicted Alejandro Kirk becoming one of baseball’s best backstops and a Postseason hero five years ago, the Pirates run by Ben Cherington have made so many poor trades and missed so many opportunities that it’s hard to give them the entire benefit of the doubt.

The Pirates have struggled for years to find a catcher who can consistently provide value on both the defensive and offensive sides of the ball. Letting a deal fall through on the one-yard line that likely would have involved Kirk is yet another massive blunder on a long list of other massive blunders since Cherington took over as GM.