Analysis: Cherington's among worst GMs in baseball history
While there were plenty of questions answered today at Ben Cherington's press conference about the firing of Derek Shelton, here's one that couldn't be: Why's Cherington still employed by the Pirates?
To start, let's just put things into perspective. Among Major League Baseball general managers with at least five years of tenure, his winning percentage is the sixth-worst all-time:
1. George Weiss, Mets, 5 years, .322 2. Branch Rickey, Pirates, 5 years, .349 3. Allard Baird, Royals, 5 years, .400 4. Chuck LaMar, Rays, 8 years, .401 5. Bobby Cox, Braves, 5 years, .402 6. Cherington, Pirates, 6 years, .410
Maybe even more striking: Cherington's winning percentage ranks 61st among general managers among four major sports leagues, including the NFL, NHL and NBA.
Why? Consider:
• He's done nothing but lose in Pittsburgh. His Pirates have finished as high as fourth twice and otherwise have owned the National League Central Division basement.
• He's invested $69 million to draft 90 players and another $26 million to sign 108 international free agents. All he currently has to show for it at the major-league level are Paul Skenes, Henry Davis, Carmen Mlodzinski and two injured players in Jared Jones and Nick Gonzales.
• Of those five, Davis is a former No. 1 overall pick slashing .133/.212/.233 and third on the organizational depth at age 25. Another, Mlodzinski, was a promising middle reliever who was moved into starting this season and has a 6.16 ERA over 30 2/3 innings.
• The recent trade messes were acquiring Bryan De La Cruz and Spencer Horwitz, but don't let recency bias prevent a look further back. Dealing Starling Marte brought 65 games over four seasons from Liover Peguero. Dealing Josh Bell brought a few ragged relief appearances from Wil Crowe. Dealing Joe Musgrove brought David Bednar and Endy Rodriguez, neither of whom approaches Musgrove's value.
• The free-agency acquisition list isn't any prettier. Among those: Rowdy Tellez ($3.20 million), Austin Hedges ($5 million), Roberto Pérez ($5 million), Jake Marisnick ($1.30 million), Yoshi Tsutsugo ($4 million), Trevor Cahill ($1.5 million), Heath Hembree ($2.13 million), Martin Pérez ($8 million), Rich Hill ($8 million), and, last but hardly least in this category, a 37-year-old Tommy Pham ($4 million) now batting .183 and playing every day.
Collectively:
• The Pirates have ranked in the bottom third of major-league hitting every year for the past six seasons. They ranked 28th in 2020 (.220), 25th in 2021 (.236), 29th in 2022 (.222), 24th in 2023 (.239) and 23rd in 2024 (.234) and they currently rank 28th at .219. In that span, they've also got the fewest (686) and RBIs (2,756).
• The fielding has been just as bad, as they have the fifth-most errors (447), a figure that obviously doesn't include other mistakes and lapses.
• The starting pitchers have the third-worst ERA (4.70), third-worst walk percentage (3.39), the second-fewest quality starts (208) and have recorded the fifth-fewest strikeouts (3,266).
• The bullpen has the sixth-most blown saves (117), the fourth-worst ERA (4.51) and has given up the most walks (1,289).
At the end of last season, when Cherington lobbied to bring Shelton back for one more season he said they'd be "accountable together." I asked him about that today to see if something had changed over the beginning of this season.
Here's his response:
"No. We’re both accountable. I am still accountable right now. We were in this together every minute up until this morning. It makes it a very difficult conversation. It makes it a very difficult choice. Certainly not lost on me that my part of that accountability, if I had done my job perfectly for five years, might not be meeting with you today. That’s certainly possible. I own that completely. This is not all on Shelty. And, I believe that it became clear to me that this was a choice, however difficult, that we needed to make. I certainly feel accountable going forward."
Nothing's more accountable than a history lesson.
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THE ASYLUM
Greg Macafee
3:20 am - 05.09.2025NORTH SHOREAnalysis: Cherington's among worst GMs in baseball history
While there were plenty of questions answered today at Ben Cherington's press conference about the firing of Derek Shelton, here's one that couldn't be: Why's Cherington still employed by the Pirates?
To start, let's just put things into perspective. Among Major League Baseball general managers with at least five years of tenure, his winning percentage is the sixth-worst all-time:
1. George Weiss, Mets, 5 years, .322
2. Branch Rickey, Pirates, 5 years, .349
3. Allard Baird, Royals, 5 years, .400
4. Chuck LaMar, Rays, 8 years, .401
5. Bobby Cox, Braves, 5 years, .402
6. Cherington, Pirates, 6 years, .410
Maybe even more striking: Cherington's winning percentage ranks 61st among general managers among four major sports leagues, including the NFL, NHL and NBA.
Why? Consider:
• He's done nothing but lose in Pittsburgh. His Pirates have finished as high as fourth twice and otherwise have owned the National League Central Division basement.
• He's invested $69 million to draft 90 players and another $26 million to sign 108 international free agents. All he currently has to show for it at the major-league level are Paul Skenes, Henry Davis, Carmen Mlodzinski and two injured players in Jared Jones and Nick Gonzales.
• Of those five, Davis is a former No. 1 overall pick slashing .133/.212/.233 and third on the organizational depth at age 25. Another, Mlodzinski, was a promising middle reliever who was moved into starting this season and has a 6.16 ERA over 30 2/3 innings.
• The recent trade messes were acquiring Bryan De La Cruz and Spencer Horwitz, but don't let recency bias prevent a look further back. Dealing Starling Marte brought 65 games over four seasons from Liover Peguero. Dealing Josh Bell brought a few ragged relief appearances from Wil Crowe. Dealing Joe Musgrove brought David Bednar and Endy Rodriguez, neither of whom approaches Musgrove's value.
• The free-agency acquisition list isn't any prettier. Among those: Rowdy Tellez ($3.20 million), Austin Hedges ($5 million), Roberto Pérez ($5 million), Jake Marisnick ($1.30 million), Yoshi Tsutsugo ($4 million), Trevor Cahill ($1.5 million), Heath Hembree ($2.13 million), Martin Pérez ($8 million), Rich Hill ($8 million), and, last but hardly least in this category, a 37-year-old Tommy Pham ($4 million) now batting .183 and playing every day.
Collectively:
• The Pirates have ranked in the bottom third of major-league hitting every year for the past six seasons. They ranked 28th in 2020 (.220), 25th in 2021 (.236), 29th in 2022 (.222), 24th in 2023 (.239) and 23rd in 2024 (.234) and they currently rank 28th at .219. In that span, they've also got the fewest (686) and RBIs (2,756).
• The fielding has been just as bad, as they have the fifth-most errors (447), a figure that obviously doesn't include other mistakes and lapses.
• The starting pitchers have the third-worst ERA (4.70), third-worst walk percentage (3.39), the second-fewest quality starts (208) and have recorded the fifth-fewest strikeouts (3,266).
• The bullpen has the sixth-most blown saves (117), the fourth-worst ERA (4.51) and has given up the most walks (1,289).
At the end of last season, when Cherington lobbied to bring Shelton back for one more season he said they'd be "accountable together." I asked him about that today to see if something had changed over the beginning of this season.
Here's his response:
"No. We’re both accountable. I am still accountable right now. We were in this together every minute up until this morning. It makes it a very difficult conversation. It makes it a very difficult choice. Certainly not lost on me that my part of that accountability, if I had done my job perfectly for five years, might not be meeting with you today. That’s certainly possible. I own that completely. This is not all on Shelty. And, I believe that it became clear to me that this was a choice, however difficult, that we needed to make. I certainly feel accountable going forward."
Nothing's more accountable than a history lesson.
Want to participate in our comments?
Want an ad-free experience?
Become a member, and enjoy premium benefits! Make your voice heard on the Steelers, Penguins and Pirates, and hear right back from tens of thousands of fellow Pittsburgh sports fans worldwide! Plus, access all our premium content, including Dejan Kovacevic columns, Friday Insider, daily Live Qs with the staff, more! And yeah, that's right, no ads at all!
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