Pittsburgh Pirates general manager Ben Cherington came into the summer with buyers at the MLB trade deadline eyeing the likes of Mitch Keller, David Bednar, Ke’Bryan Hayes, and Dennis Santana. Following a rather uneventful trade season in Pittsburgh, Cherington could reportedly be in his final months with the team.
Bob Nightengale of USA Today reported Sunday that there are already MLB rumors swirling around the league that the Pirates “will be replacing” Cherington after the season. Even if he’s retained through September, he’s widely viewed as having the worst job security in baseball.
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Cherington, age 51, was hired as the Pirates’ general manager in November 2019. Before that, he had a three-year stint as vice president of baseball operations with the Toronto Blue Jays (2016–19), and he spent more than a decade in the Boston Red Sox front office.
Boston hired Cherington as general manager in October 2011. He departed less than four years later, winning a World Series in 2013 but also missing on free-agent signings like Pablo Sandoval, Hanley Ramirez, and Rusney Castillo. Surrounding Boston’s 2013 World Series title, the team won 71 or fewer games in 2012 and 2014.
Cherington inherited a Pirates roster that went 69-93 the previous season, with its last playoff appearance coming in 2015. Entering play on August 4, Pittsburgh has a 341-478 (.416 winning percentage) record across six seasons under Cherington and is on pace to finish last in the division for the fourth time.
The Pirates didn’t trade Santana (2.27 ERA and 0.90 WHIP) or Keller (3.89 ERA and 1.22 WHIP), despite both pitchers enjoying career-best seasons and being highly coveted with multiple years of contract control. Bednar was traded to the New York Yankees. Responding to questions about why the centerpiece of the return (Rafael Flores) wasn’t a consensus top-100 prospect, Cherington said the Pirates were offered top-100 prospects but the organization wasn’t as high on those players.
“We had access to players who were ranked in the way that you were describing. We did, and we preferred this package.”
Pirates GM Ben Cherington on turning down ranked top-100 prospects in favor of other players (via MLB.com)
Even for Pirates owner Bob Nutting, six consecutive seasons of the team finishing near the bottom of the MLB standings and showing no signs of progress is likely enough for Cherington to be fired. Unfortunately for the fan base, the next general manager will likely be working under the same financial constraints as Cherington.
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