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Ben Cherington’s Best Moves as Pirates’ GM



Andrew McCutchen, Ben Cherington

Ben Cherington took over as general manager of the Pittsburgh Pirates after the 2019 season.

He was part of a complete revamp orchestrated by owner Bob Nutting. Cherington took over for the outgoing Neal Huntington, and was one of three new hires for the organization along with manager Derek Shelton and team president Travis Williams.

Since taking the reigns, Cherington has executed a number of transactions. Some of them have gone well, some of them have not. On Tuesday, we will highlight the moves he’s made that didn’t pan out. For now, lets look at some of Cherington’s best moves.


In back-to-back seasons, Cherington broke the franchise contract recordd in signing two key players to long-term deals.

At the beginning of the 2022 season, third baseman Ke’Bryan Hayes put pen to paper on an eight-year, $70 million contract which also has a club option for a ninth season.

Since the deal was signed, Hayes was awarded his first-career Gold Glove as he’s established himself as one of the best defenders in the sport. He also took a big step forward with the bat last season.

The following year, the Pirates signed left fielder Bryan to an eight-year deal worth $106.75 million. As with Hayes, Reynolds’ extension comes with a club option.

Reynolds is one of the anchors of the Pirates’ lineup and will continue to be an integral part of the club moving forward.


The Pirates found themselves with the top pick in the draft for the second time in three years after winning the first-ever draft lottery last winter.

With the top pick in last year’s draft, the Pirates selected right-handed starting pitcher Paul Skenes, who is considered to be the top pitching prospect in baseball.

While it remains to be seen how Skenes’ career will eventually play out, he gives them a potential ace of the rotation for years to come. He’s expected to reach Pittsburgh at some point this coming season.


Ben Cherington brought in Quintana on an inexpensive one-year deal prior to the start of the 2022 season.

At the time, the veteran left-hander was coming off a down stretch that was plagued by injuries. The gamble paid off.

While with the Pirates, Quintana went 3-5 with a very respectable 3.50 ERA across 20 starts. The Pirates shipped him to the St. Louis Cardinals. In return, the Pirates acquired right-hander Johan Oviedo. Although he will miss the 2024 season, Oviedo was a huge part of the Pirates’ rotation last season and figures to have a role when he returns to the mound.


Leading up to the 2021 trade deadline, the Pirates sent All-Star second baseman Adam Frazier to the San Diego Padres in exchange for three players. One of the players the Pirates received was outfielder Jack Suwinski, who was still a prospect at the time.

Suwinski has become the Pirates’ top power threat, at least in Oneil Cruz’s absence. This past year, the 25-year-old posted an OPS of .793 and belted a career-high 26 home runs.

Frazier, meanwhile, faded down the stretch with San Diego and was traded to the Seattle Mariners the following offseason.


Ben Cherington made a pair of what at the time appeared to be smaller-scale trades, but have turned into excellent returns for the Pirates.

At the 2022 trade deadline, the Pirates sent designated hitter Daniel Vogelbach to the New York Mets for right-hander Colin Holderman. Last winter, Cherington pulled the trigger on a trade of Kevin Newman to the Cincinnati Reds for Dauri Moreta.

Both Holderman and Moreta held key roles in the Pirates’ bullpen last season as back-end options. Both are expected to be contributors again in 2024.


Bringing back an all-time fan favorite (twice) would have probably been on this list regardless of performance, but Andrew McCutchen proved he still has something left in the tank.

McCutchen was brought back to the Pirates last winter on a one-year deal and hit .256 with a .378 on-base percentage and a .776 OPS in 112 games before suffering a season-ending Achilles injury.

The now 37-year-old is back again for 2024 and projects to be the primary option at designated hitter.

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