Ben Cherington: Breaking News, Rumors & Highlights

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One of the main positive takeaways from the time Ben Cherington has been the Pittsbugh Pirates‘ general manager has been the way they’ve developed talented arms all throughout the system.

Pittsburgh Pirates News / Pittsburgh Pirates on SI / October 24

Pirates Have Big Shoes to Fill in Scouting Department

PITTSBURGH — The Pittsburgh Pirates lost their most important person in their scouting department and need to make a big decision going forward. Joe Doyle of OverSlot.com reported that the Washington Nationals are hiring Pirates director of amateur scouting in Justin Horowitz as an assistant general manager.

Yoshinobu Yamamoto News / Yardbarker Quizzes

The 'World Series MVPs' quiz

MLB has awarded the World Series MVP since 1955. How many of these players can you name in six minutes?

The 'Last playoff complete game by MLB team' quiz

The 'World Series walk-off home runs' quiz

The 'Recent MLB World Series managers' quiz

Pittsburgh Pirates News / Pittsburgh Pirates on SI / September 30

Pirates President Shows Support For GM Ben Cherington

PITTSBURGH — The Pittsburgh Pirates had a poor season in 2025, but one member of the front office has faith in the team succeeding next season, with the general manager there to lead the way.

MLB News / Yardbarker

25 notable MLB Hall of Famers who never won a World Series

Among the countless Hall of Famers who never experienced the joy of winning a World Series, there are several notable legends who stand out. Here's our list of the 25 greatest.

Pittsburgh Pirates News / Bucs Dugout / September 30

Ben Cherington is back for another season with Pirates

When Don Kelly was immediately extended as the Pirates manager on Monday, it certainly felt like a positive thing on the surface. It’s safe to say that

Pittsburgh Pirates News / MLB Trade Rumors / September 29

Will Pirates GM Ben Cherington return in 2026?

He has been with the team since 2019.

Pirates remove interim tag from manager Don Kelly

Braves beat Pirates in Charlie Morton's likely farewell

Paul Skenes' latest feat shows why records shouldn't matter

25 MLB players who could be traded this offseason

The 'MLB all-time saves leaders' quiz

Pittsburgh Pirates News / Sporting News / September 29

Pirates fans want GM Ben Cherington fired despite team giving Don Kelly a contract extension

Pittsburgh Pirates fans still want general manager Ben Cherington fired.

Pittsburgh Pirates News / Pittsburgh Pirates on SI / September 26

Pirates GM Ben Cherington's Contract Length Revealed

PITTSBURGH — Pittsburgh Pirates general manager Ben Cherington has spent this entire decade in the same role, but many fans wonder how long he'll stay in the job going forward.

Pittsburgh Pirates News / Bucs Dugout / September 26

Pirates Don Kelly and Ben Cherington’s status for 2026 in question

The biggest question that will need to be answered for the 2025-2026 Pirates offseason will be if General Manager Ben Cherington will get yet another undeserving

MLB News / Yardbarker

The 25 greatest pitching seasons from the modern MLB era

America's favorite pastime has more memorable performances than any sport. As such, figuring out which pitchers had the best seasons ever is no easy task.

Pittsburgh Pirates News / MLB Trade Rumors / September 21

Pirates GM Ben Cherington discusses future, offseason plans

It’s been another tough season for the Pirates, and things went poorly enough early in the year that manager Derek Shelton was fired just six weeks into the regular season.

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The '2025 backup NFL quarterbacks' quiz

The 'World Series MVPs' quiz

The 'NFL Passing YPG leaders' quiz

The 'TDs from Josh Allen or Patrick Mahomes' quiz

Pittsburgh Pirates News / Pittsburgh Pirates on SI / September 20

Watch: Pirates GM Ben Cherington Addresses 2025 Season

PITTSBURGH — Pittsburgh Pirates general manager Ben Cherington isn't proud of how this season has gone, especially with this recent stretch towards the end of the campaign.

Pittsburgh Pirates News / Pittsburgh Pirates on SI / September 10

MLB Insider Predicts Pirates Keep GM Ben Cherington

PITTSBURGH — The Pittsburgh Pirates have struggled over the 2020s, with general manager Ben Cherington at the helm for the entirety of the decade. The Pirates have gone 358-495 overall since the start of the decade, a .420 winning percentage, with all seasons below .500.

Pittsburgh Pirates News / Last Word On Sports / August 28

Pirates GM Cherington Discussed Hitting, Free Agents with MLBTR

Pittsburgh Pirates general manager Ben Cherington recently granted a brief but wide-ranging interview to the MLB Trade Rumors podcast. Too often in his dealings with the Pittsburgh media, it seems as though he’s trying to break former Pirates manager Jim Tracy’s unofficial major league record for using the most words to say the least.

Pittsburgh Pirates News / Pittsburgh Pirates on SI / August 24

Watch: Pirates GM Addresses Recent Promotions

PITTSBURGH — Pittsburgh Pirates general manager Ben Cherington and the front office have had an eventful week, with two big roster moves in the organization.

Pittsburgh Pirates News / MLB Trade Rumors / August 11

Pirates expected to pursue help at one position in offseason

The Pirates’ 2026 infield figures to look considerably different than the group that’s been trotted out for much of the season. Pittsburgh succeeded in

Reds pull away from Pirates in slugfest

The 20 greatest MLB managers who never won a World Series

The '1979 ‘We Are Family’ Pittsburgh Pirates' quiz

Pittsburgh Pirates News / Last Word On Sports / August 1

Grading the Pirates’ Trade Deadline (or: What Was That?)

Ben Cherington just completed his sixth trade deadline as general manager of the Pittsburgh Pirates with another flurry of moves. In July, he completed six trades, giving up six players to five different teams, receiving 10 in return.

Pittsburgh Pirates News / Yardbarker / August 1

Pirates once again show they're not serious about winning

The Pittsburgh Pirates are a sham.

Pirates get solid return for disappointing former top prospect

Royals acquire grandson of Hall of Famer in last-minute trade

Career-low stat underscores slump for Mets' Juan Soto, threatens to end streak

MLB infielder gets traded across the field to other team in odd scene

Is Yankees SS Anthony Volpe starting to turn a corner?

Pittsburgh Pirates News / Pittsburgh Pirates on SI / July 30

Pirates GM in Tough Spot Ahead of Trade Deadline

PITTSBURGH — The Pittsburgh Pirates front office has a busy next two days before the end of the MLB trade deadline on July 31, including the general manager.

Pittsburgh Pirates News / MLB on ClutchPoints / July 29

Pirates rumors: The ‘awkward’ position embattled GM is in at trade deadline

The Pittsburgh Pirates are in a tough position ahead of the MLB trade deadline. Pittsburgh is sailing toward another disappointing season, under general manager Ben Cherington.

Pittsburgh Pirates News / Yardbarker / May 22

Pirates GM addresses Paul Skenes trade chatter

It seems to be a foregone conclusion that at some point over the next four or five years the Pittsburgh Pirates are going to have to trade starting pitcher Paul Skenes when he begins to price himself out of their budget. It's probably not a matter of if it happens, but probably a matter of when it happens.

Red Sox announce trade with Angels after Rafael Devers news

Juan Soto's tailspin continues with disastrous outing vs. Red Sox

The Colorado Rockies are off to a terrible, no good, start

Umpire Laz Diaz caught on hot mic admitting he screwed up a call

Can Kyle Schwarber earn $100M on his next contract?

Pittsburgh Pirates News / Pittsburgh Baseball Now / November 24

Give Ben Cherington Credit for Swallowing Pride

All general managers make mistakes. Pittsburgh Pirates GM Ben Cherington is no different. During his five years on the job, he has made his share of bad trades and free-agent signings.

Pittsburgh Pirates News / Pittsburgh Baseball Now / October 16, 2024

Ben Cherington Stands Behind Pirates’ Player Development

It is always fun when the Pittsburgh Pirates honor their 1979 team, the last one to win a World Series for the franchise. It is equally fun to hear those players’ thoughts on the current Pirates’ organization.

Pittsburgh Pirates News / Yardbarker / July 9, 2024

Why Pirates management should be furious with owner Bob Nutting

Earlier this summer, Pirates owner Bob Nutting made a rare appearance in front of the media, boldly proclaiming the team must be prepared to trade for offense before the trade deadline on July 30 at 6 p.m. ET.

Which National League wild-card hopefuls are contenders, pretenders?

Paul Skenes headlines NL All-Stars; Phillies lead with seven players

Rookie sensations: Are All-Star selections prelude to successful MLB careers?

The greatest postseason moment for every MLB team

The 'No. 1 overall pick in the MLB Draft' quiz