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On YouTubePittsburgh Pirates News / Legends On Deck / December 8
Pittsburgh Pirates Offseason Brings Importance 
The Pittsburgh Pirates‘ offseason brings importance as reports suggest the team plans to spend money. Finally, they are giving GM Ben Cherington the flexibility he has lacked since taking over in 2019.
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 8
Pirates Must Fill Coaching Vacancy in Minor Leagues
PITTSBURGH — The Pittsburgh Pirates will make coaching changes this offseason, including finding a new coach for one of their minor league affiliates. Isaac Azout of Fish on First reported that the Miami Marlins hired Greensboro Grasshoppers manager Blake Butler as their infield coach for 2026.
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 8
Every Player Pirates Could Pursue at Winter Meetings
PITTSBURGH — The Pittsburgh Pirates enter their most important time of this offseason at the Winter Meetings down in Orlando, FL with a number of players they could go after.
The 'AL and NL MVPs since 2000' quiz
How many of the AL and NL MVPs since the 2000 MLB season can you name in six minutes?
MLB News / Pittsburgh Pirates on SI / December 8
Pirates Urged to Trade for Diamondbacks Star
PITTSBURGH — The Pittsburgh Pirates are in the midst of the most important few days of the offseason at the Winter Meetings down in Orlando, Fla., where fans hope they'll make some big moves to build the roster for next season.
25 MLB players on the brink of stardom in 2026
The stars were out in full force during the 2025 World Series. From Max Scherzer in Toronto to Freddie Freeman, Mookie Betts, and of course, Shohei Ohtani, in Los Angeles, there was no shortage of the game's best under the brightest lights.
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 8
Pirates Have New Leader for 2026 MLB Draft
PITTSBURGH — The Pittsburgh Pirates have a ways to go before the 2026 MLB Draft, but reportedly will have someone new at the helm leading the way. Former Pirates director of amateur scouting Justin Horowitz departed the franchise this offseason, joining the Washington Nationals as as an assistant general manager.
Kyle Schwarber News / Pittsburgh Pirates on SI / December 8
Pirates Make Record Offer for Phillies' Kyle Schwarber
PITTSBURGH — The Pittsburgh Pirates have a huge few days coming up at the Winter Meetings in Orlando, Fla. and have already reportedly made a massive move.
MLB News / Yardbarker / December 7
Pirates reportedly make impressive offer to Kyle Schwarber
The Pittsburgh Pirates are looking to put their money where their mouth is.
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.
Don Kelly News / Pittsburgh Pirates on SI / December 7
Pirates' Don Kelly Looking to Add to Coaching Staff
PITTSBURGH — Pittsburgh Pirates manager Don Kelly has made some important moves this offseason, but still has work left to do before the start of Spring Training.
San Diego Padres News / Yardbarker / December 7
Three potential landing spots if Padres trade Jake Cronenworth
Trading Cronenworth would cut payroll, which can then be put back into the team on the mound.
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 7
Pirates Receive Winning Grade in Trade with Red Sox
PITTSBURGH — The Pittsburgh Pirates made their first big move of the offseason, which MLB insiders and national writers had good things to say about. The
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 6
New Pirates Prospect Impresses in Venezuelan Winter League Debut
PITTSBURGH — The Pittsburgh Pirates just acquired one of the better prospects in baseball and he recently showed what he'll bring next season in a recent game.
MLB News / Pittsburgh Pirates on SI / December 6
Pirates Land Padres All-Star in Mock Trade
PITTSBURGH — The Pittsburgh Pirates need additions in their lineup next season, and one San Diego Padres All-Star might serve as a good fit. Joel Reuter
Johan Oviedo News / Just Baseball / December 6
What Does the Johan Oviedo Trade Mean for the Pirates?
The Pittsburgh Pirates have had their name in the headlines all offseason long, as rumors of increased spending and big-time acquisitions have filled the winter air.
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 6
How Pirates Could Surprise MLB at Winter Meetings
PITTSBURGH — The Pittsburgh Pirates aren't normally the most active teams in the offseason, but there are some who think that they will make their biggest moves during the Winter Meetings.
MLB News / Bucs Dugout / December 6
Pirates linked in trade with Padres involving former All-Star
The Pittsburgh Pirates and the rest of the MLB are on the hot stove to try and figure out how to improve their teams for the upcoming season. The Pirates need some help in the field while the San Diego Padres could benefit from adding a starting pitcher.
Pittsburgh Pirates News / Pittsburgh Pirates on SI / December 6
Pirates' Outfield Depth Changes Heading into 2026
PITTSBURGH — The Pittsburgh Pirates have a greatly-changed outfield heading into 2026, with a recent roster move making things even more different. The Pirates placed outfielder Will Robertson on waivers, and the Baltimore Orioles claimed him on Dec.
MLB News / Pittsburgh Pirates on SI / December 5
Pirates Claim Former Giants Top Prospect Off Waivers
PITTSBURGH — The Pittsburgh Pirates needed more outfield depth heading into next season and made an addition through waivers. The Pirates announced that they claimed outfielder Marco Luciano off of waivers from the San Francisco Giants on Dec.
Marco Luciano News / MLB Trade Rumors / December 5
Can former top-100 prospect Marco Luciano bounce back with Pirates?
The Pirates have claimed infielder/outfielder Marco Luciano off waivers from the Giants.
Jhostynxon Garcia News / MLB on ClutchPoints / December 5
Pirates rumors: Pittsburgh to remain active even after Jhostynxon Garcia trade
The Pittsburgh Pirates couldn’t hide from how disastrous their season became, and that reality pushed them into MLB Free Agency with real urgency. The Jhostynxon Garcia trade signaled the first shift in strategy, a move that told fans the front office plans to stay active deep into the winter.
Pittsburgh Pirates News / MLB Trade Rumors / December 5
Pirates remain open to dealing from rotation for offense
The Pittsburgh Pirates traded back-end starter Johan Oviedo to the Red Sox Thursday, getting rookie outfielder Jhostynxon Garcia back as part of a five-player deal.
Johan Oviedo News / Field Level Media / December 4
Red Sox acquire RHP Johan Oviedo from Pirates
The Boston Red Sox continued remaking their rotation on Thursday, acquiring right-hander Johan Oviedo in a trade with the Pittsburgh Pirates. In exchange, Pittsburgh received outfielder Jhostynxon "The Password" Garcia and minor league right-hander Jesus Travieso.
Pittsburgh Pirates News / Last Word On Sports / December 4
The Pirates Were Once Stocked with Middle Infield Prospects.
By the 2021 trade deadline, general manager Ben Cherington appeared to have his Pittsburgh Pirates well-stocked with middle infield prospects. He had just obtained Diego Castillo, Tucupita Marcano, and Hoy Park in trades.
MLB News / Yardbarker / December 5
Pirates, Red Sox both rolling the dice in Johan Oviedo trade
The Pittsburgh Pirates and Boston Red Sox have seemed like ideal trade partners for more than a year now.
Pittsburgh Pirates News / Last Word On Sports / December 1
Pirates Star May Have Different Role – or Different Team – in 2026
In two preceding postseasons, it seemed a formality that Andrew McCutchen would sign for another year with the Pittsburgh Pirates. When he returned in 2023, “Cutch” made it clear he wanted to finish his career in Pittsburgh, where it started.
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