Sean O'Leary

Joined: May 25, 2024

Jul 21, 2025; Washington, District of Columbia, USA; Washington Nationals pitcher Kyle Finnegan (67) throws during the ninth inning against the Cincinnati Reds at Nationals Park

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Arkansas Razorbacks' Wehiwa Aloy (9) throw the ball to first base as Arkansas Razorbacks take on Ole Miss Rebels during the SEC baseball tournament at Hoover Met in Birmingham, Ala., on Friday, May 23, 2025.

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Sep 25, 2024; Houston, Texas, USA; Houston Astros starting pitcher Yusei Kikuchi (16) delivers a pitch against the Seattle Mariners during the first inning at Minute Maid Park.

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Oct 2, 2024; San Diego, California, USA; Atlanta Braves pitcher Max Fried (54) throws during the first inning of game two in the Wildcard round for the 2024 MLB Playoffs against the San Diego Padres at Petco Park.

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Sep 13, 2024; Denver, Colorado, USA; Chicago Cubs left fielder Ian Happ (8) makes a catch in the third inning against the Colorado Rockies at Coors Field.

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The Chicago Cubs saw an outfield mainstay win yet another Gold Glove.

Jun 8, 2024; Cincinnati, Ohio, USA; Chicago Cubs starting pitcher Ben Brown (32) pitches against the Cincinnati Reds in the first inning at Great American Ball Park.

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The Chicago Cubs looked as if they had a promising starter, but it doesn't appear he will be back in the rotation to start the year.

Iowa Cubs player Matt Shaw stands at 3rd base during the first inning against Cleveland Cubs on Thursday, Aug. 15, 2024, at Principal Park.

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These two prospects were named as MLB Pipeline standout performers for 2024.

Mar 28, 2024; Oakland, California, USA; Cleveland Guardians starting pitcher Shane Bieber (57) delivers a pitch against the Oakland Athletics during the third inning at Oakland-Alameda County Coliseum.

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The Chicago Cubs will be in the pitcher market this offseason, and there's one former All-Star who may be on their radar.

Cade Horton sits during a warmup at Four Winds Feild on June 22, 2023.

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After a disappointing first season under a new regime, the Chicago Cubs' prospects will be a huge part of 2025.

Oct 8, 2024; San Diego, California, USA; San Diego Padres pitcher Tanner Scott (66) throws in the eighth inning against the Los Angeles Dodgers during game three of the NLDS for the 2024 MLB Playoffs at Petco Park.

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One of the Chicago Cubs' biggest deficiencies in 2024 was the bullpen, but there a plenty of options on the open market.

Sep 22, 2024; Chicago, Illinois, USA; Chicago Cubs pitcher Shota Imanaga (18) throws the ball against the Washington Nationals during the first inning at Wrigley Field.

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After a terrific rookie year, the Chicago Cubs manager praised his rookie ace's ability to keep it simple.

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The Chicago Cubs continue to prove they have one of their best minor league systems in the newest top 100.

Jan 12, 2024; Chicago, IL, USA; Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel.

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After falling short of the playoffs once again, Chicago Cubs President of Baseball Operations gamve his thoughts on the season.

Sep 17, 2024; Chicago, Illinois, USA; Chicago Cubs outfielder Ian Happ (8) rounds the bases after hitting a solo home run against the Oakland Athletics during the third inning at Wrigley Field.

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In a nice gesture, a Chicago Cubs outfielder thanked the fans for their support.

Sep 28, 2024; Chicago, Illinois, USA; Chicago Cubs pitcher Kyle Hendricks (28) reacts to fans after the game against the Cincinnati Reds at Wrigley Field.

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In what might be his final season with the Chicago Cubs, a legend talks about his future with the team.

Chicago Cubs center fielder Rafael Ortega (66) celebrates with designated hitter Frank Schwindel (18) after Schwindel's two-run home run in the first inning of the MLB National League game between the Cincinnati Reds and the Chicago Cubs at Great American Ball Park in downtown Cincinnati on Tuesday, May 24, 2022.

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In 2021, the Chicago Cubs had a breakout star who was never able to replicate it, and he recently talked about it.

Sean O'Leary

Joined: May 25, 2024

Cubs 'Showed Interest In' Acquiring Former Nationals All-Star Closer

Cubs Scoop Up Golden Spikes Finalist in Latest Mock Draft

Should Chicago Cubs Pursue Veteran Left-Hander in Free Agency?

Left-Handed Ace Predicted To Land With Chicago Cubs This Offseason

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Chicago Cubs Veteran Outfielder Wins Third Straight Gold Glove

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Chicago Cubs Rookie Not Expected To Be Part of Rotation After Major Injury

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These MLB-Ready Chicago Cubs Top Prospects Absolutely Shined in 2024 Season

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Could Chicago Cubs Bolster Rotation By Signing Cy Young Ace in Free Agency?

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The Youth Movement Is Coming for the Chicago Cubs

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Chicago Cubs Should Explore Multiple Bullpen Options in Free Agency

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Chicago Cubs Manager Says ‘Simplicity’ Is Best Aspect of Ace’s Game

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Eight Chicago Cubs Prospect Land on Top 100

Chicago Cubs Executive Reflects on Disappointing Season

Chicago Cubs Outfielder Rewards Fans for Support

Chicago Cubs Veteran Talks Possible Last Start With Team

Former Chicago Cub Talks Magical Season