Ryan Pressly: Breaking News, Rumors & Highlights

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A former Toronto Blue Jay has been released. On Sunday afternoon, the Los Angeles Angels announced that Canadian right-handed reliever Jordan Romano has been released.

MLB News / Houston Astros on SI / March 15

Ryan Pressly Returns to Astros in New Role as SpaceCityHN Analyst

A former fan favorite Houston Astro, Ryan Pressly, is returning to the home he had for seven years. This time, though, he will be watching the games from a little different perspective.

MLB News / Houston Astros on SI / February 7

Former Astros Closer Ryan Pressly Reflects and Sends Message to WBC Participants

The World Baseball Classic gets underway in less than a month and the players involved couldn't be more excited. This is an opportunity many players only hope they can play in, as Team USA has compiled itself with several notable names from Major League Baseball.

MLB News / Yardbarker Quizzes

The 'AL & NL Rookies of the Year' quiz

How many of these past ROY winners since the 2000 MLB season can you name in six minutes?

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Chicago Cubs News / MLB on ClutchPoints / January 29

Former MLB All-Star Ryan Pressly gets 100% real on retirement decision

The 2025 MLB season was seemingly the last for longtime relief pitcher Ryan Pressly. He announced his retirement in mid-January after playing 13 years in the league.

Athletics News / Yardbarker

The offseason needs for every MLB team

Another MLB season is in the books. The pending lockout is hanging over the heads of players and ownership, but there could be a mad rush of moves prior to December.

MLB News / MLB Trade Rumors / January 19

Twins Hire Ryan Pressly For Player Development Role

Retired right-hander Ryan Pressly has been hired by the Twins, reports Jon Heyman of The New York Post. According to Declan Goff of SKOR North, Pressly will be working in player development with both major and minor leaguers.

Minnesota Twins News / Minnesota Twins on SI / January 18

Former Twins reliever and trade mistake joining player development staff

Former Twins reliever Ryan Pressly, who won a World Series with the Astros, is retiring from his playing career and joining Minnesota's coaching staff in a player development role, per reports.

MLB News / MLB on ClutchPoints / January 18

Twins hire Ryan Pressly after retirement announcement

Former Minnesota Twins reliever Ryan Pressly announced his retirement on Saturday, after 13 seasons in the majors. Shortly after, the Twins hired the veteran reliever to return to the organization where his career began.

Houston Astros News / Houston Astros on SI / January 17

Former Astros Star Reliever Announces Retirement From Major League Baseball

The Houston Astros have a longstanding history with some of the most prominent stars in Major League Baseball. This has been an offseason filled with moves, decisions and adjustments for many franchises across the nation, and this stands true for the Astros.

Athletics News / Yardbarker

25 MLB prospects who will make an impact in 2027

The 2026 MLB season was driven by top performances from young players, and the crop of young talent in the minors has never been greater. These 25 prospects could emerge as top MLB players in 2027.

Houston Astros News / Larry Brown Sports / January 17

Ex-Astros champion announces his retirement from MLB

The exit music is officially playing for one former Houston Astros champion. Veteran MLB reliever Ryan Pressly announced over social media on Saturday that he is officially retiring from baseball.

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Chicago Cubs News / Chicago Cubs on SI / September 23, 2025

Velocity Uptick Has Cubs Veteran Relief Pitcher Primed To Be October Weapon

Coming into the 2025 MLB season, the Chicago Cubs thought they had the backend of their bullpen figured out with the addition of Ryan Pressly, joining 2024 breakout performer Porter Hodge.

MLB News / MLB Trade Rumors / August 5, 2025

Two teams mulling interest in former All-Star reliever

Two teams are reportedly considering the addition of a former All-Star reliever.

Best MLB trades from the last decade: National League

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MLB News / Minnesota Twins on SI / August 4, 2025

Report: Twins have 'reached out' to Ryan Pressly amid bullpen exodus

According to The Athletic's Dan Hayes, the Twins' have reached out to veteran reliever Ryan Pressly about a potential reunion following last week's historic trade deadline fire sale.

Chicago Cubs News / MLB Trade Rumors / July 31, 2025

Cubs designate two-time All-Star for assignment

He has well over 11 years of MLB service time, so he can’t be optioned to the minors without his consent. In all likelihood, the DFA will end with the Cubs just releasing the veteran reliever, as he still has roughly $4.5M in salary owed to him over the remainder of the season.

Cubs acquire veteran starter from Nationals

Cubs acquire one-time All-Star reliever

Reports: Cubs acquire versatile Willi Castro from Twins

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The '1984 Chicago Cubs' quiz

Chicago Cubs News / ChiCitySports / May 14, 2025

Chicago Cubs manager sent Ryan Pressly a ‘direct’ message amid demotion

Ryan Pressly played a key role in the Chicago Cubs‘ 5-4 comeback win over the Miami Marlins in front of 38,083 fans at Wrigley Field on Tuesday night. With bases loaded in the seventh inning, Pressly was asked to step in for Julian Merryweather with bases loaded and two outs and the scoreboard reading 4-2 Marlins.

Chicago Cubs News / ChiCitySports / May 9, 2025

Chicago Cubs have a big bullpen problem, aside from Ryan Pressly

The Chicago Cubs finished Tuesday’s game against the San Francisco Giants with a “worst of times” ending to an otherwise “best of times” game. After battling back to tie the game at five runs apiece, the Cubs went into extra innings, handing the ball to closer Ryan Pressly in the eleventh to hold the Giants.

Chicago Cubs News / Athlon Sports / May 8, 2025

Cubs' Ryan Pressly Makes Promising Comments Despite Concerning Start

If there have been any issues with the Chicago Cubs throughout the early stages of the season, it's the injuries and the bullpen. The offense has played much better than most expected, and outside of a few bad games against the San Francisco Giants recently, the Cubs look to be a very good team.

Chicago Cubs News / Chicago Cubs on SI / May 7, 2025

Cubs Should Have Seen Ryan Pressly Implosion Coming With Concerning Numbers

The Chicago Cubs dealt with some underwhelming bullpen performances during the 2024 season that derailed their success. Despite overhauling the group and having nearly an entirely new group of relief pitchers in 2025, the same problems are plaguing them.

Chicago Cubs News / Just Baseball / January 30, 2025

Why Ryan Pressly Waived His No-Trade Clause to Join the Cubs

Whether or not to leave Houston for Chicago wasn’t a decision Ryan Pressly made lightly. He worked hard to carve out a long career. He worked hard to become an integral part of the Houston Astros‘ bullpen over the last 6 1/2 seasons.

MLB News / ChiCitySports / January 29, 2025

Chicago Cubs: Ryan Pressly’s role as closer may not be as secure as previously expected

The Chicago Cubs and Houston Astros have made two significant trades this off-season, with outfielder Kyle Tucker and reliever Ryan Pressly both heading

MLB News / Field Level Media / January 28, 2025

Cubs acquire RHP Ryan Pressly from Astros

The Chicago Cubs acquired right-handed relief pitcher Ryan Pressly from the Houston Astros on Tuesday. Pressly, who served as the Astros' closer for three of the past four seasons, waived his no-trade clause to allow the move to go through.