Ryan Pressly: Breaking News, Rumors & Highlights

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It was an emotional night at Daikin Park in Houston on Friday, as it marks the first time that star outfielder Kyle Tucker and closer Ryan Pressly returned to Houston since both were dealt to the Chicago Cubs.

Chicago Cubs News / Chicago Cubs on SI / June 14

Embattled Chicago Cubs Closer Credits Ian Happ for His Turnaround

On May 9, Chicago Cubs reliever Ryan Pressly was humbled in front of the fans at Wrigley Field. The 36-year-old closer, who was supposed to be their answer in the ninth inning, found himself lit up like a Christmas tree against the San Francisco Giants.

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Chicago Cubs News / ChiCitySports / June 2

Chicago Cubs: Is the end near for $14 million veteran pitcher?

The Chicago Cubs wanted a high-end closer this past offseason They made a serious play at free agent reliever Tanner Scott, reportedly offering a 4-year, $66 million contract before losing out to the Los Angeles Dodgers, who offered 4 years at $72 million, with deferred money.

Chicago Cubs News / ChiCitySports / May 14

Chicago Cubs are better than you think in one key area

The Chicago Cubs had a bullpen meltdown early last year and the team never quite climbed out of the hole that made for them. Some will even argue that that early-season bullpen collapse cost them a shot at the playoffs.

Chicago Cubs News / ChiCitySports / May 14

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 11

Demands made for Chicago Cubs to make changes after 6-2 loss to Mets

For the first time all year, the Chicago Cubs have dropped back-to-back series following their 6-2 loss to the New York Mets in front of 41,673 fans at Citi Field.

Chicago Cubs News / Athlon Sports / May 9

Cubs Predicted to Make Ryan Pressly Decision Amid Rough Start

The Chicago Cubs pulled off the best offseason MLB trade, acquiring outfielder Kyle Tucker from the Houston Astros, who is at the forefront of a potent Cubs' offense.

Chicago Cubs News / ChiCitySports / May 9

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 / ChiCitySports / May 8

‘Alarm’: Chicago Cubs have a ‘situation’ with pitcher after 9-run inning, demotion predicted

More shakeups are likely for the Chicago Cubs‘ pitching staff in the near future. In the short term, the Cubs are making their toughest choice of the season as to whether or not they will call up Cade Horton to take injured starting pitcher Shota Imanaga’s role on Saturday against the New York Mets.

San Francisco Giants News / San Francisco Giants on SI / May 7

Giants Break Longstanding Team Record in Thrilling Extra Innings Win

The San Francisco Giants knocked off the Chicago Cubs on Tuesday night by a score of 14-5 in one of the craziest games of 2025 so far, and they also made some franchise history in the process.

Chicago Cubs News / Fastball on SI / May 7

Chicago Cubs Closer Ryan Pressly Makes History With Brutal Extra-Inning Meltdown

While the Chicago Cubs' bats came through in the clutch by forcing extra innings Tuesday night, Ryan Pressly certainly didn't rise to the occasion. Chicago trailed the San Francisco Giants 5-3 entering the bottom of the ninth, until RBI singles from Justin Turner and Kyle Tucker tied the score.

Chicago Cubs News / ChiCitySports / May 7

Chicago Cubs urged to take drastic action with pitcher after 14-5 loss to Giants

The Chicago Cubs have been asking what remains of their pitching staff to step up amid injuries. It wirked well until it didn’t. The Cubs’ woes in the pitching department bit them in Tuesday’s 14-5 loss to the San Francisco Giants in front of 37,303 fans at Wrigley Field.

MLB News / Boston Red Sox on SI / May 4

Cubs Could Trade For Former Red Sox Right-Hander To Prepare For Playoffs

The Chicago Cubs’s late-inning bullpen arsenal might soon feature two former Boston Red Sox relievers. Technically, Chicago’s 36-year-old closer Ryan Pressly never played for the Red Sox’s big-league team, but he was drafted by Boston in 2007 and spent half a decade in its minor league system.

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Chicago Cubs News / Just Baseball / January 30

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

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

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.

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MLB News / Just Baseball / January 26

Astros Get Under the Tax, Trade Ryan Pressly to the Cubs

The Chicago Cubs have acquired reliever Ryan Pressly from the Houston Astros in exchange for 20-year-old pitching prospect Juan Bello. Pressly, who the Astros have aggressively shopped this offseason, will solidify the back-end of the bullpen for a team with playoff aspirations, having posted a 3.49 ERA over 56.2 innings last season.

MLB News / Yardbarker / January 27

Astros trade with Cubs sets up a potential domino effect

The Houston Astros and Chicago Cubs made a trade on Sunday that could have far-reaching ramifications.

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Houston Astros News / Field Level Media / January 26

Reports: Cubs acquiring Astros closer Ryan Pressly

The Houston Astros are dealing right-handed relief pitcher Ryan Pressly to the Chicago Cubs, multiple media outlets reported Sunday. Pressly, who served as Houston's closer for three of the past four seasons, will waive his no-trade clause to allow the move to go through, and the Astros will pay some of his remaining salary, the reports said.

MLB News / Larry Brown Sports / January 26

Cubs acquire two-time All-Star closer in trade with Astros

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MLB News / ChiCitySports / January 24

Tentative Ryan Pressly trade to the Chicago Cubs in place

A Ryan Pressly trade is looking more imminent as the Houston Astros reportedly have a tentative deal in place with the Chicago Cubs. The hold up now revolves around Pressly’s full no-trade rights. There also is competition from another mid-west team.

MLB News / MLB Trade Rumors / January 24

Report: Astros ask two-time All-Star to approve trade to Cubs or Tigers

He has full no-trade protection, and the ball is firmly in his court.

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MLB News / MLB Trade Rumors / January 23

Blue Jays have also shown interest in Ryan Pressly

If the Astros trade Ryan Pressly, the Cubs appear the likeliest landing spot. USA Today’s Bob Nightengale reported this evening that Chicago was nearing a deal for the veteran reliever.

Houston Astros News / MLB Trade Rumors / December 8

Astros reportedly 'extensively' shopping right-hander

That’s not the first indication this winter that he could be available, but it’s nonetheless notable that the club has seeming begun shopping him to rival clubs on the trade market.

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Houston Astros News / Houston Astros on SI / December 7

Toronto Blue Jays Land Ryan Pressly in Proposed Deal With Houston Astros

The Houston Astros are heading into the Winter Meetings with a lot of questions left unanswered so far this offseason. After a disappointing end to the

Houston Astros News / MLB Trade Rumors / November 6