TRADE ALERT

End of an era as Astros trade Ryan Pressly to the Cubs

Astros Ryan Pressly, Yainer Diaz
Pressly joins Kyle Tucker in Chicago. Photo by David Berding/Getty Images.

The Chicago Cubs are finalizing a trade for Ryan Pressly, adding the right-hander to the back end of their bullpen in their second major offseason deal with the Houston Astros.

Pressly has agreed to waive his no-trade clause, according to a person familiar with the situation, and there is an agreement in place between the teams, pending a review of medical records. The person spoke to the AP on Sunday on condition of anonymity because the trade had not been finalized.

Pressly had the right to block the deal because of his 12 years in the majors and six-plus seasons with the Astros. He had a 3.49 ERA in 59 appearances last year while serving as a setup man for Josh Hader.

The Cubs also acquired All-Star outfielder Kyle Tucker in a multiplayer trade with the Astros in December.

Chicago had been searching for bullpen help since it went 83-79 and finished second in the NL Central in 2024 for the second straight season. It was reportedly in the mix for Tanner Scott before he joined the Los Angeles Dodgers.

Porter Hodge had a 1.88 ERA and nine saves during an impressive rookie year with Chicago, but he likely slides into a setup role with Pressly's arrival.

Pressly is slated to make $14 million in the last year of his contract, and Houston could use the money it saved in the trade to upgrade its outfield. It also could make a renewed push for a reunion with free agent third baseman Alex Bregman.

Hader replaced Pressly as Houston's closer after he agreed to a $95 million, five-year contract last January. He had a 3.80 ERA and 34 saves in 71 games as the Astros won the AL West for the seventh time in the last eight seasons.

With Pressly on his way out, Bryan Abreu and Tayler Scott each could take on a more prominent role in front of Hader in Houston's bullpen.

Pressly, a 36-year-old Dallas native, made his big league debut with Minnesota in 2013 and spent his first five-plus seasons with the Twins. He was traded to Houston in July 2018.

Pressly rose to prominence with the Astros, becoming one of baseball's best relievers. The two-time All-Star had a streak of 40 consecutive games without allowing a run from Aug. 15, 2018, to May 23, 2019.

He was a key performer when Houston won the franchise's second World Series title in 2022. He had a career-high 33 saves with a 2.98 ERA during the regular season, and then went on a dominant run in the playoffs. He saved six postseason games, striking out 13 while allowing an unearned run and four hits in 11 innings over 10 appearances.

Pressly is 35-36 with a 3.27 ERA and 112 saves in 623 major league games. He also has 693 strikeouts and 190 walks in 650 innings.

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The Yankees host the Astros this weekend! Composite image by Jack Brame.

The Astros and the Yankees in the Bronx this weekend. Fun! And important. Both teams have been in results ruts for a while. The Astros have gone 9-16 over their last 25 games while the Yankees’ funk is longer extending, producing a 19-29 mess over their last 48 games. Despite the Seattle Mariners closing in, the Astros still lead the American League West. The Yankees’ hopes of again winning the AL East are fading toward the point of no return. They have tumbled six and a half games behind the Toronto Blue Jays and also lag three games behind the rampaging Boston Red Sox. Hence, the Yankees are under clearly more pressure than are the Astros this weekend. The pitching matchups in the first two games strongly favor the Astros. Friday night it’s Hunter Brown opposite rookie Cam Schlittler who makes his fifth big league appearance. Saturday afternoon it’s Framber Valdez versus Luis Gil, who was the 2024 American League Rookie of the Year, but missed the first four months of this season with a lat injury. Gil made his 2025 debut Sunday, and was terrible. The Astros’ quality rotation depth beyond Brown and Valdez is non-existent at this point. Their Sunday starter will be a lesser starter than the Yankees’ Max Fried. Of course, in one game you never know.

The Astros have thoroughly owned the Yankees in their most meaningful meetings over the last decade. In 2015 the ousted the Yankees in a one-game Wild Card matchup. Then came the real soul-crushers with the Astros vanquishing the Yanks in the 2017, 2019, and 2022 American League Championship Series, with it getting easier for the Astros as time went on. The 2017 series went the maximum seven games, 2019 took six, 2022 was a four-game Astros’ sweep. The regular season has been a different matter. The Yankees have beaten the Astros in 11 of 14 games over the last two years. Last season the Yankees walloped the Astros six wins to one. They only play six times this regular season: the three in New York this weekend then three at Daikin Park in early September.

Here comes the Judge

While the Astros (and their fans) endure a seemingly never-ending wait for Yordan Alvarez’s return to the lineup, the Yankees have Aaron Judge back after a 10-day stint on the injured list. Judge carries the burden of soft career postseason stats (though he has 16 home runs in just 58 postseason games and his career playoffs OPS is just 21 points lower than Alex Bregman’s), but this is a legendary player. Judge’s career OPS stands at a whopping 1.024. That number will drop during the decline years remaining in his career, but here’s the list of all time Major Leaguers higher than 1.024: Babe Ruth, Ted Williams, Lou Gehrig, Barry Bonds, and Jimmie Foxx. Those are arguably the four greatest offensive players in MLB history, plus Foxx who probably rates in the top 20. If he holds up the rest of the season, Judge is a cinch for his third AL Most Valuable Player Award in four years.

Turn back the clock

Should they choose to check it out, the Astros can watch the Yankees’ Old-Timers' Game Saturday. Though most of the greatest of Yankee legends have died, there will still be a fabulous cast of alumni who soak up cheers during introductions, with many of them then taking part in a two or three inning game. The Yankees are by far the most storied franchise in MLB. The Astros have plenty of history and beloved players over multiple generations to copy the concept, and have their own Old-Timers' Day at Daikin Park. Would it not be a blast to see Roger Clemens pitch to Craig Biggio? Roy Oswalt to Lance Berkman? As I said during our Stone Cold ‘Stros podcast this week, I wouldn’t bet against 78 (as of Friday)-year-old Jose Cruz squaring up a ball for a line drive. Make Astros’ Old Timers’ Day happen in 2026 Jim Crane!

Angry birds

The best team in the American League is Toronto, best for now anyway. The Blue Jays have been the best over the last two months-plus. The Jays woke up May 29 at 27-28. Since then they are 41-20. Over that time frame the Astros have the third-best record in the AL behind the Jays and Red Sox. A notable part of Toronto’s success the past month is Joey Loperfido. He didn’t make the Jays’ big league squad coming out of spring training, and wasn’t called up until July 6. Over 72 at bats since getting back to “The Show” Loperfido is batting .389 with a .978 OPS. Reminder that Loperfido hit .372 over his first 43 at bats with the Astros. Full credit to Joey for a magnificent month. Still, there is no reason for the Astros to be wracked with regret for having included Loperfido in last season’s trade for Yusei Kikuchi.

For Astro-centric conversation, join Brandon Strange, Josh Jordan, and me for the Stone Cold ‘Stros podcast which drops each Monday afternoon, with an additional episode now on Thursday. Click here to catch!

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