When the Cubs traded for Ryan Pressly last offseason, the move had all the makings of a savvy veteran addition. A proven postseason arm, Pressly brought with him a resume that included clutch innings with the Houston Astros during their run of American League dominance.
The hope? That he’d anchor the back end of Chicago’s bullpen and give them a reliable closer for a potential October push.
But baseball, as it often does, had other plans.
Pressly’s time in Chicago never quite clicked. He struggled to find his footing, and by the time the Cubs reached the postseason, he was no longer on the roster.
In a midseason flurry of roster moves following the trade deadline, the Cubs cut ties with the veteran right-hander. Pressly chose not to chase a comeback, announcing his retirement this offseason instead of pursuing a return to the mound - even with a potential reunion in Houston reportedly on the table.
While Cubs fans didn’t get the version of Pressly that Astros fans came to know - the one who thrived under the postseason lights - the veteran closer still made sure to tip his cap to Chicago in his farewell.
“And to the Cubs for giving me a chance to pitch for such an iconic franchise. Wrigley Field, those North Side fans … unforgettable. Thank you.”
That appreciation speaks volumes about the man, even if the numbers didn’t go his way.
Pressly’s lone season in Chicago was rocky from the start. In 44 appearances, he posted a 4.35 ERA and struck out just 15.4% of the batters he faced - a sharp decline from his days as a swing-and-miss machine in Houston.
His command wavered, and there were outings where he simply didn’t have it. A nine-run meltdown against the Giants in May and a four-run outing against the Brewers - his final appearance in a Cubs uniform - highlighted just how far off his game he was.
For the Cubs, Pressly’s short-lived tenure is less about one player and more about a broader organizational philosophy under Jed Hoyer. While the front office took on most of Pressly’s salary in that trade, it was a rare big-money bullpen swing in a system that typically prefers a patchwork approach: finding value in overlooked arms rather than investing heavily in one high-profile closer.
That strategy is on full display again this offseason. Instead of chasing another established ninth-inning guy, the Cubs spread nearly $30 million across a group of experienced relievers.
Hunter Harvey, signed for $6 million, represents the biggest bet of the bunch. He’ll be joined by Phil Maton, Hoby Milner, Jacob Webb, and returning veterans Caleb Thielbar and Colin Rea - a bullpen built more on depth than star power.
It’s a clear pivot from the Pressly experiment, and it suggests the Cubs may once again wait until the trade deadline to go searching for a true closer - if the need arises.
As for Pressly, his legacy will always be tied to Houston, where he helped close out some of the franchise’s biggest moments. His time in Chicago may not have gone as planned, but for a pitcher who gave everything he had on the mound for over a decade, he walks away with gratitude - and the respect of a game that doesn’t hand out either easily.