HOUSTON — The final pitch of the 2022 World Series left veteran right-hander Ryan Pressly’s hand and broke down and away from the Phillies’ Nick Castellanos.
Pressly watched as Castellanos reached out and poked a fly ball up the right-field line in foul territory. Kyle Tucker raced over, squeezed his glove around the ball and broke into a smile.
“I don’t think you can really top that,” Pressly said in a recent conversation with the Sun-Times. “It was amazing. And just seeing that ball going into Tucker’s glove, of all people, too, and being here [in the Cubs’ organization] with him, it was something that we’ll never forget, obviously.”
That World Series clinching out headlined the Astros’ tribute video for the pair of returning “Houston legends,” as the public-address announcer dubbed them. Snippets of that final play bookended the series of highlights that played Friday on the right-field video board in their honor.
“The people that were there, and all the hard work that team put in, the weight that lifted off their shoulders with the scandal and all that stuff, you could just tell that it was just a release of a lot of emotions,” Pressly recounted. “And I’m glad I got to experience that with them.”
The Astros acquired Pressly from the Twins — and promoted Tucker to the majors — the year after their 2017 World Series title, which was marred by their electronic sign-stealing scandal.
Houston made the playoffs all seven years of Pressly and Tucker’s tenures, reached the World Series three times and finally brought home the championship on the third trip.
Pressly, a two-time All-Star, was the Astros’ closer for that World Series run. But the team had him forfeit the job when Josh Hader joined in 2024. This past offseason, Pressly had to decide whether to waive his no-trade clause to approve his move to the Cubs.
“It was a tough decision to make,” Pressly said. “I always imagined my career ending with Houston. But it was just one of those things where I’ve always wanted to play for a historical team, too.”
Pressly has had one brutal outing in a Cubs uniform, when he gave up eight earned runs without recording an out — “career-worst, awful,” he said with a sigh. It cost him the closer role. But even with that outing, he has a 3.77 ERA. In his 32 other appearances, he has allowed only five runs (1.49 ERA).
“Obviously frustrating that one outing,” Pressly said. “But with the guys that we have in the bullpen and this team in general, it’s really easy to forget about because of how good these teammates are.”
Pitching coach Tommy Hottovy, who has known Pressly since they overlapped in the Red Sox’ organization 17 years ago, noted the value of Pressly’s experience in a bullpen flush with young pitchers and converted starters.
“He does such a good job of keeping the group together, talking about the right things, what we need to focus on,” Hottovy said. “So a testament to who he is. But the guy we hoped that he would be coming in, he’s fulfilled that, for sure.”
Now the Cubs are eying their first playoff berth since 2020.
“That’s what all our goals have been from the very beginning of the year, getting back to the postseason,” Pressly said. “And not just getting back to the postseason, but winning a lot of games in the postseason and trying to get back to the World Series. We have a lot of guys on this team who have done it, so we know what it takes to get there. Now it’s just putting the results on the field.”
The last time Pressly and Tucker won a World Series together, Tucker got to keep the ball from the final out. Sitting in the third-base dugout at Daikin Park on Friday, surrounded by Chicago and Houston media, Pressly was asked if he ever tried to wrest the ball back from him.
“I’m just glad he caught it, to be honest with you,” Pressly said. “So hopefully we can recreate that in Chicago.”