Diego Chara announced today that he will be hanging up his boots at the end of the 2027 MLS Sprint Season. It will mark the end of a legendary career with the Portland Timbers that will last 17 years, and the end of the road for the last remaining original MLS Portland Timber.
Diego Chara announces that he will be retiring at the end of the sprint season in 2027. #RCTID
— Alex Barnes (@alex-barnes.bsky.social) 2026-10-26T19:04:01.322Z
When the team announced the Monday press conference with the club legend last week fans understandably started to fear the worst. The 40-year-old stalwart had hinted in the past that his time playing soccer was going to come to end soon. But as Diego himself shared, we will be able to enjoy Chara in a Timbers shirt for one last ride.
"Being with the team for this long, being one of the original Timbers, I think this is the best way to finish my career with the Timbers," Chara shared at the press conference. But he did recognize one of the harsh realities of playing soccer at such a high level. "Once you cross the line at 35 years old, you start thinking about what's next. At some point, your body says 'it's enough', and I’m getting to that moment."
Diego Chara's accolades with the Portland Timbers are simply too numerous to fully list out. He is the club leader in appearances, starts, and was a key piece in helping Portland lift the 2015, 2018, and 2021 Western Conference Championship trophy, the 2020 MLS Is Back trophy, and of course the 2015 MLS Cup.
This season he also became the MLS leader in yellow cards shown – a stat that by his own admission he may be the proudest of. "I think the yellow cards is my favorite record. And the fans really like it too," Diego shared.
The Sprint season will be an abbreviated campaign that will bridge the gap between the end of the 2026 MLS season and the calendar flip in summer 2027. It will run from February to April, with the playoffs and MLS Cup in May. The league will then have an offseason before starting the new calendar in July.
Much more will be written in the coming months about the icon that is Diego Chara and what he means for the Portland Timbers. And while the inevitable end that we knew was coming now has a date, it's not here just yet. We are blessed to have one more campaign to enjoy The Godfather and celebrate his impact on Soccer City, USA. We all should appreciate the time while we can.
The Timbers are next in action on Wednesday October 28, when they travel to take on newly minted U.S. Open Cup Champions St. Louis City at Energizer Park. Kickoff is set for 5:30 PM PT.
