Portland Timbers captain Diego Chara to play 17th season before retiring

Portland Timbers captain Diego Chara will retire from major league soccer after the 2027 season. The 40-year-old Colombian midfielder announced the decision during a press conference on Monday, Oct. 26, 2026. He plans to play through the end of the 2027 MLS Sprint Season in May, which will conclude before the league transitions to a summer-to-spring calendar.

Chara has spent 16 seasons with the Timbers. He joined the club in 2011, becoming its first designated player when the team played its inaugural MLS match. Over his tenure, he has appeared in more than 400 matches. He holds the MLS record for the most seasons played with a single team. Chara was also named an MLS All Star in 2019.

“Once you cross the line at 35 years old, you know, you start thinking about what is next,” Chara said. “For me, I think it’s the right time to do it.”

Timbers head coach Martí Cifuentes praised Chara’s long-standing commitment to the club. “Loyalty in football is not easy to achieve, and to do it for that long a time speaks by itself,” Cifuentes said. Cifuentes noted that announcing the retirement before the start of the next season gives the staff sufficient time to select a new captain. Speaking in Spanish, Cifuentes acknowledged the difficulty of replacing such an important figure in the coming months.

During Chara’s time with the Timbers, the team captured the MLS Cup title in 2015. They also won Western Conference Championship trophies in 2015, 2018, and 2021. Chara has made two appearances for the Colombian national team in international football.

Chara said he intends to learn new skills after his playing career ends. He also expressed a desire to remain involved in the sport.