Diego Chara remembers training at a public field in Beaverton during his first year with the Portland Timbers in 2011.
The training facility where the club now practices had yet to be built. So, Chara and the rest of the Timbers would meet up at then-Jeld-Wen Field on weekday mornings and pack into several vans to make the drive out to Beaverton together.
“It’s totally different now,” Chara said.
Chara is now the longest tenured player on Portland’s roster following the departure of goalkeeper Jake Gleeson at the end of the 2018 season. Diego Valeri, who didn’t arrive until 2013, is the second-longest tenured player at the club.
During his time in Portland, Chara has experienced the highs and lows that come with playing for a young and ambitious MLS organization. The Colombian midfielder is the only player on the club’s roster that remembers the growing pains of being part of an MLS expansion team in 2011 and what it felt like for the club to hit rock bottom in 2012. That perspective has only made him prouder of the success that the Timbers have enjoyed since 2013. He has competed in four different postseason runs with the Timbers over the last six years, helping to lead the club to its first MLS Cup title in 2015.
Chara’s life off the field has also changed drastically during his eight seasons with the club. His oldest daughter, Mariajose, has grown up in Portland, while his other three children have all been born in the United States. Chara and his wife, Sindy, welcomed twin boys, Diego and Angel, last year.
“I’m proud because we grew together, side-by-side,” said Chara about the Timbers. “I feel happy for that. I think I’ve tried to continue to do my role. I think it’s a great feeling to be here.”
Chara joined Portland as the club’s first Designated Player in April 2011. Shortly after stepping off a plane from Colombia, he was thrown into his first game as a Timber, coming on as a second half substitute against the LA Galaxy on April 23, 2011.
It was the beginning of a storied career.
The 32-year-old central midfielder has made 232 appearances for the Timbers over eight seasons with the club and has developed into arguably Portland’s most important player. The Timbers have not won in their last 22 MLS games without Chara, dating back to July 2015. Chara, who has never made an MLS All-Star team, has often been called one of the most underrated players in MLS.
As Chara approaches his 33rd birthday, he still remains an indispensable figure within the club. While Timbers General Manager and President of Soccer Gavin Wilkinson said that the Timbers always have to be thinking about their succession plans, he said that Chara is not a player that can be easily replaced.
“We talk about succession planning, we believe in it, we do it, but Diego might just be a player that we may have to just ride for as long as we can and understand that we’ll have to restructure things in the midfield (when he leaves),” Wilkinson said. “He’s that good and that important to the club.”
Chara is now preparing for his ninth season with the Timbers. Even after a successful career in Portland, he still feels as if he has a lot more to give to the club. At 32, he hasn’t shown any signs of slowing down. He hopes to continue to be a leader on the field for the Timbers and help the club continue to grow and strive for success.
“I think nothing has changed,” Chara said. “I have the same energy and the same goals.”
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