PORTLAND, Ore. – Over the last month, Portland Timbers midfielder Jack Jewsbury has felt a mix of conflicting emotions.

Against the Colorado Rapids on October 1, Jewsbury, who has been with the Timbers organization since its inaugural MLS season in 2011, earned his 350th career MLS appearance, becoming only the 10th player in league history to reach that milestone.

This milestone came only two weeks after Jewsbury first announced that he would retire at the end of the 2016 season following a 14-year career that included time in Kansas City and Portland.

This Sunday, when the Timbers host the Colorado Rapids at Providence Park (2pm PT, ESPN), Jewsbury will be recognized for his distinguished career.

“Looking back on the early years, I think it was a stretch to say that I...would have played 350 games,” Jewsbury said recently. “I was fighting year after year for a contract and trying to get playing time as a young player...The first few years, not only did I not know if I was going to have a contract, but we didn't know if MLS was going to be around the next year.”

In Portland, Jewsbury found a home that welcomed him and his family with open arms but also presented one of the most vibrant markets in Major League Soccer. Before his arrival, however, the Missouri native knew little about the Rose City.

“'You're going to be blown away by the fans,'” Jewsbury remembered his friend Ryan Pore – who was on the inaugural MLS Timbers 2011 roster and had played with Jewsbury in Kansas City – telling him before the move.

For a player who had spent much of the first half of his career playing in cavernous Arrowhead Stadium, the size of the Timbers crowd and the noise of the Timbers Army exceeded his modest expectations.

“When we stepped out for the starting lineups for the Chicago game in the season home opener [in 2011], it absolutely blew me away with the support we were going to have and you could just tell that we would have something special here for a long time,” he said.

In his entire 14-year MLS career, Jewsbury has won both a U.S. Open Cup title (with Kansas City in 2004) and an MLS Cup championship (with Portland in 2015). He's logged over 25,000 minutes on the field, was named an MLS All-Star in 2011, scored 28 goals from a variety of positions to go along with 37 assists, and never once received a red card.

Calling time on such an accomplished career has been difficult for the fierce competitor.

“I think for me at my age, sometimes it becomes more about being able to leave while you're still able to contribute on the field instead of them trying to push you out the door,” he said of his retirement announcement. “You kind of do it on your own terms and I think for me at the time it made sense.”

The difficulty of that decision was visibly manifest in Jewsbury's announcement at the 2016 Stand Together Banquet. Shortly after telling the crowd that he would be retiring at the end of the season, Jewsbury paused to collect himself. In that brief instant, the crowd broke into applause as a number of people began chanting, “One more year! One more year!”

For Jewsbury, though, the finality of his decision didn't set in until he finally sat down with Timbers general manager Gavin Wilkinson and head coach Caleb Porter for a conversation he described as “surreal.”

“It's one thing to talk to your family and friends about [retirement], but to actually hear it come out of your mouth and knowing it is actually kind of sealing the deal, it's different,” he said.

So far, Jewsbury has been quiet about his future plans though he's interested in the business side of the sport and maintains that the Portland community has been deeply important to both him and his family.

“The way the city, the club, [and my] teammates have embraced me and my family has made this place truly special and it's a place that definitely feels like home for us,” he said.