Dwayne De Rosario’s career is over. The 36-year-old took to Instagram to announce his retirement after 18 years of professional soccer.

If we made one of those silly MLS Mount Rushmores, De Rosario would be on it. He won four MLS Cups and an MLS Most Valuable Player award. He was named an All-Star on seven occasions and to the league’s Best XI six times. His 104 goals are sixth-most in league history, and his 77 assists are good for 12th on the all-time list.

On top of just being flat out good, De Rosario was one of the more entertaining players in the league. He was capable of the magnificent long-range goal, dribbling through defenses or playing the perfect chip to send a teammate on goal. When he entered MLS in 2001, there was often little skill in matches, as teams relied in brute strength. But De Rosario was the outlier, skillful enough to stand out from the beginning, then continuing to wow fans as his career went on.

De Rosario also earned a reputation as one of MLS’s best big-game players. He scored the game-winning goal in MLS Cup during his rookie year and added another MLS Cup game-winner in 2007. In between, he established a pattern of showing up late in matches, as well as with playoff spots on the line, then throughout the postseason. He was frightening for opposing teams on the big stage.

Beyond being one of MLS’s best, De Rosario was also the best player Canada’s national team has ever head. His 22 goals are the most in the team’s history, and he was named Canadian Player of the Year four times. Fittingly, his last ever match came for his country, as he suited up for Canada on January 19, 2015 before walking off the pitch for good.

As MLS grows and improves, there will be a lot of great players to pass through the league. There are plenty of them now. But in the league’s first 20 years, when its existence was threatened at times and the league was trying to figure out what the hell it was, it had only a few stars. Landon Donovan was an obvious one, but De Rosario wasn’t far off. He was about as good as you could find in MLS, and a thrill to watch.

Now he says goodbye and takes a job as an ambassador for Maple Leaf Sports and Entertainment, who owns his hometown club, Toronto FC, but his spot in MLS history is forever. He was one of its first stars, and one of its most memorable.