This Week in Toronto FC History: The Dwayne De Rosario Trade | OneFootball

On April 1, 2011, Toronto FC fans woke up to news they desperately hoped was an elaborate April Fool’s prank. Dwayne De Rosario, the Scarborough-born captain, hometown hero, and the face of the franchise, had been traded to the New York Red Bulls. It wasn't a joke. It was the end of an era that was as volatile as it was brilliant, sparking a season of movement that would eventually see "DeRo" make MLS history.

To understand why De Rosario coming to Toronto in 2009 was such a massive deal, you have to look at his resume. By the time he arrived at BMO Field, he was already an MLS titan:

When De Rosario was traded to TFC from Houston in early 2009, it felt like the final piece of the puzzle. For a club that had struggled since its 2007 inception, DeRo brought instant credibility. He didn't disappoint on the pitch. He scored 11 goals in his first season and 15 in his second, often carrying a struggling roster on his back. To the fans, he wasn't just a marquee player - he was one of their own—a kid from Scarborough playing in front of the South Terrace.

However, the relationship between the star and the front office soured over contract negotiations. On September 18, 2010, after scoring a goal against his former team, San Jose, De Rosario performed one of the most infamous celebrations in MLS history. He mimed signing a cheque, a clear and public message to MLSE management that he felt undervalued compared to other stars in the league and deserved a DP contract. While some fans appreciated the honesty, the "Cheque Celebration" became a symbol of the friction that eventually led to the April 1st trade for Tony Tchani, Danleigh Borman, and a draft pick.

What followed the trade was a feat of individual brilliance that we may never see again. After a brief, productive stint in New York playing alongside Thierry Henry, De Rosario was traded again in June to D.C. United. Despite playing for three different teams (Toronto, New York, and D.C.) in a single calendar year, De Rosario was unstoppable. He finished the season with 16 goals and 12 assists, leading the league in scoring and becoming the 2011 MLS MVP. It remains the only time in league history a player has won the award while playing for three different clubs in one season.

Time, as they say, heals all wounds. In 2014, De Rosario returned to Toronto FC to finish his career where it arguably mattered most. While his role was more of a veteran presence than a primary scorer, his return allowed the club and the fans to reconcile. He retired as the club’s all-time leading scorer (a record later broken by Sebastian Giovinco).

Today, the DeRo legacy is firmly cemented in the club's foundations. He serves as a community ambassador for Toronto FC, often seen at BMO Field and working with youth through his DeRo United programs. He remains the benchmark for Canadian players in MLS, proving that a local kid could not only play for TFC but dominate the entire league.

The trade on April 1, 2011, might have felt like a cruel joke at the time, but it paved the way for a historic MVP run and a legendary homecoming that solidified Dwayne De Rosario as the greatest Canadian player of his generation.