It was supposed to be a dream come true.
A marriage made in soccer heaven. The hometown star returning back to his roots to help guide his new team to a level of success he had reached many times.
Sure, there were some good moments. The all-star appearances, the first goal at BMO Field when he headed the ball into the net against Dallas, but for Dwayne De Rosario it wasn't enough.
This was not how he had imagined it going.
On the field, De Rosario was able to forget the issues, play a game he loved in front of fans he adored. Sometimes the result would even go the team's way, but often it wouldn't and after the match, as he made the walk from the dressing room to his car, his mind would be cloudy and full of distractions about how the club was run.
"I'd definitely sit in my car and shake my head," he admitted in a sitdown with TSN.ca. "I know it was my hometown but I never wanted them to take that for granted and use that as leverage against me. I wasn't willing to stand for anything, it's who I am, I am very passionate and hungry for success."
As he started his third season with Toronto FC in 2011, it became very clear the two were heading in different directions.
De Rosario had hoped to be loaned to Celtic during the offseason but didn't get his wish and three months later he was packing his bags from Toronto for, what appeared, good.
It wasn't an April Fool's joke, but on April 1, 2011, De Rosario was dealt to New York Red Bulls for what can now be labeled nothing more than a bag of balls.
On a flight later that day, De Rosario thought he would never play for Toronto FC ever again but admitted he hoped to one day return when the direction of the club was different.
"I never closed the door and turned my back on that option. How it was presented to me this time was a situation I couldn't refuse, I always wanted to create special moments and have special memories with my hometown, Toronto FC, and I am looking to live those moments I envisioned and hopefully we can create those this season."
It is clear the Canadian international spent many hours dreaming of playing for his hometown club before it happened and it is also clear that a lot of those dreams didn't come true the first time around.
"I demand success, first and foremost from myself, but from my teammates and from the organization and to have a situation where we now have it demanded from the top is absolutely ideal. It's the right way and I am happy to be a part of that."
When Toronto FC kick off the new season in Seattle on Saturday afternoon, much of the attention will, rightfully so, be placed on star signings Jermain Defoe, Michael Bradley and Julio Cesar. The club has completely reinvented itself this winter and the return of De Rosario is almost an after-thought, a small scene in a blockbuster movie.
With De Rosario now 35 that is, probably, the right thing for a team who want to contend for the MLS Cup this season, but the 2011 league MVP believes he can still play a major part on and off the pitch.
He said: "I am really looking forward to this year. Jermain Defoe is a world class player, a winner, throughout the season it will be great to pick his brain and see how he runs and moves and create that relationship. Gilberto has a very bright future and so far I have enjoyed playing together with him. Anytime you have an opportunity to play alongside players of that calibre it is always fun, the most important thing is developing the understanding. So far its come along and we are excited to get it started."
De Rosario has been in MLS long enough to know that tough times will still come Toronto's way this season, even if they are successful.
He admits expectations are high but thinks the team is ready to drag themselves through the rough patches because of the personnel general manager Tim Bezbatchenko has assembled.
"Thankfully when we look at every position we have strong leaders. Julio Cesar to Steven Caldwell in central defence, Michael Bradley in the midfield and myself, Defoe up top, all strong personalities with experience, its important. All of these guys know it's a long season, they understand we haven't done anything yet, on paper it looks good but we have to continue to show that on a day-to-day basis and we have to work hard to accomplish something."
De Rosario's second stint in Toronto gives the club a player whose best days are clearly behind him but he still thinks his versatility can help head coach Ryan Nelsen in many areas throughout 2014.
"I don't have a specific favourite position. I like creating and scoring goals, up top, on the left, attacking mid, all these provide those opportunities for me but it depends on the team and its shape. Sometimes I am on the left and I don't really like it because I don't feel I get as much ball as I would like, sometimes I am in the midfield and you just defend a lot so that can be frustrating but sometimes, even, up top you can not get the balls, so it depends on the situation and the team."
Throughout his career, he admits he is constantly learning and developing more and more on the tactical side of the game: "Spatial awareness is a big part of my game, knowing when to leave it and attack it and I have been working with a lot of the forwards here about that as well. You want to continuously move but sometimes you need to stop and let the space develop and attack it at the right moments."
De Rosario will be hoping to find some of the space in behind Brad Evans and Osvaldo Alonso against the Sounders on Saturday. (You can read my piece on Toronto FC's strategy against Seattle here)
March 15 has been circled on the calendar for many Toronto FC fans because it is their first game but De Rosario cannot wait for the following week when he will get to pull on the red number 14 shirt in front of the home fans.
"Those fans are my family, the relationship with them means everything to me. Every time I step out for training or in a game with that badge it is for them. I do not just represent myself, I represent my direct family and the fans and I take a lot of pride in that. One day I want the youngsters to look at me and say I want to be like him, and because of that, I want to set as good an example as possible."
On paper, the words look cliché but you don't have to be around De Rosario for long to know just how much he truly means it and how much he loves his city and his club.
Toronto FC have lacked a lot of things in their short history. Above all else they have lacked wins, but in recent years there has been a distinct lack of people caring about this club.
Whether the signing of De Rosario the player turns out to be a success only time will tell, but to have a winner talk so passionately about this club is already a positive step before a ball has even been kicked.
Join Luke Wileman, Jason DeVos and myself in Seattle for Toronto FC's first game of the season live on TSN at 4:30pm et/1:30pm pt.