Since he emerged on the national team scene in the 1997 FIFA U20 World Cup in Malaysia, I've followed his career with interest. DeRo's talent was obvious to anyone who had watched him play for more than five minutes. A great dribbler of the ball with a canon for a shot and a hunger for goal, he was an extremely rare commodity amongst Canadian soccer players.
And he was a local boy.
He played briefly for the hometown side of note, back when that side of note was the Toronto Lynx. He only lasted around half a season with the Lynx, before he was snapped up by a German 2nd division side as a 19-year-old.
Things didn't work out so well, and he eventually came back to the USL, this time with the Richmond Kickers. It was there that he first displayed his ability to dominate the North American game, and after a breakout season in Virginia, he moved up to MLS with the San Jose Earthquakes.
It was De Rosario's star turn in Northern Cailfornia that really turned me into a fan of MLS. I had casually followed the league since its inception in 1996 (I can clearly remember Eddie Pope's extra time header in a torrential downpour to win the first MLS Cup), but it wasn't until I had a local hero to latch on to before my interest in the league became a vested one.
Dwayne De Rosario was that local hero.
Fast forward a few years, and TFC storms into town. The raucous crowds and fantastic feeling of supporting live, domestic top-tier football were intoxicating, but the local connection was lacking. This despite 2007's Toronto FC being far more Canadian in representation than they have been in any year since.
What was lacking was a local star.
Sure, Jimmy Brennan became beloved as the hometown captain of the side, but - God bless him - he was a journeyman midfielder-turned-fullback-turned-centre back who, by the time he made him return to the GTA after many arduous years in the second tier of England (with a brief cup of coffee in the EPL), was much more heart than ability.
So when news of DeRo finally fulfilling his destiny and coming home to star for TFC hit cyberspace, I was over the moon. I spent the day frantically keeping up with the message board chatter, madly texting everyone I knew with the good news (whether they cared or not).
De Rosario was going to lead TFC to new heights.
On the field, he did not disappoint. DeRo experienced a bit of a career rejuvenation with him hometown side, instantly becoming the attacking catalyst that TFC had so sorely lacked. There were questions about him possibly being on the decline after a couple of sublime championship years in Houston, but DeRo put those questions to rest with a 2009 season that not only set the bar for the young club in terms of goals scored, but also granted the Reds their first bit of silverware on the back of one of the most stunning individual performances in the history of Canadian club soccer.
Yet, throughout such a triumphant (personal) inaugural season, there were rumblings of discontent. Whispers of De Rosario being unhappy with his contract - one which he had signed just months before the season began - were making the rounds.
It seemed so ridiculous at the time. DeRo was living at home, making the most money he had ever made in his career, and also experiencing many more opportunities for extra income than he would have anywhere else in the world.
How could he not be happy?
Julian de Guzman's arrival at the club toward the end of 2009 as the club's first designated player seemed to be the catalyst for DeRo's financial displeasure, although the man himself was almost alarmingly quiet on the situation.
That is, until he was a guest on The Grill Room with Gareth Wheeler.
The offseason leading into 2010 was filled with more of what was sadly becoming usual turmoil for TFC. A new coach coming in, players heading out, and supporters growing increasingly restless. Throughout those winter months, what were once whispers about DeRo's monetary discontent had grown into increasingly loud chatter.
When 2010 started, the issue seemed to die down. TFC under Preki came out of the gates with a stumble, but then found their stride, all the while looking to their new captain - Dwayne De Rosario - to lead them.
And lead them he did, with goal after goal in the early going. TFC was reaching rarefied heights in MLS, with a lot of that due to the supreme scoring prowess of number 14.
Life was good for TFC, with the team cruising along in the league, and coasting through the Nutrilite Canadian Championship without giving up so much as a single goal.
Then the goals dried up for DeRo, and (is is the case), for the team as well. Players got antsy, the fans started grumbling, and yet another TFC season seemed headed for disaster.
DeRo went a long stretch without a goal, and the team suffered. Some critics pointed to his playing style as an obstacle for team success, that being that DeRo's head down-balls to the wall play disrupted any semblance of team strategy, forcing play to go through him. Thus, if DeRo stopping scoring, no one else on the team would.
After another forgettable summer, the fall months brought about a bit of a resurgence in DeRo and TFC, and the team had a faint glimmer of hope of still reaching the playoffs. They had to be pretty damned perfect down the stretch for any kind of shot, but the possibility was there.
And TFC had a new DP to help them along, the $900,000 rent-a-striker known as Mista. Surely things were once again looking up. The Spaniard's arrival pushed De Rosario down to third on TFC's wage chart, with DeRo's buddy JDG heading up the list.
DeRo seemed to have renewed sense of vigour about his game, and the goals started pouring in again. Mista, on the other hand, struggled to get into form, arriving in town out of shape and clearly rusty.
It wasn't hard to connect the two things together. Was DeRo's late season run of form an attempt by the captain to drag his team into the playoffs, much like he did on that fateful night in Montreal when Toronto won the Voyageurs Cup for the first time? Or was it more personal than that, with DeRo looking at the ineffective Mista and trying to show his bosses that he should be making that kind of dosh?
As long as the result kept coming, who cared, right?
Well, the results dried up, and it became painfully obvious that DeRo was not going to will his side into the post-season. But he would keep scoring, and in a crucial game against his old club San Jose, De Rosario scored a cracker of a goal that brought TFC back into a match in which they were being schooled.
The BMO Field crowd went crazy, sensing a faint glimmer of hope of a comeback and perhaps a miracle run that would finally see the Reds into the playoffs.
The implications of that goal were huge for the team, and everyone was so focused on the overall picture that they nearly missed it.
De Rosario, whilst celebrating an emotion-turning strike that gave his side one final longshot at turning the season around, pantomimed writing a cheque. He did this while facing the MLSE private box at the stadium, ostensibly to make sure his bosses noticed.
It was only fitting, then, that DeRo's former understudy, 27-year-old Chris Wondolowski, immediately marched down the field and put a dagger into TFC's season, while at the same time all-but-assuring San Jose's return to the playoffs as a post-expansion side.
And so it was, TFC wouldn't be advancing to the post-season, and DeRo had made his long-simmering displeasure with his contract known in a very public manner.
That brings us to this week, where it seems that DeRo had arranged a trial at Celtic without fulfilling the requirements asked of him to do so. Whether it is his agent's doing or his own, the fact remains that this current saga in the latest in what has become a disturbing trend for the captain.
Once again, supporters are talking about De Rosario and his growing discontent, at a time when they should be gearing up for the coming pre-season.
Part of that is on the TFC management, of course, who created an environment in which failure has become the norm, and the few successes are tainted with selfish outbursts from players in leadership roles.
In this writer's opinion, DeRo has flagrantly disrespected the team in his latest quest to "train" with the Glasgow giants. Sure, some could say the disrespect has been a two-way street, especially if you believe the stories about a former TFC GM's broken promises (see the Grill Room segment for more on that), but for a team that has publicly stated that it is looking for a clean break from the stench of the past four years, such disrespect from DeRo - from the captain - cannot be overlooked.
If the supporters can be so divided on the subject - and one visit to the forums will leave no doubt about that - then imagine the effect such constant distractions must have in the locker room.
It is with much sadness, then, that I humbly submit that this failed marriage between the star player and his hometown team be put to an to end.
It's such a shame, though. This could have been something very special.