I remember 2001 like it was yesterday. I was working at TSN back then (behind-the-scenes in television rather than for their nascent website) and as the Raptors stellar Playoff run wore down there was as great a sense of panic as there was of jubilation about the summer that lay ahead.

On the plus side you had a team that had just completed their greatest-ever regular season with 47-wins and was embroiled in a tense back-and-forth Conference Semi-Finals series with the Philadelphia 76ers. The Raptors were headlined by one of the biggest stars in the NBA in Vince Carter and looked like an emerging Eastern Conference power based on their 2000-01 results.

There were rifts, however. The Raptors (and their fans) were still very much haunted by Tracy McGrady’s abandonment the summer before, when he spurned Toronto’s free agency overtures and signed a six-year, $67.5-million deal with the Orlando Magic. In 2001 Carter was eligible for a contract extension but no one was sure if he’d be willing to sign on for an elongated tour of duty in Toronto after his cousin’s recent departure. Plus, the team’s success had made Toronto’s bevy of free agents (headlined by Antonio Davis, Alvin Williams and Jerome Williams) attractive to opposing teams and many thought the roster was about to be decimated despite the team’s season-long success.

In the end, of course, Carter opted to stay, and general manager Glen Grunwald offered lucrative (some would argue recklessly so) new deals to Davis and the Williamses to avoid losing them and having to reconstruct the team’s rotation. Those new deals, however, handcuffed the Raptors financially, prevented them from having the flexibility needed to pivot when the roster proved vulnerable and ultimately led to enough fruitless years that Carter would demand a trade after playing out only two years of his six-year extension.

Hindsight proved cruel for Grunwald and his decisions that summer. In addition to the expensive new contracts to his existing players, he also signed a washed-up Hakeem Olajuwon to a three-year, $18-million contract that wound up buying the team just one year of inconsistent service before Olajuwon retired in 2002. Try as he might, Grunwald was never able to dig himself out of the financial hole that he created in the summer of 2001 and he was eventually relieved of his duties in 2004 after three seasons without a Playoff appearance.

Like I said, though, I remember that summer clearly, and how that summer is frequently remembered is not how that summer played out. Or at least the cold numbers don’t do justice to the big picture that was in play in 2001.

Remember, it was in March of 2001 that it was announced that the Vancouver Grizzlies would be relocated to Memphis, Tennessee. The Raptors success in the 2000-01 season was just three years removed from what to this day stands as the most desultory in team history, the 16-66 campaign of 1997-98 (the year that Damon Stoudamire demanded a trade out of town and the club brought in their third head coach in three seasons). Plus there was the aforementioned McGrady situation and Charles Oakley’s rumoured trade demand. The team had seen some very dark times prior to their successes that season and there was a strong belief that the Raptors could not afford to lose the momentum of the 2000-01 season. They could not afford to lose another superstar, they could not afford to backslide into irrelevance, they had to capitalize on their good fortune and keep the good times rolling lest they slide back into the dark times and all of the uncertainty that comes with such a fate.

Many thought that a return to the dark times was inevitable. Davis and Alvin Williams were strong candidates to be poached away from Toronto and the assumption was that if that happened Carter would be a lock to follow them out the door. Davis, in particular, was fervently pursued by the Orlando Magic and never seemed all that interested in staying in Toronto, while Williams was strongly courted by Chicago and Atlanta. So while the Raptors may have overpaid to re-sign them (Davis’ deal with worth $64-million over five years, Williams received seven-year, $42-million contract and Jerome Williams signed for seven years at $40.8-million), it wasn’t like there weren’t other suitors vying for their services and at the time for the Raptors to retain their own they had to overpay to make it happen.

I remember that there was legitimate shock when Davis and Alvin Williams decided to re-up in Toronto. It was a little bit of a validation moment, which was of course exaggerated when Carter and Olajuwon joined them later that summer. Toronto was becoming a real NBA team, an actual player on the NBA landscape. The New York Times called them one of the favourites to win the East. That was a big deal back in 2001, one that maybe outweighed danger inherent locking up so much long-term money in such a small core of players.

So why is all of this relevant in the summer of 2014, thirteen years after the fact and a generation removed from that summer? Because circumstances have put the Raptors back in the shoes of their 2001 counterparts, and Masai Ujiri is going to have to navigate many of the same waters that Grunwald did while hopefully improving upon his outcome.

In an attempt to create as much financial flexibility as possible in his first year on the job, Ujiri assembled a robust collection of expiring contracts that was supposed to give the Raptors a boatload of cap room to play with this summer and beyond. In an unexpected turn of events, however, that collection of players turned out to be a pretty good ball club. In these Playoffs, in fact, the three players with the highest PER are Patrick Patterson (18.9), Greivis Vasquez (18.7) and Kyle Lowry (16.0) — all free agents this summer. Plus, the next guy on the list, Amir Johnson (15.9), has only a partially-guaranteed contract for next season.

This puts Ujiri into a tight corner. Does he work to keep some the most productive elements of his roster together because they created such unexpected success this season, or does he roll the dice and only bring back a select few and risk upsetting the apple cart? Keep in mind that I am operating under the presumption that at least one player of relevance will probably also be traded at some point this off-season, if only because this team is ‘good’ and not ‘great’ and further upgrades need to occur if they want to take the next step forward and with so many free agents in play there aren’t a lot of meaningful contracts left for the team to deal.

The argument for keeping the band together is obvious: this team has just completed their most successful regular season ever and is in the midst of pushing the Brooklyn Nets harder than most expected (regardless of the series outcome). Plus, guys like Patterson, Vasquez and Johnson are just good players and great fits for this team’s core, not to mention Lowry as an absolutely indispensable asset that the club now simply cannot afford to lose.

The opposing argument is that, while good, this team still has a long way to go and they need to preserve a certain amount of flexibility because they’ll still need a massive talent infusion if they want to play at the level of the NBA’s best. Like in 2001, there are sentimental reasons for wanting to keep this train rolling along, but are those reasons the most pragmatic given the longterm goals and aspirations for this club?

Of course, this isn’t 2001 and the parallels between then and now are not endless. There isn’t the same stigma against Toronto as a free agent destination as there was back then. Sure, one could still be said to exist, but that concession has to come with caveat that that stigma is only a fraction of what it once was. Secondly, contracts are not as long or expensive as they once were, especially for role players, so there is still a chance the Raptors could afford to mostly keep this group together while still maintaining enough flexibility to improve as needed.

Still, there is a fascinating debate at the heart of this issue that will be addressed by Ujiri one way or another this summer. Does he believe that there is merit in maintaining a certain level of continuity, given the successes that the club has achieved this season, or does he buy into the notion that the team hasn’t actually achieved anything substantiative yet and nothing about this team’s current assemblage should be seen as precious. I would consider that to be an overly cynical view to take in light of how little success the Raptors have seen in their nineteen-season history, but if an NBA title is all that this club can measure success by then perhaps such cynicism is validated.

In his three years with Denver, Ujiri was not noted for his sentimentality. He would gush about a player one day and trade him the next. However, Denver did not possess the same psychic scars as Toronto. Breaking up this team, or allowing it to be broken up, will come with the expectation that much better times are on the horizon. Internally there may be the belief that the Raptors haven’t achieved anything yet, but there are thousands of fans who stand outside in the cold to watch their team play from outside their arena that would disagree that nothing has been achieved. They may not be where they want the club to be yet, but they’ve struck a chord with the city and that means something, too.

In 2001, that meant that all stops had to be pulled out to keep the team together. It will be interesting to see what it means in the summer of 2014.

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