A little more than 17 years ago, the Raptors pulled off what remains the greatest coup in franchise history, signing star wing Vince Carter to a six-year, $90 million contract extension that would keep him in Toronto. The contract defused years of speculation that Carter would bolt to the U.S. as soon as he was able, chasing bigger shoe-contract riches in Chicago or New York and leaving NBA basketball in Canada — which was already losing the Vancouver Grizzlies — on life support.

"A lot of people made assumptions back then about what I wanted," Carter said recently. "But they had it wrong. I loved Toronto, and we had had a good year."

Indeed, the Raptors won 47 games in 2000-01 and were within a last-second Carter jumper of advancing to the conference finals in the East, losing to Philadelphia in seven games in the semifinals. The team acquired Hakeem Olajuwon that summer, and there was such excitement on the signing of Carter that the Toronto Sun headline read "IT’S V-DAY!" and the city’s mayor declared Aug. 1 to be Vince Carter Day in Toronto.

There is precedent, then, for a star player widely believed to be ready to bolt Toronto instead sticking with the city. For the Raptors, there is a brazen hope that the Carter history will repeat itself.

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On Wednesday, the Raptors went ahead with their desperation plan to acquire Spurs star Kawhi Leonard for their own All-Star, DeMar DeRozan, with Danny Green also coming to Toronto while Jakob Poeltl and a protected draft pick go to the Spurs.

Under normal circumstances, this would be a tremendous win for the Raptors. Leonard is one of the top two-way players in the game, a reliable scorer and consistent candidate for Defensive Player of the Year. He was third in MVP voting in 2016-17, averaging 25.5 points, 5.8 rebounds and 3.5 assists.

These are not normal circumstances, however. Leonard sat out 73 games plus the playoffs last year to rest a quad injury, and over the course of his absence, his relationship with the franchise fractured. Leonard and his agents let it be known that Leonard wanted to be traded to Los Angeles, and he owns some leverage there — Leonard can be a free agent next summer, and he could simply sign with the Lakers, who have cap space available, in 12 months.

And, league sources told Sporting News, Leonard has no interest in playing for the Raptors. There have been indications that he would sit out the entire season if necessary, and though that step would be drastic and unprecedented in today’s game, Toronto has forced the situation into uncharted territory by acquiring a player who has made it clear he does not want to be there.

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That’s where the hope that the Carter precedent might offer falls apart. Carter and Leonard are much different personalities, and while Leonard has always had a reputation as a quiet or even sullen guy, executives around the league have been surprised to see just how stubborn Leonard has been in all of this.

The Raptors surely are hopeful that Leonard can be sold on the team’s culture, on playing with point guard Kyle Lowry and the team’s talented young bench, on the uptempo system new coach Nick Nurse is implementing. They’re hopeful, too, that Leonard can be sold on the benefits of playing for Canada’s team.

It’s a fine line between hope and desperation, however, and it sure looks like the Raptors are on the wrong side of that line. There’s little chance that Leonard will stick with the team, if he plays at all. Toronto will have given up DeRozan and Poeltl for nothing.

It’s useful, too, to recall that the two high points of Carter’s time in Toronto might very well have been his win in the 2000 Slam Dunk Contest and the signing of his contract in the summer of 2001. Once that contract was signed, things took a sour turn for Carter and the team.

Olajuwon was never healthy, Carter struggled with injuries and the team made only one more postseason appearance (losing in the first round) before trading away Carter to the Nets in 2004. Oh, and one of the key players the team got from the Nets in that deal was Alonzo Mourning, who refused to play for Toronto and was waived after a two-month standoff.

The Raptors might hope that Leonard will take the Carter path and stick around. More likely, though, he’ll follow the Mourning path, and the Raptors will be left with little to show for this trade.