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By the start of the 21st century, the Toronto Raptors had grown into an NBA phenomenon. With burgeoning stars on the rise in Vince Carter and Tracy McGrady, Toronto became the talk of the NBA. After one playoff appearance, McGrady departed in free agency, leaving Carter as a solo star. With McGrady a Hall of Famer and Carter a shoo-in, one has to wonder what the duo could've accomplished together had McGrady stayed.

Ushering In A New Era

After a somewhat respectable 30-52 finish in their second season as an NBA franchise, the Toronto Raptors seemed to be on the right path. Draft picks Damon Stoudamire and Marcus Camby had shown flashes of brilliance, and with another lottery pick in the 1997 NBA draft on the way, the Raptors were compiling a youthful group of talent.

Toronto selected high schooler Tracy McGrady from Mount Zion Christian Academy with the ninth overall pick in 1997. Then-Raptors executive vice president Isiah Thomas was the mastermind behind the pick after team scout Craig Neal discovered McGrady early on. Armed with a 7'2" wingspan, an athletic frame and the ability to handle the ball, defend and shoot, McGrady was an intriguing prospect.

"I lived in the same condominium as Isiah," then-Raptors guard Doug Christie told Bleacher Report. "He called me up to his place." Thomas showed Christie tape of McGrady in high school. After a couple of minutes, Christie stared at Thomas and said, "You can get that kid?" After Thomas replied, "yes," Christie said, "If I was you, I'd get that kid because he just jumped off the screen."

Despite the addition of McGrady, the Raptors lost 19 of their first 20 games of the 1997-98 season, sapping much of the promise and hope from the previous year. Thomas abruptly resigned after a bid to purchase a controlling interest in the team failed. Stoudamire soon followed Thomas out of the door, as the 5'10" point guard was traded to the Portland Trail Blazers after indicating he would not re-sign with Toronto after the season. Coach Darrell Walker also departed, leaving assistant coach Butch Carter to take over on an interim basis.

With new owners, new management, a new coach and new players at midseason, Toronto was starting all over again. "I think the best word I can use at that time was dysfunctional," former Raptors forward John Thomas said. "We were playing in the Skydome—even our home locker room [didn't have] a sense of a true home locker room. [There were] a bunch of players that didn't necessarily understand how to vibe together."

The one major beneficiary of the massive shake-up was McGrady, although things didn't necessarily start out well. McGrady found himself in Walker's doghouse throughout his rookie season, and inconsistent playing time left the rookie at wit's end. He nearly went public to the media about disagreements with Walker, but after a conversation with Christie, he decided not to.

"Not that there isn't times that you do those sort of things and they happen, but you're a young player," Christie recalled telling McGrady. "You haven't really even played yet. It's not the time to go and just bust out and say to have this argument with the coach. You keep your head down and keep working hard. You have the talent. You should be playing. You're not, but you have to pay your dues."

Carter looked to give McGrady a fresh start with Toronto playing out a lost season. "Me having a chance to coach Tracy was a blessing for both of us," Carter said. He looked to manage McGrady's minutes so he would be able to gain experience without putting an immense amount of physical stress on his body. "The most important thing is that the first two years is letting a young player's body harden naturally," Carter said.

After the Raptors finished with the second-worst record in the NBA, they ended up with the fourth pick in the 1998 NBA draft. They had their eyes on University of North Carolina teammates Vince Carter and Antawn Jamison. "North Carolina did not want Antawn Jamison and Vince to come and work out for us," Carter said. "Antawn Jamison never did, [but] we were able to convince Vince's agent at the time to give us a chance."

The Raptors were extremely impressed. Carter (no relation to Butch) wowed the team with his freakish athleticism, and his jump shot was better than advertised. They kept their interest in Carter a secret as the Golden State Warriors, who had the No. 5 pick, wildly pursued Jamison.

"Golden State wanted to draft Antawn Jamison, and they were afraid that we knew that information and felt that we might draft Antawn Jamison ahead of them and flip-flop with somebody later in the draft like Dallas in particular," Raptors general manager Glen Grunwald told B/R. "I think that was their main concern. So they wanted to make sure that they got the player that they wanted. In order to do that, we agreed to sort of flip-flop draft picks and got a little [cash] from doing that."

The selection of Carter paired an interesting duo together. Carter and McGrady were both from the Florida area and knew of each other from playing AAU ball when they were in high school. The two also discovered that they were distant cousins.

The Rise

Over the next two seasons, Toronto underwent a massive rebuild that saw numerous veterans join the club. With Carter and McGrady on the roster, Butch Carter and Grunwald had a plan for rebuilding around their two pillars.

"[The previous season] Toronto was extremely deficient in defensive field-goal percentage, and if you lower your defensive field-goal percentage, you have to rebound those missed shots," said Carter, who was promoted to head coach. "I had built an analytical model to determine the players in the NBA on winning teams that give the largest amount of energy that was measurable in areas that would make [a team] a success."

Through that analytical model, the Raptors targeted elite offensive rebounders Charles Oakley, Kevin Willis, Antonio Davis and Dale Davis. In a one-year span, Toronto acquired three of the four, headlined by Oakley.

"Well, my goal was when I got there, I told them I'm going to bring a whole different attitude to Toronto that they never saw before," Oakley said. "It was a hockey town, so I told them every year the team will get better."

Other veterans like Muggsy Bogues and Dell Curry joined on as well. By the 1999-2000 campaign, Toronto had five players over the age of 30 who played 1,000 minutes or more. The previous season they had none.

"I think teams need a veteran presence to be successful in the NBA," Grunwald said. "I think that's forever true and still true to this day. We were trying to be successful. We had some issues in terms of retaining players in Toronto, and we wanted to make sure that Vince could be retained. And one of the ways, or factors, of that was the team needed to be successful."

As the veterans arrived, they all accepted roles as supporting cast members, allowing McGrady and Carter to incubate. During the lockout-shortened 1998-99 season, Toronto nearly made the playoffs, but a late-season swoon caused the team to fall just four games short of the postseason. Carter wowed with a yearlong dunk showcase that ended with his being named the 1999 Rookie of the Year. McGrady, who was building a highlight reel of his own, took a modest step forward in his sophomore campaign.

Surrounding Carter and McGrady was simple. Oakley, Willis and Davis played the roles of veterans who provided a physical presence in the paint. Christie was a defensive ace on the perimeter. Curry and Dee Brown provided the three-point shooting necessary to space the floor when Carter and McGrady faced double-teams.

Bogues was a steady presence at point guard, and youngsters Michael Stewart, John Thomas and Alvin Williams filled out the main roster. "Players had roles to play. It's like a music group," Oakley said. "We were like Earth, Wind & Fire. Vince and Tracy were [bassist] Verdine White and [lead singer] Philip Bailey."

When Bogues arrived in Toronto, he had an instant comparison for what he saw in McGrady and Carter. "Once we got there, we saw the ability that Tracy McGrady had and what Vince was doing and continued to do," Bogues said. "They were the two closest [to] Michael [Jordan] and [Scottie] Pippen in terms of physicality, in terms of their game and what they brought to the game."

Indeed, everyone saw what the Raptors had in their two young stars.

"The veteran guys made a pact that we're going to do all the dirty work and everything we need to do to protect these young guys because they're so talented," Brown said.

But with veteran status also came the leeway to establish how the team operated. "We had to make a rule in practice that you couldn't dunk, because [Vince and Tracy] would try some crazy stuff in practice,” Brown said. "Now you messing with the wrong people because if you dunk on Charles Oakley, Antonio Davis and Kevin Willis, you might get hurt."

They also established a culture for the team. "We were pretty strong in our leadership in terms of what we expected," Bogues said. "We wanted to make sure that they understood [professionalism] not just on the court but off the court. How to come to the game properly dressed, how we unified with one another on what we was capable of doing. We knew we had a lot of talent, especially young talent."

The team eventually saw Carter settle into the role of superhero and McGrady as his sidekick. The cousins were close and spent much of their time together, but they were also extremely competitive. "They tried to outdo each other," said Brown. "If Vince dunked on somebody during the game, Tracy's like, 'OK, I got one better than you.' Then he would try to dunk on somebody during the game."

Toronto was a surprise story during the 1999-2000 season. The Raptors finished the year with a 45-37 record and qualified for the postseason for the first time in the franchise's then-five-year history. Carter continued to widen the eyes of fans and his NBA peers alike with a wide array of gravity-defying dunks. Tracy was no slouch, either.

The highlight of the season may have been the 2000 NBA Slam Dunk Contest, one which saw both cousins enter. Carter was the eventual winner, putting on one of the best dunk contest performances ever after scoring a perfect 50 on every dunk he attempted. McGrady, finishing in third place, also held his own.

Carter immediately drew comparisons to Michael Jordan and became the talk of the NBA. A 51-point outburst on national television soon served a coming-out party for Carter's rising star. "There was days where Vince had to walk around with a hood on and his face covered because it got to the point where he was the biggest celebrity in Toronto for sure," Stewart said.

T-Mac's Pending Free Agency

Throughout the course of the 1999-2000 season, McGrady's looming free agency hovered over the Raptors. Before the season, the Raptors offered McGrady a max contract, but he declined, according to Grunwald. His game, though, took off, as he posted career numbers (15.4 points, 6.3 boards, 3.3 assists, 1.1 steals and 1.9 blocks per game) across the board.

While Toronto entertained the possibility of trading McGrady, it couldn't find any takers—not because of a lack of interest, but because of McGrady's expiring contract. "Tracy was unable to say whether or not he was unable to re-sign with us or whether or not he wanted to go to a particular team," said Grunwald. "When we were talking about trade opportunities for him during that third season, we weren't able to convince any other team that he would re-sign with them at the end of that season. That really depressed his market value."

Toronto was the victim of an era where numerous players left the team that drafted them due to the absence of restricted free agency in the collective bargaining agreement. As Toronto's season ended after a tight 3-0 series sweep to the New York Knicks, the Raptors would have their hands full as numerous teams would pursue McGrady in free agency.

The Decision and Fallout

On a cold, dark and snowy night in 1997, Orlando Magic general manager John Gabriel showed up in North Carolina on a scouting trip as he visited Mount Zion Christian Academy. "I called [McGrady's] coach [Joel Hopkins] and told him I was on my way," Gabriel said. The court was on the third floor of the school. Since it was late, the school was empty and Gabriel could not find anyone to open the door for him.

"I started throwing snowballs at a window to attract someone's attention, and someone came down and opened the door," said Gabriel. After arriving, Gabriel was informed by Hopkins that practice was nearly over and that he had to run and see a game involving the University of North Carolina. Feeling disheartened for missing an opportunity to see McGrady play live, Gabriel was prepared to leave when he discovered the coach was making the team scrimmage for two games as punishment for missing free throws.

"Tracy was playing very much the way he ended up playing as a pro, and when he couldn't get to the basket, he could pull up from three and shoot the long-range ball," said Gabriel. "He was incredibly impressive, and I guess you could say very Pippen-ish in his length and ability to handle the ball. Long strides, rebound, finish at the rim."

Though Gabriel didn't draft McGrady, he would get a chance to pursue the phenom in free agency. After pulling off a rebuild in 1999 that saw Orlando ship Penny Hardaway, Nick Anderson, Horace Grant and Isaac Austin for spare parts, the Magic set themselves up for a spending spree in the summer of 2000.

First on the list was the duo of Tim Duncan and Grant Hill. Hill was a near guarantee, and Duncan had serious interest in a partnership with Hill. McGrady was also on Orlando's radar, and Gabriel felt there was a legitimate chance of signing all three stars.

"I remember walking into Scott [Herring]'s office, our assistant GM, and we were still in the process of creating room and there was a point in time where I think that I remember us looking at each other and our eyes lighting up saying, 'You know we could probably get all three,'" Gabriel said. "I guess potentially [they] could've taken a little discount, each of the three to come together, which would've been one of the first discount of players taking a little less for the betterment of winning."

To their dismay, Duncan was soon convinced by the Spurs to return to San Antonio. That bumped McGrady up to a major priority. McGrady initially agreed to a deal, but due to a moratorium period of nearly 30 days, Orlando couldn't officially sign him. It faced threats from Chicago and Miami, both of which pursued McGrady vigorously.

"Chicago flew in on their jet to meet with him because, at that time, I think the rules were established that you couldn't fly a player on your team plane, so what teams did was fly to him," Gabriel said.

"And then on one night, I was at a dinner affair and a limo driver that was working for another company recognized me and said, 'Gabe, you better get to the airport because I just heard through the grapevine that the Miami Heat are on their way on their 727'—or whatever their jet was. And they met him out on the tarmac. I don't know if it was Pat [Riley] or not." Gabriel waited at the terminal just to make sure that McGrady still prioritized Orlando. McGrady said yes.

At the heart of McGrady's decision was the opportunity to go home. McGrady is originally from Auburndale, Florida, which is just about an hour drive from Orlando. Though he gave serious consideration to the Bulls, he couldn't pass up on a homecoming. "In the end, I think the opportunity for him to go home compelled him or drove him to go to Orlando, and it was also going to be the opportunity to play with Grant Hill," McGrady’s agent, Arn Tellem, said. "[But] I think what really drove it most was the opportunity to go home and be close to home."

What Ifs

After departing for Orlando, McGrady was expected to form a dynamic duo with Grant Hill, but it would never work out that way as Hill would miss 281 out of a possible 328 games over the next four seasons due to multiple ankle injuries.

McGrady flourished under the added pressure, leading the NBA in scoring twice during that time and creating numerous highlights as he stepped out of Carter's shadow. However, McGrady's one-man show never fared as well in the standings, as Orlando could never get past the first round of the playoffs. After Orlando went 21-61 during the 2003-04 season, McGrady became frustrated with the direction of the franchise. Soon after telling the franchise that he would opt out of his contract when eligible to do so in 2005, he was pre-emptively traded to the Houston Rockets in the summer of 2004.

Meanwhile, Carter remained an offensive force as the Raptors won 47 games during the 2000-01 season and fell just a shot attempt short of a conference finals appearance. But injuries began to take their toll, and as the veteran core continued to age, the Raptors found themselves out of playoff contention. The team traded Carter to the New Jersey Nets in 2004 after he demanded to be moved early in the 2004-05 season.

If McGrady had stayed in Toronto, the duo had a clear window of contention. While the Los Angeles Lakers were dominating their way to a three-peat in the early 2000s, the Eastern Conference featured aging contenders in the Indiana Pacers, New York Knicks and Miami Heat. From 2001-04, only two teams (the 2000-01 Philadelphia 76ers and 2003-04 Pacers) won more than 55 games.

With a developing Carter and McGrady reaching their primes, it's easy to believe that Toronto would have found themselves in a couple of conference finals appearances. "I think by T-Mac leaving, Vince got to do more, but when you have a one-two punch like that, they probably could've been one of the better one-two punches of all time," Oakley said. "Both of them athletic. Both of them could score, so it would've been nice to see them play together 10 years."

Add in a quality supporting cast and you can imagine an Eastern Conference dynasty in the making. “In hindsight, looking back, obviously I wish I had stayed in Toronto," McGrady said in a 2013 interview with the Toronto Star. "There's no doubt we could have contended for a championship. I think about that often. But if 'if' was a fifth, you know?"

Vince Carter told ThePostGame this year:

"We've talked about it plenty of times. [McGrady] says, 'I guess, maybe I should've explored it,' but at the same time, he was looking for his opportunity to be the superstar that he became. That's what he wanted.

"It's funny how back then, guys were leaving teams to go and start their own team instead of the other way around. That's just the way it was back then, and he wanted that opportunity to be the exclusive go-to guy and you can't knock him for that. ... He was taking abuse—verbal abuse—from a lot of people for doing that. And I think now, if a player were to do that, they would be respected for it. It's weird how time changes."

Toronto was just one stop in McGrady's career, and there are still many questions. "To me, the real 'what if' is 'What if [Tracy] and Yao [Ming] would've stayed healthy together,'" Tellem said of the 2005 through 2010 seasons. "I think that's the 'what if,' and I believe they had the potential to win championships together if their health had lined up.”

Tellem's point flows into a larger discussion. There are numerous 'what ifs' in McGrady and Carter's respective careers. What if Grant Hill was healthy in Orlando? What if Tim Duncan chose to sign with Orlando? What if Tracy never had his career cut short by microfracture surgery? What if Vince Carter didn't suffer knee injuries in Toronto?

They're all questions that NBA fans can fantasize about, but Vince and Tracy together for their respective primes may be the most intriguing. At one point, two future Hall of Famers—and cousins—played together in their early 20s and invigorated a dormant franchise in another country. That's a story for the ages.