Scottie Pippen and Vince Carter pairing would've led Toronto Raptors to 1999 Finals Run

In the 1997 draft, Jerry Krause and the Toronto Raptors were ready to pull a trade for a Scottie Pippen-Tracy McGrady. What would've happened if that trade did materialize?

Lazy loading placeholder

CLEVELAND, OH - JUNE 07: NBA player Vince Carter looks on before Game 3 of the 2017 NBA Finals between the Golden State Warriors and the Cleveland Cavaliers at Quicken Loans Arena on June 7, 2017 in Cleveland, Ohio. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ronald Martinez/Getty Images)

In June 1997, fresh off a second consecutive championship, Jerry Krause, who was all about rebuilding his Chicago Bulls team, had an offer ready for Tracy McGrady and the Toronto Raptors. According to Tracy McGrady on the Jump, Krause was more than interested in a McGrady for Pippen trade to happen. McGrady even said that he flew to Chicago right before the draft to do a physical and had discussions with Jerry Krause about the possibility of the move.

Of course, the deal never materialized and Michael Jordan refused any move that saw Pippen leaving. But let’s say that the deal was agreed upon, and there you have it, Scottie Pippen is a Toronto Raptor. Well, how would have this changed the career trajectory of a young Vince Carter and Toronto Raptors team that was still trying to make a mark on the NBA?

Well, let’s find out.

(This is ALL hypothetical by the way)

Lazy loading placeholder

SALT LAKE CITY, UNITED STATES: Scottie Pippen of the Chicago Bulls answer questions 10 June at a press conference before afternoon workouts in preparation for game five of the 1997 NBA Finals against the Utah Jazz to be held at the Delta Center in Salt Lake City, Utah 11 June. The series is tied at 2-2. (ELECTRONIC IMAGE) AFP PHOTO/JEFF HAYNES (Photo credit should read JEFF HAYNES/AFP via Getty Images)

June 25, 1997: The Tracy McGrady for Scottie Pippen trade happens

Pippen gets his surgery early and is ready to join the other “Star” Damon Stoudamire. They finish last place in the Eastern Conference with Pippen battling injuries the whole season. Damon Stoudamire, 1995-1996 Rookie of the year, was reportedly unhappy throughout the season and was demanding a trade. The Raptors weren’t fully ready yet to pull the plug, and they truly believed that with a healthy Scottie Pippen and a top draft pick that they could form a winning team. Pippen agreed to play one more year and wanted to sign elsewhere no matter what happens in the upcoming season (kind of like Kawhi Leonard).

Meanwhile, the Chicago Bulls don’t end up 3 peating, leaving Michael Jordan’s finals record at 5-1. McGrady had a decent season, but by no means does he replace Scottie Pippen’s presence. This means Karl Malone delivers on Sunday and the Utah Jazz claim their first championship ever

3 of 5
Lazy loading placeholder

24 Jun 1998: A picture of Vince Carter (L) being traded to the Toronto Rapters and Antawn Jamison (R) being traded to the Golden State Warriors during the NBA Draft at the General Motors Palace in Vancouver, Canada. FOR EDITORIAL USE ONLY

June 24, 1998: Toronto Raptors trade Antawn Jamison for Vince Carter in the 1998 draft

With the 1998-1999 lockout season going on, there was a lot of time for Scottie Pippen, Damon Stoudamire and Vince Carter to train together. Like Jordan instilled a winning mentality on Pippen, Pippen decided to do the same with Stoudamire and Carter. Vince Carter, who was never ever known for his defense suddenly becomes a pretty good defensive player --- he always had the athletic ability to be a great defender. And Scottie Pippen looks healthier than ever.

The Toronto Raptors would have a blistering start to the season and quickly became fan favorites. Not many teams had a 5 feet 10 point guard, a generational dunker and the best defender ever on the same team. They also had rising star Marcus Camby who led the league in blocks the previous season --- who wouldn’t have been traded because Pippen valued Camby highly.

The Raptors have exceeded expectations and have made history-making the playoffs for the first time ever. They end the season at 30-20, which is good enough for the fifth seed. They face the Atlanta Hawks who were led by Dikembe Mutombo.

4 of 5
Lazy loading placeholder

A nearly defeated New York Knicks team meets during a time-out late in the fourth quarter of the fourth game of their Eastern Conference first round play-off series against the Miami Heat at Madison Square Garden in New York 14 May, 1999. From L-R: Patrick Ewing, Allan Houston, Latrell Sprewell (#8), Larry Johnson (#2) and Kurt Thomas (#23). The Heat won, 87-72, to even the series at 2-2. Man in suit is an unidentified coach. AFP PHOTO Stan HONDA (Photo by STAN HONDA / AFP) (Photo by STAN HONDA/AFP via Getty Images)

Playoff Run against the Atlanta Hawks and New York Knicks

Although the Hawks were overwhelmed with defensive power, their offense was lacking and they had no real pure scorer as the Raptors did with Vince Carter and Damon Stoudamire. Ultimately the Raptors had enough firepower to win the series 3-1. Marcus Camby outshined the older Dikembe Mutombo and Scottie Pippen was on fire averaging 26.3 points per game in the series.

The next series saw them face a surprising 8th seed New York Knicks team who stunned the NBA beating the first seed Miami Heat --- this was the second time in history where the 8th seed beat the 1st seed. The notable thing to remember here is that the Knicks wouldn’t have had Camby, but the 35-year-old Charles Oakley instead.

Probably the most physical series for the Toronto Raptors facing the best defensive team. Camby and Pippen were effectively able to shut down Patrick Ewing and Latrell Sprewell, respectively. They ended up winning the series 4-2 despite Vince Carter struggling to get it going on offense only averaging 12.3 points per game.

5 of 5
Lazy loading placeholder

David Robinson (L) and Tim Duncan (R) of the San Antonio Spurs set their defense against the Minnesota Timberwolves at the Alamodome in San Antonio, Texas 04 February 2002. AFP PHOTO/Paul BUCK (Photo by PAUL BUCK / AFP) (Photo credit should read PAUL BUCK/AFP via Getty Images)

Toronto Raptors reach Conference final and Championship final

Now here comes the toughest challenge of all, the Indiana Pacers. A team led by Reggie Miller and their coach, the great Larry Bird. It would’ve been considered complete lunacy if you had picked the Raptors over the Pacers. But this was THE Scottie Pippen series. Scottie Pippen absolutely shut down Reggie Miller and looked like 1994 MVP candidate Pippen of old.  He was unstoppable.

The Toronto Raptors ended up winning the series 4-3, in what was an All-Time great series. Not so much for Reggie Miller who failed to have a field goal percentage over 40 percent more than once. This was also a series that caused a lot of uproar in the NBA. No fans or media members wanted to see a brand new team make it to finals, all the worse a Canadian one.

However, this is where everything fell apart for the Toronto Raptors. The Hall of Fame frontcourt of a veteran David Robinson and an up and coming Tim Duncan was too much to handle for the Toronto Raptors. Marcus Camby and Vince Carter were exposed on both ends of the floor, and Damon Stoudamire played like his nickname suggested (Mighty Mouse). Scottie Pippen, besides his best efforts, just couldn’t do it all by himself. The Toronto Raptors were swept 4-0, and this was the end of something special for the organization.

Scottie Pippen did what any other star in Toronto did at that time, sign with any other team (Portland Trailblazers), Damon Stoudamire followed Pippen’s footsteps and signed with the Portland Trailblazers also. This left all but Marcus Camby and Vince Carter as the only shining spots in Toronto. Pippen’s presence actually managed to affect Vince Carter, and he went on to make 2 all-defensive teams with the Raptors before he was ultimately traded to the New Jersey Nets. Meanwhile, Marcus Camby got traded to the Denver Nuggets when Carter got left.

Next: Pascal Siakam and Fred VanVleet are the NBA's New Emerging Duo

This was the end of an era for the Toronto Raptors and this is what could've happened if Scottie Pippen was a Toronto Raptors.