Toronto Raptors: Revisiting the ‘secret’ Scottie Pippen trade

The Toronto Raptors were once ready to trade Tracy McGrady for Scottie Pippen on draft night, but it never worked out.

The young talent on the 1997-98 Toronto Raptors painted a picture of what advancements can happen with an expansion team. Damon Stoudemire, Chauncey Billups, Marcus Camby and Doug Christie, four players who went on to have successful NBA careers, were at the forefront, and that was before Vince Carter came aboard in the 1998 draft.

The one missing player from this group, however, is Tracy McGrady, often the subject of Raptors what-ifs. Playing as an 18-year-old teenager to age 20, he left for the Orlando Magic in 2000 free agency, signing a six-year, $67.5 million contract. McGrady, speaking with Michael Grange of SportsNet Canada, has said he regrets leaving Toronto so soon.

More from Hoops Habit

• 7 Players the Miami Heat might replace Herro with by the trade deadline
• Meet Cooper Flagg: The best American prospect since LeBron James
• Are the Miami Heat laying the groundwork for their next super team?
• Sophomore Jump: 5 second-year NBA players bound to breakout
• NBA Trades: The Lakers bolster their frontcourt in this deal with the Pacers

With ESPN airing The Last Dance, though, and all the discussion of the 1990s Chicago Bulls, the Raptors have a tie to that dynasty breaking up—somewhat. As McGrady recounted to ESPN in 2016, before being picked in the 1997 NBA Draft, he had a “secret meeting” with the Chicago Bulls, as general manager Jerry Krause was prepared to send Scottie Pippen to Toronto. Michael Jordan’s input canceled the deal, and it never went public.

Well, The Last Dance unveiled just how much Krause wanted to rebuild the Bulls, despite winning the 1996 and 1997 NBA Finals. The documentary detailed tensions between management and Pippen, too, and moving him would have jumpstarted a new-look Chicago team.

But Toronto also set itself up for a push forward. Middling seasons highlighted the first two years upon arrival in the NBA, but a jump from 21 to 30 wins in 1996-97 provided some hope. This was still a young group with most of the aforementioned players, sans Billups; attendance was high (eighth in the league in 1996-97), and a lottery pick was on the way.

Pairing a well-renowned veteran with this group could have taken the Raptors to the postseason. Scottie Pippen, still just a reasonable 32 years old at the 1997 NBA Draft, was coming off averages of 20.2 points, 6.5 rebounds and 5.7 assists in the Bulls’ latest title run. Those numbers were the status quo of what became his final year with that dynasty, so Toronto was in for a dynamic all-star, whose situation was ready to burst.

This Pippen-led roster had the chance to work into the playoffs. The Raptors would have received their centerpiece, with the opportunity of challenging quality but flawed teams in the New Jersey Nets and the Washington Wizards for the final postseason spot. Actually finding their way in depends on how much Pippen transforms this team and its young supporting cast.

One thing is—likely—for sure: the Raptors never land Vince Carter.

More from Toronto Raptors

• NBA Trades: 10 Pascal Siakam deals the Raptors must consider
• Grade the Trade: Warriors become title-favs in proposed deal with Raptors
• NBA Trades: Memphis bolsters their roster in this deal with Toronto
• NBA Trades: This Pelicans-Raptors deal would send a star to the Big Easy
• 3 NBA teams facing do-or-die 2023–2024 seasons

A draft-day trade in 1998 brought one North Carolina star north of the border for another, Antawn Jamison. Swapping the No. 4 and 5 picks with the Golden State Warriors, the Raptors acquired what became their standard-bearer for the next six-plus years, nearly leading them to the Eastern Conference Finals in 2001.

Carter was highly regarded out of college, and with the Scottie Pippen-led Toronto Raptors hypothetically landing near the bottom of the lottery or as the eighth seed in the playoffs, he’s outside of their range. Although Dirk Nowitzki and Paul Pierce were the No. 9 and 10 picks, respectively, landing between No. 11 and 14 resulted in Bonzi Wells, Michael Doleac, Keon Clark and Michael Dickerson. Not exactly game-changers.

So, no Carter. No McGrady. No Pippen, too?

Chicago traded its disgruntled star after the 1997-98 season to the Houston Rockets, where Pippen stayed for just one lockout-shortened campaign. He eventually asked for a trade to the Los Angeles Lakers, hoping to play for his ex-head coach, Phil Jackson, per ESPN.com at the time. Instead, a move to the Portland Trail Blazers happened.

Whether it be the Bulls, Rockets, Lakers or Blazers, it was still Pippen hoping for a move to comfortability. Jackson became the Lakers’ coach in 1999. Assuming Pippen signs a hefty contract extension, as he did with Houston, this is just two years into his five-year pact. That means the Raptors inevitably had a move to make, as well, leaving them with their hands tied and another turn at rebuilding.

The Toronto Raptors were always going to own the short end of the stick, trade or no trade. Pippen might have provided two years, and no trade would have kept McGrady’s shelf life short. Even Carter lasted a short time before his falling out with the franchise. It took until the 2010s for the official rebound to title glory, but the path to the top had the potential to be prolonged.