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For what felt like Allen Iverson’s entire career with the Sixers, the team was looking for an ideal sidekick.

Whether it was Toni Kukoc or Matt Harpring or Glenn Robinson or Chris Webber, the right fit never seemed to come to fruition.

There was one reported attempt to trade for a Robin to Iverson’s Batman that was thwarted by Stephen A. Smith – yes, that Stephen A. Smith. If you don’t know the story, the Sixers and Raptors supposedly had a deal in place in December of 1999 which would’ve sent McGrady and a first-round pick to Philadelphia for Larry Hughes.

Smith, then a columnist for the Inquirer, reported the agreement. After the news got out there, the Raptors allegedly got cold feet. Smith has confirmed this story to be true.

So, what if that trade goes down? Do Iverson and McGrady form one of the greatest backcourts in NBA history? Does it not work because there simply wouldn’t have been enough shots to go around?

McGrady started his Hall of Fame career playing next to a superstar in Vince Carter. The duo seemed to be creating something special in Toronto, but McGrady chose to return closer to home by signing with the Magic in 2000. The only reason the Raptors explored a trade in 1999 was McGrady’s pending free agency.

While Toronto fans can ponder what could’ve been, so, too, can Lakers fans. Jerry West apparently had his eyes on McGrady coming out of high school in 1997. West envisioned McGrady forming a dominant trio with Shaquille O’Neal and Kobe Bryant.

While that never came to fruition, McGrady acknowledged that he’d heard that story before. On ESPN’s The Jump in 2017, McGrady talked about how he might’ve fit in L.A. playing next to Bryant.

“My career took a turn when I went to Orlando because I had to become a scorer because I didn’t have Grant Hill [because of injury]. I was always the player like a Scottie Pippen type – share the ball, defend the best player. That’s what I did in my three years in Toronto. I would’ve been that player alongside Kobe Bryant.”

When you look at McGrady’s final season in Toronto, it’s not hard to imagine him taking on a Pippen-like role next to Iverson. As a 20-year-old, McGrady averaged 15.4 points, 6.3 rebounds, 3.3 assists, 1.9 blocks and 1.1 steals in 1999-00. That stat line lines up favorably next to Pippen’s career averages.

But would he have been comfortable in Iverson’s shadow after seemingly not enjoying being in Carter’s? As McGrady said, he went to the Magic thinking he’d playing alongside Hill, who at the time was one of the best players in the league and still ascending. Orlando also courted Tim Duncan in that wild offseason.

The bigger question is, would Iverson have been on board with McGrady as a running mate?

It wasn’t that long ago that the Sixers thought they had a dynamic duo of the future in Iverson and Jerry Stackhouse. That situation wound up being a disaster for the Sixers as there was a constant struggle between the two over whose team it was.

“I do remember them always having kind of a fight for whose team it was going to be,” former Sixer Scott Williams said on the Sixers Talk podcast, “because it had gone from the 80’s when it was the Los Angeles Lakers and Magic Johnson or the Boston Celtics and Larry Bird to becoming Michael Jordan and the Chicago Bulls or Charles Barkley and the Philadelphia 76ers. 

“So the league started to market players differently. They started putting players in front of the teams. And I think when these guys came in here starting in the mid-90’s, they started saying, ‘I want to be that guy whose name goes before the team’s.’ So, there was always that confrontation about who’s going to be the star of the show and it didn’t lead to good chemistry among the rest of us.”

It could’ve just been those specific players that couldn’t mesh. As mentioned, McGrady signed in Orlando with the idea of playing next to Hill and also had a successful stint in Houston playing with Yao Ming. It’s feasible that he could’ve done a similar thing with Iverson.

But was that the best strategy to suit Iverson’s strengths? The team’s best playoff run happened in 2001, when a roster full of tough, defensive-minded players surrounded the high-volume shooting guard. 

Though all of us may have yearned for that perfect Iverson sidekick, maybe the fact is he didn’t need one.

“Everybody in Philadelphia always had this idea that we needed another scorer to play with Allen,” former Sixers head coach Larry Brown said on the Sixers Talk podcast. “They brought in Glenn Robinson, they brought in Chris Webber at one time, they brought in Toni Kukoc, they brought in Matt Harpring – we can go on and on and on. But it was our belief, and my personal belief, that you had to surround Allen with the right kind of guys.”

Given the way McGrady’s career went as a two-time scoring champ, it may be hard to picture it all working out.

But if he would’ve played a Pippen role next to Iverson and possibly re-signed with the Sixers the following offseason, that could’ve been a dangerous basketball team for a long time.

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