Orlando Magic losing Shaquille O’Neal to Lakers in 1996 was likened to Red Sox selling off Babe Ruth to Yankees. At Orlando, Shaq was part of a young and talented team that seem destined for years of success. However, Magic weren’t ready to give Big Aristotle what he wanted and allegedly lowballed him during contract extension talks. Despite his love for the city of Orlando, he couldn’t fathom being disrespected the way the Magic did and left for pastures new.

Leonard Armato, Shaq’s agent-turned-friend, was there through it all. While speaking to EssentiallySports’ Vishal Kolar, the Shaq brand architect revealed what went down.

If Shaq, via Armato, had his way, he would’ve ended his NBA career where it began. However, as history goes, O’Neal took the $121 million offer to play for the Los Angeles Lakers in 1996 and became a household name, adding four NBA championships to his resume. But it all could’ve been very different. Armato gave a brief timeline that showed O’Neal wasn’t even considering other offers at first.

Armato: “Shaq’s contract was up with the Magic and we started talking with them and he told me very clearly, ‘I want to stay with the Magic,’ and I said, ‘Okay, let’s do a deal with the Magic.’ So I went to the Magic and I said, ‘Okay let’s make a deal.'” Instead of offering him a max contract, which was the highest amount permitted by collective bargaining agreement, which by the way is regularly offered to any good player today in the league, they offered him less than max contract, which was highly insulting.

Magic had O’Neal’s Bird rights with the ability to pay him more than the $24.3 million salary cap to re-sign him. To Armato’s surprise, Orlando was not offering the maximum contract under the bargaining agreement. Reports have claimed that they weren’t going higher than $54 million, which Shaq felt was a big insult as other big men like Alonzo Mourning and Juwan Howard signed seven-year, $105 million deals earlier.

At that time, O’Neal had grown from a monster rookie to the star who led the Magic to its first NBA Finals and even beat Michael Jordan in the Playoffs (The only team to beat MJ’s rampaging Bulls in the postseason in the 90s). He was wanted all over the league and he knew his worth. As much as he wanted to stay in Orlando, he wasn’t going to undersell himself. So he tasked Armato with looking at other options.

Armato: “When that happened, Shaq said to me, ‘Look, go see if there’s anything else out there.'” 

Shaq became an unrestricted free agent and attracted interest from numerous teams. As soon as he gave his agent the green light, the Lakers made a move.

The Shaquille O’Neal trade from Orlando to Lakers went down in history as the Los Angeles franchise reaped rich rewards with him in the team while Magic struggled to assert themselves.

In 2006, the then Magic senior Vice President Pat Williams admitted, “To this day, we’re still digging out of that loss. It was like the Red Sox selling off Babe Ruth. They had the curse of the Bambino, and we had the curse of Shaq.” Magic remain without an NBA title while Shaq has four rings to his name.

His move to Lakers also came with a lot of skepticism. The hefty price tag carried its own weight while media also peddled that Shaq may not live up to the billing.

Shaquille O’Neal proved his worth after Lakers raised their offer

Kolar spoke about the media side of things in 1996, and it was wild, to say the least. More than the lack of max contract, it was the Orlando Sentinel poll that established that 91% of its readers thought O’Neal isn’t worth $150 million scarred him. Armato was also painted as a Hollywood broker who wanted to get Shaq more entertainment gigs. But Jerry West didn’t think the same.

The then-Lakers GM, Jerry West, had known Armato since the time he managed Kareem Abdul-Jabbar. He called Shaq’s agent with an initial $96 million offer. Armato replied his client won’t consider any offer less than the $100 million Alonzo Mourning was getting. So West traded Vlade Divac and his $8.5 million salary to get the draft pick. He used it to select Kobe Bryant and upped his offer to Shaq to $121 million for seven years.

Shaquille O’Neal accepted it and West met both Shaq and Armato in Atlanta to sign him. His love for Orlando remained though, and in 2015 he revealed his regret for leaving Orlando to go to Lakers.

During his induction ceremony in the team’s Hall of Fame, he said, “I regret it sometimes. Is this where I started and should have stayed?” I actually wish they made it a law that whoever drafts you, you’ve got to stay there your whole career.”

Despite losing to Houston Rockets in the Finals in 1995, many believed Magic had a team capable of dominating for the league for years. “That’s why I kind of regret it, because we had a young, fabulous team. We really did, and it’s a shame that we got torn apart.” O’Neal added somberly.

Shaq won three NBA titles with Lakers and added a fourth with Miami Heat in 200. But his departure from Orlando Magic will remain one of the biggest “what ifs” in NBA history.