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Five “What If?” questions from the Magic’s first 30 years

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The Magic have countless “what if” questions, but these five caught Zach’s attention

1995 NBA Finals Game 2: Houston Rockets vs. Orlando Magic Photo by Andrew D. Bernstein/NBAE via Getty Images

Throughout history, seemingly every professional team can ask “what if?” questions.

What if a key player didn’t get hurt? What if we didn’t run into a team on a crazy hot streak? What if the ball had bounced just inside the foul line, or trickled just over the lip of the rim instead of rolling off?

The list of those questions can go on and on.

For a team that has made the playoffs in half of their season since being incepted in 1989, the Orlando Magic’s list of “what ifs?” seems endless. From the loss of superstars, to missing out on one of the NBA’s greatest power forward, to a layup falling off the rim in the Finals, the list is long, and excruciating for the Magic.

But what is the biggest, and most painful “what if?” question in the Magic’s 30 year history?

5. What if the Magic didn’t lose out on the eighth seed in Shaquille O’Neal’s rookie season on the fourth tiebreaker?

Orlando Magic

After taking Shaq first in the 1992 draft, the Magic had their franchise cornerstone. O’Neal came into the league and took it by storm, averaging 23.4 points, 13.9 rebounds and 3.5 blocks per game. He was a monster on both ends, and seemingly turned the Magic from a league bottom feeder, to a threat to make the playoffs.

O’Neal proved that he could completely change a team, but also that he still needed some more help. While the likes of Scott Skiles, Nick Anderson and Dennis Scott all playing important roles that season, and beyond, the team likely had a lower ceiling with only them around O’Neal.

After missing out on the playoffs once again, and getting some favorable bounces with the pingpong balls, the Magic had the first pick in the 1993 draft. For the second year in a row, the Magic controlled the draft, and had the chance to add someone who could make a profound impact.

Enter Anfernee Hardaway.

More commonly known as “Penny,” Hardaway came in and changed the game for the Magic. His combination of size, athleticism, ball handling and scoring prowess, made him almost unguardable. He took the Magic up to another level that they likely wouldn’t have reached without him.

Hardaway raised the Magic’s ceiling exponentially. He changed a lot of things, not only with the Magic, but with the league.

And to think, the Magic were oh so close — had they beaten the Indiana Pacers one more time, or won one more game against an Eastern Conference team — they would’ve been the eighth seed, and never had a chance to get Hardaway. How different would the trajectory of that Magic team have been if they had gotten someone like Rex Walters or Greg Graham?

While it wasn’t always perfect with Hardaway, and he himself has his fair share of “what ifs,” without him, the Magic aren’t becoming an Eastern Conference powerhouse. Without Hardaway, the Magic aren’t beating Michael Jordan and the Bulls in the 1995 playoffs, leading to their first NBA Finals appearance in franchise history.


4. What if Grant Hill was healthy in his time with the Magic?

Tracy McGrady talks to Grant Hill

When the Magic signed Grant Hill and Tracy McGrady in the summer of 2000, they seemed poised to take the league by storm. As the game was evolving, and perimeter play was becoming more and more important, the Magic appeared ready to take a big leap.

Injuries had other ideas for Hill and the Magic.

After missing just 25 games in his first six seasons, Hill missed all but 48 games in his first four seasons with the Magic. Ankle injuries derailed what was one of the best growing careers in the league. Hill played in just four games his first year in Orlando, 19 his second, 29 his third.

Meanwhile, McGrady was dominating the league on a nightly basis. After showing potential of a breakout in his third year with the Toronto Raptors, McGrady took the league by storm in his first in Orlando.

McGrady jumped from 15 points per game to 26. By 2002-03 McGrady was leading the league in scoring at 32 points per game, and was arguably the best player in the league in this time period.

Yet, without his All-Star side-kick in Hill, McGrady’s work was all for nought. The prime of McGrady’s and Hill’s careers was being wasted away, all because of pesky ankle injuries.

If Hill had been healthy, would the Magic have been able to topple the likes of the New Jersey Nets, Philadelphia 76ers and Detroit Pistons? Would McGrady and Hill have formed the best 1-2 wing punch since Michael Jordan and Scottie Pippen?

The questions are endless with Hill and his time in Orlando, but it’s one that won’t soon be forgotten in Orlando.


3. What if Rashard Lewis doesn’t sign with the Magic?

Orlando Magic Sign Rashard Lewis Photo by Fernando Medina/NBAE via Getty Images

In the summer of 2007, the Magic had cap space, and were looking to replace Grant Hill who was on his way to Phoenix. Enter Rashard Lewis, the floor spacing virtuoso who was looking to cash in on his strong play with the Seattle SuperSonics.

The issue, however, was simple: the Magic already had Hedo Turkoglu, who played Lewis’ natural position of small forward. When Lewis signed with the Magic, he was adamant that he wanted to continue to play the position that allowed him to thrive in Seattle.

But, would that have been the best for the Magic? Would bringing Turkoglu, who the team had signed in free agency the previous summer, off the bench be what’s best for them?

In stepped newly minted head coach Stan Van Gundy.

Van Gundy had a vision for how the team would play around Dwight Howard, who was growing into one of, if not the best, big man in the league. He wanted Howard to command the middle and surround him with four shooters.

Once he heard Van Gundy’s pitch on play style, Lewis was immediately onboard.

“When Stan told me he wanted to move me to the four position, I was all for it,” said Lewis in 2018 before being honored by the team. “He pretty much told me he wanted Dwight to control the paint, and we’d put shooters around him, and he wanted to keep Hedo Turkoglu on the floor.

“I felt like that was our best chance to compete in the Eastern Conference and try to win a championship. When he told me that, it was like a no brainer for me. He could’ve just threw me at the four and I would’ve gone out there and played.”

If the Magic hadn’t signed Lewis that summer, would they have had the success they did? Would they have changed the way teams valued the three pointer like they did? Would they have reached their second finals in 2008/09 without Lewis?

Lewis is arguably one of the most important free agent signings in the franchise’s history, and without it, could have the league looking a lot different today.


2. What if Courtney Lee made the layup in game two of the finals?

NBA Finals Game 2: Orlando Magic v Los Angeles Lakers Photo by Noah Graham/NBAE via Getty Images

Courtney Lee didn’t play much in Game 2 of the 2009 NBA finals. After starting the game, the rookie guard logged only 11 minutes.

Three of those minutes came in the final quarter, and while he was just a rookie, he was given the opportunity to make the biggest play of the game.

After Hedo Turkoglu blocked a Kobe Bryant layup, the Magic had a chance to win the game with half a second left. It would’ve been nearly impossible to catch and shoot in that time, so Van Gundy drew up a play to get Lee a lob at the rim.

Lewis set a screen, freeing Lee up for an open lob from Turkoglu. He caught it with his head near the top of the box, and released it, but watched as the ball agonizingly fell off the front rim. While Howard cleaned up the miss, it was after the buzzer, the game went to overtime.

The Magic ended up losing by five, and went back to Orlando down 2-0.

If Lee had made that layup — or if Los Angeles Lakers big man Pau Gasol had been called for the goaltending he committed on the play — the Magic would’ve gone back to Orlando at 1-1. It would’ve changed the dynamic of the series. The Magic would’ve had the momentum, and three games at home, the place where they had wrapped up their finals birth against the Cleveland Cavaliers a week and a half earlier.

Lost in the agonizing miss from Lee at the buzzer is the fact he had a chance with 10 seconds to go to give the Magic a lead, but also missed that. Had either of those looks gone down, the Magic could have a championship banner hanging in the Amway Center, and the last 10 years could look a lot different.


1: What if Tracy McGrady hadn’t left before Dwight Howard was drafted?

Houston Rockets v Orlando Magic Photo by Fernando Medina/NBAE via Getty Images

I touched on it some above, but McGrady’s time with the Magic was, somewhat, overshadowed by the injury issues to Grant Hill. It hurt the potential the franchise had, and it wasted some of McGrady’s best years in the league.

Upon leaving Orlando, McGrady had four more productive years with the Houston Rockets. He teamed up with Yao Ming, and made a formidable duo.

Like with Hill, injuries ultimately derailed Ming’s time with the Rockets, and took away more good years from McGrady. Had he decided to stay in Orlando, he could’ve teamed with a young, talented duo of Howard and point guard Jameer Nelson, and possibly made another run.

Now, had McGrady stayed in Orlando, it’s likely the team wouldn’t have been able to sign either Turkoglu or Lewis in free agency. If they hadn’t been able to do this, would they have seen the same success they did? Would Howard have developed into the player he ultimately did?

The thought of McGrady dominating on the wing, and Howard bullying people down low is tantalizing. It could’ve given the Magic a duo, in some ways, like the one they had in the 90’s with Shaq and Penny, that possibly could’ve pushed them over the edge.


The list of “what ifs?” with the Magic is endless. These are just five, and you could likely build five off of each of these respective topics.

What are your top-five “What if?” questions about the Magic in their franchise’s history?