Greatest Orlando Magic Moment of the 21st Century

Welcome to the Greatest Moment series at Last Word On Pro Basketball, where we’ll present to you each NBA team’s greatest moment of the 21st century. From draft lottery luck, to a franchise-changing trade, to the sweet taste of a championship, every NBA team has had its own special moment to look back on.

In this edition, we’ll relive the greatest Orlando Magic moment of the 21st century: Dwight Howard‘s Superman dunk in the 2008 NBA Slam Dunk Contest.

Greatest Orlando Magic Moment of the 21st Century: Dwight Howard’s Superman Dunk

The 21st century has been both kind and cruel to the Orlando Magic fan base. The almost Tim Duncan signing, Grant Hill’s lower body, Tracy McGrady turning into an all-time great scorer, Dwight Howard coming, Dwight Howard leaving, and the mediocrity that has followed. Considering everything that has happened since 2000, there is one moment that can be universally understood as the greatest moment for the Magic in the 21st century.

The Almost Big Three

Shaquille O’Neal took the Orlando Magic from an expansion team known most for being near Disney World, to a team with a clear direction and future. Anfernee “Penny” Hardaway took that Shaq-led team and turned it into what may have been a potential dynasty. However, after it was all said and done, the Magic had zero championships and only one NBA Finals appearance to show for one of the all-time “what could have beens.” Shaq went to Los Angeles, Penny couldn’t stay healthy, and the Magic were looking at what would likely be a long road back to relevance.

Then, something magical started to happen. Tracy McGrady left Toronto after blossoming into an elite athlete and scorer to sign with Orlando. Then, Grant Hill was brought in via sign-and-trade from Detroit. And for a short period of time, it appeared as though Tim Duncan would also be joining the Magic to create, what could have been, one of the most dominant superstar trios in the league.

Unfortunately, as Magic fans know all too well, it didn’t quite shake out that way. Duncan stayed with San Antonio, Grant Hill couldn’t stay healthy, and Orlando wasn’t able to surround McGrady with enough help to propel the Magic back into NBA dominance.

What Happened?

Shaq and Penny were supposed to win multiple titles together in Orlando. Then, they were supposed to become a superteam with Duncan, Hill, and McGrady. At least the Magic were still supposed to be competitive with Hill and McGrady. People thought that the Magic would at least be competitive when Hill got healthy, after dealing with various injuries.

In the end, that never happened. Hill’s injuries continued to plague him, and the Magic had to face another rebuilding period as McGrady made public his desire to be traded after the Magic finished the 2003-04 season with the worst record in the league.

Okafor or Howard?

The Magic were back on the path to rebuilding after trading McGrady. They would need to decide who they should pair next to Steve Francis after winning the 2004 draft lottery. Emeka Okafor was coming off of a dominant college career at the University of Connecticut and was regarded as the likely first overall selection in the NBA Draft. His only competition was a high school senior from Atlanta named Dwight Howard.

The Dwight Howard Era

The Magic decided against what many considered to be the safer pick in Okafor, and selected Howard with the first pick in the 2004 draft. Howard wouldn’t have as immediate an impact as fellow prep-to-pro top selection LeBron James did during his rookie year. However, Howard quickly cemented himself as a defensive force and an emerging offensive presence.

It would take the Magic two seasons with Howard to return to the playoffs following McGrady’s exit. Being swept in the first-round isn’t what Magic fans should remember about the 2006-07 season. What should come to mind is Howard’s appearance in that season’s NBA Slam Dunk Contest. With a sticker of his own smiling face in his left hand, Howard touched nearly the top of the backboard while dunking the ball with his right. The judges must not have noticed what actually happened. It was an athletic achievement that cannot truly be appreciated until you stand under an NBA basket.

Howard did not win that year’s Dunk Contest. He did, however, take the Magic to the playoffs and gave the NBA a glimpse of what was to come.

2007-08 Season

The following season, Howard took over. He dominated on both ends of the floor nearly every night. The Magic began to come together as a team, Stan Van Gundy surrounded Howard with three-point shooters, and Howard officially became the face of the franchise.

2008 Dunk Contest

To avoid being snubbed again, Howard planned something special for the next Dunk Contest. He started out with another dunk that looked far more basic than it actually was.

It was impossible to understand and appreciate Howard’s athleticism. You had to see him in person at the time to understand. He was a 6’10” center who jumped and moved more like a small forward. Not everyone could comprehend how great of an athlete he was. 

Standing behind the basket, Howard flipped the ball off of the backboard, ducked under the basket, and windmilled the ball through with his left hand (he’s right-handed). Kobe Bryant was in the crowd and appreciated the feat. He understood the requisite size and athleticism that it took to pull this off.

The Moment: Howard’s Superman Dunk

Accompanied by his point guard, Jameer Nelson, Howard came back on the court for his second dunk. This dunk is the greatest Orlando Magic moment of the 21st century. Nelson whipped out a red cape and Howard shed his Magic top to reveal a Superman jersey. The crowd of both fans and players erupted. After tying the cape on Howard, Nelson took his spot on the baseline to deliver a perfect alley-oop for the flying Superman. Howard took off from just inside the free throw line and literally threw down the dunk. Magic Johnson‘s reactions encapsulated what the entire Orlando fan base was feeling, thinking, and doing at that exact moment.

2009 Finals Run

The Dwight Howard Superman dunk sent a spark and chill throughout the league. It was the official signal that the Magic were back. The team closed out the season with a 52-30 record and won the Southeast Division. The following season (2008-09), they finished 59-23 and made it back to the NBA Finals for the first time since Shaq and Penny.

The Magic did not win the 2008-09 championship, but fans had a new team to believe in. It was a new team that could fulfill fans’ hope of winning multiple championships in Orlando.

Fall From Grace

Just like the teams before them, this Magic team did not win multiple championships. It did not even return to the Finals. And just as Shaq and T-Mac had before, Howard went on to force his own exit.

Magic fans had to suffer through mixed messages and Howard trade rumors. After the dust settled, Howard did not leave gracefully. In one of the most awkward sports interviews ever, Orlando’s head coach, Stan Van Gundy, confirmed reports that Howard was demanding that the team hire a new coaching staff. Howard then walked into the interview and attempted to smile and charm his way through it, unaware of the comments that Van Gundy had just made. After all of the drama, the Magic needed to trade Howard.

A New Era

Dwight Howard took the Orlando Magic back to the NBA Finals and left as quickly as he came. He caused the fan base unnecessary heartache by smiling his way through his trade demands. That’s what made fans fall in love with Howard in the first place; he became the face of the franchise partly because of his personality. But ultimately, his personality led him to become one of the least popular Magic players amongst fans. Orlando might have taken Howard for granted in the same way that the city took Shaq, Penny, and T-Mac for granted. After his time in Orlando, Howard left the Magic with some future assets, draft picks, and memories of a few playoff runs.

Unfortunately for the fan base, the Magic are still in the middle of rebuilding from the Dwight Howard era. Jonathan Isaac and Aaron Gordon will need to develop into All-Star caliber players to give the fan base any hope of seeing the end of the rebuild. If either of those players does reach superstar levels, Magic fans should enjoy the ride and make sure to appreciate their time in Orlando.


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