Into the Orlando Magic-verse: Top 5 What-If’s in Orlando Magic History

In recent years, there has been an increased interest in the concept of the multiverse throughout modern-day pop culture.

Maybe you are a fan of the Marvel Cinematic Universe or the new Spider-Man Across the Spider-Verse movie each touches on this concept frequently. Or maybe you caught the Oscar Winning 2022 Movie of the Year in A24’s Everything Everywhere All at Once. Even CBS’s hit show Big Brother is capitalizing on this trend during its current season and a Big Brother Multiverse theme.

Regardless, the concept of alternate universes where things play out differently than the way we know them to is something that is become a bit of a phenomenon.

Going into the 35th anniversary season of Orlando Magic basketball, Orlando Magic Daily aims to look at the history of the franchise and celebrate all the franchise has accomplished.

But in this article, we take a deep dive into some of the biggest fork-in-the-road moments in franchise history and hypothesize what would have happened if things had gone in a different direction.

In the words of the Watcher from the MCU, “Follow me, as we ponder the question, WHAT-IF?”

Top 5 what-if’s in Orlando Magic history

What if the Magic kept Chris Webber?

What happened?

One year after drafting one of the most coveted prospects the NBA has ever seen in Shaquille O’Neal, the Orlando Magic were once again in a position of power for the 1993 NBA Draft.

On Lottery night, the Magic only had a 1 in 66 chance of their ping pong ball coming out of the hopper. Yet it defied the odds to land them the top spot in a second consecutive draft. The only question that remained was: Who should they take?

Chris Webber from Michigan’s Fab 5 team was widely considered the best player in the draft and a slam dunk to be the number one overall pick. But questions arose from many, including O’Neal himself, on how his game would fit alongside the Magic’s best player.

Despite O’Neal’s concerns and his pleas to draft fellow Blue Chips movie co-star Memphis State’s Anfernee Hardaway, the Magic drafted Chris Webber with the first overall pick and he was headed for Orlando. Until he was not.

With the third pick in the 1993 Draft, the Golden State Warriors took Hardaway and shipped him along with three future first-round picks to Orlando for Webber. The Magic appeased O’Neal and from there the rest is history.

Penny and Shaq would go on to become the most iconic duo the Magic franchise has ever seen but sadly fall short of winning an NBA Finals for Orlando.

What could have gone differently?

What if the Orlando Magic did not trade Chris Webber on Draft night? Deciding instead to pair the two similar players despite the obvious risk that came with it.

There are a couple of ways this could have gone. One is Shaquille O’Neal could have taken this as a personal slight from management. In the 30 for 30 documentary “This Magic Moment,” Shaquille O’Neal directly states he hand-picked Anfernee Hardaway as the guy he wanted to play with in Orlando.

It is conceivable to think forcing him to play with the player he was most concerned about meshing with on the court could have upset him. And it is possible the Magic would ultimately have had to choose which big man to keep happy and trade Webber anyway.

Chris Webber for his part was disgruntled in Golden State under Don Nelson and was dealt to the Washington Bullets one season later for a starter in Tom Gugliotta and three future first-round picks (including returning two of the picks they dealt to the Orlando Magic).

Maybe the Magic would not have gotten that much in return with Webber not playing the same starring role he played as a rookie in Golden State.

But What if they DID gel? What if O’Neal and Webber were the twin towers and dominated an era of basketball where big men had their highest value?

Shaq was such a dominant force in basketball history that it feels like a cold take to say he could have won a championship anywhere if he had the right pieces around him. And while Webber was not O’Neal, he was a force in his own right averaging 20.7 points and 9.8 rebounds a game throughout his pro career. He also averaged more than 1.0 block and 4.0 assists per game, proving he could affect the game without the ball in his hands.

Additionally, he played a lot of power forward during his NBA career and could have slid nicely next to O’Neal at center despite the initial concerns.

The twin towers roster would not have had the assets they received from trading Webber — but it is fun to think about what a defensive problem the two could have been together and how the NBA would have had to adapt when facing them.

Final prediction:

Contending for Eastern Conference Finals (much like the Orlando Magic did with Anfernee Hardaway) would have taken a few personnel moves from management — but the pitch of playing with two of the league’s best big men likely would have been enticing to many and easy to manifest.

The Magic would have found the right guard to complement Shaquille O’Neal and Chris Webber while also successfully defining each of their roles.

However, seeing how things played out with O’Neal and Hardaway, it is likely this team would have faced a similar crossroads. The inner turmoil would probably have risen to a place of relevance much sooner as O’Neal specifically told management he did not want to play with Webber.

Webber himself proved to struggle to find a home moving from Golden State to Washington within a year and Washington to Sacramento within another four seasons.

Even if they did not, the Magic probably still make the same financial decisions that cost them O’Neal in our version of history with salaries set to dramatically increase in the summer of 1996.

Webber and O’Neal certainly could have been a fun “what if?” story in their own right. But for Magic fans this is not the one to lose sleep over. The pairing likely would not have accounted for any championships — effectively being a less entertaining ride than the Shaq and Penny one was. And ending in a similarly disappointing destination.

Top 5 what-if’s in Orlando Magic history

What If Nick Anderson didn’t miss 4 consecutive free throws?

What happened?

In Game 1 of the 1995 NBA Finals, the Orlando Magic were up 20 points on their homecourt before everything that could go wrong did. The Magic came out in the second half flat, their lead evaporated, and with 10 seconds left in the game, they were clinging to only a 3-point advantage.

In the game’s closing seconds, Nick Anderson, the first-ever draft pick in Magic franchise history, was heading to the line to shoot two free throws and put the game away. Just making one would give the Magic a four-point lead and almost certainly a 1-0 Finals record over Hakeem Olajuwon and the defending champion Houston Rockets.

Anderson would infamously miss both, get his own rebound and head to the line once more to repeat the same situation. Once again, all the Magic needed was one free throw to clinch the game. But once again, Nick Anderson would come up short.

After Orlando missed four consecutive free throws, Kenny Smith knocked down his eighth 3-point shoot of the game with 1.6 seconds left and snt the contest to overtime.

Once there, the Magic’s psyche and confidence were shattered. Despite Horace Grant trying to get the mentality of his teammates back to a positive place, the damage was done and the Magic never re-established themselves as a presence in the series.

The Magic would lose Game 1 on an Olajuwon tip-in with less than a second left and were ultimately swept 4-0. The downfall of what could have been a special and historic dynasty for Central Florida’s team was now in motion.

What could have gone differently?

There are probably countless Magic fans who still wake up in a cold sweat thinking about it: But what if Nick Anderson made one of those four free throws?

The first piece is obvious. Orlando almost certainly wins Game 1 of the 1995 NBA Finals if Anderson does not miss all four shots from the charity stripe. Orlando may have had to sweat a bit more, but the team would still have the confidence that it could compete on this highest stage. They would still be the favorites to win the title that year.

Whether the Magic would eventually win the series or not, the element of not being swept would likely have had a positive impact on the morale of the roster. Based on the players’ comments from the “This Magic Moment” documentary, it seemed imposter syndrome hit an all-time high for the team after blowing their huge Game 1 lead.

If the Magic had stayed competitive in the series (the Magic lost Game 2 by 11 points, Game 3 by three and Game 4 by 12 – winning a title is something Shaquille O’Neal and company may have had an increased desire to accomplish together in Orlando, rather than shake their confidence in the goal entirely.

Final prediction

As the credits roll during “This Magic Moment,” Shaquille O’Neal and Anfernee Hardaway have a conversation by the pool about what things would have been like if they stayed together.

O’Neal says they would have won multiple championships and had they won then there would have never been a breakup in Orlando. Bittersweet words for any Magic fan because the truth is he is probably right.

O’Neal was destined to win titles. The “where” of it all is what is fun to consider.

The butterfly effect of Nick Anderson missing four consecutive free throws helped contribute to the Magic losing its first-ever finals game, its first-ever finals series and ultimately led to the premature loss of the best player to ever wear a Magic jersey.

Had this fork in the road gone a different way, the Magic either win the 1995 Finals and/or retain O’Neal long enough to win multiple others.

Top 5 what-if’s in Orlando Magic history

What If the Heat didn’t draft on Dwayne Wade?

What happened?

The 2003 NBA Draft is considered by many one of the deepest and most star-studded collections of prospects the NBA has ever seen. One of those stars was future three-time NBA champion Dwyane Wade.

Despite eventually becoming a Top-five pick, Wade thought the Chicago Bulls at No. 7 or the Orlando Magic at No. 15 would ultimately be his new home.

In fact, Dwyane Wade recently revealed that his fellow Marquette alum, Magic head coach Doc Rivers, hinted he wanted to trade up to five to pick him.

But that did not happen. The Magic would take Louisville’s Reece Gaines at No. 15 because it turned out the Heat valued Wade the same as the Magic did. Miami selected Wade with the fifth overall pick and set in motion one of the greatest careers of any shooting guard in NBA history.

What could have gone differently?

What if someone else available had caught the attention of the Miami Heat? Allowing the Orlando Magic to wait/trade up and land a player that could have been the franchise’s best?

Assuming he would have had a similar career to the one he had in Miami, Magic Dwyane Wade would have rewritten the entire early 2000s-2010s era of the franchise.

For starters – he and Tracy McGrady would have been on the same team for at least one year, which could have led to McGrady staying in Orlando rather than moving to Houston.

Additionally, it feels unlikely the Magic would have won the lottery the following year if they had Dwyane Wade, so Dwight Howard (arguably the franchise’s best player) probably never wears a Magic jersey in this timeline.

Even if it meant never getting Howard, most Magic fans would probably prefer a timeline where Wade was the franchise’s go-to guy and perennial representative for All-Star Weekend. Especially if it meant the possibility of the Magic becoming the benefactor of what would become one of the scariest lineups ever assembled.

Many forget that while Pat Riley is the Godfather and forever making next-level roster moves, Dwyane Wade was truly the architect of the Heat’s Big 3 as he was the one who convinced LeBron James and Chris Bosh to join him on South Beach.

Could drafting Wade have led to a scenario of the “Heatles” storyline taking place at Disney World? It is fun to imagine.

Final prediction

Dwyane Wade embraced Miami as his home immediately and spent almost the entirety of his career there. He is that organization’s most important player and possibly a top-three NBA shooting guard of all time.

If he landed in Orlando, Wade’s Magic legacy would have been much the same.

Even if it was in little old Orlando, Wade’s impact on the league and game of basketball was going to be undeniable. He was a winner in every sense of the word and even in down years consistently led his teams to the playoffs.

When he started to age and lose a step, he was never afraid to embrace the help of other stars. Proving that winning was always his number one focus and ego would never be.

Wade would have been only the third player in the organization’s history to average more than 20 points per game and more than likely would have brought other stars to Orlando to join him in pursuit of winning the Magic championships.

He almost certainly would have accomplished the goal of bringing the Larry O’Brien Trophy to Central Florida for the first time and gone down as unquestionably the greatest player in Magic History. Oh, what could have been if Pat Riley was not Pat Riley.

Top 5 what-if’s in Orlando Magic history

What If Doc Rivers allowed Tim Duncan’s family on the team plane?

What happened?

It seems crazy to imagine a time or plane of existence where it was possible Tim Duncan would have ever worn an NBA jersey aside from the black and silver of the San Antonio Spurs. But believe it or not, in the free agency period of 2000 — the same period the Magic would obtain Tracy McGrady and Grant Hill —  the Magic also were strong suitors for the Big Fundamental.

In fact, many thought it was a done deal.

The city had signs and billboards begging for Duncan to bring his talents to Orlando. The red carpet was rolled out everywhere in the Magic Kingdom in hopes of landing the future NBA legend. The organization even called in one of the city’s most famous residents in Tiger Woods to help recruit Tim Duncan during a lavish party on Disney’s campus.

Yes, just outside the happiest place on earth is where a member of the Magic organization would make a decision that fans and former players, especially McGrady, remain haunted by to this day.

In a moment that seemed to be small and quickly passing, allegedly had some of the most serious downstream effects in Magic — and frankly — NBA history.

Duncan’s then-girlfriend and now-ex-wife asked head coach Doc Rivers if family members were allowed to ride with the team on the team plane. A seemingly innocent question that Rivers would unfortunately respond to incorrectly.

He informed her this would not be permitted as only the team and front office members were allowed access to those flights and family would have to travel separately.

While never officially confirmed by Duncan or his brass themselves, this is the moment NBA fans, former Magic players and front office members alike believe changed everything.

Duncan took the weekend to consider his choice. Gregg Popovich and the Spurs got the last word. He flew to meet with Duncan in his home on the U.S. Virgin Islands. Hall of Fame center David Robinson cut a Hawai’i vacation short to join the last-ditch recruiting pitch.

That proved enough to sway Duncan to stay in San Antonio. He re-signed with the Spurs and won four more championships. McGrady would never make it out of the first round in Orlando and to this day the Magic are still looking for their first-ever NBA Finals Championship.

What could have gone differently?

Put simply, Doc Rivers could have answered that question any other way and it might have been different. Allow family members on the plane, say that it is a rule that you are willing to revisit. Heck, just lie.

From those who were in attendance, it sounds like the energy shifted the second this question was answered by Doc Rivers. So, what if it was answered differently?

In an era of the NBA where the term “Big 3” was not commonplace, The Orlando Magic were close to embracing a trend that would become a hit in the NBA a decade later. Tim Duncan, Grant Hill and Tracy McGrady on paper would have immediately made the Magic into Finals contenders and a staple in the Eastern Conference playoff picture for years to come.

Even if Hill was never fully healthy (a reality Magic fans unfortunately did see play out in real time) the idea of McGradyand Duncan sharing the same lineup is a fascinating and exciting one.

Final prediction

Knowing that Tim Duncan would ultimately go on to win five NBA Finals while also carving out a career as potentially the best power forward the game has ever seen, it is hard to believe Duncan could not have found a path to a Finals series or two in Orlando, especially in the watered-down Eastern Conference.

Pairing his mistake-free, but sometimes less-than-exciting brand of basketball, with the high-flying and athletic Tracy McGrady would have had Orlando claiming one of the more captivating dynamic duos in the history of American pro sports.

Duncan likely would have brought a championship pedigree to the Magic brand and ended his career as one of the best, if not the best, Magic player of all time.

Instead, he did all that for San Antonio and is the sole reason Doc Rivers now probably lets players family members ride on the team plane — which he did when he won the title with the Boston Celtics in 2008.

Top 5 what-if’s in Orlando Magic history

What If Courtney Lee did not miss the 2009 Finals Game 2 buzzer-beater?

What happened?

Game 2 of the 2009 NBA Finals was a classic.

The Los Angeles Lakers had a 1-0 series lead and both teams went back and forth until regulation came down to its closing seconds. In a tied contest, Hedo Turkoglu blocked Kobe Bryant on a would-be game-winning shot before calling a time-out with 0.6 seconds remaining.

From the half-court sideline, Hedo Turkoglu slapped the ball to inbound, Courtney Lee dashed from the top of the key past a well-placed Rashard Lewis screen and received a great pass from Turkoglu for an open lay-up.

The play design worked to perfection. But the ball did not go in (Pau Gasol goaltends aside). Instead, it would bounce off the glass, over the rim, and into the hands of a soaring Dwight Howard as the buzzer sounded, sending Game 2 to overtime in Los Angeles.

In overtime, the Magic would fall to the Lakers 101-96 and take a 2-0 deficit into Game 3. While the Magic would go on to win their first-ever Finals game at home in Game 3, they would ultimately lose the series 4-1.

The Magic would spend the next couple of seasons attempting to reshuffle the deck before having an ugly breakup with Howard in 2012. The former Magic center made a move that was all too familiar to Magic fans and was off to Los Angeles to play for the Lakers.

The franchise has been fighting its way back to relevance ever since.

What could have gone differently?

What if Courtney Lee’s Game 2 buzzer-beater was good? What if Orlando’s first-ever Finals win came in Game 2 on one they stole in Los Angeles?

In hindsight, the Magic’s chance to win the series felt like they plummeted after Game 2.

According to LandOfBasketball.com, teams down 0-2 in an NBA playoff series win less than 10 percent of the time, a statistic that makes the Game 2 loss for Orlando far more frustrating.

It is often forgotten the 2009 Magic were at the time the best 3-point shooting team in NBA history and had the most dominant inside force in modern basketball. They did not make it to the Finals by accident. They just had to go against one of the best ever to do it when they got there.

Had the Magic stolen Game 2 in Los Angeles and gone back to Orlando with the series tied 1-1, the Central Florida home crowd would have been electric. If you can imagine there was a road for the Magic to go up 2-1, and there was certainly a path to a Finals victory from there.

Even if the Magic had not won the series, had it been more competitive, Orlando probably does not let key pieces from their playoff run like Rafer Alston, Hedo Turkoglu or Courtney Lee move on in the fashion they did.

Or maybe they still do but find better pieces to surround Dwight with on another title run. Maybe Howard handles the following seasons differently and never leaves at all.

Final prediction:

The likeliest scenario here is the Orlando Magic probably still lose the 2009 Finals to Kobe Bryant and the Los Angeles Lakers. Even if Orlando went up 2-1, Bryant was a man-possessed on that run and it never felt like he was not the best player in the series.

The Magic even down 2-0 had their chance to tie the series. But they gave up a 3-pointer to Derek Fisher in the dying seconds (after a pair of missed free throws from Dwight Howard) and then another 3-pointer in overtime from Fisher to cement a 3-1 deficit.

There were plenty of turning points throughout that series that could have drastically changed Magic history.

Where it gets interesting is considering how management may have changed some of the moves they made after the Finals loss. And while it certainly would have, the result of this timeline probably is not much different than our own.

The reality is the 2009 Magic team was ahead of its time in some ways but existed at a bad point in history in others. It could have had a better shot to win a title in some seasons and there are others it would not have come close to making the Eastern Conference Finals (such as if Kevin Garnett were healthy for that seven-game second-round series against the Boston Celtics).

Even if it did not amount to winning the first title in franchise history, it is fair to say winning another Finals game probably would have helped prevent Dwight Howard’s ugly departure a few years later.

If the Magic lose the series in six or seven games instead of five, they probably retain many of the pieces they let go and run things back with the same or a similar team. With that added level of trust and camaraderie from a former Finals team, things probably do not break down as badly as they did between Howard and the organization.

Ultimately the Magic are still probably without a championship if Courtney Lee makes the Game 2 buzzer-beater in 2009 – but how Dwight Howard and Stan Van Gundy depart, as well as being a bottom-feeding team for the 10 years that would follow, likely play out in a much more positive way for the Magic than they did in our reality.