The Dynasty that Never Was: the 1990’s Orlando Magic

We remember the 1990’s as a great era of NBA history. Though controlled by Michael Jordan and the Bulls, the league was full of talented teams and dominant centers. But there’s one team that doesn’t seem to get much credit for the role they played in this era. The ONLY team to eliminate Jordan from the playoffs in the 1990s: Orlando. One of the league’s newest expansion teams, a few smart moves and a stroke of luck found them in the NBA Finals… but just as quickly as it came, the Magic ran out. Enjoy the story of Shaq, Penny, and the 1990’s Orlando Magic.

Chapter 1: The Start

Whenever a sports league chooses to expand, the new franchises start in a tough spot. In 1989, the NBA decided to add two new teams, expanding from 23 to 25. The cities chosen were Minnesota and Orlando. Each other NBA team got to protect eight of its players, so even the best players on the expansion teams were the ninth best players on another team. Of the twelve players that Orlando drafted, only two would stick around for more than three years. The odds really were stacked against them.

The name for Orlando’s basketball franchise was selected eight months before the NBA even announced the cities that would be getting teams. Orlando businessman Jim Hewitt and former Philadelphia 76ers general manager Pat Williams were lead lobbyists for Orlando’s potential franchise. In 1987, they held a contest in the newspaper for fans to submit ideas for the name of a potential team. A total of 4,296 entries were submitted and a committee narrowed it down to four finalists — the Heat, the Tropics, the Juice, and the Magic. During this process, the GM, Pat Williams, took his 7-year old daughter to visit Orlando. As they awaited their flight back home, she said “I really like this place. This place is like Magic.” Sure enough, Magic was also the name the committee ended up choosing. Many give the 7-year old credit for naming Orlando’s NBA franchise, but there’s no official causation between her comment and the committee’s decision.

As you may imagine, the inspiration for the name was partially inspired by “Magic Kingdom”, the prize park of Disney World, Orlando’s dominant tourist attraction. In the summer of 1989, the Magic were born. Orlando and Minnesota took turns plucking benchwarmers in the expansion draft, and were given picks 10 and 11 in the NBA draft. With the 11th pick, the Magic selected Nick Anderson, a wing out of Illinois. The first rookie in the history of Orlando basketball, Anderson would hopefully become the cornerstone of the franchise.

Chapter 2: The Struggles

Coupled with their unconventional name, the Magic sported flashy striped uniforms, dancers, and modern music at their arena and games. But despite their modern style, the on-court product was a disappointment. In its inaugural season, Orlando went 18–64, the 2nd-worst record in the NBA. No Magic player reached 20 points per game. The Magic allowed 119.8 points per game, last in the league by far. That summer, the Magic drafted Dennis Scott, a forward out of Georgia Tech, to pair with Anderson.

He would go on to average 16 points in his rookie season, but it was another player who broke out for the Magic: Scott Skiles. The 26-year old point guard averaged 18 points and 8 assists, and won the NBA’s Most Improved Player award. That season, Skiles also broke the NBA record for assists in a game, dropping 30 dimes against Denver on December 30, 1990. The Magic finished the season 31–51, but there was some hope in Orlando with Skiles and Dennis Scott.

That summer, with the 10th pick, the Magic drafted a center named Brian Williams, one of the murkiest characters in NBA history. Williams struggled with depression throughout his entire career, attempting suicide numerous times. He would be traded away from Orlando after two seasons, and ended up winning a championship with Chicago. After that, he legally changed his name to Bison Dele. Dele played one season for Detroit under his new name, posted career highs, and then retired at the age of 29 to travel the world, forfeiting the final $35 million on his contract. Dele and his brother would settle on the island of Tahiti, and in 2002, they took off on a sailing expedition and never returned. When the brother was caught trying to cash a check under Bison Dele’s name, the FBI finally caught him. Before investigation, he committed suicide in the hospital, and Bison Dele’s body has not been found to this day.

In the 1991–92 season, many of Orlando’s veterans were beginning to decline, and the Magic finished the season 21–61. Nick Anderson and Dennis Scott both looked promising, averaging 19.9 points each, at 23 and 24 years old. But they and Dele were the only players under 27 to average twenty minutes. It was clear that the Magic needed a change. They needed to get younger, and they needed a superstar.

Chapter 3: The Savior

And in the hot Orlando summer of 1992, that’s just what they got. A 7 foot 1, 300 lb superstar, to be exact. A superstar on the court, and off of it, a superstar in movies, in the rap game, and a superstar analyst. The Magic, got lucky in the lottery, and landed the #1 overall pick. It was a no-brainer. Shaquille O’Neal was coming to save Orlando basketball.

The expectations couldn’t have been higher for Shaq in his rookie season. And with a city on his shoulders, he delivered. With the re-emergence of the inconsistent Scott Skiles, and Nick Anderson and Dennis Scott fitting into roles around O’Neal, the Magic became a respectable NBA team. No longer a joke or gimmick, Orlando finished the season at .500, 41–41. Rookie Shaq easily won rookie of the year, averaging 23 and 14, Skiles posted 15 points and 9 assists, Anderson averaged 20 again, and Scott added 16. However, the Magic’s .500 record wasn’t quite good enough to guarantee a playoff spot. Tied with Indiana for the 8th seed in the East, the NBA went down its tiebreaker list. The two teams split the first four tiebreakers, and the result was decided by point differential in their head-to-head games, the NBA’s fifth tiebreaker. That went to the Pacers, and the Magic’s season was over.

Orlando really is as mystical as a major US city can be. The palm trees and perfect weather create the atmosphere for magic, and the theme parks inspire visitors to believe in miracles. And in 1993, the Magic got one. Going into the NBA Lottery with the worst chance at the #1 pick, Orlando got some ping-pong ball magic, and won the lottery. Enchantment was in the air again. The city’s 7 foot savior would get a running mate. And everyone was sure they knew who it would be.

Chapter 4: The Swap

The Fab Five took college basketball by storm. They played for the University of Michigan in the early 90’s, and many consider them the greatest recruiting class in NCAA history. In their freshman year, the 6-seed Wolverines shocked the nation by reaching the title game, where they fell to a Duke team that had gone wire-to-wire as #1 in the AP Poll. Only one team has done that since.

All five returned for their sophomore year. UM was ranked #1 before the season, and they met expectations, finishing 26–4, with a 1 seed in the tourney. Playing the role of the favorites, Michigan delivered again, making it back to the title game. This time, they faced North Carolina. We all know the infamous ending to that game. Chris Webber calls a timeout while the Wolverines are out of timeouts, down by two with 11 seconds to go, and the Tarheels win.

But Webber had been Michigan’s star player all season. Even his teammate Jalen Rose, who wasn’t lacking confidence, admitted “We were off all night, but we were still going to win and were going to win because of Chris. Then we weren’t.” Rose’s viewpoint mirrors that of everyone who had been watching all season. Webber was a first team All-American. No other Wolverine made first or even second team. He ended the season averaging 19 points, 10 rebounds, 2.5 assists, and 2.5 blocks, while shooting 62%. It was an outstanding season, and everyone saw him as the clear #1 pick in the NBA draft.

That is, everyone except the team that would be making that pick. As fans dreamed of a Shaq and Webber duo, the Orlando front office and Shaquille O’Neal himself were secret admirers of a different prospect: Anfernee “Penny” Hardaway, a 6’7” point guard out of Memphis. GM Pat Williams told this interesting pre-draft story. “We brought in Webber twice, and I think we had a very good handle on him,” Williams said, “But Penny Hardaway would not accept the fact that we were going to take Webber. He kept calling us, even on that last weekend before the draft, saying, ‘I will come back. I will do whatever you guys want. I am your player, even though you may not know it.’ Hardaway and Shaq had co-starred in the movie Blue Chips just a year before. Clearly, Penny wanted to team up with the Big Diesel, and most assume that Shaq wanted Penny too, and his opinion was highly valued in the Orlando front office. In the 90’s there were very few restrictions on pre-draft workouts. Intrigued by Penny’s comments and encouraged by Shaq’s endorsement, the Magic brought Hardaway in for a 5 on 5 scrimmage including Shaq and other Orlando players. They were blown away.

However, the Magic knew that most teams would take Webber #1, so they decided to take him, then trade him for Penny after the draft. The Warriors, picking 3rd, needed a big man. They offered the hefty price of three future first-rounders for Webber… if Penny were to fall to them at 3. On draft night, the Magic hosted an event where fans could come watch the picks go down. GM Pat Williams went onstage and announced the team would take Chris Webber, as expected. The fans went wild. The Twin Towers, Shaq and Webber, were assembled. But little did the fans know, the Magic had their fingers crossed backstage, and took a sigh of relief when Philadelphia took Shawn Bradley 2nd. The trade was happening. Williams then had to go back on stage, and announce the trade to the fans. He later said, “Well, the fans were just ready to revolt. I had to slink off the stage. They were ready to tear our arena apart.

But Orlando couldn’t be more excited about the deal. They got the player they wanted plus three first-rounders. The Shaq and Penny duo drew immediate Kareem and Magic comparisons, a dominant center and a tall point guard. With those two, Nick Anderson, Dennis Scott, and the additional draft picks, Orlando was set for the future.

Right before the 1993–94 season, the NBA world was shaken by one of the most surprising announcements in the history of sports. Michael Jordan announced his retirement from basketball at the age of 30 and coming off of three straight NBA championships. All of the sudden, the Eastern Conference, and the NBA title, was up for grabs.

Chapter 5: The Success

The 1993–94 Magic took a leap. Shaq, only 21 years old, averaged 29.3 points and 13.2 rebounds. He was 2nd in the NBA in scoring and 2nd in rebounding in only his 2nd season. Rookie Penny averaged 16 points, 7 assists, and 5 rebounds. Nick Anderson averaged 16 points with 5 rebounds, Dennis Scott scored 13, and Scott Skiles posted 10 points and 6 assists. The Skiles — Hardaway — Anderson — Scott — O’Neal starting five was one of the best in the league in an era full of talent. Orlando finished 6th in scoring, 2nd in three-pointers made, and 3rd in field goal percentage. They were exciting, and they were good, winning 50 games and finishing as the 4 seed in the East.

Finally, the Orlando Magic would be in the playoffs. The city was buzzing as it prepared for its first ever playoff series, a five-game matchup with the Indiana Pacers, the same team they had tied a year ago. Game 1 in Orlando was a close, low-scoring game. The Magic led by eight after the third quarter, but Indiana held them to 14 in the fourth, and came out with a one-point win, 89–88, despite Shaq’s 24 and 19.

Game 2 was also in Orlando. Indiana began to foul Shaq, who shot 9 of 18 from the free throw line, and only 3 of 8 from the field. Nick Anderson scored 22, but it was Penny Hardaway who went off for 31. But Indiana’s Reggie Miller one-uped him with 32, and the Pacers hung on to win the game, 103–101. At this point, Scott Skiles had been totally frozen out of the rotation. He finished the series with 9 points and 5 turnovers, playing only 20 minutes total and taking a DNP in Game Two.

After dropping two close games at home, the dejected Magic went into Conseco Fieldhouse in Indianapolis for Game 3, but the series might as well have been over already, Reggie dropped 30 again and the Pacers finished off the sweep, 99–86.

The season had been a big step in the right direction for Orlando, but they clearly needed one more piece. They had the talent, but they were incredibly young. Shaq was 21, Penny 22, Anderson 26 and Scott 25. All four had no playoff experience coming into that Indiana series.

Enter: Horace Grant. A three-time NBA champion, coming off an All-Star season, he was the perfect use of Orlando’s cap space. To clear the money, the Magic shipped Scott Skiles and a first round pick to Washington for a bench player. With Grant in the ’94-’95 season, the Magic went 57–25. Shaq averaged 29 and 11, Penny 21, 4, and 7. Grant put up 13 and 10, Anderson 16, 4, and 4, and Scott scored 13. At 22, Shaq was the NBA’s leading scorer, and finished 2nd in MVP voting. The Magic finished 1st in the NBA in points and assists, and they went into the playoffs as the #1 seed in the East, poised to make a deep run.

In March 1995, with less than a month to go in the season, a wrinkle was thrown into Orlando’s magical season. The NBA league office received a fax. It was two words long. “I’m Back”. Michael Jordan was returning to basketball.

In the first round, Orlando was matched up with the Boston Celtics. The Magic made a statement in Game 1 with an astounding 124–77 victory. To this day, that 47 point deficit is the 3rd largest playoff win in the post-merger NBA. The Magic would go on to win the series 3–1.

In Round 2, Orlando met the Chicago Bulls. MJ had only played 17 regular season games, but in the first round he reminded America of his dominance, averaging 32.3 points, 6.5 rebounds, and 5.8 assists. He also shot incredible percentages, 50% from the field and a staggering 47% from three, 8 for 17 in the four games. Wearing #45, as he had been since his un-retirement, the red-hot MJ and the Bulls were heading to Orlando hungry for title #4.

On May 7, 1995, the Eastern Conference’s 2nd round series were beginning. That night, Reggie Miller scored 8 points in 9 seconds and gave Spike Lee the choke signal. And the other matchup, Magic/Bulls, was equally as exciting. It was a close game all the way through, and with 18 seconds left, Jordan was taking the ball up with a 1 point lead. He never saw Nick Anderson coming. Anderson ambushed MJ from behind, poking the ball loose. Penny grabbed it and ran the 2 on 1 break, finished by a Horace Grant dunk with 6 seconds left. The Bulls turned it over, and two free throws made it a 94–91 final, Orlando wins.

In the locker room after the game, Nick Anderson was asked about his steal. He said, “№45 doesn’t explode like №23 used to. №45 is not №23. I couldn’t have done that to №23.” So what did Jordan do? You guessed it. Came out for Game 2 wearing #23. And he backed up it, dropping 38, 7, 4, 4, and 4 with 57% shooting. in a Bulls win. 104–94 final. The series was heading to Chicago knotted up at 1–1.

In Game 3, MJ went off again, with 40, 7, and 4, but a mulit-headed scoring effort gave the Magic the edge. They shot 50% from the field, and Shaq, Penny, Grant, and Anderson all scored 18+. Game 4 felt like a must-win for the Bulls, and they responded. 26 from Jordan, 24 from Pippen, and the series went back to Orlando, tied again. Decisive Game 5 was in Orlando. Jordan delivered again, 39 points, 54% from the field, but once again, the Magic came through. Penny, Shaq, Grant, and Scott all scored 19+, and the Bulls couldn’t stop their ball-sharing style.

In Game 6, the Magic won the series in Chicago, as four players hit 18+ yet again. Shaq finished the series averaging 24 and 13, Penny 19 and 8 assists, 18 and 11 for Grant, and 15 points per game for both Anderson and Scott. Michael averaged 31 and 7 over the series, shooting 47%, but the Bulls weren’t ready. It was Jordan’s first playoff exit since the 1989–90 season, and it would be his last in a Bulls jersey.

In the conference finals, Orlando faced another daunting challenge. The Indiana Pacers were coming off a grueling 7-game series vs. New York, and they were ready to get their chance in the NBA Finals. There was history between Indiana and Orlando. The Pacers had eliminated the Magic a year before, and the two tied for the 8th spot the season before that. Ready to finally get past Indiana, the Magic protected home court. In Game 1, Shaq dropped hung 32 and 11 on 11–16 shooting. Somehow, he presented an encore in Game 2, with 39 and 10 on 15–21 shooting. That’s 71%. Orlando was ahead 2–0, but you know what they say. The series doesn’t start til the home team loses a game. The Pacers took Game 3, and all of the sudden they had a chance to even things up. Game 4 was a slugfest. There were 52 fouls in the game. Each team had three players with 4 fouls or more, and Horace Grant and Shaquille O’Neal would both foul out. Replacing Shaq was 39-year old player coach Tree Rollins. With 13 seconds to go, Orlando’s Bryan Shaw hit a three to take the lead. Reggie came down and hit a contested three right back. The Magic had very few options on offense, and a Penny isolation resulted in a crazy contested fadeaway to take the lead back again with two seconds in the game. Indiana had one last chance for a game-winner, and drew up a play for Rik Smits, who was guarded by the 39-year old player coach Rollins, who averaged only 5 minutes in that postseason. Smits got Rollins on a pump fake, and hit a buzzer beater for the win. Series tied.

Back at home for Game 5, Shaq re-established his dominance, dropping 35 and 13. Orlando won the game, and had a chance to clinch the series back in Indianapolis. But Reggie and the Pacers had other thoughts. Miller scored 36 on 6–10 from three, Rik Smits added 22 and 10, and for the 6th straight game, the home team won.

In Game 7, Orlando held Reggie to 5 of 13 shooting, and Indiana shot 21% from deep. All five Magic starters scored in double figures, and they shot 57% as a team as opposed to Indiana’s 37%. It wasn’t close. 105–81, and the Magic were heading to the NBA Finals.

Chapter 6: The Shock

Basketball’s biggest stage. Orlando was here. A 5-year old franchise already in the NBA Finals. Whether it was great front office work, incredible lottery luck, or magic in the Orlando air, who can really say. But ready or not, the reigning champion Houston Rockets were coming to town for Game 1. Two of the best centers in the game would be battling it out, Shaquille O’Neal vs. Hakeem Olajuwon. In Game 1, Hakeem dropped 31, 7, and 6 assists. Shaq? 29, 16, and 9 assists. With around a minute to go, Shaq got Hakeem jumping on an up and under, and put the Magic ahead, 110–107. The teams traded misses, and Houston was forced to foul with 11 seconds in the game, sending Nick Anderson to the line with a three point lead. All he had to do was make one. Just one. That would make it a two possession game.

Anderson’s first free throw missed off the front rim. Now he had to make the second… but he missed it off the front rim. The rebound went through the hands of the Rockets, up in the air, and it fell into Nick Anderson’s lap. He was fouled again, 7 seconds left. Another chance. All he has to do is make one. Anderson bricks the first free throw. That’s three in a row. With one last chance, he rises, shoots, and bricks it again. 0 for 4. Houston timeout, and Kenny “The Jet” Smith hits a buzzer beater three to send it to OT, where the Rockets win the game, 120–118.

Orlando came up just short in Game 2. Shaq dropped 33, 12, and 7. Penny 32, 5, and 8. But the rest of the Magic went 15 of 42 from the field, while the duo went 24 of 43. That’s 56% for Shaq and Penny, 36% for the rest of the team. The two stars scored over half the Magic’s points on the same amount of attempts. The role players couldn’t come through. Meanwhile, Hakeem drops 34 and 11, and the Rockets leave Orlando with a 2–0 lead.

Despite admirable efforts from Shaq and Penny, the Rockets would go on to sweep Orlando, 4–0. Hakeem averaged 33, 12, 6, 2, and 2, eye-popping numbers. Shaq, Penny, and Horace Grant delivered for Orlando. 28, 15, and 6 for Shaq on 60% FGs. 26, 5, and 8 for Penny on 50%. 14 and 12 for Grant, on 53%. Nick Anderson and Dennis Scott shot 36% and 31% respectively. But the craziest stat is the fact that Shaq was 22 and Penny was 23. It was Shaq’s third season and Penny’s second. Despite the loss, Orlando was set to challenge Jordan until his retirement with such an incredible duo.

Nick Anderson shot 70% from the line that season. It was uncharacteristic for him to miss four free throws in a row. How fitting that the first player Orlando ever drafted is the one to choke away their first Finals appearance. To be fair, Game 1 isn’t the entire series, but it was Anderson and Scott, the first two Magic rookies, who lost the 95 Finals for their franchise. I guess everyone’s luck runs out at some point.

Chapter 7: The Sweep

Believe it or not, the Magic came back stronger in 1995–96. With the same core, they won 60 games, Shaq made his 4th All-Star game in his 4th season, and Penny made it too, his 2nd appearance in 3 seasons. The 60–22 Magic were the 2 seed in the Eastern Conference. They swept Detroit in Round 1, then beat the Hawks in 5, and in the conference finals, met a familiar foe: MJ and the Bulls.

After last year’s tough loss at the hands of Orlando, the Bulls responded by breaking the NBA’s win record, going 73–9. Jordan won MVP, and Chicago was once again the team to beat. But the Magic were 1–0 in playoff series against MJ, and they were confident they could get back to the Finals, where they had unfinished business.

The Bulls blew out Orlando in Game 1, 121–83, and Horace Grant suffered an elbow injury. The Magic assumed it was just a sprain, but X-Rays revealed hyperextension, and he was ruled out for the season. Orlando fought in Game 2, but came up short. In Orlando, the Bulls held the Magic to 67 points in Game 3, and finished them off in Game 4.

Once again, Shaq and Penny played well. O’Neal averaged 27, 11, and 4 in that series on 62% shooting. Hardaway averaged 26, 4, and 5, shooting 48%. Once again, it was Scott and Anderson that struggled. Scott shot 27% and Anderson 31%.

With the season abruptly over, all eyes turned to the summer and Shaquille O’Neal’s free agency.

Chapter 8: The Sellout

All talks between Shaq and Orlando were centered around the big man re-signing. As long as the Magic offered enough money, it was a no-brainer for the Big Diesel to stick around. The Magic had Shaq’s Bird Rights, meaning they could go into the salary cap to sign him. Because there was no max salary, Orlando could have “thrown a blank check at Shaq… and I believe, ended the negotiations before they started”, according to Joel Corry, a consultant working with Shaq’s agent at the time.

But instead, Orlando offered Shaq $54 million over 4 years, less than Alonzo Mourning and Juwan Howard had just received. When O’Neal was insulted by the offer, the Magic defended themselves by “criticizing Shaq’s rebounding and defense”, according to Corry. He argues that Orlando’s mistake was pitting themselves as Shaq’s enemy, and negotiating against him, rather than taking care of him.

But they weren’t the only team that wanted the All-NBA 24-year old. The Lakers got into the mix, trading expensive Vlade Divac to Charlotte for a pick. This trade was meant to create space for Shaq. With the pick, LAL took an 18-year old shooting guard named Kobe Bryant.

At this point, Orlando started to offer Shaq more money… but not a lot more, just enough to outbid the other teams. Once again, not treating him like a franchise player. Things got worse when Orlando Sentinal conducted a fan poll, asking whether Shaq was worth $115 million. In an era where players were starting to see more and more money, fans were shocked and appalled by the numbers they were seeing, and 90% of Orlando fans voted “no”.

Between the fans’ disapproval, the disappointing amount being offered by Orlando, and the adversarial style through which the Magic were negotiating, Shaq had had enough. He signed with the Los Angeles Lakers in July 1996.

Throughout the NBA’s history, there has been “Restricted Free Agency” for players coming off of their first contract, like Shaq was in ’96. This concept allows the team that drafted the player to match any contract offer, and keep the player. However, one year before Shaq hit the market, players threatened a lockout over the CBA negotiations, and Restricted Free Agency was eliminated as part of the deal.

Two years later, Restricted Free Agency was reintroduced. Shaq’s free agency came in the only window where Restricted Free Agency didn’t exist. The only time in the history of the league, that this would be possible, was between 1995 and 1998.

In the first season without Shaq, the Magic finished with a barely winning record and were eliminated in the first round. Penny was an All-Star again. But in 1997, at 26 years old, he suffered his first of many knee injuries, playing only 19 games. He was never the same. Never made another All-Star game, never reached the same numbers.

Chapter 9: The Speculation

So what are the odds of Nick Anderson missing all four of those free throws? Or Shaq’s free agency coming in the only 3-year window in NBA history where he would be unrestricted?

What would’ve happened if Anderson makes one? Orlando would be up 1–0, maybe Anderson wouldn’t shoot so awful in the series and the rest of his career. Or what if Horace Grant wouldn’t have hurt his elbow in the Chicago series? What if Shaq had re-signed?

The possibilities are limitless, and the potential was sky-high. The Magic made it to the Finals with 22-year old Shaq and 23-year old Penny, both All-NBA first team at that incredibly young age. They could’ve challenged Jordan. They could’ve taken over the East. They could’ve won multiple championships.

But you know what they say. Easy come, easy go. It was Magic that brought these two young superstars to an expansion team in Orlando, and at some point, the luck runs out.