Recently, I came across the “ESPN 30 for 30” Documentary of the Orlando Magic from the mid-90’s. There are many people that consider this team the best to never win a championship.

They were a cultural phenomenon with the style of their uniforms. Next, to Michael Jordan, Penny and Shaq were the most marketable stars in the league at this time. Shaq and Penny were fan favorites in the NBA Jam video games. Penny had his alter-ego Lil’ Penny (voiced by Chris Rock). The Magic had all of the pieces in place to take the place of the Jordan-led Bulls as the next NBA Juggernaut.

The tag-team of Shaquille O’Neal and Anfernee “Penny” Hardaway were extremely promising. Penny Hardaway was a Point Guard that stood 6’7″. His size caused people to compare him to the legendary Earvin “Magic” Johnson because of his size. Magic himself was a Point Guard that stood 6’9″. People thought that he could even surpass Magic in some ways. Yes, Penny was that good. On the other hand, you have Shaq, who was a 7’1″ Demolition Machine. O’Neal was poised to become the Greatest Center of All-Time as he was heavily compared to the likes of Wilt Chamberlain and Kareem Abdul-Jabbar. Shaq would go on to become the closest thing to Wilt in the Modern Era, so all was not lost.

Since Shaq’s retirement, there has not been a Center that has come remotely close to achieving what he has achieved as players of his mold have become extinct. Today’s fans may only see him as an out of shape commentator joking with Charles Barkley on TNT, but Shaq was a menace in his younger days. When you are looking to build the typical basketball team, you would start with the Center and a Point Guard. Shaq and Penny fit those requirements perfectly.

Orlando traded Chris Webber on draft day for Penny to create that nucleus. This team was the biggest threat for his Airness heading into the future, as they were aiming for Chicago’s throne. They had all of the tools to be the 90’s Hip-Hop version of Showtime.

Then, you add supporting pieces around them such as Dennis Scott, Brian Shaw, Horace Grant and Nick Anderson that you could count on to get the job done. Horace provided the championship experience that they needed, as he won the first three championships being the third wheel on the aforementioned Bulls team.

Magic’s Lakers and Bird’s Celtics dominated and defined the 1980’s. Jordan’s Bulls defined the 1990’s. The Shaq & Kobe Era Lakers did that in the early 2000’s, along with Duncan’s Spurs. Orlando fans will always live with the painful idea what Shaq & Penny could have done for the Magic in the late 90’s heading into the new millennium.

The Magic had youth and a very strong upside in their favor. Shaq was one of the top two scoring leaders and a top 3 MVP Candidate in Jordan’s absence. They conquered the East, as Shaq basically made players like Patrick Ewing and Alonzo Mourning his whipping boys. The Magic went through teams like the Knicks, Hornets, and the Pacers on their journey. Orlando’s crowning achievement came when they defeated an all-time great Chicago Bulls team that won three straight titles.

In fairness, Jordan was still shaking off his rust as he was still not in the proper shape for Basketball. Unfortunately, this team lacked maturity. They lacked the experience and mental toughness to handle the mantle that was theirs to take. The Magic would lose to the Rockets in the Finals thanks to Hakeem Olajuwon. On top of that, Clyde Drexler & co, surprised rising star Penny Hardaway and the rest of his cast of characters as the Houston Rockets swept the Magic in the Finals.

To make matters even worse, Nick Anderson bombed from the free throw line as he missed all four free throws. Anderson was not Rick Barry or Larry Bird from the free throw line, but he was passable at 71%. Suddenly, Nick transformed into Shaq when he stepped up to the line as his misses were another crack in the team’s armor. Anderson fell apart psychologically and never recovered.

In 1996, Orlando went 60-22 as they were right after the history-making 72-10 Chicago Bulls Powerhouse. Penny was breaking out even more into a star, as both he and Shaq would make the 1996 Dream Team in the Summer.

Sadly, everything came crashing down in the 1996 Eastern Conference Finals. Chicago returned with a vengeance, as they defeated the young Orlando Team. The Chicago Bulls dominated the Orlando Magic by defeating them in only four games to advance to the NBA Finals. Meanwhile, Dennis Rodman rendered Shaq as ineffective. Orlando was once a team of promise, but they failed to reach their full potential. The Chicago Bulls continued to prove why they were the Best Team in Basketball during the 90’s. Michael Jordan would further cement his case as the Greatest Player of All-Time

The internal conflict would tear the team apart, as their Franchise Star would leave for Hollywood and establish his place among the great champions in NBA History with a new dynamic perimeter player named Kobe Bryant. They would become what Shaq and Penny should have become had things fallen into place. Shaq would become one of the top players of the 2000’s, as he would lead the Lakers to 3-Straight Championships. Shaq’s run in the Finals was comparable to Michael Jordan’s first three-peat years.

O’Neal was clearly a magnet to championship success, as he made any perimeter player around him better (Penny, Kobe, Wade). Shaq became the Shawn Michaels to Penny’s Marty Jannetty. He is, in fact, the most destructive force on a Basketball Court that this generation has seen. On the other side of the coin, the Orlando Magic would quickly fall on their face. In the span of one season, the Magic went from being in the Conference Finals to not making the playoffs.

Penny was given a larger load to carry because of the potential that he had. He was the flavor of the month. However, that flavor left a bad taste in everyone’s mouth as Penny’s body slowly started to break down. Hardaway would join the Phoenix Suns by 1999. He would show flashes of who he was but was never the same player as a result of injuries. O’Neal and Hardaway would cross paths in the playoffs, as Shaq’s Lakers destroyed Phoenix 4-1. Penny would look at Shaq and Kobe’s duo as a reflection of what he and Shaq once shared, as well as what they could have shared.

If the Orlando Magic stayed together?

The Magic were already second place in the Eastern Conference behind Chicago. Penny was coming off of his best season. Shaq was taking the throne as the Top Center in the league, as Olajuwon, Ewing, and Robinson would soon fade not long after that. However, Orlando Management told Shaq that he was not worth $100 million.

However, there were players like Alonzo Mourning and Juwan Howard that received that much money (Zo/$105 million, Juwan/$101 million respectively). Shaq may have had his issues controlling his ego, but he was well worth that kind of money. With all due respect to Zo and Howard, but they were not even in the same category as Shaq as players. They were not even in the same library as Shaq, let alone in the same book as him.

Shaq was drawing worthy comparisons to Kareem, Wilt, and Russell at the time. The NBA showed how much they invested in Shaq by naming him one of the 50 Greatest Players!! Even though the decision was premature at the time, Shaq fulfilled his potential and even more as he became one of the consensus Top 10 Players of all-time. With that said, Shaq was shortchanged as the team offered him $80 million instead. The way that they showed their “appreciation” or lack thereof was to underpay him. On the other hand, Jerry West offered Shaq a much greater deal that he richly deserved as the Lakers offered Diesel $120 million. The rest is history.

Orlando’s championships went out West. Let’s say that Orlando swallowed their pride and paid Shaq what he deserved. Then, they could bring in the right role players to take the places of Dennis Scott and Nick Anderson. If Penny stayed healthy, he could have had the storied career that Kobe Bryant has enjoyed. Instead, he has become an urban legend like Connie Hawkins.

If things continued to go well, they could have Tracy McGrady to continue the legacy. As long as the right personnel moves were in place, Orlando could have made their mark as one of the perennial dynasties in NBA lore. Even if they snatched at least two or three, that would be fine. Instead of joining the ranks of the greatest dynasties, this Magic team joined the ranks of the 80’s Rockets, 2000’s Blazers, and 2000’s Kings as teams that had what it took but shot themselves in the foot. They were a walking championship waiting to happen. Once again, “What if?”