What if Shaq and a Healthy Penny Hardaway Stayed Together?

There might not be an NBA player who played with a better collection of teammates than Shaquille O’Neal.

He played with Kobe Bryant, Karl Malone and Gary Payton in Los Angeles, Dwyane Wade and Alonzo Mourning in Miami and Steve Nash and Amar’e Stoudemire in Phoenix.

Then later in his career there was LeBron James in Cleveland and Boston’s “Big Four” of Kevin Garnett, Paul Pierce, Ray Allen and Rajon Rondo.

But before all of those hall of fame players, there was Anfernee “Penny” Hardaway who O’Neal teamed up with during his days with the Orlando Magic. Though Penny may not be a household name these days, he needed no introduction during the 1990’s.

Everyone knew Penny Hardaway in the 90’s, it was hard not to. He had his own Nike sneakers, a puppet named “Lil’ Penny” that took the nation by storm. Oh and he was one of the league’s most exciting stars. His pinstriped number one Magic jersey was one of the top selling jersey in the mid 90’s as well.

On the court, Penny was a rare point guard. Standing 6’7″ the initial comparison was to Magic Johnson, but their games were not very alike. While not Magic, Penny was dynamic in his own right and was on a hall of fame trajectory prior to his injuries that derailed his career.

So what if Penny had stayed injury free? Does Shaq stay in Orlando? Do they win a championship before Shaq eventually outgrows Orlando? Based off the answer Shaq gave in a 2018 interview with CBS, he certainly believes they could have.

“All I was thinking was [we were] the new Magic and the new Kareem. When we played together it was awesome. He was Kobe before Kobe. So I think if we had stayed together we definitely would have gotten one. Maybe two.”- Shaquille O’Neal.

Early years of Shaq and Penny


The first three seasons of the Shaq and Penny duo were dynamic. By 1995-96 Penny made back to back All star games averaging 21 points and 7 assists per game. Averaging 27 points and 12.5 rebounds per game, and making the all star game all 4 years of his career, Shaq has already cemented place in the league.

The duo lead the Magic to their first postseason berth in 1994 and then an NBA Finals appearance the following year. However, they were swept by Hakeem Olajuwon’s Houston Rockets. Unfortunately that was the short lived peak of the duo as Penny began facing injuries soon after, and Shaq went to Los Angeles in 1996.

What if things were different?

Let’s reimagine the offseason when Shaq left for the bright lights of Los Angeles. This time he signs an extension with the Magic, putting faith in both the organization and Hardaway. Hardaway also avoids the string of injuries and is a healthy blossoming star.

The Magic’s taste at another NBA Finals appearance would be on hold as Michael Jordan and the Bulls were in the process of their second three-peat. There was just no way any team was getting in the way of the Bulls dynasty for those three season. But in 1999, the year after Jordan retired for the second time, the window would be open.

Rather than the New York Knicks representing the Eastern Conference in the finals against the San Antonio Spurs, it is Shaq and Penny’s Magic.

The Magic likely bring the Magic their first NBA title against the David Robinson and young Tim Duncan led team. Penny would have dominated the back court matchup against the 5’10” Avery Johnson and un-athletic Steve Kerr.

There was no stopping prime Shaq, he was single handily destroying teams. With the Eastern Conference post MJ being so weak, it is safe to say the conference belonged to Orlando for as long as Shaq was there. By the 2000 NBA season, Shaq has become the most dominant player the league has ever season. I expect the Magic to go back to back as NBA champions, winning the 2000 title, capping off his first MVP season.

The Shaq and Penny Split Still Occurs

How long could the big fish stay in the small pound that is Orlando? There is only so many times you can go to Disney a week and there is not much else to do in Orlando.

Despite the success the duo had in Orlando, I don’t See Shaq and Penny going on a Shaq and Kobe type run. I can’t See Shaq staying in Orlando long enough for them to even attempt a three peat.

So I think Shaq still ups and leaves Orlando after the 2000-01 NBA season. He would have got too popular, too famous to live comfortably in a small market city with nothing really happening. Plus the rise of Kobe into a top level player combined with the attraction of Hollywood would for sure lure Shaq to Los Angeles.

Regardless, Shaq’s legacy in Orlando would be great. He put the franchise on the map, winning two titles. He also leaves them in good hands with a healthy Penny Hardaway. While still being salty that they lost an all time greta player, the wound wouldn’t be as deep knowing Penny was there to carry the weight of the franchise.

While doing so, he would be on a hall of fame trajectory and one day be elected to the prestigious group. Going down as one of the best and most unique guards of his era, the legacy of Penny would be more than “what if” scenarios.

In case you Missed them:

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Unappreciated players of the 2000’s 


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