With the 15th overall pick in the 2020 NBA Draft this October, the Orlando Magic have a chance to select a young player who can help the franchise escape the treadmill of early playoff exits, sub-.500 records, and high lottery picks that they have been stuck in for years.

The Magic made the playoffs in the last two years and are fresh from a first-round exit at the hands of the Milwaukee Bucks. But this relative success is a far cry from their best years in the league, which included a trip to the NBA Finals and ended when Dwight Howard left in the summer of 2012. 

Since then, the team entered a rebuild, and not all of their draft picks have panned out, continuing a long history of misses in the draft. The Magic also drafted players who went on to reach greater heights when they were traded to other teams like Chris Webber, Victor Oladipo and Domantas Sabonis.

Nonetheless, the team also had some success in the draft since the franchise joined the NBA in 1989, including the players who gave their fans countless memories and postseason success. Here are the five greatest draft picks in Magic history: 

5. JJ Redick

Taken by the Magic with the 11th overall pick in the 2006 Draft, Redick didn’t have a great start to his NBA career, averaging only six points in just under 15 minutes a game during his rookie season. The former Duke Blue Devil played for an Orlando team that was a playoff contender and didn’t give him a lot of playing time, which was compounded by his struggles on defense. 

Redick eventually hit his stride as he grew more accustomed to the NBA’s style of play. He adjusted into his role as a shooter that spaces the floor and gives Dwight Howard room to operate. He improved in each of his seven seasons with the Magic, putting up his best numbers in the 2012-2013 season, when he averaged 15.1 points on 45% shooting along with 2.4 rebounds and 4.4 assists per game.

Unfortunately, this was also when the Magic dealt him to the Bucks at the trade deadline. He would go on to play pivotal roles for the LA Clippers, Philadelphia 76ers, and New Orleans Pelicans, but Redick proved that the Magic made the right call by picking him on Draft Night in 2006. 

4. Nick Anderson

Anderson is likely still remembered for missing four free throws in the dying seconds in Game 1 of the 1995 NBA Finals against the Houston Rockets, but that shouldn’t take away the fact that he was one of the Magic’s best draft picks. With the franchise joining the league as an expansion team in 1989, Anderson was Orlando’s first-ever draft selection, as they took him with the 11th overall pick in the NBA Draft that year. 

Anderson quickly rewarded the franchise's faith in him by being one of the few bright spots on a Magic roster that experienced the growing pains of being an expansion team, averaging 11.5 points on 49% shooting during his rookie season.

Orlando’s early losing seasons gave them high draft picks like Penny Hardaway and Shaquille O’Neal. Anderson he fit into the role alongside the team’s stars as they became one of the league’s best young teams. Anderson would go on to play 10 seasons for the Magic, averaging 15.4 points, 5.4 boards, and 2.8 assists. Although he never made the All Star Game or won any major award, he proved that the franchise was on to something when they made him their first draft pick in their history.

3. Dwight Howard

Magic, Lakers, Dwight Howard

His messy exit from Orlando and his later career as a journeyman are what some people might remember from Howard, but he also gave the Magic some of their best years as a franchise. Taken with the first overall pick straight out of high school in the 2004 NBA Draft, Howard was immediately thrust into the spotlight as a 19-year old and delivered for the Magic. He led the team to five playoff appearances in his eight seasons in Orlando, while becoming not just a menace on the defensive end, but also one of the league’s best players.

At the time, the Magic were stuck in the doldrums since the days of Shaq and Penny, but big man out of Atlanta gave the team its longest sustained success as a franchise, including their second Finals stint in 2009. While in Orlando, Howard was a six-time All Star and won the Defensive Player of the Year Award three years in a row.

He made the All-NBA First Team five times and led the league in rebounding for four seasons. Despite going on to play for other teams, Howard remains the franchise leading in minutes played, points, rebounds, and blocks, firmly cementing his place as among the best Draft picks in team history.

2. Penny Hardaway

Magic, Penny Hardaway, Michael Jordan, Bulls

Fans eagerly anticipated who the Magic would pick in the 1993 NBA Draft to pair alongside young big man Shaquille O’Neal. So there was some surprise when Orlando traded first overall pick Chris Webber to the Golden State Warriors, who had selected Penny Hardaway out of Memphis at third overall. But Hardaway wanted to play with O’Neal, and he quickly proved that the Magic were right in their decision, as his game blended seamlessly to that of O’Neal. He averaged 16 points, 5.4 rebounds, and 6.6 assists his rookie year and helped the Magic reach the playoffs for the first time in franchise history.

In his six seasons in a Magic uniform, Hardaway was a four-time All Star and made the All-NBA First Team twice and the All-NBA Third Team in 1997. Together with O’Neal, he helped Orlando reach new heights, and continued to play at a high level even after he left. Some of his seasons in Orlando and later in his career were mired with injuries, but still doesn’t diminish what Penny was able to achieve when he played for the Magic. 

1. Shaquille O’ Neal

Magic, Shaquille O'Neal

Even now, more than 24 years after he last put on an Orlando Magic uniform, Shaquille O’Neal continues to cast a large shadow over the team that drafted him with the first overall pick in 1992. That was a night that changed the Magic franchise and gave them a franchise cornerstone that their team could build around.

He averaged 23.4 points, 13.9 rebounds, and 3.5 blocks in his rookie season, winning the Rookie of the Year Award and becoming the first rookie to be selected in the All Star Game as a starter since Michael Jordan in 1985. 

His dominance would continue in the succeeding years, as led the Magic to the playoffs in three of his four seasons, including their first Finals appearance in 1995. He went on to average 27.2 points, on 58% shooting to go with 12.5 rebounds and 2.5 blocks in his four seasons in Florida. He may have played just four seasons before bolting for the Lakers, but Shaq was also to do so much in such a short amount of time, making him the clear pick as the Magic’s best draft pick in its history.