10 Worst free agent signings in Orlando Magic history

Luke Ridnour Orlando Magic (Photo by Sam Greenwood/Getty Images)
Luke Ridnour Orlando Magic (Photo by Sam Greenwood/Getty Images) /
8 of 11
Jonathon Simmons, Orlando Magic
SAN ANTONIO,TX – NOVEMBER 4: Jonathon Simmons #17 of the Orlando Magic drives on Patty Mills #8 of the San Antonio Spurs at AT&T Center on November 4 , 2018 in San Antonio, Texas. NOTE TO USER: User expressly acknowledges and agrees that , by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ronald Cortes/Getty Images) /

The 10 worst free agent signings in Orlando Magic history

4. Jonathon Simmons

3 years, $20 million in 2017

Remember Jonathon Simmons? He burst onto the scene with the San Antonio Spurs in the middle of the 2010s, earning a shot at a bigger role with the Orlando Magic. It felt like a big deal that an up-and-coming player would give a rebuilding team like the Magic a shot.

That did not end well, though, and essentially ushered in the end of Simmons’ NBA career.

After going undrafted in 2012, Simmons battled his way through the barely solvent American Basketball League and the NBA D-League (that is what it was still called) before earning his chance with the Spurs. San Antonio poached him from Brooklyn’s Summer League squad in 2015 and Simmons earned Championship Game MVP honors with the Spurs, who quickly signed him to a real deal.

He was a key bench cog for San Antonio during his two seasons with the team, averaging about six points per game in each of the two years. He was offered a $1.6 million qualifying offer in 2017, but San Antonio withdrew that offer and let him walk.

Two days after the Spurs withdrew the offer, Orlando handed Simmons a three-year, $20-million contract. And for the first few months, that deal seemed to be a good one, with Simmons regularly dropping more than 20 points, including a career-high 29 in December. In February 2018, he soared even higher with a 34-point performance.

He managed to exceed that one more time and averaged 13.9 points per game in his first season in Orlando. But he continued to struggle behind the arc, which only got worse the following season when he shot 22.9 percent from three in 41 games, never scoring more than 18 in a contest.

Approximately halfway through the deal, the Magic sent Simmons to the Philadelphia 76ers for a couple of picks and Markelle Fultz. That may be Simmons’ best contribution to the Magic, as Fultz has proven to be a possible long-term backcourt option in Orlando.

As for Simmons, he played 15 more games with the Sixers that season and hasn’t appeared in an NBA game since. He currently plays for the Shanxi Loons in China.