1 player at each position that the Spurs should have kept around

Shooting Guard - Jonathan Simmons (2015-2017)

Jonathan Simmons and Coach Gregg Popovich had a great relationship, and you could tell Pop thought a lot about Simmons beyond the court. When Simmons and the Spurs matched up, the two shared a genuine embrace almost every time.

By all accounts, losing Simmons was a tough pill to swallow for the Spurs. After first standing out with the Austin Toros, Simmons finally got an opportunity to play with the Spurs in 2015. When he got his chance, Simmons displayed fearlessness and was constantly playing tough on both ends of the floor, which Spurs coaches loved. Never averaging more than seven points in his two seasons as a Spur, Simmons still had a handful of big performances in his time.

You could tell by watching Simmons play that he could have been a part of the starting rotation if he had been given more floor time. But no matter how well he played, Simmons never got substantial minutes, prompting him to welcome the idea of signing elsewhere when he became a free agent.

Simmons would go on to sign a multi-year contract with the Orlando Magic, where he shined bright in his first season there, doubling his points per game total from the previous year. Simmons could be the biggest "what-if" on this list, regardless of where he is currently playing, which is overseas with the AI Riyadi Sporting Club in Europe.