San Antonio Spurs miss no. 2: Jason Kidd
Now, this is a bigger name. The Spurs rebounded just fine from losing out on Jason Kidd, going on to win two more championships in the following four years. But if the Spurs had signed Jason Kidd in 2003, who knows the level of dynasty the Spurs would have reached beyond its already lofty heights.
Fresh off the 2003 NBA Finals win at Kidd's expensive, the Spurs could have added that year's MVP runner-up to the team. This was a man who brought a team that featured Kenyon Martin as arguably their second-best player and featured guys like White Mamba Brian Scalabrine in prominent roles.
As someone who thinks that Tim Duncan could have excelled even further had he been surrounded by more perimeter shooting, defense, and playmaking from the guard positions, it really had me thinking Kidd would have been the ultimate missing piece of a trio that would have dominated the league for a decade.
What about Tony Parker? This is where it gets tricky. There were certainly rumors swirling that in 2003, the Spurs would have had to trade Parker to get the financial space needed to sign Kidd. But these rumors don't necessarily check out.
For starters, the Spurs have vehemently denied this, saying it was their plan all along to keep a Parker and Kidd backcourt with Manu likely maintaining his 6th man status. Coach Popovich and the front office even went a step further, saying the plan was to have Parker play as more of a slashing shooting guard on offense early in his career while learning firsthand from one of the best playmakers of all time in Kidd before ultimately taking over point guard duties.
The real reason Kidd never signed with the Spurs was he wanted to try winning on his own as opposed to going to a team with an established superstar, the same challenge Giannis Antetokounmpo took on earlier this year.
But Kidd would not win his sole NBA championship until years later in 2011 as somewhat of a shell of his former self after joining forces with Dirk Nowitzki and a deep Mavericks team. Kidd himself has since come out and regretted his decision in a major "what if" moment. You're not alone, Jason!