6. Jason Kapono
Kapono was the second pick in the second round of the 2003 draft, and it took a few years and three different teams before the 6’8 forward broke out.
He was playing for the Heat in his fourth season where he averaged 10.9 points in 26.4 minutes per game while shooting 49.4 percent from the field and an absurd 51.4 percent on his 3-point attempts. The Heat were swept by the Bulls in the first round of the playoffs, and Kapono barely played, but that did not stop him from scoring a life-changing contract in the 2007 offseason.
The 6’8 forward earned a four-year $24 million, which was the full mid-level exception back in 2007. He continued to be an elite shooter, but he did not fill a need in Toronto. Kapono’s defense was porous and his offensive production dropped off. He played his best in the 2008 playoffs, but the Raptors were bounced by the Magic in the first round.
Toronto dipped in the standings in 2009 before trading Jason Kapono to the Philadelphia 76ers in the offseason. He shot the 13th-best 3-point percentage in NBA history, but his contract was a regret for the Toronto Raptors. They needed shooting, so it made sense for Bryan Colangelo and the team. Sadly, Kapono was just so one-dimensional that things did not go as planned.