5. The Meh-rice Harkless deal
A fairly underwhelming place to start, but these kinds of nothing deals were exactly the problem at the height of the Orlando Magic being a complete afterthought.
Maurice Harkless was a decent rotation player in the NBA. There was nothing spectacular about him, but to play 201 games for the organization is not nothing.
So to give him up for a second-round pick with relatively heavy protections was just weird. Surely there was a better deal out there than this?
Harkless went on to play even more games for the Portland Trail Blazers (274), and also appeared in 33 postseason contests, including their run to the Western Conference Finals in 2019.
This deal came at a time when the Magic were giving away OK players like Shabazz Napier, Kyle O’Quinn and Moe Harkless for absolutely nothing at all.
The logic was likely that a second reboot was coming for the roster, and we know that it did.
But the inability to turn a rotation player like Harkless, as well as the others named here, into anything that could help them in the long term was criminal. Front office ineptitude at its finest.