The 5 worst NBA trade deadline deals ever

4. Tobias Harris to the Pistons; Brandon Jennings, Ersan Ilyasova to the Magic

To be clear, the Detroit Pistons were right to make this move even if it was never going to put them over the edge. In essence, they were offered a young player who was already locked in to a reasonable contract for two lesser players, both past their best, who could kindly be described as spare parts. How could they possibly have said no?

It’s the Orlando side of this deal that seals its place on the list. Rarely has there been a deal that so accurately magnified the stifling lack of clarity that was driving an organization’s decisions.

Three-and-a-half games back of the eighth seed, Magic general manager Rob Hennigan decided to trade in a talented combo forward, who had just signed a new contract the previous summer, for a pair of veterans who he believed could help the team press on with a post-season push.

The veterans in question were Brandon Jennings and Ersan Ilyasova, both of whom had been favorites of then Magic head coach Scott Skiles during his time in Milwaukee. Harris had also played for Skiles with the Bucks, yet having not fit his coach’s eye was traded to Orlando in another short-sighted deal.

If the deal was intended as a sign of trust and faith in a coach who was going to be around long-term, perhaps it would have been excusable. Instead, Skiles resigned as head coach just three months later.

Quoted by ESPN at the time, Hennigan explained his motivation for making the trade:

"“I think we’re right in striking distance for a playoff spot. We feel like our team has played well the last few games, and we just have to sustain that momentum and add to that momentum. The goal is to make the playoffs and the goal is to win, and that’s what we’re trying to do. We see Brandon and Ersan as really good fits, both short-term and long-term for us. We also were able to open up some flexibility this summer in the cap-space realm, if we decided to go that route. It sets up a few different ways we can play this.”"

The Magic would finish the season nine games back of the eighth seed in 11th place. At the end of the season, Ilyasova was moved as part of a draft night trade and Jennings left in free agency. Orlando invested their cap space in creating a center log-jam, and have struggled into the current season as they lack a smaller forward capable of stretching the floor. You know, a Tobias Harris-type.

Turning young assets into nothing but cap space, and then going on to use that to create further problems is quite the feat. I’d guess the Magic would like to have this one over.