4. Brent Barry
February 19, 1998: Traded Isaac Austin, Charles Smith and a future first round pick (Brian Skinner) to the Los Angeles Clippers for Brent Barry.
At the time of the trade, this risky move certainly raised a few eyebrows. Purely from a team point of view, the Heat were in the midst of a 55-win season. They won at the time a franchise best 61 games the previous season.
Personnel-wise, center Isaac Austin was in career-best form, despite the accompanying low-post presence of Alonzo Mourning. A future role as a sixth man could definitely have been worth exploring.
Further, although Skinner was no difference maker, he did carve out a 14-year career as a solid veteran presence.
And yes, it’s true that Barry was in the midst of a career-best season when the trade was made. However, the Heat already had two incumbent outside shooters in Voshon Lenard and Dan Majerle. Acquiring another outside shooter was not exactly a pressing matter.
It could be argued that Barry may have been utilized as another ball handler. But with all-star point guard Tim Hardaway still at the top of his game, those opportunities were always going to be limited.
The upshot of the trade resulted in Barry playing 17 games for the Heat, averaging 4.1 points per game. He would later sign with the Chicago Bulls as a free-agent in the offseason.
Whilst it’s certainly hard to predict how trades will pan out, this was not a good return on investment.
Next: Trying to appease LeBron