The 20 worst free agent signings in NBA history

#3. Derrick Rose: 5 years, $95 million

Former number one overall pick Derrick Rose is another surprise inclusion on this list, but it is unfortunately well warranted. After winning league MVP at just 22 years old, he signed a 5-year, $95 million rookie max extension in 2011, using a new rule nicknamed the Rose Rule. The then-newly created rule allowed eligible players on their rookie deals to sign extensions starting at 30% of the salary cap.

It’s hard to blame the Bulls for wanting to keep Rose for as long as possible, and it wasn’t like he was injury-prone prior to signing his massive extension. Actually, he initially proved surprisingly durable, missing just six games through his first three seasons.

That didn’t last, of course. He got injured in Game 1 of the Bulls’ first-round series against the 76ers in 2012. Rose missed the remainder of the playoffs and all of the 2012–13 season. He then came back for the 2013–14 season only to be later ruled out for the rest of the year with a right meniscus tear. In 2014–15, Rose tore his right meniscus again and missed significant time.

After several injuries, it was clear that he was not the same player, so Chicago traded him to the Knicks. There, he played well before a left meniscus tear ended his season. Rose ultimately missed 256 games in the five seasons after signing his max extension. To Rose’s credit, after missing 62% of his team’s games over that span with four different leg injuries, he would later evolve into a capable role player, but he failed to live up to the contract that was named after him.