10 Worst free agent signings in Rockets history

4. Scottie Pippen

After being largely underpaid through his first 11 years in the NBA, Scottie Pippen finally got the payday that he had been pursuing, albeit from the Houston Rockets. The Rockets acquired Pippen in a sign-and-trade deal that sent Roy Rogers and a second-round draft pick in the 2000 NBA Draft in exchange for the 7-time All-Star and 7-time All-Defensive ace.

Pippen's new contract with the Rockets paid him up to $82 million over the course of five years, with $15 million in incentives, giving him $11 million annually, which was an incremental increase over his $2.6 million annual figure. Rockets forward Charles Barkley, re-structured his contract to pave the way for Pippen to land his payday and form a supertrio in the Space City. 

Unfortunately the experience of the Rockets' Big Three didn't quite go as planned, as the team went 31-19, good for fifth-best in the West, landing them a playoff matchup against the Los Angeles Lakers, who eliminated them within just 4 games. Pippen struggled to find his shot in the series, shooting 32.9 percent from the floor and 27.3 percent from deep.

For the season, Pippen averaged 14.5 points (his lowest scoring average in the previous nine years), 43.2 percent from the floor (career low), along with 6.5 rebounds and 5.9 assists.

Pippen demanded a trade after his lone season in Houston, in part because of a clash he had with the aforementioned Barkley. On October 2nd, 1999, the Rockets dealt Pippen to the Portland Trail Blazers for Kelvin Cato, Walt Williams, Stacey Augmon, Ed Gray, Brian Shaw, and Carlos Rogers, washing their hands of the Hall of Famer.