4. Scottie Pippen

Ride: Gulfstream II private jet, 2002
Complex Says: Hall of Famer and six-time NBA champion Scottie Pippen has compiled a long list of bad business investments over the years. One of those investments was a $4.3 million Gulfstream II jet he bought in 2002. Apparently, Scottie had been taking so many charter flights to and from Portland while playing for the Trail Blazers that in 2002 a pilot convinced him it would be a good idea to invest in his own private jet. After the aircraft had already been purchased, it was revealed that necessary repairs on the engine costing roughly $1 million had gone unnoticed due to a missed inspection. Rather than pay for repairs, Pippen grounded the plain and sued his attorney for $8.2 million. It wasn't until last year that Pippen was finally awarded $2 million for the fiasco surrounding a plane that it appears he never took on a flight.