During his 17 year NBA career with the Chicago Bulls, the Portland Trailblazers and Houston Rockets, Scottie Pippen cemented a reputation as one of the greatest and most admired NBA players of all time. However, his reputation with restaurant waiters, bar staff and others in the service industry was much less than stellar where he earned the nickname, "No Tippin' Pippen". There is even something called "The Official No Tippin Pippen Thread" on the Web where various waiters and others share their bad experiences with Scottie Pippen's cheapskate ways.
In Portland, some local restaurants claimed that Pippen would spend as much as $800 on food, but only leave just a $25 tip. And, at a TGI Fridays in Chicago, a bartender claims that Scottie Pippen and B.J. Armstrong came in with a group of girls, and Scottie Pippen bragged about "I don't tip anyone. I'm saving my money". Meanwhile, B.J. Armstrong was very nice. He spent $300 on drinks and food, most of it for others, and tipped $100 as well. He told staff at TGI Fridays not to take it personally about Scottie Pippen's penny pinching ways.
THE CHICAGO TRIBUNE's Steve Rosenbloom once noted that it's always something with Scottie Pippen, and it "always seems to be money". Back in 2000 when the Trailblazers were playing the Timberwolves in Minneapolis, Pippen wanted a local bar to run the Lennox Lewis-Michael Grant Heavyweight fight, however the bar wanted to refuse because of the $750 licensing fees for bar use. After an argument, the bar ran the fight that only lasted just two rounds, then Pippen felt ripped off and didn't want to pay. Finally, after another argument with Pippen, the bar charged him half price, losing 50% on the deal.
Horace Grant, a former Chicago Bulls teammate also affirmed that the "No Tippin' Pippen" reputation was well earned, despite the fact that Pippen was his friend. But, it was claimed that Michael Jordan was worse yet when it came to tightwad ways.
After his retirement, Scottie Pippen didn't do so well financially with his investmests despite earning $120 million during his career. He unsuccessfully sued a law firm that he claims lost $27 million of his money in bad investments and was in debt for a Grumman Gulfstream II, a private jet that he bought. One source believed that he could not withstand a $5 million lawsuit financially and really needs to play basketball again to pull himself out of his debts. But, that seems impoosible for a 45 year old player who had to cut short his last season of basketball back in Chicago in 2004 because of injuries.
Scottie Pippen's financial woes will never match those of Mike Tyson though. Although, he earning as much as $400 million during his career, Tyimpossibleson was thoimpossibleught to be worth only about $700 at one point because of his financial problems and bad mismanagement.
What happens to old basketball players? Well, they don't always retire wealthy in the sun somewhere, even when cheap as heck and penny pinching.