Scottie Pippen Gulfstream II- Following a career in which he earned some $120 million in salaries, the former Chicago Bulls forward famously partnered with a few businessmen in 2002 to buy a Gulfstream II corporate jet. Pippen's original stake in the plane was only to be $1 million, but when the other investors defaulted, the six-time NBA champ was left alone with the $5 million tab. Pippen sued his lawyers for legal malpractice in the deal years ago and, remarkably, was rewarded $2 million when the jury reached a verdict in the case earlier this year. That should go a little ways to easing the pain over the other $27 million the All-Star has blown on bad investments.
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