Scottie Pippen finally got the money he felt he always deserved when he signed a $67 million deal with the Chicago Bulls before being traded to the Houston Rockets in 1999. Armed with a new contract, Pippen’s lifestyle has also changed.
Pippen bought a $10 million yacht, named it Lady Larsa and then built a huge house in Fort Lauderdale. But there was one luxury he always wished some of his more well-off friends had – a private jet.
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The “Air Pip” deal disaster.
Because he didn’t have a plane, Scottie flew on charter flights. On one of his trips, he met a Florida charter operator named Craig Frost, who piloted his own jet. In early 2002, Frost convinced Pippen that instead of spending a lot of money on chartered flights, he might as well buy his own plane.
And because Frost was in the charter business, he offered Pippen a deal to make him co-owner of a Grumman Gulfstream II jet that Scottie had flown and liked. According to the agreement, Pippen would pay him $4.375 million as his share of the cost of the plane. In return, he could use it as needed, and if he didn’t have a trip, they could lease the jet and split the profits.
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To finance the cost, Pippen and his then-wife, Larsa, established “Air Pip” LLC and borrowed the $4.375 million from JODA LLC, an aircraft finance company based in Chesterfield, St. But by September 2002, Larsa called Scottie’s investment adviser, Bob Lunna, and told him that they believed Frost was not maintaining the plane properly and that she no longer felt safe flying in their own plane.
“We should never have bought this plane,” Larsa said, according to Lunn. “We hired you to prevent us from making decisions like this. You’re supposed to protect us from ourselves.”
Related: “He’s a different man” – Scottie Pippen on Dennis Rodman’s true personality
Court cases followed
Pippen stopped making payments on the loan in 2003, citing that he had been defrauded by Frost and Lunn. The following year, the lender sold Scottie’s promissory note to a bank, which then sued the company for non-payment of the debt.
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Through his lawyers, Pippen argued that he was the victim of a conspiracy orchestrated by people he trusted to make the deal — namely Frost and Lunn. He lost the case and later an appeal was made to pay $5 million.
After losing the appeal in 2007, Pippen sued Frost and won a $2.37 million judgment against Frost and his company, CF Air. In 2010, Scottie also filed a lawsuit against the Chicago Law Firm Pedersen & Houpt for failing to closely supervise the purchase of the plane. Pippen asked for $8 million from that malpractice case and was awarded $2 million instead.
In retrospect, Scottie essentially recovered the $4.3 million through the two court cases he won. But it came after years of litigation and legal costs.
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Although Scottie made over $109 million during his 18-year NBA career, he would have saved himself millions if only he had listened to Lunn, who claimed that in 1999 he had advised Pip not to buy a jet because of maintenance costs. But Scottie didn’t listen.
“He’s a big dog,” Lunn said. “His friends are flying in private jets; he wants to fly in a private jet. It was an ego thing… He kept flying me. He had a serious ambition to have his own plane.”
Well, the “big dog” learned his lesson the hard way.
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Related: Larsa Pippen admits dating married NBA sharpshooter in 2020 was a mistake: ‘I had a COVID brain’
This story was originally published by Basketball Network on January 24, 2026, where it first appeared in the Off The Court section. Add the Basketball Network as a Preferred Source by clicking here.