Scottie Pippen got the money he always felt he deserved when he signed a $67 million contract with the Chicago Bulls before being traded to the Houston Rockets in 1999. Pippen’s lifestyle also changed with the new contract.
Pippen bought a $10 million yacht, named it the Lady Larsa, and then built a large house in Fort Lauderdale. But there was one luxury he always wished some of his best friends had – a private jet.
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“Air Peep” deal disaster
Because he did not own a plane, Scott 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 more 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 co-own the Grumman Gulfstream II jet he flew and that Scotty flew and loved. According to the agreement, Pippen will 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 travel, they could rent a jet and share in the profits.
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To finance the cost, Pippen and his then-wife, Larsa, formed “Air Pip” LLC and took out a $4.375 million loan from JODA LLC, an aircraft finance company based in Chesterfield, St. Louis. But by September 2002, Larsa called Scotty’s investment adviser, Bob Lunna, and told them that Frost had not properly maintained the plane and that he did not feel it was safe to fly in his plane.
“We should never have bought this plane,” Larsa said, according to Lun. “We hired you to prevent us from making such a decision. You must protect us from ourselves.”
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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 Scotty’s promissory note to the bank, which sued the company for default.
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Through his lawyers, Pippen argued that he was the victim of a conspiracy orchestrated by people he believed to be complicit — meaning Frost and Lunn. He lost the case and successfully appealed to pay $5 million.
After losing an appeal in 2007, Pippen sued Frost and won a $2.37 million judgment against Frost and his company, CF Air. In 2010, Scottie filed a lawsuit against Chicago law firm Pedersen & Houpt for failing to closely monitor aircraft purchases. Pippen sought $8 million from that malpractice suit and was awarded $2 million instead.
In retrospect, Scotty essentially repaid the $4.3 million through two court cases he won. But it came after years of lawsuits and legal expenses.
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Although Scottie earned more than $109 million in his 18-year NBA career, he would have saved himself millions in unnecessary expenses if he had listened to Loon, who claims that in 1999 he advised Pip against buying a jet because of the maintenance costs. But Scott didn’t listen.
“He’s a big dog,” Lun said. “His friends are flying in private jets; he wants to fly in private jets. It was an ego thing … he kept beating me. He had big ambitions to have his own airplane.”
Well, “Big Dog” learned his lesson the hard way.
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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.
