Scottie Pippen finally got the money he thought he deserved when he signed a $67 million contract with the Chicago Bulls before being traded to the Houston Rockets in 1999. With the new contract, Pippen’s lifestyle has also changed.
Pippen spent $10 million on a yacht, named it Lady Larsa, and then built a large house in Fort Lauderdale. But there was one luxury he always wished some of his wealthier friends had – private jets.
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‘Air Pip’ causes disaster
Since Scotty didn’t own a plane, he flew on a charter plane. On one trip, he met a Florida charter operator named Craig Frost who flew his own plane. In early 2002, Frost convinced Pippen that instead of spending a lot of money renting a plane, he should buy his own plane.
Since Frost was in the charter business, he offered Pippen a deal to make Pippen a co-owner of a Grumman Gulfstream II jet, which he had flown and which Scottie had also flown and liked. According to the agreement, Pippen will pay him $4.375 million as his share of the aircraft costs. In return, he gets to use it as needed, and if he’s not traveling, they rent the plane and share the profits.
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To pay for it, Pippen and his then-wife Larsa formed “Air Pip” LLC and loaned $4.375 million from JODA LLC, an aircraft finance company based in Chesterfield, St. Louis. But by September 2002, Larsa called Scotty’s investment adviser, Bob Lunna, to tell him that they believed Frost was not maintaining the plane properly and that she no longer felt safe flying in her 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.”
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Court case follows
In 2003, Pippen stopped repaying the loan on the grounds that he had been deceived by Frost and Lunn. The next year, the lender sold Scotty’s promissory note to a bank, which then sued the company for unpaid debt.
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Pippen argued through his attorney that he was the victim of a conspiracy hatched by people he trusted with the deal, referring to Frost and Lunn. He lost the case and later appealed for $5 million.
After losing his appeal in 2007, Pippen sued Frost and won a $2.37 million settlement against Frost and his company, CF Air. Scotti also filed a lawsuit in 2010 against the Chicago law firm Pedersen & Houpt, accusing it of failing to closely monitor aircraft purchases. Pippen sought $8 million in damages from the medical malpractice case, but was ultimately awarded $2 million.
Looking back, Scotty essentially recouped $4.3 million through the two lawsuits he won. But this comes after years of litigation and legal fees.
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Although Scottie made more than $109 million during his 18-year NBA career, if he had listened to Lunn, he could have avoided unnecessary millions of dollars in spending. Lunn claims he advised Pip in 1999 not to buy a jet because of the maintenance costs. But Scotty didn’t listen.
“He’s a big dog” Lunn said. “His friends were all flying around on private jets; he wanted to fly around on private jets. It was an ego thing… He kept knocking me out. He had this huge ambition to own his own plane.”
Well, Big Dog learned that 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 article was originally published by Basketball.com on January 24, 2026, and first appeared in the off-court section. Click here to add Basketball Network as your preferred source.
