Property is always a good investment, and, over the years, Scottie Pippen has poured some of his fortune into his homes. Since Pippen got his big break with the Chicago Bulls, it makes sense that some of his major investments would be in the Windy City. In 2021, Pippen sold his Highland Park home for just under $2 million. He had originally bought the home back in 2004, but kept it as an investment property after moving to Los Angeles years later. Before closing the sale in 2021, he teamed up with Airbnb and rented the home out to curious fans as part of a promotion for the Tokyo Olympics, per People.

Though Pippen is a gracious host when it comes to his property, he's also fiercely protective. In 2018, he took Lindsay Glazer and Jacob Woloshin to court for alleged damage to one of his Miami properties. The couple rented the property from Pippen for $30,000 a month for a period of six months between 2017 and 2018. When they left, Pippen claimed they left the place in disrepair. The couple allegedly damaged furniture, stole property, failed to clean and pay utilities, and allowed their child to draw in the walls, per Radar. All in all, Pippen said the damages were assessed at just over $109,000, which was the amount he was requesting in the suit. In 2022, he dropped the legal action without any further conflict.

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