Vince Vaughn owns what is known as the most expensive condo in Chicago. Vince Vaughn’s address in Chicago is at a three level penthouse on the top floors of the Palmolive building at 159 E Walton Place. That address is famous for once being the Playboy Building. In fact, Vince Vaughn’s office in his condo is where Hugh Hefner’s office used to be.

The condo is 12,000 square feet and boasts five bedrooms, four full baths, four half baths, two fireplaces, and three valet parking spaces.

Vince Vaughn bought the condo in 2006, right before the market crash, for $12 million. Now he is selling it, and asking $13.9 million.

Chicago Now reports that Vaughn has been trying to sell the place for a while now, and had originally asked a whopping $24.7 million back in 2011. Over the years that followed, the price dropped again and again. First to $18.4 million. Then $16.75 million. Then $14.9 million.

At this rate, Vince Vaughn is going to end up taking a bath on this investment, if he hasn’t already. Vaughn is an Illinois native, hailing from Lake Forest on Chicago’s north side in the North Shore area.

Vaughn made news recently when HBO announced that he would be joining Colin Ferrell, Rachel McAdams, Taylor Kitsch, Kelly Reilly, and Afemo Omilami in the second season of their hit show True Detective.

And just this week, it was announced that Vince Vaughn would act as Grand Marshal for the Daytona 500 on Fox.

“Last year was an exciting one for NASCAR, and I can’t wait to help kick off the 2015 season as the Daytona 500 grand marshal,” Vaughn said. “The Daytona 500 is one of the biggest events in all of sports, and I feel honored to be able to be a part of it in it in such a major way.”

Vaughn joins a list of celebrities who have acted as Grand Marshal at the Daytona race, including: James Franco, Chris Evans, John Travolta, Ben Affleck, Nicolas Cage and True Detective season one alum Matthew McConaughey.