In a move that blends basketball rivalry with big-city philanthropy, Cleveland Cavaliers owner Dan Gilbert is making sure his team has plenty of support on the road—by busing hundreds of fans from Cleveland to Detroit for the playoffs.

Gilbert, the chairman of Detroit-based Rocket Companies and a major force in downtown Detroit's revival, has organized free bus trips for about 500 season ticketholders to attend Game 5 of the second-round series against the Detroit Pistons at Little Caesars Arena. The gesture includes a pregame party at Gilbert's own event space, The Beacon, complete with free food, drinks, and entertainment.

For Gilbert, it's a chance to cheer for his Cavaliers while staying connected to his Detroit roots. "Dan Gilbert is amazing," said Cavaliers fan Michael Meyer, sporting a T-shirt Gilbert provided that reads "Beat Detroit!" "He transformed everything with our team. He gave us a ride up. He fed us lunch. He fed us dinner and then he brought us to the game."

But not everyone is intimidated by the show of support. Pistons fan Stacey Sorak, whose seats were right behind the section reserved for Cavaliers fans, remained unfazed. "It doesn't matter, we're still gonna win," she said. "We silenced them pretty quick last time they were here."

The bus trips are part of Gilbert's ongoing commitment to the Cavaliers' fan base, echoing the same energy he's brought to revitalizing downtown Detroit over the past decade. With more than 100 properties redeveloped in the Motor City, Gilbert knows a thing or two about building momentum—both in real estate and on the court.