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T-Pain and Wyclef rock the Preakness Stakes in front of athletes and Bravo stars

May 20, 2025
in News
T-Pain and Wyclef rock the Preakness Stakes in front of athletes and Bravo stars
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Preakness Stakes
It was a weekend of festivities at the Preakness Stakes, the the second leg of the Triple Crown. AP

Performances by Wyclef Jean and T-Pain marked the last running of the Preakness Stakes at Pimlico race track in Baltimore before its shuttered for a years-long reconstruction.

“You all got dressed up for this,” a shorts-clad T-Pain told a crowd of equestrian VIPs and socialites trackside. “Do I need to put on pants?”

T-Pain
T-Pain performed his hits trackside for a crowd of VIPs. Getty Images for 1/ST

The rapper sang hits like “Buy U a Drank” and “Bartender” after the big race that saw Umberto Rispoli gallop into a win on Journalism.

Before the main race, Wyclef Jean performed for an audience that included a number of politicos including the city’s Mayor Brandon Scott and Governor Wes Moore, as well as a number of Ravens and Commanders athletes.

Wyclef Jean
Wyclef Jean also took the stage to sing hits like “Hips Don’t Lie.” Getty Images for 1/ST

The “Guantanamera” singer also gave a shout out several times to 1/ST CEO Belinda Stronach, who just sold the track to the state for $1 with the promise they will redevelop the site for hundreds of millions of dollars.

“Summer House” star Jesse Solomon was spotted rocking out on stage with a large group during the first song.

He was later seen hanging out with “Bachelor” alum Jason Tartick and TikToker Jon Bouffard during the concert, which also drew “Love Is Blind” cast members Micah Lussier, Brittany Mills and Alex “AD” Dillon.

Jesse Solomon
Bravo star Jesse Solomon was in the crowd. Getty Images for 1/ST
Bobby Flay
Bobby Flay is very involved in the racing world. Getty Images for 1/ST

Former NFL player Cam Newton, former Yankees pitcher CC Sabathia, NFL Hall-of-Famer Ray Lewis, and NBA star Carmelo Anthony were also spotted in the VIP 1/ST Chalet area, as was celebrity chef Bobby Flay.

“I have been following [racing] since I was a teenager,” Flay told Page Six. “My grandfather took me to Saratoga Springs and I just fell in love with it, It’s a fun sport and fun event.”

Flay owns a minority stake in breeding operation WinStar Farm and has owned a number of horses including fillys More Than Real, Pizza Bianca, and 2015 Grade 1 winner Dame Dorothy. He also owns a part of 2016 Belmont Stakes winner Creator.

Belinda Stronach
1/ST CEO Belinda Stronach owns the licensing rights to the Preakness Stakes and the Pegasus World Cup in Florida. Scott Quintevalle
Cam Newton
Cam Newton was spotted taking in the races. Getty Images for 1/ST

His horse Candied claimed victory in the Allaire du Pont Distaff Stakes at Pimlico over the weekend.

When it comes to betting, Flay told us he looks at “past performances,” but assured newbies: “Just pick your favorite name or color of the silks. You’ll be fine.”

The day before the main event — known as the Black-Eyed Susan Stakes where the female horses take the track — spies spotted the “Real Housewives of Potomac” filming in the VIP section with a witness telling us they were surprised it was “so scripted.” “They don’t talk to each other when the cameras aren’t rolling,” they said.

On Saturday night, following a long day of cheering on the ponies, racing insiders head to an after party at the Elk Room where Stronach, who has the ownership rights to run the Preakness and the Pegasus World Cup in Jupiter, Florida, was spotted on the dance floor grooving while her son Frank Walker DJ’d the bash.

The post T-Pain and Wyclef rock the Preakness Stakes in front of athletes and Bravo stars appeared first on Page Six.

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