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Top comedian, 101-year-old veteran will team up to lead 2024 Gasparilla parade

The 2024 Gasparilla Parade of Pirates is set for Saturday, Jan. 27.

TAMPA, Fla. — It's the start of a new year, which can only mean one thing — Tampa Bay is gearing up for another Gasparilla Pirate Fest.

On Tuesday, Ye Mystic Krewe of Gasparilla announced that Tampa native and top stand-up comedian Bert Kreischer will be returning to his hometown on Saturday, Jan. 27 to serve as the grand marshal for the Parade of Pirates.

You may know Kreischer from his major motion picture, “The Machine," or his most recent Netflix stand-up special "Razzle Dazzle," which has charted in the top five stand-up specials on the streaming service. 

Kreischer, who was named the Just for Laughs Fest Stand Up Comedian of the Year in July, is also fresh off a sold-out show at Amalie Arena. 

"Get ready, Tampa. I'm partying hard," Kreischer said in a video announcing his role as grand marshal.

"There's no better person who embodies the pirate culture and a love of Tampa than the one and only Bert Kreischer," Ye Mystic Krewe of Gasparilla Captain Truett Gardner said. "All I have to say is look out Tampa Bay! We look forward to Bert's energy and hometown pride to lead this year's festivities for a lively crowd along Bayshore Boulevard."

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And Kreischer won't be alone at the head of the parade. He'll be teaming up with this year's honorary community hero: 101-year-old World War II US Army “Buffalo Soldier” Roy J. Caldwood.

Credit: Seminole Hard Rock Gasparilla Pirate Fest
World War II US Army “Buffalo Soldier” Roy J. Caldwood

Caldwood became a medic during the war in the 92nd Infantry Division, the only Black Infantry Division in WWII deployed for combat in Europe. He volunteered to stay in a village under German attack to aid a sick Italian man, earning Caldwood a Bronze Star. 

After the war, Caldwood had an award-winning career as an Assistant Deputy Warden and Program Director at Rikers Island for 21 years. 

“Mr. Roy Caldwood’s bravery and compassion is the definition of a community hero,” said Steve Bonner, the president of Seminole Hard Rock Hotel & Casino, which is sponsoring the event. "Even at 101, Mr. Caldwood continues to serve as a community justice advocate and share his learnings with as many people as possible."

Starting at 2 p.m. on Jan. 27, Kreischer and Caldwood will lead more than 115 parade floats, 53 krewes, seven marching bands, and the infamous Ye Mystic Krewe of Gasparilla pirates down a four-and-a-half-mile parade route along Bayshore Boulevard. 

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