Tampa Rough Riders donate over 10,000 Teddy bears to people who ‘need a little love’ each year

The Rough Riders still parade proudly down the palm tree-lined streets of Tampa — armed these days with cuddly Teddy bears instead of Teddy Roosevelt’s fearsome calvary horses. 

Roosevelt’s legendary legion of marauders attacked and captured San Juan Hill in Cuba during the Spanish-American war in 1898. 

The larger-than-life American hero, just 39 years old at the time, parlayed the victorious assault into the governorship of New York, the vice presidency and then the Oval Office — all in less than three years. 

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He staged his forces in Tampa before setting sail for Cuba during a war that transformed geopolitics 125 years ago. 

The Rough Riders of today are a Tampa “krewe” that honors the unit’s memory and the city’s role in American military and presidential lore. 

Bob Moeller is president of the 1st U.S. Volunteer Cavalry Regiment Rough Riders, a “krewe” of Tampa residents who donate over 10,000 Teddy bears each year to “anybody in need of a Teddy bear and a little bit of love.” (Kerry J. Byrne/Fox News Digital)

They collect and distribute more than 10,000 Teddy bears each year for needy local children and families — among other charitable endeavors and civic activities. 

“We will distribute them to children’s hospitals, VA centers, assisted living centers,” Lt. Col. (ceremonial) Bob Moeller, president of the 1st U.S. Volunteer Cavalry Regiment Rough Riders, told Fox News Digital.

“Tampa Rough Riders distribute stuffed animals to ‘anybody in need of a Teddy bear and a little bit of love.’” — Bob Moeller

“Pretty much anybody in need of a Teddy bear and a little bit of love,” he added, of those the groups will help.  

Teddy bears, beloved by generations of children, are named for Theodore Roosevelt. The very first Teddy bear was sold 120 years ago, on Feb. 15, 1903, while President Roosevelt sat in the White House. 

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Krewes such as Moeller’s Teddy bear-hugging Rough Riders are civic and charitable organizations that march in local parades, host celebrations and otherwise lend a festive air to a community. 

Scenic Plant Hall, the main building for the University of Tampa, was formerly the Tampa Bay Hotel. Teddy Roosevelt stayed at the hotel while preparing to lead the Rough Riders in their assault on San Juan Hill in Cuba. (Kerry J. Byrne/Fox News Digital)

Each krewe typically sports celebratory costumes. 

The Rough Riders wear tan-and-blue late 19th-century U.S. Army calvary uniforms with tropical headgear made popular by the Hero of San Juan Hill.

“Tampa is rife with krewe life,” Tampa magazine wrote last year. 

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“People with common interests gather in these social and philanthropic membership organizations and have a blast along the way.”

The Tampa Bay Buccaneers of the NFL call their season-ticket holders “krewe members,” in deference to local tradition. 

“Tampa is rife with krewe life.” — Tampa magazine

The Rough Riders’ sprawling clubhouse in Ybor City features parade floats outside and an entire storage space inside with Teddy bears sorted by size from small to jumbo — the biggest stuffed bears as large as full-grown men. 

Moeller’s Rough Riders, founded in 1978, serve a dual role of charity and preserving American lore. 

The 1st U.S. Volunteer Cavalry Regiment Rough Riders are a Tampa krewe that celebrates the life and legacy of Teddy Roosevelt and his Rough Riders, while conducting charity work around the city. Their sprawling clubhouse includes murals and dioramas of the Rough Riders’ assault on San Juan Hill in Cuba during the Spanish-American War. (Kerry J. Byrne/Fox News Digital)

“They really did ride through Tampa,” said Moeller. “This is a real part of our history.”

Florida’s City by the Bay is filled with monuments that memorialize the Rough Riders and their charge up San Juan Hill on July 1, 1898. 

Ornate Plant Hall, the main building on the beautiful University of Tampa campus, was the Tampa Bay Hotel in the late 1800s. Roosevelt used it as his headquarters while in the city. 

“The Rough Riders who ‘could whip Caesar’s Tenth Legion’ brought enduring fame to Tampa.” — Historical marker

“Tampa was a cluster of old weather-beaten houses floating on an ocean of sand” when Roosevelt and the Rough Riders arrived by train on June 3, 1898, reads a historical marker in Ybor City, Tampa’s popular old-world neighborhood. 

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“The Rough Riders who ‘could whip Caesar’s Tenth Legion’ brought enduring fame to Tampa.”

Krewes are common around the Gulf of Mexico, most notably in New Orleans, where they’re essential to Mardi Gras celebrations.

A historical marker in Ybor City, Tampa, memorializes the city’s role as the staging area for the assault on San Juan Hill in Cuba by Teddy Roosevelt’s Rough Riders in the Spanish-American War. (Kerry J. Byrne/Fox News Digital)

Tampa krewes play a key role in Gasparilla, the city’s raucous annual pirate festival. 

Founded in 1904, it is the annual highlight of Tampa’s community-wide social calendar and is organized by Ye Mystic Krewe of Gasparilla.

Moeller, who was born and raised on Staten Island, New York, likens krewe culture to the mummers of Philadelphia and the United Kingdom. 

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“While krewes exist around the country, they are prevalent in Florida, with around 130 krewes running,” Tampa magazine reported last year. 

“The krewe scene is especially thriving in Tampa.”