Puerto Rico Surf Legend Honored: "He Rode That Wave Straight to Heaven"

Back in October, a tragic accident rocked the Puerto Rico surf community.

Robert “Bobby” Oldsman passed away while surfing one of the island’s heaviest waves, Tres Palmas in the Rincón region, during what forecasters were calling 10-to-15-foot waves. He reportedly hit his head on his surfboard, and was unable to be rescued.

Bobby O, as he was affectionately known, was 72 years old. And following his passing, the local surf community gathered to celebrate his life with a traditional paddle-out.

“He really was a legend in the Rincón community,” Bobby’s daughter, Olivia, told SURFER. “He was an epic surfer charging Tres Palmas even at almost 72 years old. It seemed he was aging backwards. He looked 45 (I swear it was the ocean), absolutely hilarious, a caring friend to so many, and an awesome dad. He lived life stress-free. He was so happy every day to be alive. When he wasn’t surfing, he was riding his Triumph Scrambler through the mountains of Puerto Rico with his best friends Dennis Ritch (another surf legend in Rincón), Dave Barry, and others.”

Tres Palmas is often considered Puerto Rico’s premier spot for big waves, often compared to the North Shore of Oahu’s Sunset Beach. The wave breaks in deep, open-ocean waters with a channel on one side, but during certain swells, sneaker sets that can consume the entire lineup. And Bobby O loved surfing there, among other PR spots.

“When he passed, he was having an amazing session,” Olivia added. “He was also in the best shape, physically and mentally, that he’s ever been in. His friends said he was all smiles, having the time of his life. He has surfed Tres for a long, long time (15ish years), so this wasn’t anything out of the ordinary. He had his morning coffee; it was right where he left it. He went to do what he loved more than anything in the world, at his favorite place in the world.

“He literally has the horizon of Tres Palmas tattooed on his chest over his heart. If he could’ve chosen a way to go out, it would’ve been this way. He said goodbye to the guys in the lineup (only seven, as it was pre-season), rode one in on the inside, slipped, and must’ve gotten clocked in the head with the board, and just wasn’t seen in time. He was face down for too long. He wore a flotation vest, and when he was found, the leash was still attached. I know my dad and he had more heart and soul than anyone I knew, and loved us so much. He would’ve made it in if he was conscious. He rode that wave straight to heaven.”

Dennis Ritch, one of Bobby O’s Puerto Rico pals, remembered:

“We lost a real gem of a person. Bobby O checked out of this world doing one of his favorite things - surfing at Tres Palmas in Rincón PR. A lifelong surfer, Bobby O split his year running his business White’s Catering on Cape Cod in the summer and surfing the cold waters of Wellfleet, MA. The rest of the year he spent in paradise at his Rincón home nestled in the mountains with a view of…you guessed it…Tres Palmas.

“He surfed, he sailed, he rode motorcycles, he danced, he cooked great meals, he made friends everywhere he went and he did it with style. He was…Peter Pan. He wanted everyone to enjoy life as much as he did. He always got so excited when his daughters Olivia, Tessa, and his son in law Taner were coming to town. The amount of people who came to his celebration of life pig roast and paddle out at Playa Marías (another one of his favorite spots) and the smiles, tears, hugs and kisses that were shared are a testimony to his impact on the lives of so many.

“The world needs more Bobby O’s. I sure Miss this one.”

Rest in paradise, Bobby O.