Florida Keys

Ex-con accused of stealing boat for Cuba trip gets 5 years


An ex-con who stole a Key West charter boat last September saying he was headed to Cuba to seek political asylum will serve five years in prison after admitting to grand theft in court, where he represented himself.

Stephen Leonard, 41, a truck driver originally from New York City, never fought the charge at the Monroe County Courthouse, where on Aug. 3 Judge Wayne Miller refused to toss out his initial plea of no contest and sentenced him to state prison.

Since his arrest Sept. 17, 2015, when state and federal agencies caught up with him on the water, Leonard hasn’t denied he boosted another person’s 31-foot Yellowfin vessel from the Hurricane Hole Marina on Stock Island.

“His intent was to seek asylum in Cuba,” said Assistant State Attorney Paunece Scull. “The court had him evaluated and he was found competent to proceed. He has written numerous letters to the court and to me with reasons from fleeing the state – federal judges were after him and he stole a semi truck in New York.”

Leonard spoke of having lost his wife and children to legal woes.

He currently has two cases pending in U.S. District Court, one accusing the Monroe County Sheriff’s Office of poor medical care and the other asking a judge to move his case from state to federal court, claiming the waters where he was arrested were within federal jurisdiction.

On Aug. 3, Leonard represented himself, so the prosecutor had to hand him the paperwork — including the state’s recommendation he serve five years in a case where he faced up to 30 — which onlookers said caused Leonard to become emotional and plead for clemency.

“For awhile the public defender was appointed and he wanted them off the case,” Scull said. “He pled back on Oct. 7, 2015, and it just was in limbo this whole time until Aug. 3 when he was finally sentenced.”

Leonard has at least 15 prior felony convictions including aggravated battery of a pregnant woman in Miami-Dade County.

Security video showed someone taking the boat at 5:30 a.m. the day of the theft. By 3:30 p.m., staff at the Key West Harbor Yacht Club on Stock Island called the Sheriff's Office to report the boat was being fueled up at their marina and they had heard the boat was stolen and recognized it when it came in.

Deputy Spencer Curry arrived just as the stolen boat was leaving and yelled at the operator, later identified as Leonard, to stop but the boat sped off.

Staff at the yacht club reported Leonard asked how much gas he would need to get to Cuba.

Leonard was charged with a first-degree felony because he stole a vessel worth over $100,000 and caused damage to it when he went screaming out of Stock Island’s yacht club.

“There is some amazing video of it,” Scull said. “He leaves at such a high speed.”

Gwen Filosa: @KeyWestGwen