When police motored out to the yacht, George Huguely V jumped into the Atlantic Ocean and began swimming to shore, according to the Palm Beach Sheriff's Office.
The family's 40-foot yacht, named "The Real Deal," was a quarter of a mile off shore from the glamorous Ritz Carlton Hotel, police said.
No arrests were made, and Huguely was picked up by a passing boater without injury. The incident occurred not far from the family's million-dollar estate in the wealthy coastal town of Manalapan, Florida
Also in 2008, Lexington, Virginia, Police Officer Rebecca Moss wound up on the ground, wrestling with Huguely during an arrest in 2008 that ended with a conviction for public intoxication and resisting arrest.
Moss said she was forced to use a Taser on the 6-foot-2, 209-pound Huguely after he hurled racial and sexual obscenities at her and threatened her life, telling the officer, "I'll kill you. I'll kill all of y'all. I'm not going to jail."
Huguely had two other run-ins with the law. In September 2007 he was booked for reckless driving after speeding at 70 mph in a 55 mph zone. In November 2007, he was arrested for possession of alcohol as a minor when he was 19.
Both Huguely and Love came from a world of privilege, each attending elite private high schools in the Washington, D.C., area.
Enjoying vacations in Palm Beach and being cared for by a nanny, Huguely came from a long line of Huguely men, many of whom are successful businessmen. His high school, the Landon School, has an annual price tag of nearly $30,000.
Love was raised just outside of Balitmore, in Cockeysville, Maryland, and attended the girls' school Notre Dame Prep. Her father, John Love III, passed away in 2003 from prostate cancer.