Lawyer Ron was bred and owned by James T. Hines, Jr., an entrepreneur who started his first company, Premium Allied Tool, in Owensboro, Kentucky, in 1966 and turned it into a multimillion-dollar business.

Hines became involved in thoroughbred horse racing in 1995 but died at the age of 69 in a drowning accident in his home swimming pool on February 20, 2006, just before Lawyer Ron's victory in the Rebel Stakes.

In the 2006 Grade III Risen Star Stakes held at Louisiana Downs on January 14, Lawyer Ron broke well and was second heading into the first turn.

Heading down the stretch, Steppenwolfer made a strong challenge for the lead, but Lawyer Ron held him off to win by 3/4 length.

In the 2006 Grade III Rebel Stakes held at Oaklawn Park on March 18, Lawyer Ron got a poor start and was trapped against the rail in fifth.

Lawyer Ron was then challenged by Private Vow coming out of the second turn but pulled away and won by 2¾ lengths over a late-surging Steppenwolfer.

On August 25, 2006, Lawyer Ron won the inaugural running of the St. Louis Derby at Fairmount Park Race Track in Illinois.

Ridden by John Velazquez and hard to handle in the early part of the race, on September 30 Lawyer Ron lost to Curlin by a neck in a stretch duel in the Grade I Jockey Club Gold Cup at Belmont Park.

On February 11, 2007, Lawyer Ron, who continued to be rank throughout his career (probably contributing to his loss in the 2006 Breeders' Cup Classic which went to Invasor), was ridden by jockey John Velazquez for an optional/allowance claiming race at Gulfstream Park.

Although previously a headstrong horse, he settled early and moved to the lead on the outside passing the three-eighths pole and entered the stretch with a clear advantage.