In Florida, Cruguet was hired to ride for Horatio Luro at Hialeah Park Race Track and began to achieve success in the ensuing years.

In 1969, he won a major Grade I race aboard Arts and Letters when he replaced Braulio Baeza due to another commitment, riding the future Hall of Fame colt to victory in the Metropolitan Handicap at Belmont Park.

[1] The 1970 U.S. Champion two-year-old colt, ridden by Cruguet in all his starts, went undefeated in his short career but in his three-year-old season was injured in March 1971 while preparing for the Wood Memorial Stakes.

In a move still written about today, with 20 yards to go to the finish line in the Belmont Stakes, Cruguet stood up in the stirrups, raised his right arm over his head, and jubilantly gave the crowd a victory salute by waving his whip in the air.

Slated to ride a three-year-old filly trained by friend John Paul Pucek, he postponed his comeback attempt due to bad weather and concerns over the youth of the horse.

He also planned to attempt a comeback during the 2011 Arlington Park meet as part of a special "Legends" race in support of the Permanently Disabled Jockeys Fund on August 12, but also had to withdraw from that event citing health concerns.