Leslie Stewart, born on March 21 in Laventille, Trinidad and Tobago, emerged as one of the most accomplished light heavyweights to represent the Caribbean on the international stage. Standing at 6 feet 2 inches with a 74-inch reach and an orthodox stance, he built a career marked by resilience, technical skill, and battles with some of the sport's elite. Stewart debuted on January 29, 1982, in Port-of-Spain, stopping Michael Hospadales via a fourth-round TKO in a six-round bout, setting the stage for a career that spanned 18 years.
The early phase of Stewart's career saw him dominate the local circuit in Trinidad, winning his first 11 bouts and capturing the Latin American Light Heavyweight Title in his eighth fight by knocking out Carlos Flores Burlon in four rounds. After establishing himself regionally, Stewart transitioned to the United States, defeating Elvis Parks in Miami Beach by a ninth-round TKO in his 12th fight. Shortly after, he claimed the USA Florida State Light Heavyweight Title by outpointing James Salerno on November 10, 1984.
By 1985, Stewart had added the WBC Continental Americas Cruiserweight Title to his collection with an eighth-round TKO over Mark Frazie in Trinidad. He further unified this title with the USA Florida State and WBC Continental Americas Light Heavyweight Titles by defeating Chris Wells via a sixth-round TKO in Fort Lauderdale. Later that year, he claimed the Commonwealth Light Heavyweight Title with a points victory over Lottie Mwale in Port-of-Spain, solidifying his reputation as a top-tier contender.
Stewart's first attempt at a world title came on February 9, 1986, against Marvin Johnson for the vacant WBA World Light Heavyweight Title. In a gruelling fight at the Market Square Arena in Indianapolis, Stewart held his own but was ultimately stopped in the seventh round due to cuts. Undeterred, he rebuilt his career with five consecutive wins, including victories over notable names such as Uriah Grant, James Salerno, and Fulgencio Obelmejias.
On May 23, 1987, Stewart achieved his greatest triumph, defeating Marvin Johnson in a rematch in Port-of-Spain to claim the WBA World Light Heavyweight Title. Johnson could not continue after the eighth round, marking Stewart's ascent to the pinnacle of the division. His reign, however, was short-lived; he lost the title to an undefeated Virgil Hill on September 5, 1987, in Atlantic City by a fourth-round TKO.
Stewart's pursuit of another world title saw him face Donny Lalonde on May 29, 1988, for the WBC World Light Heavyweight Title. Fighting in front of a home crowd in Port-of-Spain, Stewart was stopped in the fifth round. Later that year, he dropped a close split decision to Bobby Czyz and, in 1989, was stopped in the eighth round by Michael Moorer in a bid for the WBO World Light Heavyweight Title.
In the 1990s, Stewart continued competing at a high level, facing top contenders such as Anthony Hembrick, Guy Waters, and Henry Maske. Notable victories included a unanimous decision over Drake Thadzi in 1991. Despite these successes, he struggled to regain the consistency of his peak years, suffering losses to rising stars and established champions.
Stewart's final professional bout occurred on January 15, 2000, at Radio City Music Hall in New York, where he lost a unanimous decision to Billy Lewis. He retired with 31 wins (20 by knockout) and 12 losses from 43 bouts, leaving behind a legacy as one of Trinidad and Tobago's most respected boxers.