Sugar Ray Robinson

Using Ray Robinson's AAU card, Smith Jr. continued to fight on the so-called bootleg circuit. It was a bootleg operation because the fighters, who were presumed to be amateurs, pocketed $10 per win. Still fighting under the alias of Ray Robinson, Smith Jr. picked up the nickname of Sugar when a local sports editor in Watertown, New York, remarked of Robinson "That's a sweet fighter you've got there…," to which a fan rejoined, "As sweet as sugar." Still growing, and training in earnest, Robinson brought his weight up to 118 pounds and continued undefeated throughout his years as an amateur boxer. Thus, the career of Sugar Ray Robinson was born.

In 1939 then eighteen-year-old Robinson, weighing just under 116 pounds, defeated Louis (Spider) Valentine for the featherweight championship in the Golden Gloves competition. In 1940, at 126 pounds, Robinson won his second Golden Gloves championship, this time as a lightweight. Leaving behind an amateur record of eighty-five undefeated bouts, including sixty-nine knockouts—with forty in the first round—he hired Curt Horrmann as a manager and turned professional that year. Sugar Ray Robinson made his debut as a welter-weight on October 4 at Madison Square Garden in a bout against Joe Echeverria. Robinson won by a knockout in the second round of the scheduled four-round fight, and took a purse of $150. Just four days later he defeated Silent Stefford in Savannah, and once again it was a second-round knockout for Robinson.

Robinson earned a modest reputation and on July 21, 1941, he fought in a main event for the first time, in a contest with Sammy Angott, the reigning lightweight champion of the National Boxing Association. Angott had agreed to the fight only in a non-title bout. Robinson as a result had to weigh more than 136 pounds in order to be heavier than a lightweight. After tipping the scale at 136¹/₂ pounds at weigh-in, Robinson won the ten-round decision and pocketed a $6,000 purse for the affair. He finished the calendar year with three more knockouts and two ten-round decisions in his favor.

In 1942 Robinson signed with agent Mike Jacobs who wasted no time in contracting a fight with Jake LaMotta on October 2, 1942 in New York City. Robinson took the 10-round decision but four months later suffered the first loss of his career, in a re-match with LaMotta in Detroit on February 5. After defeating Jackie Wilson two weeks later in New York, Robinson dealt LaMotta a second defeat on February 26 in Detroit in a ten-round decision. On February 27 Robinson reported for induction to the U.S. Army as Private Walker Smith Jr., in compliance with a call to the draft.