In 1936 he teamed up with his friend Walter Hagan to win the Inverness Invitational Four- Ball, a year after it had been won by Tommy Armour and Bobby Cruickshank, for what turned out to be Hagen’s last win on tour.
However, even by this early stage, it was clear that Ky’s fondness for drink was becoming a problem. It was said that the easiest way to beat Laffoon on the course was to get him into a bar the night before. As might be expected with such a larger-than-life character, he was immensely popular with his fellow pros, and many would seek him out for swing tips and to revel in his company. In particular, he and Armour were often together drinking and gambling.
1938 saw a relatively sober Ky win the Miami Four-Ball with Dick Metz, then he beat Sam Snead in the Cleveland Open in remarkable fashion. On the 18th, Snead hooked his approach towards the clubhouse and the ball shot through the open door of the men’s locker room and out of bounds. In between his two wins, Ky shot his career best score – a 61 at his home club, Schifferdecker Golf Course, in Missouri.
In 1940, in the US Open at Canterbury Golf Club, Ky became part of Major history when he was one of six players who were disqualified for teeing off early. Having seen a storm brewing, they wanted to get ahead of it but were warned by the marshal that they should play at their official time. They teed off 15 minutes early anyway and their subsequent eviction sparked a national outcry as one of the group, Ed “Porky” Oliver, shot a 71 to tie the winning score but was kicked out of the play-off regardless.