Bill Holland began his Indianapolis 500 career at the end of an era which crowned three three time winners. He very easily could have been one of them. In 1936 Louis Meyer became the first three time winner. Between 1937 and 1948 Only five drivers won the race. Wilbur Shaw and Mauri Rose won three times, Floyd Roberts and George Robson each won a a race, and Floyd Davis was the co-winner with Rose in 1941. But Holland just as easily could have been a three time winner as well.

From 1947-1949 Lou Moore’s Blue Crown Spark Specials, a Deidt chassis powered by an Offenhauser engine, , dominated Indianapolis. Rose, who co-won the 1941 race in a Moore car, the last race before World War II, was back with the team, paired with rookie Holland in 1947. It was a formidable but volatile combination.

In the 1947 500 Holland took laps 24-59. Rose led the next 26 laps. Holland regained the lead on lap 86 and appeared to have the race well in hand. Late in the race with a 1-2 finish fairly secure,  Moore instructed the crew to put the letters “EZY” on the sign boards for both cars. Holland thought he had a lap lead on Rose. When Rose passed him on lap 193, Holland thought Rose had unlapped himself. The pass was for the lead. Rose became a two time winner. Holland assumed he had won and learned he did not as he pulled into his pit.

“It’s the lousiest deal I ever got,” he said later.

The 1948 500 had the same result but less dramatic fashion. Rose won by more than a minute and Holland didn’t lead a lap.

In 1949 Holland took the lead on lap 55 and didn’t relinquish it the rest of the race. With rose running second, both drivers were again give instructions to slow down. Rose continued to gain ground on Holland, who was probably not going to get caught again. The last lap drama was avoided when Rose dropped out of the race with eight laps to go. Moore fired him after the race.

For the 1950 race, Rose drove for Howard Keck, who a couple years later hired Bill Vukovich. Holland finished ahead of Rose again, but Johnnie Parsons won the race and Holland was second in the rain shortened race. Holland led eight laps, from lap 110-117. Parsons took the lead back and was leading when the race was called after 138 laps. Could Holland have caught Parsons? Possibly, but we will never know. Parsons was driving with what his crew thought was a cracked engine block. Their strategy was to lead as much as they could to collect lap prize money. If the engine blew, at least the lap prize money would salvage part of their day.

Holland ran just one more 500 Mile Race in 1953, finishing 15th, dropping out after 177 laps with a cam gear problem. He had been suspended in 1951 for driving in a  race in Florida which was not sanctioned by USAC.

Holland’s record in his first four 500s was three seconds and a win. This definitely puts him in some select company. Holland is in the same conversation with Shaw and Vukovich when the discussion turns to drivers who should have more 500 victories than they do.