"Milton was born in St. Paul, Minnesota, on November 14, 1893. He began his career in racing in 1914, competing on dirt tracks in the Midwestern United States. By 1917, he was competing nationwide, and earned his first major win at a track in Providence, Rhode Island. In 1919, he was one of the dominant figures in American racing, winning five of the nine championship races including the International Sweepstakes at Sheepshead Bay, New York, and making his debut at the Indianapolis 500. Later that year he suffered severe burns when his car burst into flames during a race at Uniontown, Pennsylvania. He returned to the track the following year to win the Universal Trophy on June 19 before winning the 1920 United States National Driving Championship.
Milton was a starter in the Indianapolis 500 eight times, earning the pole position once, and finishing in the top five on four occasions. He drove for Duesenberg his first time in 1919 and again the following year when he finished third. In 1921, the twenty-seven-year-old Milton won the celebrated race driving a straight-eight Frontenac built by Louis Chevrolet. In 1922 fuel tank problems forced Milton out of the race after only forty-four laps, but he came back in 1923 driving for the H.C.S. Motor Co. with a Miller 122 and won the race for the second time. His last was the 1927 Indianapolis 500 where he finished eighth.
At the 1936 race, Milton returned to the Indianapolis Motor Speedway to drive the Packard 120 Pace Car. At his suggestion, the tradition of giving the race winner the Pace Car began that year. In 1949 Milton was appointed chief steward for the Indianapolis 500. Health problems forced him to retire in 1957."