Rollie Free was a thirteenth century man stuck in the twentieth century. He was all about honor and bravery. Free was mild mannered unless someone questioned his ethics or his courage, or challenged his “castle” (Indian motorcycles). He was ready to fist-fight over such matters, and people knew this. Brash and authoritative, Indian dealer Free was fond of taunting local Harley-Davidson speedsters with words like: “You got a hundred bucks, Jughead? You want to run against my Indian Chief, my Indian Four, or my Indian Scout? Pick one.” Once, upon goading a Harley rider into a match race, Free opened his wallet, and showed that he had $300 to wager. Of significance, $300 was the dealer cost of Free’s new Indian. The Harley rider agreed to a race. Free said, “Let’s see the money.” The Harley rider said, “It’s a gentlemen’s bet.” Free retorted, “I never had a gentlemen’s bet with a Harley guy in my life! I want the money up.”

 Free enjoyed making brash statements, then proving he was right. Sometimes the proof was on a document that he would hand you. Other times Free had to demonstrate to skeptics just how unbelievably fast he could make Indian motorcycles run. Free had customer Indian bikes – fenders, lights, saddlebags, and all -- that had more top speed than Harley racers or a certain stripped-down Harley that was the official record holder. There’s something to be said for being faster than the “fastest.” Bound for Daytona Beach and an attempt to beat the Harley 750 cc record, Free told his wife “If I don’t beat them [Harley-Davidson] by ten miles an hour, I won’t even come home.” He bettered the record by “only” nine and a half miles an hour. But Free then displayed a letter from the weather bureau which validated his statement that 17 mile an hour crosswinds were to blame. “I wasn’t worried about getting a record, I could beat [the Harley record] with my wife on back of the machine [Indian].”

Yet the frisky Free had a softer side. “Chief” Free was kind and generous to members of his Indian “tribe.” If a customer got behind on motorcycle payments, Free wouldn’t repossess the motorcycle. He would keep accepting partial payments and late payments until the customer got past some rough point in his life. Free almost never cursed, and never in front of women. He was big hearted. When he topped a rival’s American speed record but by only four-hundredths of a mile-per-hour, he asked that he and the rival be listed as co-record-holders.

 Rollie Free claimed he was no salesman, that he had to have a demonstrably superior product in order to sell it. He was guilty of excess modesty. The man could sell anything, especially himself. How else, having never before raced a car of any kind in even a local-yokel contest, how else could Free have talked himself into a starting spot in the 1930 Indianapolis Five Hundred? How else, seventeen years later, for his second car race, could he have re-sold himself to Indy officials for another go at the Five Hundred?

Though the four-wheeled Indy bouts were sideshows to his motorcycle career, the two races, the 1947 race especially, speak volumes about Rollie Free’s courage. Racing once every seventeen years, against guys who did it three times a month for a living, Free was in sixth place at 220 miles when the engine failed. His simple thought process was clearly on display: “If the guy in front of me can, then I can.”

In 1948, Free made the famous “bathing suit” record at Bonneville, his slippery body enabling him and the Vincent H.R.D. motorcycle to exceed the then “magic” 150 miles an hour. Asked about the risk of 150 mph near-naked riding over the sharp salt crystals, a risk increased by Free’s style of flat-out chin-on-the-tank feet-out-the-back, Free responded: “I would’ve stood up on the bike, if that would’ve made it go faster.”

 In 1949, Rollie Free witnessed Englishman Noel Pope’s Bonneville World Record attempt with a streamlined Brough-Superior. After crashing the machine, Pope vowed he would never again ride a fully enclosed motorcycle. In 1950, Rollie Free made an attempt on the BMW-held World’s Record, using a Vincent enclosed in a streamlined shell. After losing control and skidding over a mile, Free nonchalantly went about the task of removing the damaged enclosure, and soon was setting a series of American records with the naked bike. Free vowed to solve the streamlining problem and return for another World Record attempt.

Yet, for all of Rollie Free’s Indian and Vincent record setting, and his side adventures like the two Indy Five Hundreds, Free never brought up any of the go-fast subjects. On first thought, one supposes, at least regarding Free’s well known motorcycle adventures, that Rollie was simply cagey because he knew that people would quickly draw upon his reminiscences. Yet, there must have been some modesty in play. For one friend recalls that he knew Rollie for years before the friend learned about the two Indy races!

In 1953, came Rollie Free’s last big thirteenth-century act. He was at Bonneville to re-run the Vincent streamliner. While Free was practicing with the naked bike, the referee suggested that Rollie practice under the clock in order to raise his American records. Thus, Free set his last record during a bout of sun stroke while “running on auto-pilot.” After a hospital stay in Salt Lake City, Free returned home to Hollywood, California, to find a very upset wife. The couple had never had children, and so had poured out their affection upon each other. They were madly in love, in other words. If the Knight’s Lady was upset, it was up to the Knight to fix this. Then and there, after so many record runs, amid a serious and promising program to capture the world’s record, then and there Rollie Free told his wife that he wouldn’t race again.