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Ral designed an unorthodox roll that enabled his brother to keep his head at least two feet above the ground, relatively safe from impurities. Parr would begin in a sitting position, flop over sideways until his weight rested on his hands and knees, and then flop back to a sitting position. Roche called this method "a good, ground-covering roll."
In practice sessions, Parr would execute four rolls, rest for a few moments, and then repeat the pattern. Soon he had mastered the technique and was able to gain four feet going uphill and five feet on a downgrade with each roll. A date was set.
Despite Parr's desire to discourage undue publicity, news of the roll's date leaked out. On the evening of Monday, May 18, about 100 reporters, friends and other spectators gathered at the Elkridge Kennels to witness Parr's historic attempt.
He arrived wearing ankle-high golf shoes, ribbed woolen socks, khaki knickerbockers, a heavy woolen sweater and a plaid golf cap. He had attached football pads to his elbows and pillows to his knees. After wrapping his hands in linen bandages, he pulled on a pair of work gloves.
Parr started to roll at eight sharp. The first part of the course, along the club's gravel driveway, was the most perilous. As one reporter noted,
Parr was a big man, "weighing something like 175 pounds." Despite his padding, he cut his left knee during the first hour.
At 11:35 p.m., having traveled exactly four-fifths of a mile, Parr rolled into a little tent equipped with medical supplies. Society physician R. Tunstall Taylor examined the athlete: pulse rate, 72. After rubbing Parr's knees and arms with alcohol, Taylor pronounced him fit to continue, and Parr resumed rolling at 12:20 a.m.
An hour later at least 30 spectators were still around. A member of the opposition camp—those who had wagered that Parr would fail—followed in a Thomas Flyer touring car to make sure the rules were observed. Friends, walking ahead with lanterns, removed stones from the course, and one, D. Harry Mordecai, carried a mattress for Parr to rest on periodically.
By 3 a.m. Parr had rolled a little more than halfway. He was beginning to weaken and was resting after every third, rather than fourth, roll. But at 4:15 a.m. he seemed to regain enthusiasm as he rolled past the gates of Attica, the home of Robert Garrett, an investment banker and an heir to the Baltimore & Ohio Railroad fortune. One of Parr's friends called out "Good!" after every roll.
"The rolling might be good, but the resting part is much better. At least it seems so to me," Parr said. "Some of you fellows are hardhearted wretches. You haven't got a bit of sympathy for a man when he's down."