1928 Cleveland
Cleveland introduced its first four cylinder in 1925, but struggled due to a smaller engine than rivals Henderson and Ace.
In 1926, they changed engine design to an inlet-over-exhaust valve configuration and a displacement of 45 cubic inches. In 1927, the displacement was increased to 61 cubic inches making it a true competitor to Henderson and Ace. The 4-61 had a top speed of 90 mph and was the first American motorcycle to use a front brake.
By the year this bike was built, Cleveland was in financial trouble and offered itself to Harley-Davidson. Harley-Davidson considered the offer due to Cleveland's already present competition to Indian's Ace based Fours. In the end, Harley-Davidson declined in favor of developing their own Four. In 1929, just a short time after the Wall Street Crash, Cleveland went out of business.