Cleveland Brothers Equipment Co., Inc. can trace its origin back to 1937 when Bob and Roy Cleveland started a landscaping contracting company. The company evolved through the years working on numerous high profile jobs. In search of new opportunities, Bob and Roy took over the Caterpillar dealership in Central Pennsylvania.

On Jan. 1 1948, Cleveland Brothers was formed. In 1965, Roy stayed at Cleveland Brothers while Bob moved to New York to pursue other dealer opportunities. Bob and Roy's father, C.W. "Dad" Cleveland, was hired as the purchasing agent for the company. Roy's son, Jay, began working at his father's company in 1961. In 1963, Bill Kirchhoff married Jean Cleveland, Roy's Daughter.

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