Benedum's career got a lucky start after a chance encounter on a train with a superintendent of the South Penn Oil Company. Benedum was known for his negotiating skills and his success as a wildcatter. He is said to have found "more oil in more places than anyone in history." With his long-term business partnerJoe Trees, Benedum created the Benedum-Trees Oil Company. The famous partnership started with the purchase of an oil lease in Pleasants County, West Virginia. The first well on this lease began producing in 1896; soon six other wells became active. The profit from this lease allowed Benedum and Trees to purchase a dozen additional leases in West Virginia. In 1911, the company moved into the Benedum-Trees Building in downtown Pittsburgh. Benedum and Trees were instrumental in 1943 in the first oil discovery in Florida in Collier County. Trees, however, had died a few months before the oil began to flow. The company was responsible for the discovery of the famous Yates Oil Field in Texas. The business was so successful that Benedum appeared on a list of the seventy-six wealthiest Americans in 1957. He was proclaimed West Virginian of the Year in the same year for leaving much of his wealth to the improvement of the state. Benedum was a Democrat and donated heavily to the party. The New York Times described him as a "friend" of President Roosevelt. Benedum made a particular effort to convince African Americans, who at that time largely identified with the Republican party, to vote Democratic.
Legacy and philanthropy
Benedum never retired. Even though he was very wealthy and eighty-seven years old, The New York Times reported in 1956 that he continued to work seven days a week. In 1910, Benedum sold an oil lease which he had procured in Caddo Parish, Louisiana, for $7 million. There he met one of his younger associates, Clem S. Clarke of Shreveport, whom he encouraged to run in 1948 as a Republican for the United States Senate against Russell B. Long. Clarke, who attended Benedum's 80th birthday party in 1949, recalled of his mentor, Benedum:
There were governors, senators, men of industry, and I've never heard from any group of men in my whole life the amount of nice things that these people had to say about Mr. Benedum during that birthday dinner.... Mr. Benedum has been known around Pittsburgh and around the industry as a maker of millionaires. He hasn't tried to keep it all to himself - he's taken other people in with him. All of his associates that have been with him have all turned out to be millionaires or almost millionaires and some of them have made several millions of dollars by sticking to him and working with him. I think that's extremely commendable, because I've known in my life a number of great men who have been moneymakers, but a great portion of them have always wanted to get all of the money for themselves. They didn't want anybody else to share it with them. So I think it's extremely commendable that Mr. Benedum has never been a man who wanted to make all the money....
Benedum donated to many charitable causes during his lifetime. He was responsible for the construction of a civic center and a Methodistchurch building in his hometown of Bridgeport, West Virginia. The wealth from the Benedum estate was placed in a foundation named for the Benedums' son: the Claude Worthington Benedum Foundation. Benedum directed that the foundation use the money for causes local to Pittsburgh and West Virginia. When Benedum died in 1959 he was living in the mansion which he had constructed in Pittsburgh at Woodland Road and Fifth Avenue. He is interred at Homewood Cemetery.
