When the League needed an attorney, Wheeler went to law school, studied for four years while working for the League and became an attorney. Eventually he prosecuted over 2,000 dry law cases.

Wheeler perfected the powerful political machine of the League. Early in his career with the League, he rode a bicycle from house to house to defeat a state senator who was not a friend of the League. Politicians realized very quickly that he was a man to be feared. When he moved to Washington D.C., his political presence was felt in the highest levels of government in this country. In 1919, he became legislative superintendent for the League and is largely responsible for helping to draft the 18th amendment and the Volstead Act.

During prohibition, he sought strong enforcement legislation and policies.

He was vigilant in guarding the League's interest in Congress. According to the Standard Encyclopedia of the Alcohol Problem, Wheeler dealt with Congress and other branches of the government using "the card-index system of keeping tabs on public officials and of rallying supporters when needed."

Upon the death of Purley Baker in 1924, Wheeler was able to wrest control of the League's policies from his rival Ernest Cherrington, the proponent of an education policy. Wheeler's behind-the-scenes maneuvering resulted in the election of Francis Scott McBride as national superintendent.

By 1926, Wheeler was facing strong opposition by some members of Congress who were questioning the spending by the League in some congressional races.

Wheeler's health was frail and by the following year he had to retire to his vacation home in Little Point Sable, Michigan, in order to try to regain his strength. A tragic set of circumstances ensued. His wife was burned by the gasoline stove in the kitchen and fled through the house with her clothes on fire as her father suffered a fatal heart attack attempting to help her. She died the following day. Within weeks Wheeler himself died.