[1] Canfield worked in various jobs prior to running a small faro parlor in Pawtucket, Rhode Island which eventually led to his arrest.
However, gambling was illegal in the United States and in 1885 he served a six-month sentence in Rhode Island jail for violating gaming laws.
Canfield invested an estimated $800,000 in enhancing the building and the grounds of Congress Park to bring them up to the standards of the top European establishments.
In 1902–3, he added a dining room to the back of the Clubhouse fitting it with stained glass windows and an early form of air conditioning.
The elegant atmosphere made the cream of society feel welcome to bet their money on the Clubhouses's many games of chance.
The clientele during this period included not only members of wealthy families like the Whitneys, Vanderbilts and J. P. Morgan's, but gambling legends like Diamond Jim Brady and John Warne "Bet-a-Million" Gates, and prominent entertainers like Gates' girlfriend Lillian Russell and impresario Florenz Ziegfeld.
Canfield owned a number of fashionable gambling houses in New York, Rhode Island, Saratoga Springs and Newport.
In December 1902 his New York clubhouse at 5 East 44th Street in Manhattan was raided, and Canfield, who was not actually arrested, escaped to England where he lived for the next four and half months.
A few months before his death, he sold his collection of etchings, lithographs, drawings and paintings by Whistler to the American art dealer Roland F. Knoedler for $300,000.
According to Alexander Gardiner, Canfield returned to Europe to sit for Whistler at the New Year in 1903, and sat every day until 16 May 1903.
[3] After Canfield's untimely death in 1914, Genevieve and their children, Grace and Howland, lived comfortably on the fashionable East Side of Providence, through the benefit of her late husband's will.