Born in Louisville, Kentucky, Flannery studied at the Chicago Art Institute then went into advertising, working his way up to a vice-presidency of Young & Rubicam. Retiring in 1941 to devote his time to painting, Flannery received commissions from prestigious owners and breeders, including Greentree Stables and Alfred G. Vanderbilt. In his one-man shows at New York’s Kraushaar Galleries, he documented American racing with an insider’s eye.
Flannery spent most of his professional painting career working for Greentree Farm in Saratoga Springs, NY, Aiken, SC, and Lexington, KY. The majority of the paintings he produced, depicted Greentree subjects.
When Flannery passed away, his agent Kraushaar Galleries called New York horseman Mr. Walter Jeffords who pretty much bought everything in the studio. Mr. Jeffords sold a group (10-12 pieces) of paintings to Mr. John Gaines, Gainesway Farm, Lexington,KY. His work has pretty much remained in these three collections.