He then studied law with John Edward Parsons, was admitted to the bar in 1875, and formed a partnership with Albert Stickney.

Shepard was a delegate to the National Convention of the "Gold Democrats" in Indianapolis, which nominated the Palmer/Buckner ticket for the 1896 United States presidential election.

In 1897, Shepard supported Seth Low, who ran on the Citizens Union ticket for Mayor of New York City at the first election under the Consolidation Charter.

In 1901, despite Shepard's reformist record, Tammany boss Richard Croker had him nominated as the regular Democratic candidate for Mayor.

Mark Twain, an avid supporter of Seth Low, said of Edward M. Shepard: "A Tammany banana is a strange thing.

Shepard had been considered the frontrunner for the gubernatorial nomination, but Tammany boss Charles Francis Murphy preferred Dix.

At the onset of 1911, the Democrats having a majority in the Legislature, it was generally believed that Shepard would be elected US Senator from New York to succeed Republican Chauncey M. Depew.

But Sheehan remained in the field, and after 74 days of deadlock, James A. O'Gorman was elected as a compromise candidate on April 1.