On and off for two decades, the affable Mr. Rodham has tried to use his connections with his sister and his brother-in-law, former President Bill Clinton, to further a business career that has seen more failures than successes. The connections to the Clintons have given Mr. Rodham, a self-described “facilitator,” a unique appeal and a range of opportunities, like addressing Chinese investor conferences and joining an advisory board of a company seeking permission to mine for gold in Haiti. When Mr. Rodham was short on cash in 2010, Mr. Clinton helped get him a job for $72,000 a year raising investments in GreenTech Automotive, an electric car company then owned by Terry McAuliffe, an old friend of Mr. Clinton’s and now the governor of Virginia. A government investigation in March found that GreenTech, which sought green cards for its Chinese investors through an American government program, had received special treatment in the handling of its visa applications. The report described instances when Mr. McAuliffe and Mr. Rodham contacted an official from the Department of Homeland Security to complain about the pace of the visa process. Tony Rodham has lived in the shadow of his sister. He never finished college, and he worked at a variety of jobs — as a prison guard, private detective and at the Democratic National Committee — until after the Clintons were in the White House, when he became a consultant and deal broker. He was once married to Nicole Boxer, the daughter of Senator Barbara Boxer of California. He lives with his second wife, Megan, and two young children in a large house on a hill in Vienna, Va., a suburb of Washington. He was married to Megan Madden, whom he wed in 2005 following a divorce from his first wife, Nicole Boxer. Rodham was the father to three children: Zachary Boxer Rodham, Simon Rodham and Fiona Rodham.