[3] His older brother, Robert Flanagan, also entered politics, but as a Republican serving in the Maryland House of Delegates and as that state's Secretary of Transportation from 2003 - 2007.

In 2002, Flanagan made a bid for the Democratic nomination for State Treasurer but was defeated by Senator Jeb Spaulding, who went on to win the office.

[5] He was not easily observable from the roadway, and hung upside down in subfreezing temperatures for 18 hours before someone spotted his car and he was rescued.

[5][6] On December 4, 2006, Flanagan had another car accident when he went off the road while turning onto I-89 in South Burlington.

In failing health for the last decade of his life, Flanagan died on November 3, 2017, aged 66, at a nursing home in New Hampshire.