ALBANY — As a former aide to both Andrew M. Cuomo and his father, Todd R. Howe built a reputation as a prominent lobbyist in Albany and Washington, with top clients like the Metropolitan Museum of Art and major developers in upstate New York.

Trading on his connections as a Cuomo loyalist, Mr. Howe was seen by many as a reliable conduit to the governor’s office. Now, amid a sprawling federal investigation into the Cuomo administration’s marquee economic development projects, he has emerged as one of its top focal points.

The allegations against Mr. Howe, who has not been charged with a crime, are not clear. But a review of court documents and public records found that his professional persona masked a history of chaotic and slipshod financial dealings, including a 2003 bankruptcy and nearly $400,000 in federal tax liens and other judgments against him.

Though he looked every bit the prosperous Beltway insider, with large homes in the Maryland suburbs and children in elite New England boarding schools, he appeared to be often short of money, dodging tens of thousands of dollars in bills from a long lineup of local car dealerships and home-improvement businesses.