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Throughout his career he waged many failed campaigns for political office, including unsuccessful bids as "Honest Abe" for the U.S. Senate in 1974 (defeated in Democratic primary), for the New York City Council, for Manhattan Borough President in 1997, for Lieutenant Governor of New York, for New York State Comptroller in 1998, and for Mayor of Miami Beach, Florida.
A 1999 audit of the agency by New York State Comptroller Carl McCall found many instances of patronage and mismanagement.
In 1912, he ran on the Progressive ticket for New York State Comptroller, but was defeated by Democrat William Sohmer.
A 2007 investigative audit by the New York State Comptroller found that the majority of SUNY campuses had, in violation of the Federal Clery Act, underreported crimes and failed to disclose required safety and security policies.
Samuel J. Pitcheralle is the Treasurer of Saratoga County, New York appointed after Christopher Callaghan retired in 2006 to run for New York State Comptroller.
In response, the Tammany-allied State Comptroller William Sohmer moved to freeze payrolls for state highway and prison projects, and the State Senate under the leadership of another Tammany officer Robert F. Wagner refused to approve the Governor’s appointments to the New York Public Service Commission.
In 1979, he became the County Executive of Erie County, New York, succeeeding Edward Regan, who stepped down to become New York State Comptroller.
He was appointed as Acting Treasurer in 2006 by Governor George Pataki to fill out the remaining months of the term of Christopher Callaghan, who had retired to pursue a bid for New York State Comptroller.