Gerald F. "Gerry" O’Leary (August 7, 1932 – May 23, 2014) was an American politician from South Boston, Massachusetts.

[1] A student athlete, O'Leary ran the 400 metres at English and played running back for the Holy Cross football team.

He ran for the United States Senate in 1972, but lost to Middlesex County District Attorney John J. Droney in the Democratic primary.

He resigned on October 4, 1980, after being arrested and charged with attempting to extort a $650,000 kickback from a school bus company.

[3] He pleaded guilty to violating the Hobbs Act and was sentenced to eighteen months in prison.