Political Career
Degnan began his political career in 1999 when he was elected to the first of what would be four terms as a Brewster Village trustee.
In his first year in office, Degnan opposed plans by Putnam County to expand Brewster's social services center, expressing concern that an expanded center would exacerbate illegal immigration in the village and require taxpayers to pick up the tab for services provided to non-taxpaying day laborers. In 2000, though Degnan estimated that 300 day laborers could be found on the streets of Brewster in a given day, he again opposed a proposal by the Putnam County executive to construct a day laborer hiring center in Brewster for similar reasons. In time, Degnan would come to view a hiring center as a way to reduce the loitering and crime which many village associated with day laborers. But in 2000, he remained opposed.
In 2005, Degnan challenged the eighty seven year old, six term incumbent Cesar for the mayorship of Brewster. As a result of New York's electoral fusion system, Cesar ran as a Conservative and Independent; Degnan, on the Democratic and Republican lines. In the end, Degnan defeated Cesar, then New York's oldest sitting elected official, by 97 votes.
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