His chief opponent in the primary was James Edward Doyle, whose campaign was managed by Patrick Lucey.
In 1957, Proxmire won a special election to the United States Senate and named Day as his legal counsel in Washington, D.C.
During this period, he was chair of the Madison Public Housing Authority, which during his tenure built the first public housing units in Madison; served as special counsel to Governor John W. Reynolds in the 1964 reapportionment case before the Wisconsin Supreme Court, which became the first state court in the nation to reapportion legislative districts on the basis of one person, one vote.
He also represented the mayor of Madison in a civil action challenging his right to go forward with the building of the Monona Terrace and served on the Board of Regents of the University of Wisconsin System from 1972 to 1974.
His name appears on a Bicentennial commemorative plaque in the capitol rotunda, along with an original copy of the Wisconsin Constitution of 1848.