He ran for Governor of Maryland in 1966 as an Independent after the Democratic Party nominated segregationist George P. Mahoney as its candidate.
Had the 10% of the vote received by Pressman instead gone to Mahoney, Spiro Agnew would have lost the 1966 gubernatorial election by a narrow margin.
Pressman returned to the Democratic Party following his victory and won six additional terms as Baltimore City Comptroller.
We have a city that is bloomin’/But Randy Newman isn’t human.” [1] During the 1970s, when the Baltimore Colts owner Robert Irsay and Baltimore Orioles owner Jerold Hoffberger were seeking major upgrades to the outdated Memorial Stadium or the building of a new stadium, Pressman opposed using public money to build a replacement.
The measure passed 56 to 44 percent, effectively destroying any chance of a new, modern sports complex being built in Baltimore.