Marshal for the Eastern District of Wisconsin form 1952 to December 31, 1955, after which Michalski was elected Sheriff of Milwaukee.
In 1918, he became an apprentice machinist, and continued in that profession, except for a brief time (September 1, 1933 - January 1, 1935) as an inspector for the State Athletic Commission.
During this period, he ran a liquor store on Mitchell Street for five years, and made investments in South Side real estate.
Michalski, described as "a large man with a booming voice... known in the political arena as a fiery orator", became known for his malapropisms (asked about how he felt, he reportedly replied "My syracuse veins are bothering me").
")[7] He was a delegate to the 1964 Democratic National Convention, nominally pledged to favorite son Governor John Reynolds as a presidential candidate.