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In page Milwaukee:

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Milwaukee has a history of giving long tenures to its mayors; from Frank Zeidler to Tom Barrett, the city had only four elected mayors (and one acting) in a 73-year period.[1] When 28-year incumbent Henry Maier retired in 1988, he held the record for longest term of service for a city of Milwaukee's size,[citation needed] and when Barrett retired in 2021, he was the longest-serving mayor of any of the United States' 50 largest cities.[2]