Retro Romance

Bad-Boy Mayor Seeks a Wife

Renegade mayors are nothing new, and you don’t need to look to major cities – like Toronto – to find them. Even small cities can lay claim to notorious figures. Newburyport’s infamous example is Andrew “Bossy” Gillis, who ran for mayor 20 times from 1928 to 1958 and held the office for six terms. As the story goes, he initially entered politics after being told by the sitting mayor that he couldn’t open a gas station in the town’s Market Square. Gillis supposedly punched the incumbent, and then promptly ran for office. He was elected and opened his gas station despite lacking the required permit. As a result, Gillis spent 60 days in jail, performing his mayoral duties by telephone.

Gillis used to say that he settled more disagreements through fistfights than discussions. But he didn’t limit his pugnaciousness to politics; he was equally obstreperous when it came to romance. In 1930, Gillis traveled to California to find a wife. In an interview with the Palm Beach Post, he proclaimed: “Blondes won’t do. In the first place it is my observation that they are not good housekeepers, and in addition they go to bridge teas, and no wife of mine is going to be a bridge tea hound. I’ve decided to give all the brunettes and red heads who can qualify as good lookers an even chance.” He went on to describe himself as “Aged 33, healthy as they make them, and a darn fine fellow.”

Gillis’ unlikely luck won out: A dark-haired woman found a way to love him despite his flaws, and marriage seemed to do him a world of good. A 1937 issue of the Reading (Mass.) Eagle newspaper reported Gillis as saying, “My wife is the woman behind the throne. She tamed me.” Time magazine agreed, writing in 1949: “Bossy still looked as seedy as Burpee’s spring catalogue, and he fitted into the gentle, museum-piece decor of old Newburyport, Mass., like a prime bull at a vegetarians’ convention. But the coming of middle age, a wife and a new black bowler had smoothed some of Bossy’s sharp edges.”

The public got a glimpse of the grit that did the smoothing when his bride made her own bid for the mayoral seat in 1937. The Nashua Telegraph captured her in a classic Mae West moment: “I don’t tell what my move is going to be before I make it. In checkers, if I’m going to take two men I take them and tell about it afterwards.”

*Sources include Time magazine, Reading Eagle, Nashua Telegraph and Newburyport Daily News. Top photo: Andrew “Bossy” Gillis ran for mayor of Newburyport 20 times between 1928 and 1958 and held the office for six terms. Courtesy photo.