First term (1906–1908) In
December 1905, Fitzgerald was elected
Mayor of Boston. In the process, he made an enemy of the powerful Lomasney by opposing one of Lomasney's lieutenants,
Edward J. Donovan. After Fitzgerald beat Donovan in the mayoral primary, Lomasney endorsed the Republican candidate,
Louis Frothingham, and delivered 95% of the vote in his usually Democratic ward to Frothingham. However, the Republican vote was split between Frothingham and judge
Henry Dewey, who ran on the Populist ticket after losing the primary. Fitzgerald won despite Lomasney's undermining, though only with a plurality of the vote. Another opponent of Fitzgerald's during the campaign was
P. J. Kennedy, a behind-the-scenes Democratic figure. They later became allies. In 1914, their families were united when P. J.'s son
Joseph P. Kennedy Sr. married Fitzgerald's eldest daughter
Rose. Fitzgerald was the first American-born
Irish Catholic to be elected mayor. He lost the 1907 election in part because his opponent, Republican
George A. Hibbard, promised he would "clean up [Fitzgerald's] mess." With control of the city and state Government, Republicans revised the city charter to curb the power of the Irish Democratic ward bosses like Fitzgerald and Lomasney. They eliminated the large common council, replaced the board of aldermen with a nine-seat
city council, extending the mayor's term to four years, and making all offices formally non-partisan, removing the advantage of party recognition in the predominantly Democratic city.
Second term (1910–1914) In 1910, Fitzgerald ran for mayor again. His campaign was almost scuttled by a bribery scandal involving no-bid contracts with kickbacks during his first term. Fitzgerald escaped prosecution, but made a long-term enemy in
Daniel H. Coakley, an Irish lawyer who had defended one of the key figures in the business. In addition to his rivalry with Lomasney, Fitzgerald now also had to contend with the rising star of
James Michael Curley of Roxbury, who was kept out of the race by assurances that Fitzgerald would serve only one term. Fitzgerald won a narrow victory over
James J. Storrow, a stiff Protestant Republican
Boston Brahmin. Early in his first term as Boston's mayor, Fitzgerald had formulated a plan to revitalize the commercial importance of the city under the banner of "a Bigger, Busier and Better Boston." This plan was not pursued by Hibbard but gained traction after Fitzgerald's return to office. Fitzgerald was able to persuade businesses and the Massachusetts legislature to invest $9 million for improvements to the port by 1912. Within a year, the investments began to pay off in the form of new port traffic to and from Europe. In 1914, Fitzgerald broke his promise to Curley and attempted to run for a second consecutive term. Curley made common cause with Daniel Coakley, and they secured Fitzgerald's withdrawal by threatening to expose a dalliance he had with a
cigarette girl, Elizabeth "Toodles" Ryan—who was only 24, the same age as Fitzgerald's daughter Rose—at a local gambling club. Curley was elected in
January 1914 to his first of four terms as Boston mayor. == Later political career ==