This is the story of a self-educated, charismatic, gifted leader who overcame personal tragedy in childhood and was elected the youngest mayor of a major city in America at age twenty-six. It is the story of a reformer who possessed a genius for politics. James K. McGuire (1868–1923) was elected mayor of Syracuse three times as a Democrat in a Republican bastion. As a candidate for governor in 1898, he nearly derailed the rise of Theodore Roosevelt. His ideas and positions informed the candidacy of William Jennings Bryan in his quest for the presidency and the platform of the Democratic Party in those elections.

James K. McGuire is often overlooked as a key figure of Irish nationalist politics, yet the issue defined his life for over three decades. As the title implies, he had multiple careers, each overlapping the others.

James mark Sullivan was part of the post-famine Irish immigration to the United States in the late 19th century. Overcoming family misfortune, he moved from newsboy to journalist to Yale-educated lawyer. Relocating to New York City, his association with Tammany Hall involved him in the "Crime of the Century" Becker-Rosenthal murder case, a role not previously explored. Sullivan's involvement won him a patronage appointment as ambassador to Santo Domingo. Scandals about graft and corruption forced his resignation. However, another factor which contributed to his dismissal, unexplained until now, was his effort at subversion of his government's policy of neutrality, which was connected to his ties to Irish nationalism. He later established the first indigenous Irish film company with a pronounced Nationalist agenda, making several films which are now classics of the silent film era. Following the death of his wife and son during the influenza epidemic of 1918, he returned to the United States. Failing to revive his legal career, he removed to Florida, dying in relative obscurity.

Along with his close comrades Michael Collins and Eamon de Valera, Harry Boland (1887-1922) was probably the most influential Irish revolutionary between 1917 and 1922. His sway extended to almost every aspect of republican activity. Already prominent as a hurler before 1916, he was convicted and imprisoned after an energetic Easter Week. He subsequently became Honorary Secretary of Sinn Fein, T.D. for South Roscommon in the First Dail, President of the Irish Republican Brotherhood's Supreme Council, and a republican envoy in the United States between May 1919 and December 1921. He broke with Collins over the Treaty, but became the chief intermediary between the factions. Early in the Civil War, however, he was killed by National army officers in the Grand Hotel, Skerries. Boland's influence was the product of charm, gregariousness, wit, and ruthlessness. After his rebel father's early death, Boland's mother raised him in a spirit of intransigent hostility to Britain. Yet he was also stylish, cosmopolitan, and humane. His celebrated contest with Collins for the love of Kitty Kiernan is perhaps the most intriguing of all Irish political romances. Attractive yet elusive, his personality helped shape the Irish revolution. David Fitzpatrick's biography draws upon documents in Irish, British, and American archives, including his American diaries and thousands of letters to, from, and about Boland. Extensive use has been made of family papers and de Valera's vast archive on the Irish campaign in America. These and other recently released documents illuminate the inner workings of Irish republicanism, and the critical importance of brotherhood in the revolution. As an old-fashioned republican and advocate of 'physical force', Boland is still venerated as a martyr by revolutionary republicans. Yet, in his conduct, he practised the ambiguities associated with Sinn Fein in today's Northern Ireland. Doctrine was subordinated to the twin quests for republican unity and political supremacy, entailing reiterated compromise, systematic duplicity, and mastery of propagandist techniques. If his outlook seems archaic, his practice was astonishingly modern. Harry Boland was a forerunner for Adams and McGuinness. -- Publisher description.