James Aloysius O’Leary

James Aloysius O’Leary (April 23, 1889 – March 16, 1944) was an American lawyer, businessman, and Democratic politician who served as a United States Representative from New York for five consecutive terms from 1935 until his death in 1944. Over the course of his decade in the House of Representatives, he contributed to the legislative process during a significant period in American history, representing the interests of his constituents through the Great Depression and the early years of World War II.

O’Leary was born on April 23, 1889, in New Brighton, Staten Island, New York. He received his early education at St. Peter’s Academy and Augustinian Academy, both on Staten Island, and later attended Westerleigh Collegiate Institute. In addition to his formal schooling, he pursued the study of law, laying the groundwork for a professional career that combined legal training with business and politics. His upbringing and education in Staten Island helped root his later public service in the local community he would eventually represent in Congress.

Before entering national politics, O’Leary established himself in business on Staten Island. He became active in the real estate and insurance fields, gaining experience in local commerce and property matters. In 1917 he joined the North Shore Ice Company, a significant local enterprise, and advanced within the firm to become its general manager and vice president. He held those executive positions from 1920 to 1934, overseeing operations during a period of economic expansion in the 1920s and the onset of the Great Depression in the 1930s. His business background and legal training provided him with practical experience in management and finance that would inform his later legislative work.

O’Leary’s first major foray into electoral politics came with an unsuccessful campaign for a seat in the New York State Senate in 1930. Although he did not win that race, the campaign increased his political visibility and strengthened his ties to the Democratic Party in New York City. Building on this experience, he sought federal office a few years later, as the political landscape was being reshaped by the New Deal and the Democratic Party’s growing dominance in national politics.

In 1934, O’Leary was elected as a Democrat to the United States House of Representatives, beginning his congressional service on January 3, 1935. He served continuously in the House from 1935 to 1944, winning reelection to a total of five terms. As a member of the House of Representatives during the New Deal era and the early years of World War II, he participated in the democratic process at a time of profound economic and geopolitical change. Throughout his tenure, he represented his New York district’s interests in Congress, aligning with the Democratic Party and contributing to legislative deliberations on domestic recovery, social policy, and national defense.

O’Leary’s service in Congress extended over nearly a decade, from 1935 to 1945 as recorded in some contemporary accounts, though his actual tenure ended with his death in 1944. He remained in office until March 16, 1944, when he died in West New Brighton, Staten Island, while still serving as a Representative. His death in office placed him among the members of the United States Congress who died while still holding their seats during the first half of the twentieth century, and it brought to a close a career that had combined business leadership with sustained public service.

O’Leary’s family continued to play a role in New York and national politics after his death. His great-grandson, Vito J. Fossella Jr., later served as a Republican member of the United States House of Representatives, representing New York’s 13th congressional district from 1997 to 2009. This multigenerational involvement in Congress underscored the enduring political legacy of James Aloysius O’Leary and his family in the public life of New York.