Jared Flagg began studying art when he was thirteen, under the guidance of his elder brother, George. He also seems to have enjoyed some instructional contact with his uncle Washington Allston. By 1837 he had attained sufficient skill to set up his own practice as a portraitist, in Bridgeport, Connecticut; he made his first appearance in an Academy annual exhibition the same year. He was briefly in New York but, finding no encouragement for his career there, moved on to Newark, New Jersey, where he worked for about a year. By the spring of 1840 he was established in Hartford, where he had his first real success with a commissioned portrait of Judge Samuel Hitchcock, president of the Yale College School of Law.
In 1841, with his career as a portraitist progressing adequately, Flagg married. His wife's death two years later, combined with a pursuit of the formal education he had missed in classes at Hartford's Trinity College, led him into the study of theology and, in 1854, ordination in the Protestant Episcopal Church. In 1855, after a brief period as the minister of the church in Birmingham, Connecticut, he was called to Grace Church in Brooklyn. He was its rector until 1863, when he resigned from the ministry to return fully to painting.
Throughout these years of study and service in the church, Flagg did not relinquish-nor, seemingly, much diminish-his activity as a painter. His work was not seen in Academy annuals between 1840 and 1847, the year following his second marriage. But from 1848 until 1852 he maintained a studio in New York and was again a steady participant in Academy exhibitions, mainly showing portraits, from 1847 through 1859. Flagg's work was not again seen in annuals until 1865. The coincidence of much of this period with the duration of the Civil War is probably less significant than its encompassing of his wife's illness, his decision to give up the ministry, and his departure from Brooklyn.
After leaving the ministry, Flagg returned to New Haven, which would remain his principal home for the rest of his life. His second wife died in 1867; he remarried in 1869. In 1872 he took a studio in New York and resumed regular participation in Academy annuals, which continued through the year before his death.
In his later years, Flagg wrote a biography of his uncle, The Life and Letters of Washington Allston, which was published in 1892. Although he was a successful portraitist in his own day, it is perhaps by this book that he is best remembered.
JPH