Kessler grew up in New York City in a Jewish family. He was a volunteer spear carrier and prop boy at the New York Metropolitan Opera as a teenager, and he had classical training as a singer. He worked selling cloth at the Sample Shop as a young adult, and he married his wife, Sonia, while working a range of modest jobs.
He attended graduate school at Harvard University, but after finding enough success as a poet he left doctoral studies and landed at Binghamton University, where his students included Camille Paglia (1964-1968). Paglia later wrote that the biggest impact on her thinking were the classes taught by poet Milton Kessler:
The way I was trained to read literature by Milton Kessler (at Harpur College, part of Binghamton University), who was a student of Theodore Roethke, he believed in the responsiveness of the body, and of the activation of the senses to literature. And oh did I believe in that. Probably from my Italian background -- that’s the way we respond to things, with our body. From Michelangelo, Bernini, there’s this whole florid physicality leading right down to the Grand Opera, the great arias.
Kessler had a brief bout with thyroid cancer, an affliction he shared with poet Paul Blackburn. Boarding a bus after a visit to Binghamton, Blackburn told Kessler, "How warm to share a common disease." Blackburn died not long after.
- "Zero". The Los Angeles Times. September 2, 1990.
- Free Concert: New and Selected Poems. Etruscan Press. 2002. ISBN 978-0-9718228-4-9.
- Riding first car: learning the boxes. Black Bird Press. 1995. (Chapbook)
- The Grand Concourse. State University of New York at Binghamton. 1990. ISBN 978-0-938621-02-7.
- Sailing Too Far. Harper & Row. 1973. ISBN 978-0-06-012354-3.
- Woodlawn North. Illustrator Robert Ernst Marx. Impressions Workshop. 1970. ISBN 0-932052-68-1.
- Called home: a sequence of poems : 1964-66. The Black Bird Press. 1967. (Chapbook)
- A Road Came Once. Ohio State University Press. 1963.
- "Poet Power". The New York Review of Books. August 22, 1968.
- "An Interview with Camille Paglia," Bookslut, April 2005
- "The Milton Kessler Memorial Prize for Poetry", Harpur Palate
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