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Dennis Jacobs is a life-long New Yorker, born during an air raid blackout on February 28, 1944, raised on the Upper West Side, and educated in City schools from kindergarten through college. His paternal grandfather came to the United States from Poland before the First World War and settled in Belair, Ohio. His father, Harry N. Jacobs (1910-93), came to the United States in 1920.


His parents met in Toledo, and settled in New York in 1936, where his father opened a linens and domestics shop on Broadway at 95th Street. An older brother, Barry Jacobs (1940- 2012), practiced ophthalmology in Boston.


The Jacobs family moved to Queens in 1955. Jacobs attended Forest Hills High School (class of 1960), where he worked on the school newspaper; the faculty adviser of The Beacon, James J. Kernan, was teacher, mentor and a lifelong influence on his writing. At Queens College (class of 1964), he majored in English and realized in his French and Latin classes that he would always be monolingual. When he was a teenager, a summer job as a messenger in Manhattan took him all over the island and inspired a continuing interest in the City’s history and buildings.


He was awarded a master’s degree in English literature by New York University (1965), and worked there toward a doctorate, but did not complete a dissertation. He concentrated on early English prose and Victorian novels.


In a brief first career, he taught in the English Department of Queens College and at the Nassau Police Science Academy, and for a summer at Prairie View A&M College in Texas. In a talk delivered long afterward to a bar association, Judge Jacobs complained that his time as a graduate student and English teacher had rendered him a compulsive proofreader, and morbidly sensitive to solecisms and mixed metaphors. He cited one lawyer, who told a judge that his question had hit the nail on the coffin; and another lawyer, who gloated that his adversary had inflicted this self-inflicted wound on himself.


In 1970, he enrolled at New York University School of Law, where he became a Pomeroy Scholar and a member of the Law Review. A particular influence was his first-year contracts teacher, Professor Sylvester Petro. On graduation in 1973, he joined Simpson Thacher & Bartlett as an associate. The following year, he married Judith Weissman, who was then a preceptor in French at Columbia College, and who went on to a career in university development.


At Simpson Thacher, he started as a corporate transactional lawyer, but soon came to the conclusion that he was not cut out to update utility bond indentures. He then joined the litigation department, and dealt over the ensuing years chiefly with cases involving securities, antitrust, contracts, insurance and reinsurance. He was elected to partnership in 1980.


In March 1992, President George H.W. Bush nominated Judge Jacobs to the Second Circuit. He was confirmed in September and assumed office on December 8.


Judge Jacobs was appointed a member of the United States Judicial Conference Committee on Judicial Resources in 1997, and was chair from 1999 to 2004. In 2006, he became chief judge of the Second Circuit for a seven-year term. The chief judgeship largely coincided with the six-year renovation of the 1935 Thurgood Marshall United States Courthouse at 40 Foley Square, a project suited to Judge Jacobs’s interest in New York City and its landmarks. For that work, the judge was awarded the 2014 Chairman’s Award of the New York Landmarks Conservancy.


Judge Jacobs was honored by the Green Bag for his John F. Sonnett Memorial Lecture, delivered at Fordham Law School in 2007. The lecture, The Secret Life of Judges, identified an insidious judicial bias in favor of the legal profession and in favor of legal proceedings and legal principles as solutions for everything. Another lecture, Lawyers at War, cited the estrangement between elite law and the military professions, and warned of the resulting danger to national security and effective civilian control of the military. In The Pardon Power: The Power Nobody Wants, a speech first delivered in 2003 and several times thereafter, the judge deplored the neglect of the pardon power as a corrective when the judicial system misfires.


In 2009, St. John’s University conferred on him the honorary degree of Doctor of Laws.