Osterweis was the author of numerous books and articles focused on the history of the American South and on New Haven, Connecticut.
[1][2] During his ten years in the cigar business, Osterweis pursued his interests in history and American Jewish history, writing two biographies about prominent Jewish Americans, Judah P. Benjamin, Secretary of State for the Confederacy, and Rebecca Gratz, a philanthropist and social activist from a prominent family in Philadelphia.
Gratz, reputed to be the inspiration for Sir Walter Scott's Rebecca in Ivanhoe, was a friend of Washington Irving's tragically short-lived fiancée, Matilda Hoffman.
Osterweis taught and coached several future national leaders in public speaking, including William F. Buckley Jr., Edwin Meese, David Boren, John Kerry, and George W.
[6][7] The Osterweis Debate Tournament at Yale for high school students in Connecticut is named in his honor.
[10] Osterweis owned the first (and only) female bulldog to serve as Yale's mascot, selected in 1975 to celebrate co-education at the formerly all-male school.
On November 10, 1979, the New York Times reported that a group of Princeton University students posing as Yale cheerleaders kidnapped Handsome Dan XII, aka Bingo Osterweis, the evening before the Yale-Princeton football game.
Yale got its revenge on the field, beating Princeton 35–10, and Bingo was returned safely to Osterweis after the game.
He was vice president of Temple Mishkan Israel (1943–44), a Reform congregation that his family had been involved with since its beginnings in the mid-19th century.