Cornell Law School and An Off-season Law Practice
While playing for the Orioles in the 1890s, Jennings and John McGraw both attended classes at St. Bonaventure University. After the 1899 season, Jennings was accepted to Cornell Law School. He managed the Cornell baseball team while studying law and concluded that he was well-suited to being a manager. While at Cornell, he joined the Phi Delta Theta fraternity chapter there. Jennings continued as a scholar-athlete until the spring of 1904, when he left campus early to manage the Orioles. Though he never finished his law degree at Cornell, Jennings passed the Maryland bar exam in 1905 and started a law practice. He continued to work at his law practice during the off-season through the remainder of his baseball career.
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