We at Flamingle HQ think this is an excellent question, as there are two potential answers — and we at Flamingle HQ love multilayered answers. If you mean, “Who was the UW’s longest-serving chief executive?” then the answer would be Charles Van Hise 1879, 1880, MS1882, PhD1892. He held the top post from April 21, 1903, until November 19, 1918, 15 years, six months, and 29 days. He’s known for earning the UW’s first doctoral degree (in geology) and promoting the Wisconsin Idea. He might have kept on going as the UW’s leader, but he died of complications after surgery for a nasal infection. But Van Hise wasn’t the UW’s “chancellor.” His title was president. If you mean, “Who held the title of chancellor for the longest?” then the answer is Irving Shain, who held that title form September 9, 1977, to December 31, 1986, or nine years, three months, and 23 days. Rebecca Blank, who recently occupied Bascom Hall's big office, comes in just behind him. She was the university’s top administrator from July 23, 2013, until May 31, 2022: eight years, 10 months, and nine days.