[63] Late in his tenure, Wilson had a confrontation with Andrew Fleming West, dean of the graduate school, and also West's ally ex-President Grover Cleveland, who was a trustee. Wilson wanted to integrate a proposed graduate school building into the campus core, while West preferred a more distant campus site. In 1909, Princeton's board accepted a gift made to the graduate school campaign subject to the graduate school being located off campus.[64]
Wilson became disenchanted with his job due to the resistance to his recommendations, and he began considering a run for office. Prior to the 1908 Democratic National Convention, Wilson dropped hints to some influential players in the Democratic Party of his interest in the ticket. While he had no real expectations of being placed on the ticket, he left instructions that he should not be offered the vice presidential nomination. Party regulars considered his ideas politically as well as geographically detached and fanciful, but the seeds had been sown.