He served as chancellor of the University of Wisconsin–Madison from 1964 to 1967 and also led that institution through a period of campus unrest—including, in one instance, writing a personal check to cover bail for students arrested during a demonstration.

[8] Fleming met Aldyth Louise "Sally" Quixley, a fellow student from Rockford, Illinois, in 1935, when they were both working in the dining hall at Beloit College, and they dated seriously his final two years of school.

[13] After President Franklin D. Roosevelt re-established the National War Labor Board, Fleming used his connections with two University of Wisconsin law faculty members who were involved with its formation to secure a junior position with the organization, beginning in April 1942.

He returned to Washington from April to September 1950 to serve as executive director of a wage control board President Harry Truman had created at the onset of the Korean War, and during this time he also began to work as an arbitrator.

When the University of Illinois offered a position as a full professor and director of the Institute of Labor and Industrial Relations, he accepted, effective September 1952.

In 1957 he became a professor of law and continued to have time off to perform arbitration work, and in 1963, the president of the University of Wisconsin system called to offer him a new position.

[27] At their January 10, 1964, meeting, the board of regents of the University of Wisconsin named Fleming a professor of law and provost of the Madison campus, effective that September 1.

[29] The University of Wisconsin system was expanding rapidly at this time, and part of Fleming's job was ensuring that the Madison campus, which generated most of the revenue, kept an appropriate share of money for its own needs.

His restraint was widely praised at the time, with the Milwaukee Journal saying the university had "shown the nation that a student protest can be a legitimate exercise in democracy, not a disruptive episode in bitterness".

[33] On February 22, 1967, police arrested seventeen protestors who refused to leave an engineering building at the end of a sit-in protesting Dow Chemical's on-campus recruiting.

Following a meeting at Detroit's Hotel Ponchartrain that was almost entirely occupied by discussion of how to handle student protests, Briggs offered Fleming the position while driving him to the airport.

[12] The regents created the position of president-designate for Fleming beginning in September 1967, in order to give him four months of planning and orientation before he assumed his full duties on January 1.

A student protest that October which disrupted a meeting between engineering faculty and Rear Admiral Samuel Brown demonstrated to the community the differing approaches of the outgoing and incoming administrations.

In his own response to the incident, Fleming emphasized its positive aspects, pointing out that all parties acted with restraint, there was no violence, and the police were not involved; at the same time, he called for increased student participation in decision-making.

"[40] Shortly after Fleming took over officially in January 1968, he removed Cutler as vice president for student affairs; Cutler's earlier writings had expressed support for free expression on campus, but his actions in office, including an attempt to ban sit-ins in 1966 and his cooperation in providing the names of "subversives" to the House Un-American Activities Committee, did not fit into Fleming's philosophy of a restrained and dignified atmosphere of debate.

"[45] A similar building occupation later that month at Columbia University was resolved through police intervention that left hundreds of students and faculty members injured.

[46] In dealing with campus protests, Fleming favored a strategy of not letting minor differences become major incidents that would in turn serve as recruitment material for demonstrators.

It's not a big job to throw the dirt back in the hole ..."[48] Fleming himself described the Vietnam War as a "colossal mistake" at a teach-in September 1969 and called for the unilateral withdrawal of U.S.

[52] Ann Arbor's chief of police, Walter Krasny, broadly agreed with Fleming's flexible approach, later writing:[53] Somebody's going to come out on the short end if you don't have some passive type of resistance.

"A bomb placed under an Army staff car parked outside the campus ROTC offices in June 1969 caused damage but no injuries.

Later that month, two nights of impromptu partying that blocked off South University Street near the president's house was met with teargas fired by sheriff's deputies.

In his autobiography, Fleming says students came to his house with teargas in their eyes, which he let them into the kitchen to wash out, after which he went out and persuaded the deputy chief of police to withdraw, saying the sheriff, Douglas Harvey, had been "itching for a confrontation" and reacted beyond what was necessary.

BAM protestors picketed outside buildings, addressed classes, and engaged in protest actions such as blocking intersections and stopping drivers entering parking garages to discuss the strike's demands.

Further negotiation between Fleming and BAM leader Ed Fabre resulted in an agreement; BAM leaders organized a celebration, and the board of regents issued a statement that praised both the Black students and Fleming while directing a barb at other protestors:[58] ... the public should take note that the black students have, unlike many of the white radicals who seem bent on destruction for its own sake, been pursuing the legitimate objective of trying to make more educational opportunities available for their people.

He oversaw the introduction of affirmative action programs, a campus-wide restructuring of salaries and compensation to address gender inequalities, and the construction of several major campus buildings, including the Hatcher Graduate Library, the Bentley Historical Library, the Power Center for the Performing Arts, and a building for the schools of architecture and art.

[61] In the fall of 1977, Fleming was approached with job offers to lead the State University of New York and the Center for the Study of Democratic Institutions in Santa Barbara, but declined.

Fleming's first project as director was to enlist former CBS News president Fred Friendly to produce a series of televised seminars on the Constitution.

[64] Historian Nat Hentoff called the Fred Friendly Seminars, which began with that 13-part series, The Constitution — That Delicate Balance, "the most valuable, quintessential American television I have ever seen".

From 1985 to 1990, he served as Michigan Governor James Blanchard's representative to a group trying, ultimately unsuccessfully, to reform the state's medical malpractice system.

"[70] Other contemporaries from the protest era have a negative assessment, such as former SDS members Eric Chester, who "found him to be a rigid personality, unwilling and unable to engage in a genuine give and take", and Gary Rothberger, who called Fleming a "cold dude who didn't care about anything else other than carrying out his assignment" and said of his passivity towards alleged police brutality during the South University riots, "He did nothing when he could have spoken out.