Richard C. Lee, a New Haven mayor who directed the city’s efforts at redevelopment and was its dominant political force for almost two decades, died of natural causes Sunday morning at the age of 86.

Lee, who served eight terms as mayor from 1954 to 1969, initiated much of the development that shaped modern New Haven, making the city a model for both the benefits and pitfalls of urban renewal. A charismatic and often controversial public figure, he became one of the most influential mayors in the country, bringing unprecedented amounts of federal funding into the city.

Lee was on a first-name basis with former President John F. Kennedy, and he had ambitions for statewide or even national office. He was a pioneer in looking at cities and urban planning in a new way, but he hesitated at trumpeting New Haven as a model for other American cities.

“For everything we’ve done, there are five things we haven’t done, or five things we’ve failed at,” Lee said. “If New Haven is a model city, then God help urban America.”

Born in 1916, Lee was raised in a poor, devoutly Catholic household in a working-class area of New Haven. After graduating high school, he was hired as a reporter for the New Haven Journal-Courier after he falsely claimed he was a good typist. After quickly teaching himself to type on a borrowed typewriter, he began covering the City Hall and police beats, developing a vast knowledge of city affairs.

Kevin Miller, a longtime family friend of Lee’s, said the former mayor retained his almost encyclopedic knowledge of the city and its inhabitants long after he left politics.

“You could sit and talk to him, and he was like a walking, talking, living history book of New Haven,” Miller said. “If you mentioned a person’s name, he’d tell you about their mother, their father, where they came from, the things they did.”

At the age of 23, Lee became a city alderman, winning election in a heavily Democratic ward. In 1942, he became the chief of Yale’s wartime news digest. Although Lee was not college-educated, his work with the news bureau brought him into close contact with the University and developed connections that later served him as mayor.

When Lee first ran for mayor in 1949 at the age of 33, he lost by only 712 votes out of 70,000 cast. To add to Lee’s disappointment, he later learned that one supporter had gotten drunk on Election Day and failed to deliver a group of absentee ballots that would have more than closed the margin of victory. In 1951, he ran again, losing by two votes.

Two years later, when Lee was finally elected mayor in his third campaign, he had combined his Ivy League contacts and ideas with his command of old-fashioned Democratic machine politics.

“It took me a long time to get to be mayor and when I finally made it, I made up my mind that I wasn’t going to be an ordinary mayor,” Lee said.

The focal point of his tenure in office quickly became his efforts at urban renewal. His first project was to redevelop the Oak Street area, building an enormous office building and modern apartments with millions of dollars of aid from the federal government. Later projects included the construction of two large department stores, a shopping mall, and a 19-story hotel.

Lee’s efforts in the Dixwell neighborhood exemplified his approach to urban planning. In an attempt to clear the neighborhood’s slums, Lee attracted a shopping mall and a state-of-the-art apartment complex to Dixwell, while a local elementary school gained national attention for being open 16 hours a day for recreational activities.

Featured on the cover of Time magazine, Lee’s vision of the Elm City became a model for other cities seeking to reverse urban decay. His connections with Kennedy and Lyndon Johnson led to New Haven serving as a testing grounds for many social programs of the 1960s, while earning New Haven the highest amount of federal money per capita among all American cities.

Miller said Lee once told him that he would receive calls in the mayor’s office from Kennedy’s secretary, asking Lee to come down to the White House for dinner. Lee would travel down to Washington, D.C., and eat with Kennedy — even helping the president with his back brace before he went for an after-dinner swim.

Robert Dahl, a Yale professor of political science who published a landmark study of Lee in 1961, said Lee’s political skills greatly aided him in his ambitious plans for redevelopment.

“As a mayor, he was extraordinarily gifted at putting together a coalition of diverse interests and carrying through a program,” Dahl said.

Yet while Lee’s administration was largely focused on ambitious plans for developing New Haven, Lee was known for concerning himself with even the most minor aspects of city administration. One letter Lee wrote to the dean of the Art and Architecture School at Yale illustrated his concern with the city’s aesthetic appeal.

“Please look at the west wall of your building at York and Chapel across from Paul Rudolph’s new monument. The drapes are dirty, untidy, and pulled awry — a completely magnificent structure with very poor housekeeping,” Lee wrote.

Towards the end of Lee’s tenure, however, his efforts at urban renewal were overshadowed by growing racial unrest within the Elm City. Riots broke out in 1967, and suffering from poor health, Lee decided not to run for re-election in 1969. He was later given a fellowship from Yale after he left office and taught undergraduate courses at the University.

Robert Ellickson, a Yale Law School professor who has studied urban change in New Haven, said Lee determined the development of the Elm City since the 1950s.

“Mayor Lee was the giant figure of the second half of the 20th century in New Haven,” Ellickson said.

The renewal effort itself has earned mixed reviews from later historians and politicians. Yale art professor Vincent Scully wrote that the buildings Lee commissioned “develop a quality at once cruelly inhuman and trivial.” Dixwell, where Lee directed many of his efforts, became mired in crime and poverty by the late 1970s.

“He had a belief that if you changed physical circumstances, crime would go down,” Ellickson said. “What he didn’t realize — was that there were less destructive ways of doing things.”

Yet Dahl said Lee was an important mayor because he sought to address problems of urban decline.

“He was among the very first — for better or for worse — to engage in a large-scale program of urban development, and that attracted attention across the country,” Dahl said. “He was animated by a strong desire to improve his city.”

Yale President Richard Levin said Lee’s personal characteristics aided his long career in New Haven politics.

“He was a very warm, outgoing personality,” Levin said. “He had a huge inventory of friends and acquaintances. He very much relished his public role.”

Raymond Wolfinger, a professor of political science at the University of California at Berkeley who spent five months trailing Lee in 1958, said Lee was never comfortable with some aspects of elected office, despite his firm command of politics.

“Although he made a very large number of speeches, he was always very nervous,” Wolfinger said. “He told me that every time he gave a speech he sweat through his suit out of anxiety.”

Lee is survived by his wife, Ellen, and a son and two daughters.