McKeldin challenged Democratic
mayor of Baltimore Howard W. Jackson in the 1939 election, but was defeated. He subsequently challenged the incumbent
governor of Maryland, Democrat
Herbert R. O'Conor, in
1942, but lost by five points. McKeldin would ultimately be elected mayor of Baltimore in 1943 on his second attempt. During his first term, he oversaw the construction of Friendship Airport, now
Baltimore-Washington International Airport, in
Anne Arundel County. McKeldin ran for governor again in
1946, challenging
William Preston Lane Jr., but was defeated again, by a wider margin than in 1942. He ran for governor a third time in 1950, defeating Lane in a rematch. As governor, McKeldin endeavored to improve the state highway system by establishing the
Baltimore Beltway (now Interstate 695), the
Capital Beltway (Interstate 495), and the
John Hanson Highway portion of
U.S. Route 50. He was a staunch supporter of interstate cooperation, saying once: "I rode by train over several state borders. I carried no passports. No one asked me to identify myself. No one had the right to. This is America." He was also an advocate for
civil rights for
African Americans, and received the
Sidney Hollander Award for his pro-civil rights efforts. He was also a supporter of Israel. In 1952, McKeldin was a major figure among moderate Republicans who
campaigned for
Dwight D. Eisenhower to receive the Republican nomination for President, and would deliver the principal nominating speech for Eisenhower at the
1952 Republican National Convention in
Chicago. In
1954, McKeldin was re-elected governor against the
president of the
University of Maryland, College Park,
Harry C. "Curley" Byrd, who had controversially resisted desegregating the university. After his second term in
Government House, McKeldin returned to his law practice in Baltimore; he was succeeded as Governor by Democrat
J. Millard Tawes. In
1963, McKeldin returned to public service after being narrowly elected to a second non-consecutive term as mayor of Baltimore. In his second term, his administration focused on the
urban renewal of the city's
Inner Harbor. In 1964, he decided to support Democratic candidate
Lyndon B. Johnson over Republican
Barry M. Goldwater in the
presidential election, due to Goldwater's opposition to the
Civil Rights Act of 1964. In 1966, the city council voted to condemn and demolish 700 homes in the
Rosemont neighborhood to build the
Interstate 170 "highway to nowhere" that McKeldin had conceived with urban planner
Robert Moses in 1941. McKeldin's second term as mayor ended in 1967, and he did not seek re-election. McKeldin remains the last Republican mayor of Baltimore to date; indeed, he is the last Republican mayoral candidate to win even one-third of the vote in the city. He was the first Republican governor of Maryland to be re-elected, and the only one until
Larry Hogan was re-elected in
2018. ==Personal life==