Chiles was born in Polk County, near Lakeland. He attended public schools in Lakeland, then went on to the University of Florida, graduating in 1952. Following his college years he went to Korea as an artillery officer in the United States Army.
After the war, Chiles returned to the University of Florida for law school, graduating in 1955; he passed the state bar exam that year and went into practice in Lakeland.
In 1958, Chiles, a Democrat, was elected to the state House of Representatives. He served there until 1966, when he was elected to a seat in the state senate, which he held until 1970. While serving in the state senate, Chiles served on the 1968 Florida Law Revision Commission.
During his time in the state legislature, Chiles continued to work as a lawyer and developer back home in Lakeland. He was one of the initial investors in the Red Lobster restaurant chain.
In 1970, Chiles decided to run for a seat in the United States Senate. At the time, despite his 12 years in the state legislature, he was largely unknown outside his Lakeland-based district. As a political gimmick and to generate some media coverage across the state, Chiles embarked upon a 1,003-mile walk across Florida.
The walk, which took 91 days, earned him the nickname "Walkin' Lawton," a name that was to follow him throughout his political career. Along the way, Chiles earned the name recognition he sought, becoming a legend in Florida politics. In journal entries, Chiles wrote that sometimes he walked alone, while other times he met ordinary Floridians along the way. In later years, Chiles would recall the walk allowed him to see Florida's natural beauty, as well as the state's problems, with fresh eyes. The gimmick worked, and Chiles was elected easily.
Chiles was re-elected to the U.S. Senate twice, in 1976 and 1982. Chiles, never flashy, was considerate a moderate lawmaker who rarely made waves. He served as the the Chairman of the Special Committee on Aging of the 96th Congress (1979-1981), and in the 100th Congress (1987-1989) served as the chairman of the influential Senate Budget Committee.
Chiles underwent quadruple-bypass heart surgery in 1985. After his recovery, he became increasingly frustrated with the slow pace of work in the Senate, complaining that it was too difficult to get anything done. He announced in 1988 that he would not seek re-election that year. (Chiles was succeeded by Connie Mack, III.)
After the surgery, Chiles developed clinical depression, and was treated with Prozac, at the time a very controversial drug. He retired from the Senate in 1989 and intended to retire from politics entirely. However, several supporters convinced him to enter the 1990 Florida governor's race against Republican incumbent governor Bob Martinez.
Chiles ran a campaign to "reinvent" the state's government, and defeated the relatively unpopular Martinez to take office in 1991. During his first term as governor, Chiles managed to accomplish very little. Although he developed ambitious health-care and tax reform packages, neither passed the state legislature. The early years of his term were troubled by a national economic recession that severely damaged Florida's tourism-based economy, and by Hurricane Andrew, which struck near Homestead in August, 1992.
Chiles ran for re-election in 1994 against Jeb Bush. A Republican tide swept the country in that year, and Bush ran ahead of Chiles for much of the campaign. Then, with only a few weeks left before the election, Chiles responded to a reporter's inquiry about his floundering campaign by saying that, "The old he-coon walks at midnight," an old Southern reference to the oldest and wisest racoon in a pack. The metaphor pointed up Bush's status as a political novice who was largely pre-scripted. Chiles came from behind to win a narrow victory in the election.
Chiles' second term as governor was notable, as he was the first Democratic governor in state history to have a legislature controlled by the Republican Party. However, he had some successes. Together with state Attorney General Bob Butterworth, Chiles sued the tobacco industry, winning an $11.3 billion settlement for the state. He also won approval for a $2.7 billion statewide school construction program.
In 1995 Chiles sought treatment for a neurological problem, after he awoke with nausea, slurred speech, and loss of coordination. He recovered fully.
In 1998, Chiles, who was term-limited, supported his Lieutenant Governor, Buddy McKay, for governor in a campaign against Jeb Bush. Bush scored an easy victory over McKay, who ran what is generally considered a rather poor campaign.
On December 12, 1998, less than a month shy of retirement, Chiles suffered a heart attack while exercising. He was found next to an exercise bike in the gymnasium of the governor's mansion. Funeral services were held at Faith Presbyterian Church in Tallahassee, following a funeral procession that traced part of his walk from the 1970 Senate campaign, from the panhandle town of Century to Tallahassee.
Chiles was known as a health care and children's advocate throughout his career. He emphasized health coverage for the uninsured and led a campaign to create the National Commission for Prevention of Infant Mortality in the late 1980s. In 1994 he fought for the creation of regional health care alliances throughout the state, which allow small businesses to pool their health care dollars and broaden coverage while saving money. He also created the Florida Department of Elder Affairs.
In 1992, Chiles created the Florida Healthy Start program, to provide cut-rate prenatal and infant care to poor mothers across the state; since the program's inception the state's infant mortality rate has dropped 20%. In 1996, Chiles appointed a Governor's Commission on Education to examine the state's school system. One of the significant reccomendations that came from that commission eventually led to the highly controversial 2002 state constitutional amendment restricting Florida's school class sizes.
"To be a successful state, we must nurture successful children."
"I didn't come to stay. I came to make a difference."