Bennett was set to run for a 23rd term in 1992 in the newly renumbered 4th District against Jacksonville City Council president Tillie Fowler, his strongest Republican opponent in decades. However, he abruptly ended his bid for reelection when his wife became ill in the spring of 1992. Fowler went on to win in November. At the time of his retirement, he was the second longest-serving member of the House (behind only fellow Democrat Jamie Whitten). He is still the longest-serving member of either house of Congress in Florida's history. Proving just how Republican this district had become, the Democrats have only fielded a candidate in the district five times since Bennett's retirement, and none of them have cleared the 35 percent mark.