Brown, while still on his honeymoon, decided to run for governor the next year just 10 weeks ahead of the primary with little preparation or connections, and he merely looked like an amusing sideshow against the apparent frontrunners. Brown also used his first days on the campaign trail to announce he was considering selling the Celtics, an announcement the Boston Herald American greeted with the headline, “John Y. Wants to Sell Celtics —Hooray!” (He went on to do so later in the year.)
But the wealthy Brown, who toured the commonwealth by helicopter, spent an enormous $1.5 million during his quick sprint to the nomination and beat out Louisville Mayor Harvey Sloane 29-25. The Democratic nominee had an easier time against the Republican standard bearer, former Gov. Louie Nunn, who tried to frame the race as “Kentuckians against the others.” Brown, though, scored a 59-41 win over Nunn, whom The New York Times said “has a reputation for increasing taxes and was never widely regarded as a promising candidate” in what was still a heavily Democratic state.
The new governor, whose tenure coincided with a national recession, was quickly talked of as a potential 1984 presidential candidate, with the Wall Street Journal running a profile with the headline, “From Fried Chicken to the Governorship; Is White House Next?” However, his national ambitions were derailed over news about his gambling, and, occasionally, huge losses.
Brown was additionally harmed when he was linked to two federal investigations, though while a matter involving drugs and gambling impacted his friends, he was never charged. Brown, who suffered serious health issues while in office, also was very much a hands-off leader, which allowed the legislature to exert more power over state affairs than it was accustomed to.
State law at the time prohibited governors from seeking a second consecutive term, and Brown was conceded by Lt. Gov. Martha Layne Collins, a fellow Democrat who spent 500 days as acting governor while he was out of state. Brown ran again in 1987 when he was next eligible in another crowded primary, and this time, his main adversary appeared to be Lt. Gov. Steve Beshear. This time, though, a different wealthy businessman, Wallace Wilkinson, slipped in and nudged past Brown 35-26 before winning the general election.
Brown, who never sought office, remained angry at Beshear decades later after his old adversary was finally elected governor; Brown refused to become part of his inaugural committee, saying, “I don't respect him. I don't want to be part of it. I'm not really interested in being politically correct.” However, he relented after Beshear secured a second term four years later; Brown’s son, former state Treasurer John Y. Brown III, said that shortly before his death, Brown called Beshear “the greatest governor in (his) lifetime.”