Why has Kentucky never reelected a Republican governor?

[The Arizonan]

I find it strange that Kentucky has never reelected a Republican governor considering that it is a red state and Republicans hold most of the statewide offices, most of the House seats, and both Senate seats. Is it because Kentucky still has ancestral Democratic character downballot?

[Roll Roons]

They only started allowing governors to run for second terms in 1992, and both of the Republican governors who have gotten elected since then have been horrifically unpopular. Plus Kentucky's Republican trend at the state level is actually pretty recent. Democrats held the State House until 2016, and Cameron will be the first GOP attorney general since WWII.

[Amenhotep Bakari-Sellers]

Dems elect statewide Dems, Conway lost because 2015 was a GOP good yr, after Trump, the GoP is in tatters; as a result, McConnell will have a Bruce Lunsford race on his hands in 2020

[Tender Branson]

Because they all SUCKED.

[Skill and Chance]

They only started allowing governors to run for second terms in 1992, and both of the Republican governors who have gotten elected since then have been horrifically unpopular. Plus Kentucky's Republican trend at the state level is actually pretty recent. Democrats held the State House until 2016, and Cameron will be the first GOP attorney general since WWII.

This.  Almost entirely because they had the VA rules until the 1990's. 

[Indy Texas]

Because Republican governors insist on implementing Republican policies, which have little to benefit most people in Kentucky.

They soured on Bevin because they elected a Tory Man and were then inexplicably shocked that he would implement Tory Measures.