Lowell Weicker was a liberal Republican in the Senate, at least from the Watergate days through ‘88. Sometime after he lost to Lieberman, he ran for the governorship of Connecticut, and won. So, we can also ask, how much good was he able to get done as governor?
Well, for one, he’d likely be re-elected in 1994 and 2000, though I’m not necessarily sure beyond that. Either way though I think it’s likely that at some point he pulls a Jim Jeffords and becomes an independent caucusing with the Democrats.
Perhaps the least illogical of taxes!He was one of Connecticut’s most consequential governors, pushing through the state income tax. . .
He would almost certainly be primaried by 1994, by which time Connecticut Republicans had moved to the right. He might have to run for re-election in 1994 as an independent as Lieberman was later to do in OTL. Whether he would succeed or not depends on whether he gets enough Democratic support--in other words whether Democrats were willing to vote for him as overwhelmingly as Republicans did for Lieberman in OTL in 2006. https://en.wikipedia.org/wiki/United_States_Senate_election_in_Connecticut,_2006
My question is by who? None of the CT congressional delegation at that time was really that much more conservative than he was...
Why does a challenger have to be a member of Congress? (Though Gary Franks seems to me to be considerably to the right of Weicker). There are plenty of state legislators, wealthy business people, etc. The point is that Weicker himself recognized that the Connecticut GOP was becoming inhospitable to liberals like himself by not running as a Republican when he ran for governor in 1990.