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Spoiler alert: all five Democrats representing Connecticut in the House of Representatives will win re-election. This has been a given every single election since the last Connecticut Republican member of Congress, Rep. Chris Shays of the 4th district, was defeated by Jim Himes in 2008. But just because something is true today doesn’t mean it will be so in the future.

What would it take, then, for Republicans to win a seat in Congress?

I could go the snarky route here and just say “be a completely different party,” and honestly that is true in a very real sense, but I’m going to try and take this seriously.

Let’s just assume right from the start that we’re talking about the 2nd, 4th, and 5th Districts only, here. The 1st and 3rd, which represent Greater Hartford and Greater New Haven respectively, are so far out of reach for Republicans at this point that they could run the pope and still get only about 40% of the vote.

All three of the remaining districts are currently beyond Republican reach, but for different reasons. I wrote about this in 2018, when I pronounced all three of these “pretty darn safe” for Democrats, for now. If anything, they’ve only gotten safer, since.

There are a few general things that would need to be true for any Republican to have a shot at any of these three seats; a non-presidential election year, deep voter disillusionment with Democrats, a less-toxic national Republican Party that embraces moderates, a strong and well-known candidate, and either a very unpopular incumbent or an open seat with a weak opponent.

Other than that, the needs become situational.

The 4th District, which is in lower Fairfield County along the coast, has been growing steadily more Democratic over the past 20 years as the moderate patrician conservatives of the old guard give way to highly-educated upper middle class liberals. Greenwich, once a bastion of Republican support, voted for Hillary Clinton in 2016 and sent Democrats to the General Assembly for the first time in decades in 2018.

A Republican who wanted to be successful here would have to be moderate-to-liberal, much like Shays or his predecessor, Stewart McKinney. The GOP base in this district isn’t large enough to do otherwise. He or she would have to get those college-educated white voters to come back to the fold with common sense fiscal conservatism and social liberalism. In today’s GOP such a person wouldn’t get past the primaries, so that would be a very difficult step one.

The 5th District is a hodge-podge of different types of places. There are four medium-sized cities: Danbury, New Britain, Meriden, and (most of) Waterbury. These cities tend to vote Democratic and are very much the anchors of the district – U.S. Rep. Jahana Hayes grew up and taught in Waterbury. What swung this district from Republican to Democratic in 2006 was the Farmington Valley’s switch from red to blue, which began in the Iraq War and has solidified since. Again, this is a swing in college-educated white people in wealthier areas.

The 5th is the home of the Republican “heartland” of the state, which is centered around conservative Naugatuck Valley towns like Plymouth, Thomaston, and Watertown. But that heartland isn’t getting any bigger, so a base strategy won’t work here, either. A smart, moderate campaign with a populist touch might gain some traction, though. A Republican who is acceptable to the Whole Foods crowd would have a chance, given the right circumstances.

Then there’s the 2nd District. This district, which covers almost the entire eastern half of the state, goes through periods of being hyper-competitive followed by long stretches of invulnerable incumbents. We’re in the latter right now, due in large part to Rep. Joe Courtney’s savvy understanding of what makes his constituents tick. But the makeup of the 2nd is what makes it possible for Republicans to win. Donald Trump won Windham County in 2016, and parts of the district around Norwich appear to be trending more Republican lately.

The 2nd also doesn’t have a big city or populous, wealthy suburbs full of newly-converted Democrats. Instead, it has small farming towns, old mill towns, military towns, blue-collar suburbs, and smaller cities like New London, Norwich, and Willimantic. Bread-and-butter economic issues, social moderation, and a strong military appeal would go a long way. Just ask Rob Simmons.

This theoretical Republican might be the only one to get past the primary. If Joe Courtney ever steps down, this district could be one to watch.

None of this could happen now. Both parties would have to be different. Republicans especially would have to learn from their past mistakes. But if they can do this, and the stars align perfectly, one or more of these seats can be theirs for the taking.


Susan Bigelow is an award-winning columnist and the founder of CTLocalPolitics. She lives in Enfield with her wife and their cats.

DISCLAIMER: The views, opinions, positions, or strategies expressed by the author are theirs alone, and do not necessarily reflect the views, opinions, or positions of

Susan Bigelow

Susan Bigelow is an award-winning columnist and the founder of CTLocalPolitics. She lives in Enfield with her wife and their cats.