WOW have long been Republican Counties, but they weren't as supercharged for the GOP decades ago as they were in the Bush/Obama eras. At that point the country was a vastly different place and Waukesha was less different than upscale suburban counties in other metropolitan areas.
The real question I guess is why WOW was trending right while most northern suburbs were trending left through the Clinton/Bush/Obama years.
Yeah, if anything, the Chicago suburbs just to the south were more like the WOW suburbs of the day, the hyper Republican bastions that were even more conservative than their already conservative peers. This was especially true of DuPage County, which hosted some of the most blisteringly right-wing suburbs in the country right alongside Orange County in California (Goldwater won both by double digits).
I’ve heard it said that at least part of the reason for the continuing stalwart tendencies of the WOW suburbs is due in part to the old-school political dynamic between the managerial class that has a disproportionate presence in WOW and the labor class located mainly in Milwaukee. Another explanation I’ve heard relates to the ample presence of conservative talk radio in the region, but I suspect that’s more likely to be a symptom rather than a cause. There has to be a deeper root reason to WOW’s stubborn conservative bent. I’d be curious to hear your take, TJ.