Have Faith in Massachusetts

Roughly speaking, until the years just after World War II, Massachusetts had a deserved reputation as one of the most conservative states in the union: consider, if you will, Calvin Coolidge as governor, and the existence of the New England Watch and Ward Society (for those of you who don't recognize that, they were the driving force behind banning books in Boston).

So here's the challenge: how does one have Massachusetts hang on to that old school Yankee/Brahmin conservatism to this day? If somehow you can (1) make the Kennedy clan similarly conservative, and (2) get the Kennedy clan into the GOP, and do it plausibly, that's icing on the cake.
 
The problem is that once the Irish Catholics outnumber the Brahmins it will be very difficult because of the Great Depression. The Brahmins would have to become more socially flexible and religiously/ethnically tolerant. With "No Irish Need Apply" signs still around prior to WWII, doesn't seem like anyone's willing to dump the bigotry. You would need a prominent Brahmin to emerge and do a Vandenberg- say that times have changed and a political alliance is necessary. Problem is the same as in the South- no one wants to publicly step over the red line and break that fundamental social more. Eventually, among the Kennedys, the Brahmins would accept Joe Jr. and Jack (not Bobby or Ted, for a variety of reasons best summarized as "too much South Boston, not enough Harvard") as members in their ranks.

With regards to the Kennedys: that's easy. Joe Sr. was a generous donor to the Massachusetts GOP in the 1920s IOTL. Just have him not jump ship for FDR in '32 and get him elected Republican Governor of Massachusetts in 1936. Then HCL dies in a car crash in 1952- a special election is held, which then-Congressman Joe Jr. wins against an unknown GOP opponent. If Joe Jr. lives Jack will not go into politics. Both Joe Jr. and Bobby could easily be diverted into the GOP IOTL given their political beliefs- RFK could've done so in the early 1950s but family mores, which he would never break, made that a non-starter. If the whole family is Republican, then that's not an issue.
 
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