I'm only 20, and I totally get the reference. But yeah, I agree, the generations have 'forgotten' what scum Teddy was/is. Why Massachusetts continues to reelect this guy, I'll never know...
The large majority of the public forty years and younger wouldn't know the reference without the thought completed. I'd give 3 to 1 odds that when the two headlines were tested to a mailing list that the complete-thought headline would pull a larger response. Probably by five times or more response.