...who, I might add, famously admitted he didn't know any poor people growing up...vetoed the Children's Healthcare Initiative with the claim that Americans needed to pull themselves up by their bootstraps. His dad, H.W., campaigned on the notion of working class Americans learning to pull themselves up by their bootstraps. Interestingly, I can find no instance of Reagan using the term, but the media frequently applied it to describe him based on his "aw, shucks" public persona.
A bit of bootstrap trivia: We say that we "boot up" or "reboot" a computer based on the phrase, too.
Originally, a computer would be powered up and just sit there. An initial set of instructions for the CPU had to be hand-fed in using switches so that the computer would how know to load a program off a storage device to be able to accomplish a thing. In the 1950's, around the time the first operating system was created to allow more than one program to run at a time, the idea came about to hardwire those initial instructions to read a storage device. That hardwired code could be initiated at the press of a single button instead of arduous switch-flipping to set the bits for each step of the instructions and then execute them. This was known as "bootstrap" code since it allowed the computer to run the operating code by itself. Soon even the single button push was automated by a small circuit so that upon power up, the bootstrap code would automatically run, and the computer would "boot" itself into an operational state. By the 80's the term "boot" and "reboot" had entered pop culture & colloquial speech outside of the original computing subcultures. It's interesting how the timing coincides with the rebirth of use by modern politicians. President Carter even mentioned it in his 1980 debate with Reagan.