Does it really count as by-the-bootstraps if someone else is doing the pulling?  

For my seminar on F. Scott Fitzgerald, the first thing I had to read was Horatio Alger’s Ragged Dick (which is not a euphemism for a venereal disease).  From what I understand, that book is one of the founding texts of the so-called American Character.

In it, Richard “Ragged Dick” Hunter is an orphaned bootblack in NYC and by self-denial and careful saving he is able to bring himself up from poverty and become ‘spectable.  It was hilarious, as Dick is one funny motherfucker.  But he really didn’t get there all by himself. Along the way, he’s given clothes and money and a job by some very philanthropic rich people and a  preacher.

I can see the influence in the Gatsby character, another by-the-bootstraps kind of kid, helped along by a rich guy, but Fitzgerald subverts this by having Gatsby’s gain ill-gotten and illustrates that the veneer of the ‘spectable people is just that, veneer, surface, an act.