Originally published in 1960, later reissued in 1987 by Black Lizard, Whittington’s The Devil Wears Wings has all the attitude you want from a novel of this time period. Buz Johnson is a down on his luck former Major who now works in a small Gulf Coast Florida town teaching whoever how to fly. He has to take it from his boss Smiling Jimmy because no one else will have him and his drinking problem. It’s all sour and going nowhere for Buz, a fact that Whittington’s writing captures so well. He has Judy in the wings (so to speak), but they’re no good together and he wants no one else.
In walks a fine solution to his problems, a mysterious gentleman who could be a CIA operative or some other black ops crew. Someone has been watching Buz and sizing him up. What follows is not a spy versus spy adventure, but a bank caper that somehow is so complicated that it involves stealing two planes and getting away with the dough with no one the wiser. It’s a Three Stooges kind of robbery though far more than Jesse James.
It’s a caper story with great characterization and buildup, but has quite a bit of comic relief among the clamor of the robbery.