Through the balance of the 1930's, Annie meets up with all kinds of assorted swindlers and murderers. Some of the swindlers, it turns out, are not the villains which they originally appear to be. Gray lets it be known, that at times, some bad guys might be better than supposedly good guys. As a f'rinstance (as Annie would say), in 1933, C.C. Chizzler practically made a slave of Annie with a phoney contract. But Chizzler himself was "had" later on by good-buy con-man Goldbrick Jack. In 1936, Annie and Jack Boot are at odds with a murderer, Horace Gila (as in "Monster"), who had framed Jack Boot for said murder some thirty years previously. As is typical in the Gray judicial system, Gila meets his match in a good, old fashioned shoot-out. The calvary in this case turns out to be the state Governor! Another murderer meets his end (though we never really find out what his end was), in a 1938 sequence featuring Uriah Gudge, a wealthy but miserly man in the same mold as Phineas Pinchpenny. Also like Pinchpenny, Gudge has many skeletons to hide. Those skeletons haunt him into his mysterious "disappearance."
In December of 1938, Annie meets up with possibly the most horrific villain which Gray has concocted: The mysterious Axel. We're not quite sure where Axel hails from, though it's most certainly a European country. And it might not be so coincidental that his name is so similar to "Axis," as in the "Axis Powers." His interest in Annie, at this time, is simple for the millions of dollars in ransom which he could collect from "Daddy" Warbucks; after which he would "dispose of the brat."