On the surface, it might seem that Judy Jones has the freedom. After all, she has money and position enough in society to skim off the cream of everything "good" in the world. She need not work; she is effortlessly beautiful. Judy has the freedom (and time) to crook her finger, bat her eyes, and have men faint at her feet.
Dexter, on the other hand, initially seems much less free. He is far below Judy in social status (he is a caddy at the course where she plays) and has almost no money. His freedom is much more limited than Judy's. He has to work hard and do "dexterious" social climbing. (My thinking is that his name is a pun.)
It does appear for a time that Dexter has done well in a society that allows freedom. He seems to embody the "American Dream" of success...from humble status he rises to the top of his field, briefly wins the girl, gets lots of money.
In the end, however, freedom for both Judy and Dexter seems pretty hollow. Judy ends up in a bad marriage and "old at twenty-seven." Dexter winds up in a gray and humorless office building, without Judy. He longs for the days where he still had hope. For FSF, then, at least in this story, the American Dream may be just that: a dream. Sure, you may be "free" to dream it, but what has it really to do with reality?