Anything you could describe the young woman as, instead of young, that alludes to a flaw that will be fixed? What caused her to decide? The logline reads more like an inciting incident/catalyst than a logline itself. It might start something like “When a delusional songwriter gets in a car accident, she has to x to avoid y or z will happen.

Hi John – great story idea! I agree with Philippe that the ingredients are there but the hook is missing. Right off the bat “watches” is kind of a vanilla verb. If you keep this logline, maybe a more vivid verb is in order? Also, I assume he’s playing, not watching? Also for the adjective, compulsive, my head jumps right to “degenerate gambler that’s destroyed his life and those around him” so if that is not the character you are going for, you may want to take another look. If he’s caution to the wind, maybe “reckless” or if he’s actually good at it, maybe find something to show that?

I get that you are trying to portray the story is being told in flashbacks but maybe that is not necessary for the logline? Maybe try and do the logline in linear format and then use the flashbacks as storytelling mechanisms in the screenplay?

Here’s a quick-take:
As a lifetime of self-inflicted debt catches up to him, a degenerate gambler goes all in (insert: at the card table (maybe)) to clear his name from a homicidal bookie.

Is that helpful?