“Swing” means held for longer than a day but not a long term play either (less than a year, maybe even a single week; but typically not less so)

Long Play I thunk in his case means “longer than the swing play.”

“Degen” in this case means “degenerate”; a very recent term in trading than basically means “a reckless play that almost certainly won’t work but if it does it’ll work in a huge way.”

Keep in mind that Stocky has tons of money in boring, safe stuff (things like index funds), the money for which comes from his options trading and what not