"Halloween" Jack Paris (#62) says:
When you lose this Thug gain $20,000.
Do I gain $20,000 from using "Gambit" #27 which says to gain $30,000 by discarding a card from my hand, making it a $50,000 gain?
What about If I have Insurance office played, which allows me to place 2 markers for losing a thug/holding, would I get 2 markers for this discard?
Gambit is discarding, not "losing" (so, no). Losing a thug only happens to thugs in play.