Crossword puzzle clue "having financial trouble like a gossip columnist"

Having financial trouble, like a gossip columnist?

"Gossip Girl" character who [spoiler alert] turned out to be the true identity of Gossip Girl...but "Gossip Boy" doesn't sound as good

Having financial trouble, like the hangman?

Having financial trouble, like a chambermaid?

Having financial trouble, like a London landlord?

Having financial trouble, like an author?

Having financial trouble, like a communist?

Having financial trouble, like a quarryman?