When Gambler gambles someone, it's like the night has ended and simultaneously another night has started. Roles like Priest receive the "At the confessional nights..." system message, roles like Dreamer receive a legit dream mid-night too, so what happens is that Trickster visits twice when Gambler is active, and it seems the first visit (coincidental with Gambler gambling) has landed you on Granny, making you die.
