Grifter

[TcK421]

To all those wondering about this particular trophy, you might have noticed that there seem to be almost no wheel gambits in the game with Huge Success cards. As it happens, there seems to be only about 3 or 4 gambits where you can get Huge Success results on wheels and they are all late game. There is one in the river crossing on the second floor of Judgement, and another if you run away from the Prison Mage encounter on the second floor of The Sun. Another is in the Far North encounter, but if you earn this card's token it is no longer available to you.

 

So right now, it is a bit of a grind to get this, but the Steam version received a patch a few days ago that added a Huge Success card to the wheels on the Field of Fae and Plague encounters, so you might want to wait for this update to hit PS4 to grind this one out. Just thought I'd post this because I figured other people would be wondering about the lack of chances to progress this trophy, good luck everybody.

[Rally-Vincent---]

Field of Fae has got a huge success card on the wheel (just saw it by chance), but of course, you'll have to win the card chance game first to get there.

[Willstown]

If you have the Cold Hearth expansion then doing Keturah's named bounties will result in a fair few wheel gambits.

[Willstown]

Finally got this one last night after coming back to the game.

 

As the 1st OP mentions the 'Plague' encounter has a huge success.  You can get multiple plague encounters in the 2nd level of the Chariot challenge, grinding this seems to be the best approach.