A Fine Night of Debauchery is the 51st main story mission in Red Dead Redemption 2 (RDR2). This walkthrough will guide you through all objectives of A Fine Night of Debauchery Main Quest including all Gold Medals for 100% completion.
A Fine Night of Debauchery is unlocked after completing The Gilded Cage.
Quest Giver: Trelawny
Chapter: 4
Region: Lemoyne
Gold Medal Requirements:
- Win the game of Poker without Strauss’s help
- After your cover is blown, escape the boat in under 35 seconds
- Get 5 headshots
- Complete the mission without taking any health items
Starting Location: Saint Denis, Lemoyne
Talk to Trelawny
Meet up with Trelawny in Saint Denis to run a con job on a riverboat casino, but first he thinks your outfit needs some work.
Follow Trelawny to the tailor, and buy the fine three-piece town suit, called ‘The Wittemore’. Luckily there will be no cost to you.
Next, follow Trelawny to the barber to get your hair cut and a proper shave, so that you don’t look like a vagrant.
Properly cleaned up, follow Trelawny to a carriage that will take you to the docks in style.
Unfortunately, you will have to leave your weapons behind, so be on your best behavior.
Trelawny lets you know that the dealer is in on the game, and Strauss will be giving you signals about how to bid, but in order to fulfill the gold medal requirements, you won’t be taking his directions. Keep walking with Trelawny until you sit down at the poker table.
Play Poker
- GOLD MEDAL: Win the game of Poker without Strauss’s help
Having the dealer in on the scam makes this gold medal requirement easy to achieve. The key is to not even wait for Strauss’s suggestions, and certainly never press the 
/ 
button. On the first hand fold, because it is automatically a losing hand.
Most of the players will leave at this point, leaving you alone with Desmond Blythe. For this hand and every hand that follows, just keep going all-in until Blythe busts.
After he busts, he’ll bet his watch from the safe upstairs, and again go all in.
After you win again, follow the pit boss upstairs to get the watch. Conveniently, Javier will be posing as a guard and join the pit boss as an escort.
The pit boss will utter some casual racism while waving a gun around, greatly diminishing any remorse you might feel for his upcoming beating.
Wait for the pit boss to open the safe.
Javier will clock the other guard in the face, while you dissuade the pit boss from doing anything stupid.
Press 
/ 
to disarm the pit-boss and take his gun, then loot the safe. As soon as you do, you will snap into Dead Eye.
Looks like the pit boss had two guns. I can’t say that I’m sorry things went this way.
Finish looting the safe, then follow Javier. Be sure to holster your gun out of view. He will lead you down two flights of stairs.
Keep following Javier into the main room, where Trelawny is having an argument at the bar with Blythe.
Just as you’re trying to defuse the situation, all hell breaks loose.
- GOLD MEDAL: After your cover is blown, escape the boat in under 35 seconds
- GOLD MEDAL: Get 5 headshots
- GOLD MEDAL: Complete the mission without taking any health items
This time limit is ridiculously tight. Immediately go into Dead Eye and try to get as many headshots as you can. There should be enough guards visible in the room to immediately get at least three on your first pass.
Get out of cover and immediately start moving towards the stairs. Go into Dead Eye and shoot the two guards coming down the stairs to complete your five headshots.
Ignore everything else, and sprint for the door to the right of the stairs, and turn left.
Follow Javier and Trelawny off the edge of the riverboat and into the river.
Another flawless Trelawny plan. Mission complete!
This finishes A Fine Night of Debauchery main mission in Red Dead Redemption 2. Now the next quest Horsemen, Apocalypse starts.
Next Up: Horsemen, Apocalypse
For more Walkthroughs with all gold medals, check out the complete Red Dead Redemption 2 Story Walkthrough.
How to get the suit back? Can’t find it anywhere. Is it mission only?
Mr. Pinto, thank you for asking that because my bot found it and I think it is only mission specific. From research and and my own exp, I found that although the suit had disappeared at the end of the mission I had gained the shade of blue for my Opulent vest.
Like stated in the guide the time limit is ridiculous. I had to retry it multiple times, going through all the early slow-paced BS again just because the escape point refused to trigger even though I had already killed (and headshot) 5 guards, forcing me to go back and kill one more…
The key to getting the time limit is not using dead eye because the kill cutscenes take too much time. When you’re behind the bar, get 3 or 4 headshots without deadeye and then start running towards the exit on the right side. I killed two more on the stairs in deadeye while i was going to the exit and then made a dash for the water.
I had the same thing happen to me like 3 times, I’d get all 5 headshots immediately, run up, and nobody would follow me until after my timer started beeping, at which point I’d just let myself be killed to try again. I don’t understand, you have to stay right next to them until a certain time, or until a certain number of guards are dead? Or you just can’t get ahead of the rest?