StartPlaying logo
The Greatest Gamble

The Greatest Gamble

Dungeons & Dragons 5e on Roll20, Discord

Price per player-session
You will be charged when a session starts



  • Duration: 3.5 to 4.5 hours

  • Number of players: 2 to 6 players

  • Experience required: Open to all

Price per player-session

About the adventure

The Deck of Many Things is a magical item that few have the privilege of gambling on with their characters. This set of adventures will follow the characters as they discover a strange card that leads them on a wild adventure suitable for the Deck of Many Things. When assembled, the goal is to have a couple more adventures to allow the players to ultimately experience the repercussions of drawing the card, whether it be clearing out a keep, living life on a higher level than everyone else, or having to deal with some devil that wants your demise! Unfortunately, the deck still has wildly magical properties while it is apart. Even the possession of a card is enough to warp the battlefield in strange new ways that can help or hinder the wielder. What do you think? Will you dive right in and test your fortune? After assembling the deck, the idea is to have an additional adventure or two after. After all, there is no truer victory than one whose consequences you get to experience firsthand. Will you lay claim to a keep infested with monsters, have death wished upon you by a powerful fiend, or grow significantly in power? There are many possibilities that await in this adventure and it's up to the nature of fate to determine which one you'll live.

Professional Game Master

Terence T.

10 years as a TTRPG player

2 years as a Game Master

0 games hosted

Terence T. profile

Additional Details

How to prepare

You will need to be able to use Roll20 and Discord. Players are required to also have a basic understanding of the rules.

What I provide

My Roll20 Pro subscription will allow me to set up interesting battlefields, and the maps I make using Inkarnate will help bring the players into the game.

Gameplay details

After a tremor shook an old mage's tower and caused it to collapse, many an adventurer is seeking to salvage what the old wizard may have had. You are one such group. The idea is that the campaign goes from 3rd level to around 7th or 8th level. While I will try to incorporate everyone's preferred playstyles, there will be a slight emphasis on combat. Not enough to choke out the other pillars, but enough to point out. The individual cards of the Deck of Many Things will be able to fundamentally change how a battle can be fought when initiative is rolled. This may require players to think on their toes as the tides shift in and out of their favor.

Content warnings


Safety tools used


How will character creation work

Characters will start out at 3rd level. I'm open to discussion on whether players want to roll their stats or use Point Buy. No races with a permanent fly speed. Add 10d10 GP to starting wealth. Characters will be created either during a session 0, or before than depending on circumstances. Characters will use Roll20.

Players can expect

  • Combat/Tactics: High
  • Roleplay: Medium
  • Puzzles: Low
  • Experience Level: Open to all

Find Dungeons & Dragons 5e Game Masters

Check out some of our GMs
See all

Browse Games by System

What's StartPlaying?

Tabletop Roleplaying Games Run by Game Masters
  • Find a game to join solo or search for a professional game master for you and your friends/coworkers/family.
  • Book your session and wait for the Game Master to approve you.
  • If you don't have a blast with your first game, your next game is on us.