Gambling build ideas wanted.

[KyleG]

I want to create a character who likes to gamble and likes the finer things, so if it's not something extravagant he has just brought he's spending it gambling either for another big win or an unfortunate day (doesn't get him down). Characters that spring to mind are Bond, Gambit and Mollymauk not neccessarily for the gambling aspects but general attitude and persona.
I could play it as purely roleplay but inquisitive rogue might be kinda cool to play into the gambler.
Then there is the suave side, that bond or gambit side, thats more charisma so maybe i should lean in there with swashbuckler or swords bard.
Could go another route and lean into the lucky side of being a gambler, portent, maybe a halfling, maybe lucky feat.
Could play up the showman aspect, a performer, and go trickster or soul knife or a bard, eloquence maybe.
Im picturing him as a bit of a risk taker, egging on an opponent be it in combat or at the table.

So what do you think would be a good approach?

[JackPhoenix]

Have the gambling be a part of the character's background and personality, not their entire gimmick. Pick the Lucky feat, maybe, if that's how you want to go, and then build a normal character.

[llama-hedge]

You could consider a mildly refluffed wild magic barbarian. JoCat's most recent campaign had a character like that, although I haven't kept up with that in ages.

The subclass leans into the chance aspect, while barbarian's natural durability means you can afford to step into harm's way and live to tell about it afterwards.

I haven't played a wild magic barbarian myself, but I was in a party with one in a campaign that ran from 1 to 20 and the player seemed like he was having a good time. We had good access to magic items but I don't recall any points where the build underperformed despite minimal optimisation.

[LudicSavant]

I want to create a character who likes to gamble and likes the finer things, so if it's not something extravagant he has just brought he's spending it gambling either for another big win or an unfortunate day (doesn't get him down). Characters that spring to mind are Bond, Gambit and Mollymauk not neccessarily for the gambling aspects but general attitude and persona.
I could play it as purely roleplay but inquisitive rogue might be kinda cool to play into the gambler.
Then there is the suave side, that bond or gambit side, thats more charisma so maybe i should lean in there with swashbuckler or swords bard.
Could go another route and lean into the lucky side of being a gambler, portent, maybe a halfling, maybe lucky feat.
Could play up the showman aspect, a performer, and go trickster or soul knife or a bard, eloquence maybe.
Im picturing him as a bit of a risk taker, egging on an opponent be it in combat or at the table.

So what do you think would be a good approach?

Characters like Gambit often don't have on-the-nose gambling-based powers. And I'm sure you'll get a lot of those sorts of recommendations (Wild Magic and the like) anyways, so I'll go off on a bit of a different route.

You picture a risk taker, egging on an opponent. So how about a character who literally dares enemies to hit them, betting on who will give out first -- can they take that next hit, or will their enemy go down to Armor of Agathys or Hellish Rebuke?

And besides, what greater gamble than thinking you can out-play the devil? I'm thinking a frontline retribution tank with a dash of Warlock. Could make it a Bardlock if you like.

[Derges]

One option might be the wild magic sorcerer. It can be very fun and, with the playtest text change, not entirely DM-dependent.

Another could be a wizard with a deck of cards. You can take it full Yu-gi-oh "King of games" or a modern stage magician (which might be closer to your bond vibe). You can create real spell cards and use them as your spellbook or just as a gimmick.

[Lvl 2 Expert]

I've had twice in my current character's career that I didn't really know what spell to pick. Because there were multiple good options, I already got the ones I really wanted and I wanted to avoid metagaming too much. So I had a clairvoyant NPC (who was nowhere near the action nor invested in my spell choices) draw a card. The card my DM drew determined my choice, according to a small list prepared for the occasion. I might want to revisit this concept one day, getting all my spells at random through drawing regular playing cards or spell cards or by rolling dice. That might work as part of your character too. Maybe an Arcane Trickster or something? Especially if you're worried the spells will be bad or it will feel like too much of a central gimmick? Whatever happens, you'll still have a playable rogue with some appropriate skills and feats.

[Zetakya]

Don't underestimate the advantage that simple divination magic would give to a professional gambler. Especially if you had Subtle Spell.

You could also outright cheat by using minor illusion magic to change cards to whichever one you wanted it to be.

[5eNeedsDarksun]

My first question would be: Are you going to cheat, or not?

The build looks a lot different if you are, leaning into things like expertise in Slight of hand or Subtle spell.

[KyleG]

My first question would be: Are you going to cheat, or not?

The build looks a lot different if you are, leaning into things like expertise in Slight of hand or Subtle spell.

I'm not picturing him cheating physically, a little gamblers luck, maybe a little psychic info if i could subtle be telepathic.

[Corran]

I want to create a character who likes to gamble and likes the finer things, so if it's not something extravagant he has just brought he's spending it gambling either for another big win or an unfortunate day (doesn't get him down). Characters that spring to mind are Bond, Gambit and Mollymauk not neccessarily for the gambling aspects but general attitude and persona.
I could play it as purely roleplay but inquisitive rogue might be kinda cool to play into the gambler.
Then there is the suave side, that bond or gambit side, thats more charisma so maybe i should lean in there with swashbuckler or swords bard.
Could go another route and lean into the lucky side of being a gambler, portent, maybe a halfling, maybe lucky feat.
Could play up the showman aspect, a performer, and go trickster or soul knife or a bard, eloquence maybe.
Im picturing him as a bit of a risk taker, egging on an opponent be it in combat or at the table.

So what do you think would be a good approach?
Hmmm, involve some other pc's on it. Have two* pc's vouch for you and help you get out of whatever trouble you get into (work with the DM to figure out how much time these troubles are happening on screen and how much off screen; eg they could just be the little silly bit you have to deal with just before the start of some adventures). And have one pc who will lure (ideally out of pettiness) yours back into that lifestyle whenever your pc is even thinking of making a fresh start.

*Why two? So you give the other players enough room to differentiate their treatment of your character's flaw should they want to. For example, one is a dear friend who wants to help you (and acts in direct contrast with the third pc who wants to keep you gambling). They'll drop resources and even put their reputation in line to save you from whatever trouble you managed to get yourself into. The second is someone who is willing to make an effort at getting you out of dodge just because you are useful but at the same time they wont go the extra mile to save you from whatever negative consequence might be in store for you (eg beating, flogging, whatever). And on that note, it would be good if your character can fill some distinct niche that the other party members dont. Eg tracking, or disarming/detecting traps, healing, ect. Lots of niches really, but some are are more easily acknowledged and observed than others.

[Heavenblade]

A divine soul sorcerer halfling with lucky, bountiful luck, second chance, and the right spell picks (Bless, feather fall, etc ), especially with stuff like magical guidance and seeking/heightened spell metamagic, you can play an extremely lucky guy

A really fun character to play.

[Dice Goblin]

One option might be the wild magic sorcerer. It can be very fun and, with the playtest text change, not entirely DM-dependent.

Another could be a wizard with a deck of cards. You can take it full Yu-gi-oh "King of games" or a modern stage magician (which might be closer to your bond vibe). You can create real spell cards and use them as your spellbook or just as a gimmick.

Currently have a rogue/wizard playing a magic card thrower in our camapign, they are just epic!

[Snig]

Isn't there a new feat or subclass related to card throwing?

[Snig]

http://dnd5e.wikidot.com/rogue:wild-card

[Mastikator]

I'm not picturing him cheating physically, a little gamblers luck, maybe a little psychic info if i could subtle be telepathic.

Halfling with the Lucky feat. Divine soul sorcerer for the favored by the gods ability. Detect thoughts is a 2nd level sorcerer spell and can be made subtle, while only reading surface thoughts it is not detected by the target.

Magical guidance at 5th level is also a light-lucky ability that sorcerers get.

Edit-
Noble background for the gaming set proficiency, and your character was lucky to be born into wealth. And there is the trope of the noble who spends time with the common folk especially to gamble.

Or spy/criminal background for a gaming set proficiency and thief's tools.

Also catapult is a 1st level sorcerer spell and you can catapult dice, gaming cards, etc.

[thoroughlyS]

The variant downtime activity for gambling (Xanathar's Guide to Everything p.130) lists three skills for the activity: Wisdom (Insight), Charisma(Deception), and Charisma(Intimidation). I would recommend making a character that has proficiency with all three skills, so they can sit in at basically any table to wager, regardless of game. If I were to make a character that played up these vibes, I would actually do a spirits bard. It would give you the ability to use a tarokka deck as a focus, and you can get expertise in two of those skills, not to mention that both gamblers and bards benefit from high CHA. As a fun extension of the concept, the spirit bard's subclass feature is built around a die roll.

[KyleG]

Currently have a rogue/wizard playing a magic card thrower in our camapign, they are just epic!
My curiosity is peaked...care to share the details?

[KyleG]

The variant downtime activity for gambling (Xanathar's Guide to Everything p.130) lists three skills for the activity: Wisdom (Insight), Charisma(Deception), and Charisma(Intimidation). I would recommend making a character that has proficiency with all three skills, so they can sit in at basically any table to wager, regardless of game. If I were to make a character that played up these vibes, I would actually do a spirits bard. It would give you the ability to use a tarokka deck as a focus, and you can get expertise in two of those skills, not to mention that both gamblers and bards benefit from high CHA. As a fun extension of the concept, the spirit bard's subclass feature is built around a die roll.

Good thinking. I will lean into that. Not sure about the spirits bard but bard certainly seems a good contender.

[Boverk]

Could maybe reflavor magic stone as throwing cards?

[Lvl 2 Expert]

I'm not picturing him cheating physically, a little gamblers luck, maybe a little psychic info if i could subtle be telepathic.

Detect thoughts? You "only" get surface thoughts without the victim finding out what you're doing, but "okay, jack and ace of clubs" is about as surface as thoughts get.

[Kane0]

Homebrew on the table? Because i remember seeing a college of fortune bard somewhere that looked really fun