Chance Encounter

Whenever you win a coin flip, put a luck counter on Chance Encounter.
At the beginning of your upkeep, if Chance Encounter has ten or more luck counters on it, you win the game.

Tavern Scoundrel

Whenever you win a coin flip, create two Treasure tokens. (They're artifacts with "{T}, Sacrifice this artifact: Add one mana of any color.")
{1}, {T}, Sacrifice another permanent: Flip a coin.

Krark's Thumb

If you would flip a coin, instead flip two coins and ignore one.

Wizard Class

(Gain the next level as a sorcery to add its ability.)
You have no maximum hand size.
{2}{U}: Level 2
When this Class becomes level 2, draw two cards.
{4}{U}: Level 3
Whenever you draw a card, put a +1/+1 counter on target creature you control.

Fiery Gambit

Flip a coin until you lose a flip or choose to stop flipping. If you lose a flip, Fiery Gambit has no effect. If you win one or more flips, Fiery Gambit deals 3 damage to target creature. If you win two or more flips, Fiery Gambit deals 6 damage to each opponent. If you win three or more flips, draw nine cards and untap all lands you control.

Ral Zarek

+1: Tap target permanent, then untap another target permanent.
−2: Ral Zarek deals 3 damage to any target.
−7: Flip five coins. Take an extra turn after this one for each coin that comes up heads.

Planar Chaos

At the beginning of your upkeep, flip a coin. If you lose the flip, sacrifice Planar Chaos.
Whenever a player casts a spell, that player flips a coin. If they lose the flip, counter that spell.

Talisman of Creativity

{T}: Add {C}.
{T}: Add {U} or {R}. Talisman of Creativity deals 1 damage to you.

Okaun, Eye of Chaos

Partner with Zndrsplt, Eye of Wisdom (When this creature enters, target player may put Zndrsplt into their hand from their library, then shuffle.)
At the beginning of combat on your turn, flip a coin until you lose a flip.
Whenever a player wins a coin flip, double Okaun's power and toughness until end of turn.

Zndrsplt, Eye of Wisdom

Partner with Okaun, Eye of Chaos (When this creature enters, target player may put Okaun into their hand from their library, then shuffle.)
At the beginning of combat on your turn, flip a coin until you lose a flip.
Whenever a player wins a coin flip, draw a card.

Game of Chaos

Flip a coin. If you win the flip, you gain 1 life and target opponent loses 1 life, and you decide whether to flip again. If you lose the flip, you lose 1 life and that opponent gains 1 life, and that player decides whether to flip again. Double the life stakes with each flip.

Krark, the Thumbless

Whenever you cast an instant or sorcery spell, flip a coin. If you lose the flip, return that spell to its owner's hand. If you win the flip, copy that spell, and you may choose new targets for the copy.
Partner (You can have two commanders if both have partner.)

Stitch in Time

Flip a coin. If you win the flip, take an extra turn after this one.

Chaos Warp

The owner of target permanent shuffles it into their library, then reveals the top card of their library. If it's a permanent card, they put it onto the battlefield.

Squee's Revenge

Choose a number. Flip a coin that many times or until you lose a flip, whichever comes first. If you win all the flips, draw two cards for each flip.

Yusri, Fortune's Flame

Flying
Whenever Yusri, Fortune's Flame attacks, choose a number between 1 and 5. Flip that many coins. For each flip you win, draw a card. For each flip you lose, Yusri deals 2 damage to you. If you won five flips this way, you may cast spells from your hand this turn without paying their mana costs.