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Commander
Flying When Hidetsugu and Kairi enters the battlefield, draw three cards, then put two cards from your hand on top of your library in any order. When Hidetsugu and Kairi dies, exile the top card of your library. Target opponent loses life equal to its mana value. If it's an instant or sorcery card, you may cast it without paying its mana cost.
Acquire Pain
{T}: Add {U}. {2}{U}: Put an hour counter on Midnight Clock. At the beginning of each upkeep, put an hour counter on Midnight Clock. When the twelfth hour counter is put on Midnight Clock, shuffle your hand and graveyard into your library, then draw seven cards. Exile Midnight Clock.
Creature
Whenever you draw a card, put a +1/+1 counter on Chasm Skulker. When Chasm Skulker dies, create X 1/1 blue Squid creature tokens with islandwalk, where X is the number of +1/+1 counters on Chasm Skulker. (They can't be blocked as long as defending player controls an Island.)
When Woe Strider enters the battlefield, create a 0/1 white Goat creature token. Sacrifice another creature: Scry 1. Escape—{3}{B}{B}, Exile four other cards from your graveyard. (You may cast this card from your graveyard for its escape cost.) Woe Strider escapes with two +1/+1 counters on it.
Erase all Joy
Know your Pain
Look at the top five cards of your library. As many times as you choose, you may pay 1 life, put those cards on the bottom of your library in any order, then look at the top five cards of your library. Then shuffle and put the last cards you looked at this way on top in any order.
Land
More Pain
Whenever you cast a noncreature spell, create an X/X blue Shark creature token with flying, where X is that spell's mana value. Cycling {X}{1}{U} ({X}{1}{U}, Discard this card: Draw a card.) When you cycle Shark Typhoon, create an X/X blue Shark creature token with flying.
Multiply the Pain
You may have Flesh Duplicate enter the battlefield as a copy of any creature on the battlefield, except it has vanishing 3 if that creature doesn't have vanishing. (A permanent with vanishing 3 enters the battlefield with three time counters on it. At the beginning of your upkeep, remove a time counter from it. When the last is removed, sacrifice it.)
Changeling Whenever you cast an instant or sorcery spell, if it targets one or more other permanents you control, create a token that's a copy of one of those permanents. When a spell or ability an opponent controls causes you to discard this card, create a token that's a copy of target permanent.
Protect the Pain
You may exile two blue cards from your hand rather than pay this spell's mana cost. Gain control of target noncreature spell. You may choose new targets for it. (If that spell is an artifact, enchantment, or planeswalker, the permanent enters the battlefield under your control.)
Cast this spell only during the declare blockers step on an opponent's turn. Remove all attacking creatures from combat and untap them. After this phase, there is an additional combat phase. Each of those creatures attacks that combat if able. They can't attack you or planeswalkers you control that combat.
Recall the Pain
Put target creature card from a graveyard onto the battlefield under your control. It gains indestructible. If it's your turn, scry 2. (Look at the top two cards of your library, then put any number of them on the bottom of your library and the rest on top in any order.)
Until end of turn, target creature you control gains "When this creature dies, return it to the battlefield tapped under its owner's control, then create a Wicked Role token attached to it." (Enchanted creature gets +1/+1. When this Aura is put into a graveyard, each opponent loses 1 life.)