mtg whenever you draw a card deal damage Rogue's Gloves [Jumpstart] Question about "Whenever an enchanted

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Though this works better in 1v1 where the life total is 20

You're probably more familiar with "during your upkeep" than any cards with actual printed upkeep costs nowadays, but the concept is the same whatever it's called

The latter would be determined by ease of resolving it and difficulty in removing it

15 Jarad, Golgari Lich Lord The Classic Golgari Commander One of the most straightforward commanders on this list, Jarad, Golgari Lich Lord is a commander who wants as many creatures to be in your graveyard as possible