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A boast ability can be activated at any point after the creature with that ability has been declared as an attacker

(2) Each time your opponent activates a card or effect, this card gains 300 ATK

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So either you'll be stuck grinding for hours or get lucky in winning, doing it over and over until you can manage to save some DP and construct a better deck to use, which will make battles easier

Lillies popularity as a character from Sun & Moon, combined with the emotional resonance of the Trainers Pokmon mechanic, creates a level of demand that keeps this cards floor high

That being said, lifegain decks do have better options for commanders than Frodo