Messara Escardos ultimately won his bet.
But he failed to predict many factors.
The first is that the boy’s parents feared him so much that they plotted to dump their Magic Crest somewhere from where it could never be retrieved.
Flat’s parents went to an underground casino famous among the mages of their region and lost everything they had on purpose, leading them to need to mortgage their Magic Crest as compensation for their gambling debt.
Messara would have appreciated the amazing irony, as the casino was run by one of his old friends, the one known as the Dark Lord of Finance.
But this miscalculation was trivial. In fact, Flat, with the help of his friends, took the Fem’s Casa challenge and got his Crest back.


Fate/Strange Fake: Volume 7, Bridge: "Messara Escardos"