localizing historical allusions (Waterloo; Honnoji)

Question

English occasionally uses "Waterloo" idiomatically to refer to a situation where someone meets their (ultimate) defeat. (historical allusion to Napoleon's defeat at the Battle of Waterloo)

"That playboy fell hard for Susan. He finally met his Waterloo"

"This is your Waterloo. Soon, you'll be Napoleon Blown-apart." (Sideshow Bob)

My question: would a nativized version work in Japanese? I've toyed with the idea of using Honnoji, in reference to Oda Nobunaga's defeat.

(1) ?「裁判で勝ちつつあってから、田中対鈴木事件は先生の本能寺だった」

　　("After a string of victories in court, the lawyer met his Waterloo in the case of Tanaka v. Suzuki.")

(2) ?「俺は世界一の魔導師！この決闘はお前の本能寺だ！」

　　("I am the world's best wizard! This duel will be your Waterloo!")

Answer 1

You cannot use 本能寺 like that. In addition, 本能寺 is associated with surprise attack rather than ultimate defeat to me. Even if you used an explicit analogy marker (eg 彼にとって本能寺のようなものだ, まるで本能寺みたいなことになった), people are unlikely to understand what you want to mean. And 魔導師 usually refers to Western-style wizards, who don't usually know 本能寺 in the first place :)

A similar word in Japanese is perhaps 天王山【てんのうざん】, which sometimes refers to "decisive stage/battle" without using ～のような.

ここが天王山だ。 This is the make-or-break stage.

I'm not aware of any place name which can mean ultimate defeat on its own in ordinary conversations.