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It's either one of two.

Gemfire. A simplefied strategy game like Romance of the three kingdoms. It was on the SNES by Koei. We must of beaten that game over a couple hundred times from grandschool through JR High. With me playing it in highschool to.

Or Civ 2, which i played nearly every day for a year or two.

Third place is probably Front Mission 3. Since i've beat that game 4-6 times at about 30-50 hours a playthrough