Rome-Persia is an interesting and arguably worst-case quagmire. For a mere worse case, a few decades ago is more than enough: https://en.wikipedia.org/wiki/Ir

Rome-Persia is an interesting and arguably worst-case quagmire. For a mere worse case, a few decades ago is more than enough: https://en.wikipedia.org/wiki/Iran-Iraq_War https://en.wikipedia.org/wiki/Iran-Iraq_War