Medieval 2, Total War.
Playing as England, I'm attacked by France then threatened by the pope (who I elected!) to cut that shit out or I'd get excommunicated. I do as he says, meanwhile France builds up a huge army and almost steamrolls one of my castles. Striking back after the mandatory 7 turns the pope told me to wait, I proceed to take every single settlement the Frenchies have with my king, now a uber-general at the age of only 29. The final castle I take from them has a single pair of ballistae, and in the beginning five minutes of the attack gets a lucky shot on my general and kills him instantly. I still take the castle though, and make plans to bring a new general to the front to attack Milan, who's giving me funny looks.
The faction heir, now newly appointed king I send from Paris to Metz (The castle I just took) to support the troops and make sure they don't turncoat. I send him with a few hundred knights, figuring that a two turn journey can't be that dangerous. As soon as I send him on his way, he's ambushed by a
full stack of rebel armored swordsmen.
Holy Shit. He dies as I try to withdraw him from the battle, using the other knights as bait, again from a lucky shot by some peasant archers.
Finally, deciding that I have had enough of this bullshit, I gather up a huge-ass two stack army, with my 16 year old newly fledged king, and send them on their way from London to deal with those rebel fucks. As soon as the army touches down in northern France, boom, earthquake. It kills half my dudes, turning a 7,000 strong army into about 3,500. For those of you who are not aware of the frequency of earthquakes in France, here's a picture:
Earthquakes are most frequent around the areas directly bordering those lines. Needless to say, I'm a bit pissed off.
Now I don't even have enough men to take the first Milan city. Figuring I can still retrain them, I send the army back to a nearby castle. It's a two turn trip. Praying and crossing my fingers, I click the 'end turn' button. Boom, king assassinated, remaining army turncoats, and Spain, France, and Scotland all invade at the same time. Cue throwing monitor through window.