For me:
1. Napoleon- This guy was a hero of mine as a kid when I thought war heroes were nearly gods on earth in a way... and now that I've lost that believe- I STILL FREAKING LOVE NAPOLEON! The man is AMAZING! Short (ok, ok, YES, he WAS average height for his time, but this is Napoleon, the short reference MUST be made!) but always confident, so intelligent, so complicated... and he was one of those leaders that just CARED for the folks on his side. He cared about France. He cared about his family. He cared about the JEWS, for heaven's sake, how often has THAT happened with a military leader in Europe, especially up to Napoleon's day, he got them out of the ghettos in Western Europe. And, of course, his men LOVED him, I mean LOVED him... they'd have to to have put up with marches through Italy and Egypt and Russia. Yes, he lost in the end, but I still think that he's one of the greatest military minds ever (doing one of my "Rushmores" again, I'd pick Napoleon, Alexander, Caesar, and then likely Ghengis Khan, maybe subbing out Khan for Ike or MacArthur or Patton if a modern leader were called for) and this is who I'd have WANTED to serve under. I'm a weakiling, I'll admit it, I suck at so many things you need to be a good soldier and I'm not great medically at all, I don't know HOW our soldiers do it overseas (kudos to them, a bigtime ALUTE to them, whatever your opinion of the war, you HAVE to respect these guys, what they have to do and the fact that they can do it is AMAZING and a testament to their great will and character)... but I have to say:
If given the chance, I'd work my ass off as hard as possible and even learn French if I had to, I'd want to march with the Master! ;)
2. Horatio Nelson- Odd my top 2 are from the same era, same war... and on the opposite sides. But Nelso is amazing, too, and if I were going to fight a sea war, I'd want him as my leader, for three main reasons- brilliant leader, fascinating man that strikes me as sort of the Captain Picard of naval warfare, and if I had to go to war on any ship, my choice WOULD have to be the HMS Victory... the USS Enterprise (the real WWII battleship, though in a couple hundred years if Kirk or Picard need recruiting... just no red shirt for me! lol) comes a close second and I almost picked it, but the leader just doesn't stand out. The Enterprise and Vicotry are EASILY the two greatest ships in naval history, and it'd have been hell but maybe an amazing hell to serve on either... but given the choice, I'll take Nelson and the victory.
3. Washington- OK, 3 picks in the late 18th-early 19th century era in a row to start the list, can you guess my favorite what era I'd have loved to have been in war-wise? ;) some say Washington as a general is overrated- to that I say, in true American fashion, BULLSH*T! Yes, he lost and lost and LOST, but he hung in there and, more importantly, what made him great and one I'd have loved to serve with, he made his MEN hang in there... Valley Forge, more than any other battle, was maybe Washington's greatest victory in the Revolution. The fact he kept a bunch of farmers and artisans that had been beaten and beaten by the British and were now hunkered down in freezing cold from deserting, that the Continental Army stayed intact at all... WASHINTON. The famous crossing the Delaware, coupled with Valley Forge- showing whey he was a great general, a great soldier's general, and the perfect man, once the war was done, to be Father of Our Country. We ALL love ya, George (and we're all sorry your country's been messed up so badly... blame the last guy in office, he stole your name, George, but mostly blame both parties for being so partisan, Red or Blue... you were Red, White, and Blue forever, you knew better than to be partisan, you didn't even really have a party!) ;)
4. Alexander- I have a cheat in this one, because I picked him for a few reasons here, one sort of... well, decide for yourself: personality, cool period of time, tutored by Aristotle (if I could've met HIM!)... and, yep, NEVER LOST! That's ALWAYS a plus side when you're choosing a commander, right? :D
5. Theodore Roosevelt- A bit of a cheat, maybe, but I'm taking the pick anyway- TR IS AMAZING! He was my favorite president as a kid; as an adult, I still idolize he and his distant cousin FDR. This pick is completel because of TR; the war was short, but in Cuba, and disseas-riden, and hot, and humid... but for the chance to be there with THEODORE ROOSEVELT... THAT would be amazing!
Honorable Mentions- Caesar, Eisenhower, Patton, MacArthur, the WWII USS Enterprise and her captain