: A military commander with ridiculously formidable tactical prowess.
- Straight: Leonard Lebowitz is the greatest tactical mastermind known to man, and lead Japan to win WWIII.
- Exaggerated: Leonard Lebowitz is the greatest tactical mastermind known to man, and lead his Ragtag Bunch of Misfits to win WWIII though Gambit Roulettes after Gambit Roulettes. Not for his country, but for himself against the entire world. In fact, the chaos that ensued after war was also part of his plans, despite sparking out of a comment during a mass funeral.
- Downplayed: Leonard Lebowitz is an amazing commander, whose victory record is impressive. Were it not for two incidents when a completely unexpected ambush had been arranged by unaffiliated soldiers, he would have a perfect battle record.
- Leonard lives in a world of supers, and his power is sheer tactical brilliance.
- Leonard Lebowitz was a real person, and he was just that good.
- Inverted: Leonard Lebowitz is the most incompetent general known to man.
- Leonard Lebowitz proves himself to be a ridiculously brilliant tactician... but the heroes beat him anyway through the power of teamwork/friendship/rock n' roll.
- Leonard Lebowitz has been fed intelligence from spies - he knows ahead of time exactly what his enemies plan to do.
- Double Subverted:
- Parodied: Leonard Lebowitz is soooooo brillant, that he wins WWIII single-handedly using only a tank, a dozen rounds, and some cocoa powder.
- Zig-Zagged: Leonard Lebowitz leads his army into WWIII and loses to the weakest general's army in the war, who end up being outwitted by Lebowitz and forced to join his army and admit defeat, only to have everyone in WWIII sign peace treaties before Lebowitz could rejoin the war.
- Averted: Leonard Lebowitz is an ordinary general; not an idiot, but not infallible either.
- Lebowitz is the main character of a wartime propaganda piece, and showing him do anything but win would send the wrong message.
- The work is an After Action Report of a strategy game, and the player in question really is that good.
- Leon Lebowitz is based off a historical general. However, the writer decided to exaggerate his competence.
- Lampshaded: "Oh come on, you couldn't have possibly planned that!"
- Invoked: Lebowitz's superiors realize he's unbeatable and purposely send him into vitally-important but impossible battles.
- Exploited: Jack is a Magnificent Bastard who knows nothing about warfare, so he decides to use personal measures to set up all of Lebowitz's victories to end in him assuming power by manipulating background items but not the war itself.
- Defied: The main character goes out of his way to out-smart Lebowitz.
- Discussed: "Seriously though, Lenny...don't you find it kind of weird that we can't even beat you in coin tosses?"
- Conversed: "Come on, this war movie is totally unrealistic! There's no way that Lebowitz guy could have planned that well!"
- Deconstructed: Leonard Lebowitz is a sociopathic Death Seeker Blood Knight, and burns down villages in hopes that someone eventually rises to defeat him.
- Reconstructed: ...and he dies happy when someone does.
- Plotted a Good Waste:
, you Magnificent Bastard
, I READ YOUR BOOK!