Ulysses S. Grant vs Jesse James army battle

[JHG]

Ulysses S. Grant 
He was the living legend, the scourge of Spotslyvania, the seizer of Vicksburg, Unconditional Surrender incarnate…who would write his memoirs while suffering from cancer.
Abilities: >average physical ability, horsemanship, generalship, swordsmanship, marksmanship, fear factor, super sobriety(just kidding!), charisma
Jesse James

The violent tempered outlaw is prepared to go BLASTING OFF AGAIN!
Abilities: >average physical ability, horsemanship, marksmanship, charisma, stealth, deception

Jesse James has the entire James-Younger Gang(~15 men at peak) Grant is leading 100 soldiers to suppress any Neo-Confederate rebellions and to stop the gang-alive or dead.

[JHG]

Grant probably takes it even if his men have the Pattern 1861 Springfield. He's a far smarter general with far better men while James merely has outlaws so...
"WE'RE BLASTING OFF AGAIN!" Jesse James said calmly

[JHG]

I’m thinking Grant grants any death wishes here.

[JHG]

Unconditional surrender granted.

[JHG]

Jesse James may have better weaponry but he's a far inferior general.

[Kyng]

Yeah, this just sounds like a curbstomp in Grant's favour, TBH. Even if you make the numbers equal (and keep the disadvantage in weapons), I suspect Grant would still win due to superior organisation and training.

[JHG]

Yeah, this just sounds like a curbstomp in Grant's favour, TBH. Even if you make the numbers equal (and keep the disadvantage in weapons), I suspect Grant would still win due to superior organisation and training.

“WE’RE BLASTING OFF AGAIN!” He said calmly.