Jack Theodore Brennan

Name: Jack Theodore Brennan

Gender: Male

Other names: Dagger-Jack

Jackie (by P.J. and Esme)

Junior (by PJ, Esme and Cesare)

Class: Outlaw, bank robber

Age: 22 years old

Body Type: Long and lanky, with the amount of muscle that a life with physical labour would bring a man.

Height: 6’

Complexion: Tanned and leathery from sun exposure

Hair: Dark brown and usually nicely trimmed, despite a life on the run. Jack also sports a styled mustache and goatee, which he keeps as neat as possible.

Eyes: Grey

Scars: Many, most prominent ones are bullet wounds from the Civil War, which he was caught and forced to enroll in.

Relationship Status: Single

Personality: Unlike the other people in the gang that Jack is a part of, Jack is very outgoing and charismatic. His spontaneous and wild personality often brings him into troubles that he doesn't always have the smarts to get out of. Jack is also a notorious womanizer, often finding himself attracted to both the easy-going women of the night, but also the more prim and proper daughters of wealthy townspeople.

Likes: Most noticeably, Jack likes pretty women and cheap booze. These vices has brought him in trouble before, and he therefore often turns to gambling saloons. Over the years, he's found that gambling might bring trouble, but not as much as a jealous husband or over-protective father.

Dislikes: Jack strongly dislikes any authority other than P.J. - the leader of the gang. As a child of a dysfunctional orphanage, Jack doesn’t believe in the idea of "a few men doing the best for many men."

History
Born September 12th, 1848.
Not much is known by Jack's early life, other than he was placed as a foundling at an orphanage in Kentucky at the age of two. He has no memory of his true parents, who left no evidence of their identities with the boy.

After a year, Jack was moved to another orphanage in Georgia, where he met and befriended a girl named Maggie, who was of a similar age as him.

The new orphanage was far from ideal - beatings and abuse were on the menu more often than hot food, and the children were rented out to do cheap labour. Jack never saw a dime of what he earned as a chimney sweep, cattle herder, paper boy and whatever else he did. He started making his own money at the age of six, when he and Maggie would team up and pick pockets. Maggie would usually distract a wealthy mark by pretending to be sad or lost, and Jack would pick their pockets while they were occupied. They were caught a few times and beat for their behaviour, but it only made them better at their craft.

In 1855, at the age of seven, Jack ran away. For months, he lived off of petty thievery, before advancing to home burglaries. Maggie stayed behind at the orphanage, advancing from pickpocketing to scamming and cons.

Along the way, he crossed paths with criminals PJ ‘Madman’ Meyer and Cesare ‘The Sicilian’ Carini. At the time, Jack was a skinny, hungry boy around 8 years old, and saw the two men as a ticket to dinner. He was caught red-handed while trying to sneak a few coins from PJ’s pocket, and given two choices which were to be decided with a coin-toss: walk away unharmed, or lose the hand that had been stealing. The coin never got to five it’s final verdict, however, as Jack snatched the coin mid-air and ran off. His nerve and will to risk his life and limb impressed the two outlaws, who allowed him joined up with them. While he was a child, the men attempted to drop Jack off at several orphanages, but he always found their way back to them. Eventually, they decided to stop trying, and Jack has traveled with them ever since.

Just before his sixteenth birthday in 1864, Jack was caught and charged with horse theft and armed robbery. Instead of being sent to the gallows, he was shipped off to the fronts of the Confederate Army, where he participated - and was wounded - in The Battle of Opequon.

Jack and Maggie’s paths would eventually cross again. In early 1863, Maggie joined up with the gang, spending most of her time as a ward and project of Esme Butler (nee Black, later Donaldson, currently Black-Wilkerson), until 1865 where she disappeared.