Ryan met and fell in love with a pretty, quiet nurse of Cuban descent, named Maria de Mederez. She had dark hair, was of petite stature and her family immigrated from Cuba when Castro took power.

Even though they were both of the Catholic faith, both families disapprove of the couple. Still, nothing could stand in the way of their love, they wed and promptly started a family.

The marriage was a happy one despite an early tragedy. Maria bore their first child, a son. Unfortunately, he was a sickly baby and soon died. They then preceded to have four girls. So it was with some surprise and much joy that their last child turned out to be a very health baby boy. They gave him an Irish name, since it sounded more American than a Cuban one. Both had felt the sting of prejudice because of their nationality and religion and wanted their son to have every advantage in life.

Young Jack grew up in the tough working class Southie but did well. He excelled in sports as well as school. But he did even better with the ladies, which would have his mother in a panicked state every time he went out with a girl, worried about her baby's 'purity'.

He graduated South Boston High School with fine grades and through some miracle, his parents had saved enough money to send him to Boston Unirversity, instead of the local state school, Umass-Boston.

Jack went to B.U., majoring in Criminal Justice and minoring in History and Military Tactics. He once had thought of going into law enforcement but all future plans were put on hold when tensions rose in the Middle East. Jack felt it was his duty to serve his country and enlisted in the army. His parents were aghast for the obvious reasons but even if their patriotism didn't prevent them from strong opposition, it would have done little good.

Staff Sgt. Brannigan served well in Desert Storm, was awarded a purple heart and came back to the U.S.A. full of hope. However his hope was soon dashed when he came home to the news that his father had died, dead of a massive heart attack while Jack was overseas. Due to the fact that he was in battle and his location was to be a secret, he couldn't be told about the death before hand.

Saddened over his father's passing and disillusioned with life, he would eventually wander to Macao, a Portuguese colony off the coast of China. Macao was favorite tourist spot and Jack had visited there during his army stint. It was also a hotbed for organized crime and Brannigan put his talents to work in a whole new field. A favorite among Macao's Asian gangsters for various tasks, he eventually came home to Southie.

Jack's mother had already died, thus adding to his sliding towards crime. And soon after, finally sealing his fate, Jack Brannigan caught up with his childhood friend, Liam, "William" O'Reilly. Liam was now the head of the Irish Mob in South Boston, following James J. "Whitey" Bulger's fleeing to avoid indictment. Jack rose through the ranks, eventually becoming Liam's most trusted advisor. It was at this time that he became familiar with the drug trade, supposedly banned within the Italian Mafia.

When Liam met up with some major legal trouble, his organization was scuttled for the most part. However, Brannigan was able to take what resources he had and apply them to corner the Northern New England's drug trade. While not as lucrative as that of the trade in Metropolitan Boston, it was much easier to control and he knew that fighting wars over the big city is where Liam went wrong.