Born on 27th April, 3236 on a farm on the planet Nirvana in the Phekda system, his life was going to be interesting whatever direction it took. At the time, Phekda was one of the most notorious anarchy systems in the northern inhabited sectors. James was the last born in his family, all born by natural childbirth, the typical farms on Nirvana having a standard of living roughly comparable to farms of the mid twentieth century on Earth. His three older brothers were all ideally suited to farm labouring, being what James's father affectionately termed "strong in t' arm but thick in t' head". As the quirks of natural reproduction would have it, James was physically quite different from the rest of the family. He grew up to be thin and lanky, but with a cunning mind and lightning reflexes. Cruelly bullied by his siblings, James longed to leave the surly bonds of planetary gravity and make his living as a bounty hunter. The life of the bounty hunter seemed romantically exciting to the eyes of most planet-bound dreamers, and his desire to become one was fuelled when his best friend was murdered by Senator Johnson's strongmen during a dispute over land ownership rights.

At the age of seventeen standard years, James left home for the city of Newtown in Nirvana. In a stunning display of bad judgement typical to naturally-conceived teenagers, he conned a loan shark into lending him the money to buy a Saker Mk III. James left a simple "goodbye" message to his family back at the farm, and departed for Alioth by buying a ride with a bounty hunter. Once at Alioth, he purchased the Saker Mk III and began an adventure that would nearly cost his life on several occasions. He had no intention of paying the loan shark back, especially since the shark's sister happened to be Senator Johnson.

As James matured, his natural cunning and snake-like reflexes eventually earned him an Elite rating, several scars, and great respect amongst his fellow bounty hunters. In 3268 at the age of 32, he joined the AJN intelligence branch at Titican. Not long after joining, he discovered an INRA plot to destabilize the Alliance. He led a small team that foiled this plot and earned a great deal of recognition from the military leadership. This resulted in gaining the command of the starship Fearless, which he commanded from 3272 until being made Fleet Admiral at the age of 44. In 3294, Admiral Winston decided it was time to step down and lead a less stressful life, and became Commander of the TSCA. As well as performing administrative duties, he also was the TSCA's chief Check Pilot, and occasional instructor.

It was while giving a stage check to a bomber crew that James Winston died in tragic circumstances, aged 67. After dodging the bullets of pirates, spies and assassins for decades, he and the bomber crew he was supervising were killed instantly when their Courier slammed into an asteroid in the Gateway system, less than 10,000km from Dublin Citadel. The cause was a faulty valve in the control system - in deep space something that could be handled with ease, but which had disasterous consequences while flying low on a simulated bombing run.