The Formula Junior race at Brands Hatch in 1963 that saw Mike Hailwood, piloting a Brabham in his first try at four wheel competition, finish fifth is remembered today only for being the advent of the British two-wheel ace's star-crossed Grand Prix career. However, the winner of that event went on to achieve considerable renown in another field, in the process drawing the attention of Scotland Yard and the Buckinghamshire CID.

Roy James, by many accounts including Hailwood's, showed great promise as a racing driver. He had begun in karts. At Brands Hatch in '63 he was early into a 17 for 19 streak in Formula Junior. But he faced the same hurdle that most up-and-coming drivers not independently wealthy face: where will the money come from? The fact that racing demands significant capital investment can be attested to even by those who have never had to deal with Bernie Ecclestone. Niki Lauda got himself fearfully in debt before he hit the big time. Nigel Mansell once mortgaged his home to keep racing. James, apparently larcenous by nature or upbringing, seems to have decided at a tender age to obtain his funds by methods requiring neither interest payments nor restoration of principle.

By 1962, car theft and second-story work had already earned him periodic confinement as a guest of Her Majesty's Government. In that year he and his mate, Micky Ball, like James short of stature and ethics and long on driving ability, made off with 144,000 pounds Sterling worth of someone else's jewelry in Monte Carlo. Upon their return to England they fell in with a gang planning to knock over an armored truck payroll shipment at Heathrow in November. They were assigned the duty of getting the money and the thugs away from the scene of the crime in two stolen Jaguars. In accomplishing this James was able to display some of his motoring skills. While exiting through a gate in the airport's perimeter fence he bounced off of an Austin A40 trying to block his way, but was able to keep going (here I shall stalwartly resist making any comparison with Jerez, 1997, except to observe that, although fraud was committed in Spain, at least nothing was stolen). Once on the main road he quickly overtook Ball, but, in a nervy move, balked traffic in the middle of an intersection whose light had just turned red allowing Ball and the money to get through. The robbery was a brutal affair, assorted clerks and armored truck guards having been coshed with homemade blackjacks, and netted the gang only 62,000 pounds. In the ensuing investigation Scotland Yard's Flying Squad recognized James and Ball as the only usual suspects possessed of the sort of flair displayed in the getaway. Ball quickly caved in, in the process betraying a couple of the other perpetrators but not James. Only Ball wound up doing any time. James used part of his share of the loot to purchase the Brabham that got him going in Formula Junior.

Buoyed by the notoriety of, if not the financial return on, the airport job, the gang set its sights higher. They planned to hit a night train [What would later come to be called The Great Train Robbery] that allegedly carried millions of pounds in bank reserves from Glasgow to London. They brought in another London gang in order to obtain the services of one of its members, a florist accomplished at rigging railroad signals to stop trains. Ball, indisposed as a result of the Heathrow affair, was not in on this one, but Roy James was, in the process sinking his fledgling racing career while becoming a party to one of the most famous crimes ever committed.

To James's credit he doesn't seem to have catered much to the personal assaults inherent in stealing from people. Thus it was that he volunteered to master the art of decoupling railroad coaches, this activity being necessary to the planned robbery in order to facilitate moving the locomotive and mail coach away from the balance of the stopped train to a location offering road access for the getaway vehicles. He and a couple of other gang members were able to practice unnoticed in London rail yards until they achieved the desired expertise. His study of railroad technology also convinced James that he could operate the hijacked diesel locomotive should the driver prove to be uncooperative. Under a ruse he even hitched a short ride in a locomotive out of Euston station in order to   observe the operation of the controls. However, movement of the locomotive and mail coach was so vital to the success of the enterprise that the gangs elected, despite James's ardent disapproval, to bring in an elderly train driver hankering after a little adventure to do the job. James was undoubtedly unhappy in the gangs' choice of vehicles as well. Not Jaguars this time, but two old Land Rovers (only one of which was stolen) and an army surplus truck. The gangs also declined to exploit James's road racing talent. Due to the imposing bulk of the material they intended to steal and the impossibility of Ball providing assistance to James in any long distance getaway, the gangs decided to purchase a small farm house near the proposed site of the robbery to serve as a staging point. From here the caper would be launched, and here the money would be stashed until things settled down. At least James was spared the indignity of being given charge of the proposed transport away from the farm house for the money: a horse trailer.

The whole gambit was meticulously planned, and testament to the adage that if criminals would put half as much effort into legitimate work as they put into crime, they could be rich without the inconvenience of having to go to jail. The train was duly stopped by rigging the selected signal, which was located on an isolated stretch of track in Buckinghamshire. The fireman was abducted as he returned from the signal's disabled call box. The cab was stormed and  the driver bashed nearly to unconsciousness. James and another gang member decoupled the back end of the train on cue. The gangs' driver was unable to get the locomotive moving, as was the train's groggy driver, until enough vacuum developed, but this did not upset the schedule. The thieves smashed their way into the mail coach, then formed a bucket brigade to get the money bags moved from it to the army surplus truck. They were even disciplined enough to leave some money behind when their prearranged time limit had been reached. They convoyed back to the farmhouse as the sun was coming up. Roy James, in the most famous drive of his life, motored along with uncharacteristic sedateness at the wheel of a Land Rover. Bear in mind that this was August of 1963 and you realize that they got away with a staggering amount of money: 2.5 million pounds.

In complex undertakings people can make mistakes; and, as James could have attested to based on his motor racing experience, if they make mistakes where the risk factor is high the consequences can be severe. One of the robbers told the train crew to remain still for 30 minutes, clueing the police to the possibility that the gangs were hiding out near by. At the farm house some of the robbers occasionally forgot to wear their gloves, thereby leaving behind fingerprints. Others elected to paint the truck since it had been seen by one of the train's crewman. Paint drops and splotches wound up in assorted places including on the bottoms of shoes. Mail bags from which money had been removed were disposed of haphazardly

The thieves, spooked by radio reports that the police were scouring the general area, made an early, disorganized exit from the farmhouse, ultimately abandoning the horse trailer plan. James retrieved his personal Jaguar, made high speed runs between London and the farm house carrying money, and spent an entire working day at his garage in order to avoid arousing anyone's suspicion by an unexplained absence. He nevertheless found time to deliver 12,500 pounds of his own proceeds to Micky Ball's home.

When the Buckinghamshire police, acting on a neighbor's tip, discovered the farmhouse with its embarrassment of evidence, the game was up. Part of the gang members' problem was that, having made careers of crime, they were by no means strangers to the authorities. They fell like dominos. James decided he would turn himself in after the trials of those who were caught early, but on the night of December 3rd, 1963, the house where he was hiding was surrounded by scores of police. Calling on his experience as a cat burglar he tried a dash across the rooftops and a daring thirty foot leap to the ground, but to no avail. He, along with the most of the rest, received a 25 year sentence  for conspiracy and a 30 year sentence for armed robbery, to be served concurrently. In August of 1975 he became the first of the train robbers to be released on parole, only to discover that a friend who had been entrusted with his cut of the stolen money had spent it while James was in prison. His old friend Micky Ball had long since adopted a new name and prospered in legal business.

Roy James was probably the most intelligent of the train robbers, but it would seem that he took second place to no one in bad judgment. Once upon a time he shared the track on even terms with the likes of Brabham, Hulme and Stewart. What he might have accomplished in motor racing had he mapped the course of his life more carefully became only a "what if."