But his scam was finally exposed by a ticket inspector and, in an out-of-court settlement, he paid Southeastern trains back the £42,550 in dodged fares and £450 legal cost within three days.
The cost of a standard-class single fare from Stonegate - where the average home cost half a million pounds - to London is £24.50 while an annual season ticket costs £4,548.
According to a report in the Sunday Times, the senior executive is believed to have travelled into London without buying any ticket and avoiding detection from 2008 until the end of last year.
He was able to get off his train at London Bridge and cross a platform to catch a service to Cannon Street - again avoiding having to go through any barriers.
At Cannon Street, he used an Oyster card to exit the barriers, paying the then maximum £7.20 fare incurred when a passenger taps out without having tapped in.
But on November 25 last year a ticket inspector standing next to the barriers spotted he had paid £7.20 and not the £2.30 for a single ticket.
After being challenged, the passenger later admitted to dodging the correct fare on five journeys between London Bridge and Cannon Street.
However, suspicious investigators for Southeastern discovered that the man had for a number of years up until 2008 been purchasing an annual ticket from Stonegate.
And within five days of being caught out at Cannon Street, the executive renewed his season ticket, leading Southeastern to believe he had been dodging the fare for his commute for five years.
Despite never admitting to this, the executive offered to settle the matter out of court and paid up within three days of being notified by the train operator the total owed in dodged tickets.
Southeastern, who has not named the man, said all passengers have the option to avoid prosecution and settle out of court.
The train company told the Sunday Times that the executive wanted to protect his identity because he was concerned about the impact it would have on his job.
A spokesperson added: "All customers have the option to settle out of court and in this case he chose to pay the settlement fee that we put to him.
"The customer wanted to protect his identity and did not admit to evading fares for five years at any point during the process."
However, critics have questioned why the fare dodging executive was allowed to escape being prosecuted and remain anonymous.
Manuel Cortes, leader of the TSSA rail union, said in the report: "It is not only extraordinary that the biggest fare dodger in railway history got away with it for so long, but has also now escaped criminal prosecution as well."
- Daily Mail
