But now the 28-year-old from Barnsley's life has changed for the better after he won £1million on the National Lottery.
The groundworker, who played for Sheffield United before recurring injuries saw him drop into non-League and eventually quit, has now spoken fully about the incredible circumstances of his jackpot win for the first time.
Mr Kennedy almost left the winning ticket in a shop and only bought it in a change from his usual habits because he forgot what day it was.
He and partner Kay Yoxall, 25, now plan to travel the world.
The couple regularly play Euromillions Lucky Dip on a Friday, but when they asked for their usual ticket, the shopkeeper pointed out it was actually a Saturday and they bought a Lotto Lucky Dip instead.
The tickey matched two numbers in the Lotto draw, entitling them a further free Lucky Dop - which Mr Kennedy claimed but then almost left on the counter before a shop assistant at the post office in Dunsville, Doncaster, called him back. This ticket matched the five main numbers and the bonus ball on November 10 - netting them £1million.
He checked the numbers in the lunch cabin during a break on the building site he was working on, and initially his father, who works with him, did not believe he had won.
His colleagues only believed him when he called the National Lottery to confirm his prize.
Mr Kennedy said: “I was confused at first and just couldn’t be sure it was a winner. Despite all the checks it isn’t until you hear on the phone that it is a £1m win that you really believe it. Making the call in front of my mates and colleagues was brilliant and I immediately took them to the pub for a celebratory pint.”
The couple had always discussed the plan if they won big on the National Lottery while at work. Miss Yoxall said, “When he called and said come home I still wasn’t sure. I could hear all the lads in the background and felt sure it was a wind up. My brother works with Terry and it was only when he Facetimed me that I could see it was true.”
They immediately escaped the wind and rain for a week in Tenerife, returning home to get their win paid out, before heading to Dublin for a long weekend. Plans are now afoot for the couple to, Covid permitting, travel the world.
Mr Kennedy said: “I don’t enjoy building sites during the winter so am planning to get away and see the world. Kay can take a break from work so we’d love to go across America, see Australia and also south east Asia. We already have New York booked for January. The ideal plan would be never to work a British winter again!”
The former footballer ended his professional career with Harrogate Town in 2018.