The 23-year-old midfielder was stuck between a rock and a hard place trying to force his way into the Stamford Bridge first team since breaking through their academy ranks in 2006.
Shipped out on loan far and wide, from Bournemouth to Burnley, the England Under-21 international has finally found home under Nigel Adkins' wing at St Mary's where he played every game of the Saints' promotion push last season.
And after making it into Stuart Pearce's Team GB squad for London 2012, the Carshalton-born star can hardly believe his luck.
"It's been a great season for me," said Cork. "It was a tough choice about what to do - whether to leave Chelsea or not and where would be the right place.
"But to have a successful season at Southampton and get promoted and then to top it off with an Olympic call was a great year and one I'll never forget.
"I'm really looking forward to the Games. I hope we can have a successful team - I don't think we'd be here to just be a part of the Games, we're here to achieve something as well. That's what the manager shares as well and hopefully we can do something good."
Things could have been so different for the versatile Cork as in March 2011, he suffered a heart scare while playing for Pearce's England Under-21 side against Iceland at Preston's Deepdale Stadium and was hospitalised.
A high heart rate resulted in an overnight stay but having seen the ramifications of Fabrice Muamba's cardiac arrest while playing for Bolton against Tottenham in March, Cork is counting his lucky stars that he is able to compete at all this summer.
"Things like that do bring it back to you about what a great opportunity you've got," he added. "You can't take anything for granted because you might not be here tomorrow. It does make you think how lucky you are to be involved in a set-up like this.
"I played for the Under-21s at Preston against Iceland and I don't know if it was viral thing, but I remember going through the first half and thinking my heart was beating so fast.
"I was asked if I could see it through to half-time, but I remember just aching. My heart rate wouldn't come down and I was having palpitations and had to go to hospital.
"I stayed overnight and eventually my heart-rate came down. It was a bit scary, but it's all sorted again. If it happens again, that's when you start to worry.
"Luckily for me, mine wasn't as nearly as bad as [Fabrice] Muamba's, but it was horrible to see what happened to him on the pitch and hearing everything about it. He's alright now though hopefully."
Cork has been with the squad for a week, training alongside the likes of Manchester United legend Ryan Giggs and the Southampton ace revealed the experience has been everything he expected.
"It has been immense," he added. "We have had a great week and it couldn't have gone any better really. We needed to train hard and gel as quickly as possible and we have done just that.
"It has been amazing, not just for me, but for everyone else as well."