However, Bertrand was used sparingly during his time at Chelsea before sealing a switch to Southampton in 2015, where he has since gone on to become one of the Premier League's finest left-backs.
And he says he needed to leave Chelsea in order to further his career, revealing he never truly felt the west Londoners' “full support”.
Recalling his move to Southampton from Chelsea in an interview with the Daily Mail, Bertrand said: “I wanted to feel like a footballer. I didn’t necessarily feel like a footballer at Chelsea.
“It was emotional in terms of Chelsea being the club I had been at since I was young and taken part in one of their most historic moments.
“There was the emotional attachment but from a football perspective it was a no-brainer [to leave].
“When I was there (Chelsea), whenever I did get the chance to play I never felt the full support to relax and enjoy my football.
“The times I did play it was like an audition. And that is never healthy.
“As a young player coming through you want the club to be stable enough to say, “We trust in you, go out there and play”.
“You don’t want to make a young player feel on edge. I wanted that consistency — and for people to judge you they need to see you consistently.
“Southampton has given me a fantastic base in being able to do that and progress.”
Bertrand was named in the PFA Team of the Year for the 2014-15 campaign after playing a key role in helping Southampton finish seventh.
He has also become a regular in the England national team setup since joining Southampton, scoring in the Three Lions' 4-0 victory over Malta earlier this month.