Fresh off a flight from London to Chicago, former Chelsea captain Gary Cahill sat down with FotMob to talk about his time at the club, the trophies he’s won, and the current crop of stars at Stamford Bridge.
By Alex Roberts
Gary Cahill was speaking in Chicago at The Famous CFC presented by Coors Light, the last stop of Chelsea FC’s international fan engagement events in the 2025/26 season. The Famous CFC gives Chelsea fans from across the globe the chance to meet up with fellow Blues and enjoy Q&As, quizzes, games, and the opportunity to take a picture with the Premier League trophy.
Now 40, Cahill saw and it all during his time in West London. Played under seven managers, won eight trophies, and inherited the captain’s armband from John Terry before leaving the club he grew to love back in 2019.
Let’s rewind a little, though. Cahill joined the Blues in January 2012, heading down the M6 from Bolton to put pen to paper on his first Chelsea contract. A few months later, he was playing in and winning a Champions League final.
“It was a crazy rollercoaster for me. I came mid-season to Chelsea, obviously given the opportunity, I jumped at it and came down,” Cahill said. it was a mental six months going on to win the FA Cup and Champions League.”
For the first half of the season, Cahill had been at Bolton, the club he had called home for four years. Chelsea were an entirely different ballgame though, and the centre-back learned that if he didn’t swim, he’d sink… quickly.
“I think the first thing that stood out for me going into the football club and the dressing room itself was that winning mentality, that kind of hunger to succeed and push yourself. I always said I went in as a bit of a sponge, to look at these players and see how they worked, what they did, and how they’ve won so many things.
“There were pure, world-class international players in the dressing room. Then, the football club in general has an expectation to do well. and win, and that was bred into the players. That was my first impressions of going to the club.”

It didn’t take long for him to adapt. Cahill would go on to play 45 or more games in his first three full seasons at Chelsea, establishing himself as key player for the club, all the while learning the ropes from the greatest captain the club had ever seen, John Terry.
Terry left Chelsea in the summer of 2017, signing for Aston Villa where he would play out the final season of his career. Under Antonio Conte, they had just become champions, and the dressing room was packed with quality and big personalities.
Eventually, Conte landed on Cahill as his next captain. It was obvious, really. “Yeah, big shoes to fill,” Cahill chuckled. “In my first season I didn’t need to be the leader because there was already loads of them there. I think it gave me the opportunity to learn, to go about my business a bit quieter.
“When you fast forward season after season, I felt like I grew into that role. I had a good upbringing in that sense. I was under the leadership of one of the best captains the clubs has ever had. So, to learn from him, and not just him, there were plenty of leaders in that dressing room, I felt ready for it.
John didn’t play as many games as he previously had, so I was captain on the pitch while he was still club captain. That little transition there gave me the opportunity to grow into the role. To the point where when I was given it, I was experienced enough. I just felt more rounded as a player and person.”
Cahill was the last Chelsea captain to lift the FA Cup. It’s a tournament that holds a special place in English football, the original, the best, there isn’t much like it nowadays. Getting your hands on that famous old trophy isn’t easy.
Eden Hazard scored from the penalty spot to bag a 1-0 win over Man United in the final. If we’re being honest, it wasn’t the best game, but Cahill didn’t care, he had won his second FA Cup since joining Chelsea.
I love the FA Cup,” he said. “Obviously, I’m an Englishman so I’ve been watching it since I’ve been at school. It’s a massive, massive competition and it was one of the proudest moments of my life, lifting the FA Cup as captain.
“We lost it the year before to Arsenal. These opportunities don’t always come by, you really never know if you’re going to get this opportunity again, and you need to have that mindset, I think.
“You can be nervous, have those butterflies and think ‘I need to respect the fact we’re in an FA Cup final. This may never come round again. It’s a great opportunity to go out and do something great.’”
Current captain Reece James had the opportunity to end Chelsea’s ‘Wembley curse’ on Saturday (May 16) as they lined up against Pep Guardiola’s Man City. Unfortunately for the Blues, Antoine Semenyo’s sublime backheel was enough to take the trophy up north.

That’s seven defeats in their last seven finals at the ground, four FA Cups and three League Cups. It’s a far cry from the all-conquering sides that Cahill was a part of, as well as the ones that came before him, even if some of those losses have been… controversial.
“It’s hard to put your finger on just one thing that’s gone wrong,” he said. I think it’s just a learning process for a young squad going through these moments and they’re developing all the time.
“But they need to make sure they learn from them. I use the example of myself as a player, when I lost that FA Cup final against Arsenal to then have that chance again the next year, I felt ‘This has to go our way.’
“Don’t keep reliving them but remember them, if that makes sense. We talk about this young squad, and they need to keep developing. Still, they need to grow, but to grow you have to go through good moments and bad moments.”
Cahill may have hung up boots, but his relationship with Chelsea didn’t end there. Nowadays, he’s a club ambassador, meeting fans, going to events, and helping those who may not get the chance to go watch their side week in and week out.
Chelsea are a global brand now, undeniably one of the biggest clubs in the world, and events like the one Cahill was at in Chicago have become a regular occurrence. Football is ultimately about community.
“We’re doing a famous CFC event at Joe’s Bar, which is great. There’ll be hundreds of Chelsea fans there. It’s incredible to now get the chance to go into these environments, because I obviously didn’t as a player.
“And it’s only growing, which is a great thing. Chelsea are huge around the world but I’ve certainly seen it (grow) over the last few years that I’ve been able to come here. I was here a couple of years ago as well it’s growing all the time so for us to put on these events it gives us a chance to connect with these fans.”
Regardless of the result against City, meeting a bonafide Chelsea legend, alongside a couple of cool, crisp Coors Lights, would have made it memorable. Of course, the recent Xabi Alonso announcement probably lightened the mood too.

(Images from Victoria McDonald / Chelsea Football Club, additional images via IMAGO)
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