Chelsea has had several exceptional leaders during the Premier League era, with the majority of them guiding the Blues to a trophy or two.
Cesar Azpilicueta is the current captain of Chelsea, and he won the Champions League in May 2021. He isn’t, however, the most decorated Chelsea manager in the previous three decades, which is unsurprising.
During the Premier League period, we ranked all six of them from worst to best.
6. Andy Townsend
Townsend led Chelsea to their first Premier League campaign in 1992-93, but only finished in 11th place.
To be fair, this was a different era: Stamford Bridge had a dog track around the pitch, Ken Bates ruled the club like a brick on top of a Victoria Sponge, and they’d only recently been promoted to the Premier League.
In the summer of 1993, Townsend joined Aston Villa, and the former Republic of Ireland international helped his new side win the League Cup the following season. By putting his Tactics Truck on the goal line, of course…
5. Gary Cahill
After John Terry left Chelsea in the summer of 2017, Cahill took over as captain, following a guard of honour that Terry could well be continuing today if he had his way.
When the former Bolton defender took over as captain, they were league winners, but manager Antonio Conte left the club in disarray following a disappointing 2017-18 season.
Maurizio Sarri replaced Conte in 2018, but Chelsea finished third in the league after another poor season.
Chelsea’s present iteration, on the other hand, is a trophy-laden monster, with Cahill leading the side to FA Cup and Europa League victories during his time as captain.
He went to Crystal Palace in 2019 and is now in charge of Bournemouth’s Championship promotion push.
4. Cesar Azpilicueta
The current armband bearer has a long way to go to match some of his predecessors’ achievements… Azpilicueta was able to win the Champions League after impressing in the final.
Azpilicueta shined against Manchester City in the 2021 final, putting the Premier League champions at bay with ease.
Despite the club’s ups and downs over the previous decade, the long-serving defender has been a rock of stability since joining Chelsea in 2012.
The Spain international’s contract expires this summer, and his future is uncertain, but there’s no disputing his place in Chelsea supporters’ hearts.
3. Dennis Wise
Wise played for Chelsea for 11 years, winning two FA Cups, a League Cup, and a UEFA Cup Winners’ Cup.
Wise is the club’s second-most successful captain, and all of those championships came before Abramovich, making them all the more difficult.
When you consider this, as well as the midfielder’s commitment to the cause and unappreciated passing ability, it’s no surprise that Wise’s stock at Chelsea continues to rise.
Chelsea legend Dennis Wise became a Blue on this day in 1990! pic.twitter.com/dSBN7y7aEa
— Chelsea FC (@ChelseaFC) July 3, 2017
2. Marcel Desailly
Desailly, one of the best defenders of his time, played a key role in Chelsea’s awkward transformation from mysterious entertainers to Premier League giants.
Although he was released by Jose Mourinho in the summer of 2004, the World Cup winner had already sealed his place in Chelsea legend.
1. John Terry
Captain, leader, and legendary figure all rolled into one. And the only option to be in #1 on this list.
Simply stated, without Terry leading the charge and scoring crucial headed goals, Chelsea’s 21st-century success would be difficult to imagine.
Terry’s achievements at Chelsea are unlikely to be replicated – winning 16 major trophies while captaining a team separates you from the pack.