Ranking every Chelsea captain of the PL era from worst to best

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Chelsea captain John Terry lifts the Premier League trophy after the victory over Sunderland, May 2017.

Chelsea have had some legendary leaders during the Premier League era – and the majority of their captains have led the Blues to some sort of silverware.

Cesar Azpilicueta is the current wearer of the captain’s armband at Stamford Bridge and lifted the Champions League trophy in May 2021. But, unsurprisingly, that doesn’t make him the most decorated Chelsea leader over the past three decades.

We’ve ranked all six of them during the Premier League era from worst to best.

6. Andy Townsend

Townsend led Chelsea into their inaugural Premier League campaign but the side would only finish 11th in 1992-93.

To be fair, this was a different era – Stamford Bridge had a dog track running around the pitch, Ken Bates bestrode the club like a brick on top of a Victoria Sponge and they’d only been promoted to the top flight in 1989.

Townsend left for Aston Villa in the summer of 1993 and the former Republic of Ireland international helped his new team win the League Cup the following season. Presumably by parking his Tactics Truck on the goal line…

5. Gary Cahill

Cahill became Chelsea captain after John Terry left in the summer of 2017 – following a guard of honour that could well be carrying on now if Terry had his way.

They were league champions when the former Bolton defender took the captains armband but an underwhelming 2017-18 season saw manager Antonio Conte depart the club under something of a cloud.

Maurizio Sarri replaced Conte in 2018 but Chelsea would only finish third in the league after another inconsistent campaign.

But the modern-day iteration of Chelsea are trophy-hoarding monsters and Cahill led the side to the FA Cup and Europa League titles during his time as captain.

He left for Crystal Palace in 2019 and is now leading Bournemouth’s Championship promotion charge.

4. Cesar Azpilicueta

The current wearer of the armband has some way to go to match the achievement of some of his predecessors… but at least Azpilicueta lifted the Champions League trophy after starring in the final.

Azpilicueta performed brilliantly against Manchester City in the 2021 showpiece, keeping the Premier League winners at bay with consummate ease.

The long-serving defender has been a beacon of consistency since joining Chelsea in 2012, even if the club have enjoyed a number of highs and lows over the past decade.

His contract runs out this summer and the future of the Spain international remains uncertain – but there’s no doubting his place in the hearts of Chelsea supporters.

3. Dennis Wise

A club legend at Stamford Bridge, Wise spent 11 years at Chelsea and won two FA Cups, a League Cup and a UEFA Cup Winners’ Cup.

That trophy haul means that Wise is the club’s second most successful captain in their history – and all those honours were won pre-Abramovich, making them feel that bit more hard-won. 

When considering this alongside the midfielder’s commitment to the cause and underrated passing ability, then it’s no surprise that Wise’s standing at Chelsea remains so high.

2. Marcel Desailly

One of the greatest defenders of his generation, Desailly served Chelsea well during the period where they made the awkward transition from enigmatic entertainers to Premier League heavyweight.

He was jettisoned by Jose Mourinho in the summer of 2004 but the World Cup winner had already made himself an indelible part of Chelsea folklore.

Marcel Desailly points and shouts during a Chelsea away game against Aston Villa in February 2002.

READ: A tribute to Marcel Desailly, ‘the rock’ on which Chelsea built their success

1. John Terry

Captain, leader, legend. And the only possible choice to top this list.

Put simply, it’s impossible to imagine Chelsea enjoying their 21st-century success without Terry marshalling the troops and popping up with crucial headed goals.

It’s unlikely that Terry’s achievements will ever be topped at Chelsea – winning 16 major trophies as captain tends to set you apart from the field.


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