Every captain in Chelsea F.C. history

Bentley, a forward, was the first captain for Chelsea. He took on the role starting with the 1953-54 season, but he had been with the club since 1948. Things panned out well immediately, as Chelsea won their first top-level title in the 1954-55 season. Bentley left the club after the 1955-56 season, though, but didn’t go far. He moved on to Fulham, where he played 142 league games, and then ended his playing career with QPR, who was a third-division team at the time.

Bentley left Chelsea as the aging core that had been at the center of the club started to dissipate. Armstrong was part of that core as well, having also started with Chelsea in 1946. The wing back played 402 league games for Chelsea, and he became captain after Bentley. However, after one season as captain he left as well. In fact, Armstrong decided to emigrate to New Zealand, where he lived out his days.

Saunders represented something akin to a youth movement at captain, as he hadn’t been with the team since, you know, the end of World War II. He joined Chelsea in 1953, the same time Bentley became the first captain. Saunders was one of two players to play in every game for the title-winning club. He took over as captain in 1957, but retired after the 1958-59 season, meaning he only had the role for two seasons. Saunders was only 31 when he retired.

Man, if you played for that 1954-55 title team at Chelsea and stuck around, you got to have your chance to play captain. Blunstone is the fourth member of that team to serve in the role. Playing the now-antiquated position of “outside left,” Blunstone left his hometown club Crewe Alexandra as a teenager to join Chelsea. Leading the club into a new decade, he took over as captain for the 1959-60 season, and stayed in the role until he retired at the end of the 1963-64 season. Blunstone would then get into coaching, and managed Brentford for a few seasons.

If you are not a Chelsea fan of a certain age, Venables is probably the first name you recognize. It’s not so much because of his play, though he did play in over 100 games with Chelsea, Spurs, and Queens Park Rangers. Venables was captain of Chelsea for two seasons, but a row with manager Tommy Docherty over breaking curfew immediately soured his relationship with the club and he left after the 1965-66 campaign. While he was a fine player, Venables is best remembered as a manager. In this role he would excel at Barcelona and Spurs, and would go on to manage England.

We promised stability at captain for Chelsea, and here is where that starts to prove itself. Players like Harris aren’t around much anymore. They called him “Chopper,” and he was an old-school “hard man.” The defender was popular with the Blues, though. He first appeared for the club in the 1961-62 season, and Harris took over as captain for the 1966-67 campaign. Harris served in that role until the 1979-80 season, even as the club bounced down into the second division a couple times. “Chopper” would make almost 700 appearances with Chelsea before he left the club, but that was for third-division Brentford, where he served as a coach as well as a player.

Replacing a legend like Harris was not going to be easy. Also, Chelsea was in the Second Division at the time. Droy, one of Harris’ defensive partners, got the nod. He was captain during the club's tenure in the Second Division. Droy helped get the club promoted at the end of the 1983-84 season. The next year, he was replaced as captain, loaned to Luton Town, and would move on to Crystal Palace in 1985.

Another defender, Pates, was considered more befitting a captain for a First Division club. In fact, he actually got the role during the 1983-84 season, taking over for Droy. The defender would stay in the role as the team returned to top-level football, and was captain through the 1987-88 season. After 346 appearances with Chelsea, he moved to Charlton Athletic, and he became a bit player for several seasons around English football.

Roberts’ greatest success came at Tottenham Hotspur, where he played over 200 league games as a defender. After that run, he went to Rangers, and then Chelsea, relegated to the Second Division, brought the veteran in to try and right the ship. The Blues slapped the armband on him, and Chelsea was promoted in his first season with the club. He stuck around for one more season before heading for West Brom. Roberts had a journeyman managerial career, including interesting stints with Pakistan and Nepal’s national teams.

Chelsea broke new ground by naming a non-English captain. Nicholas was Welsh! How continental! The defensive midfielder, who had 73 caps with Wales, was at the end of his career. For sake of perspective, Nicholas made his professional debut with Crystal Palace in 1976. He only served as Chelsea’s captain during the 1990-91 season, his last with the club. After retiring, Nicholas would manage a few teams in his native Wales.

Chelsea’s getting more international by the moment. Townsend played internationally for…Ireland! Townsend played 70 games for Ireland, but he was an interesting choice for a captain. The midfielder had a real journeyman career, making between 71 and 134 league appearances for five clubs. Townsend captained Chelsea for two of the three seasons he was there, but then he moved on to Aston Villa. You may have seen him on ITV or BT Sport in more recent times.

After being part of perhaps the last successful run for Wimbledon, Wise moved to Chelsea prior to the 1990-91 season. Thus began an iconic, successful run. While he would not take over as captain until 1993, when the Premier League had begun play, he would serve in that role until the end of the 2000-01 season. The central midfielder helped lead Chelsea to two FA Cups in that time. After his lengthy tenure with Chelsea, Wise would actually find a way to keep playing but have even more say in the club. He was a player-manager at Millwall, Southampton, and Swindon Town.

For the first time, Chelsea named a captain from mainland Europe. Desailly, while born in Ghana, played internationally for France. Quite a bit, in fact. That’ll happen when you are considered an all-timer at both centre back and defensive midfield. He joined Chelsea from vaunted AC Milan, and he helped usher in the modern era of Chelsea football. Desailly was captain from 2001 until 2004. At that point, he had lost a step and was done internationally. He basically retired, which is to say he went to play in Qatar.

The third of Chelsea’s three longtime captains, and the most successful of the bunch, Terry is in the running for the best centre back of his generation. Some consider him the best Englishman at that position of all time. It did take Terry a second to find his footing, and he even was briefly loaned to Nottingham Forest in 2000, which is funny in hindsight. Once he grabbed a spot in the starting lineup, though, he held it with gusto. Terry made 717 total appearances with Chelsea, and served as captain from 2004 until 2017.

Chelsea didn’t look far to replace Terry. They just looked to the guy standing next to him. Cahill, Chelsea’s other centre back, was tapped for the role. While he wasn’t quite on Terry’s level, Cahill got 61 caps with England and was quite good. He was captain for two seasons, but effectively only for one. Cahill was captain during the 2017-18 season, but then in 2018-19 Maurizio Sarri took over as manager, and he did not like Cahill. The Englishman was effectively relegated to the bench and left for Crystal Palace to continue his career.

While Cahill was still captain during the 2018-19 season, since he was usually on the bench, Azpilicueta was typically wearing the armband, since there has to be a captain on the pitch. That made him an easy choice to take over the role full-time for the 2019-20 season. The Spanish international would serve as captain when Chelsea won the 2020-21 Champions League, and he served the club quite well. After a decade with the club, Azpilicueta left on good terms after the 2022-23 season to head back to Spain, where he currently plays for Atletico Madrid.

Chelsea needed a new captain for the 2023-24 season, and once again it went with a defender. This time, it was James. Only 24, he’s already made 16 appearances for England, and over 100 Premier League appearances for Chelsea. Could he be the next long-term captain for the Blues? Well, given how erratic the club’s ownership has been, the odds are against it, but he has the talent, and youth, to make it happen.