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All-Time Premier League: Chelsea

The pick of the Pensioners

Our next stop is in the West End of London, where in 1904 Gus Mears purchased the Stamford Bridge Athletics Ground, with the intention of adding soccer to the programme. Having tried and failed to agree terms with Fulham, he decided to form a first-class club of his own – and he wanted to attain first-class status immediately. At the time, promotion to the Football League was won not automatically on the pitch but in an end-of-season election in which the worst teams in the League were pitted against promising non-League clubs. Such a system was obviously open to abuse, with little to stop the clubs forming a cartel, but Mears managed to circumvent that obstacle. He secured the signatures of several famous players, promising them that their registration would not be retained if he failed to win them election to the League. The League, whether impartially impressed or enticed by the gate money such stars would bring in, endorsed his club’s candidature. Thus, without a single season of play behind them, the “Pensioners” were in the big-time.

They have never lost their first-class status since. They have been signing star players ever since, from Fatty Foulke to Francesc Fabregas, and have developed a fair few of their own along the way. Yet their history, perhaps more than that of any other club in this collection, illustrates that star power alone is not enough - for in spite of their being able to boast of such players as Vivian Woodward, Alex Jackson, Hughie Gallacher and Tommy Lawton, it took them fifty years to win their first championship; and in spite of the efforts of Alan Hudson, Peter Osgood, Glenn Hoddle and Gianfranco Zola, it would be fifty more before they won a second. Constructing the best possible combination of all those who have called Stamford Bridge home is a tricky task, but here is my best attempt.

1. In goal, it’s not as tricky as it later becomes. As impressive as Vic Woodley’s 19 consecutive caps for England in the thirties are, and as awe-struck as I was in my primary school days by the spectacular saves of Carlo Cudicini, both are benched thanks to the enduring excellence of Peter Bonetti. Although he is most famous today for his errors in a World Cup quarter final in 1970, the fact that he was chosen to play when Gordon Banks fell ill speaks volumes about his ability. English football fans in general may remember him as the man who lost the World Cup; but those who watched him week after week remember him as “The Cat,” the man whose acrobatics in the Chelsea goalmouth were one of the great spectacles of soccer.

After coming up through the youth team, he made his first-team debut in 1960, and would remain the club’s first-choice goalkeeper for nineteen years. The team he entered was a struggling one, and in ’61-’62 Chelsea were relegated from the First Divison; but they spent only a solitary season in the Second, and, back in the First, they soon began challenging for cups and championships. In ’64-’65, they won the League Cup and made a run at a domestic treble, eventually finishing third in the First Division and losing to Liverpool in an FA Cup semi-final. Two years later, they went one better in the FA Cup, reaching the final.

Bonetti, with his agile saves and long one-handed throw-outs, was one of the biggest reasons for the team’s success; and when Chelsea finally did win the FA Cup in 1970, no player could have deserved it more. His performances throughout the season were good enough to make him the runner-up to Billy Bremner in the voting for the Footballer of the Year award. It was Bremner’s club, Leeds United, whom the Pensioners faced in the final. Almost single-handedly, he held them to a 2-2 draw in the first match with a series of saves. The replay has gone down as one of the dirtiest Cup Finals in history, and Bonetti did not escape the rough play. Injured in a challenge with Mick Jones, and targeted thereafter by the Leeds forwards, he held them off on one good leg, saving shots from Peter Lorimer and Terry Cooper as Chelsea won 2-1.

His lowest moment in football, the World Cup match against Germany, came that summer, but Bonetti bounced back, helping his team to the finals of two more cup competitions in the next two seasons. In 1971, they beat Real Madrid in Athens to win the European Cup Winners’ Cup, holding on to a half-time lead thanks to Bonetti’s superb second-half display. In 1972, they reached the League Cup Final again, only to lose to Stoke City. After the club suffered relegation in 1975, he left to join the North American Soccer League’s St. Louis Stars. The only man in the team to live up to the name, he helped the Stars to the semi-finals of the league’s championship play-offs; but he was back at the Bridge before long. He rejoined Chelsea after that solitary summer, and within two years had helped the club win back its place in the First Division. He retired in 1979, having made 729 first-class appearances for the club, a record for a goalkeeper, including 208 clean sheets. Petr Cech, who broke his shutout record in 2014, will make it a close contest when he becomes eligible; but for now, Bonetti stands above all competitors.

2. In 2005, as Chelsea Football Club celebrated its centenary, its supporters voted for their own greatest XI. With Paulo Ferreira, a European champion the year before at both club and international level, the incumbent on the right side of defence; and with memories of Dan Petrescu still fresh in the minds of many; the man who received the most votes was a Scotsman who won as many caps in his career as Ferreira had in one year.

Steve Clarke never had the wider reputation of Petrescu or Ferreira, but at Stamford Bridge he is known as one of the greatest defenders in Chelsea’s history. Whether in a three-man or four-man defence, whether as an overlapping wing-back or as a staying-put centre-back, Clarke, the Cesar Azpilicueta of the nineties, was a key player in Chelsea’s first team for eleven years.

Like Bonetti, Clarke joined a struggling Chelsea team; and like Bonetti, he got his reward in the end. Signed from St. Mirren in January 1987, he found himself fighting off relegation. In his first half-season, he helped the team to safety, and his performances were good enough to earn him a place in the Football League XI for its centenary match against the Rest of the World. The reprieve was short-lived, lasting only one season, but so was the spell in the Second Division that followed. For Clarke and the club, the successful promotion campaign would mark the beginning of a decade-long upward climb. As a raider whose runs forward provided plenty of goals for his colleagues, he helped his team back into the First Division at the first attempt, earning his first five international caps in the process, and to a fifth-place finish the following season. In ’93-’94, as Chelsea reached the FA Cup Final, his performances earned him the club’s Player of the Year award and a brief recall to his national team after a six-year absence.

As his age advanced, and as Petrescu arrived to compete for his place in the lineup, he became a more conservative kind of player, frequently moving into the middle. Under player-managers Ruud Gullit and Gianluca Vialli, the team built on the improvements made by Glenn Hoddle; and major honours came Clarke’s way at last. He had missed out on the Full Members’ Cup Final in 1990 and lost the FA Cup Final in 1994; but in 1997 and 1998 he earned winner’s medals at Wembley as Chelsea twice beat Middlesbrough to take the FA Cup and the League Cup respectively. His last game for the club, a 1-0 win over Stuttgart to win the Cup Winners’ Cup, was his greatest success of all.

One can see why the Chelsea fans voted for him; but if one goes back further into the archives, one finds a right-back who may have been even better. Little film footage exists of Peter Sillett playing; but if one is to believe his contemporaries, that fact is to be considered a loss to the game. Billy Wright considered Sillett his equal, and Stanley Matthews described him as the best full-back he ever played against. His clever positional play compensated for a lack of pace; and although full-backs in the fifties rarely got forward in free play, Sillett offered an attacking threat from deep positions. His captain, Roy Bentley, described him as one of the best passers of a ball he had seen, capable of hitting hundred-yard passes with pinpoint accuracy. With his fearsome long-range shot, he was deadly in dead-ball situations, and it has been said that opposing teams used to line up defensive walls when he took free-kicks as far as 40 yards from the goal. Exaggeration, perhaps; but there was certainly something to exaggerate. His 34 goals for Chelsea were a club record for a defender until surpassed by John Terry.

Playing for Chelsea between 1953 and 1961, Sillett made 260 top-division appearances for the club, two more than Clarke; and every major milestone in Clarke’s record has something analogous in his own, although he experienced them in the opposite order. Major club honours? Check. Sillett was part of Chelsea’s first championship-winning team in 1955, scoring six goals, including the penalty-kick against the Wolves that gave the Pensioners a decisive advantage. A short-lived spell in his national team? Check. His performances in the title-winning campaign earned him a call-up to the England team for a three-game tour of Western Europe. An all-star game? Check. Sillett was selected to play for Great Britain against the Rest of Europe. A continental final? Check. Playing for the London XI, he made it to the two-legged final of the first Inter-City Fairs Cup, although he didn’t play in the second game. Relegation? Check. After suffering a broken leg at the star of the ’61-’62 season, Sillett watched on as Ken Shellito replaced him and his team-mates fell into the Second Division.

So, who was better? Individually, Sillett might have the edge; but with this team using a four-man defence, strategic considerations favour Clarke. In Sillett’s time, the W-M formation was ubiquitous, and full-backs were something halfway between wing-backs and centre-backs. Although he probably could have played in a wider position, there is no need to guess about Clarke. More important is Clarke’s overlapping ability. With a narrow, albeit fluid, forward line, width from deeper positions is needed, and Clarke is the man to provide it.

3. On the left, width will not be a problem. Ashley Cole was once an Arsenal man through and through; but it was for Chelsea that he played the most – and, one could argue, the best. In 2006, when he left the club he had supported since childhood, he was already one of the world’s best left-sided defenders. He had played for England in three international tournaments, and been named in the Team of the Tournament after the second. He had been named in the PFA Team of the Year in three years, and in the UEFA Team of the Year in one. He had won the Premier League twice, the Community Shield twice and the FA Cup three times. Yet at Chelsea, one could argue that he became even better.

At Arsenal, his attacking abilities had been on full display. Under Jose Mourinho’s management, and subsequently under Avram Grant, he was restrained from advancing as frequently, but his positional play in defence developed further. He was one of the few defenders in the game capable of containing Cristiano Ronaldo; and when he did go forward, he had lost little if any of his attacking threat. He won the FA Cup four more times, giving him a record seven winner’s medals in the competition. In 2006-’07, he won the League Cup, with his new team beating his old. In 2009-’10, he scored a career-best four goals and won his second League and Cup double, along with another Community Shield. At the end of 2010, he was voted into the UEFA Team of the Year again; and in 2010-’11, he made it back into the PFA Team of the Year. He also won continental competitions, something he had never quite managed at Arsenal, with the European Champions’ League in 2011-’12 and the Europa League in 2012-’13.

With Arsenal: 228 games, 9 goals, 7 trophies, 5 all-star teams

With Chelsea: 338 games, 7 goals, 10 trophies, 2 all-star teams

It’s close, but for the purposes of this league, I’m counting him as a Chelsea player. That being decided, the question of who should defend the left wing for Chelsea’s all-time XI is not close at all, Eddie McCreadie and Graeme Le Saux being left some way behind. Sillett, capable of playing right-back or left-back, can substitute for Cole or Clarke as and when the need arises.

4. If he glances to his right on one of his runs forward, he’ll see a familiar face. Ken Armstrong, John Hollins, Ray Wilkins, Ruud Gullit, Dennis Wise, John Obi Mikel and (more recently) N’Golo Kante have all done credit to Chelsea in deep midfield positions; but only one Pensioner had a position named after him. Claude Makelele, correctly enough, claimed not to have invented anything, but such was his success as a defensive shield and deep-lying playmaker that he became synonymous with the role.

Perhaps he would have been understood better if he had worn a different shirt number, or if those who called it “the Makelele role” had read their history. If they had heard of Luisito Monti; Nestor Rossi; or Chelsea’s own Nils Middelboe, the Danish banker and amateur footballer who entertained Stamford Bridge between 1913 and 1922 but wouldn’t travel for away games; they would have known better. If anything, what he did was revive a role that English football had forgotten. He wore a right-half’s Number 4 shirt for Chelsea and a left-half’s Number 6 for France; but perhaps it is by splitting the difference that one can best appreciate his place in the game’s history. Jonathan Wilson has drawn parallels between Jose Mourinho’s 4-3-3 formation and Karl Rappan’s verrou, in which Makelele would have played the part of the attacking centre-half.

The French international served as the pivot of Mourinho’s team. Sitting at the base of a midfield triangle, he shielded his central defenders and provided the principal link between the backs and the forwards. Conserving his energy with his team in possession, he became a tireless runner when the opposing team had the ball, and was ideally positioned to break up attacks before starting them for his own side with an understated creativity. His short passes were unspectacular, but they were almost always the right passes.

Not everybody appreciated him. When Real Madrid sold him to Chelsea, Florentino Perez claimed that they wouldn’t miss him at all; but the record tells a different story. With Makelele, they had won six major honours in three years, including two Spanish championships and the European Champions’ League. Without him, and without having signed a suitable replacement, they lost their domestic dominance to Barcelona. Before Makelele’s arrival at Stamford Bridge, Chelsea had not won a League championship since 1955. With him, they won two in five years, along with an FA Cup, two League Cups and a Community Shield.

Coincidence? I don’t think so. Among all those contending for the Number 4 jersey, Makelele takes the prize – even though I’ve half a mind to make him Number 5.

5. But let us stick with what has become British tradition and give that number to a stopper.

As Bonetti battled on in that famously physical Cup Final replay, Ron Harris was in the thick of the fray. An inspirational captain and as tough a tackler as anyone on the pitch, Harris showed both sides of his game over the two matches. In the first, it was his quickly-taken free-kick that led to Tommy Hutchinson’s levelling goal; and in the replay, it was his tackle on Eddie Gray that reduced the Leeds outside-left to a spectator. Those two games were the most famous of 795 first-class appearances, still a club record, which Harris made in Chelsea colours between 1961 and 1980. He played in all 42 League matches in three separate seasons, and in at least 40 ten times. Primarily a central defender, he could play in almost any position; and in the days before squad numbers, he wore every number between 2 and 10 at least once. One could make a case for him at any defensive position, although he’d have to be careful about his tackling wherever one played him.

Another Harris, John, was also a tough tackler but, to judge by his record, a fairer one, earning just one caution in his Chelsea career compared to Ron’s 40. Loaned to Chelsea by Wolverhampton Wanderers during the Second World War, he signed on a permanent basis in September 1945, and remained at Stamford Bridge for eleven years. He played in 41 League games in each of the first three seasons after the competition resumed and 31 in ’54-’55; and his 14 goals in first-class competition equal the later Harris’ tally in 364 games – more than 400 fewer than Ron. He might well have been a better player than his later namesake, but besides mere statistics I can find little information about him. While he is sent to prove himself in the reserve team, Ron gets the start at centre-half.

6. John Terry was to more recent Chelsea teams what “Chopper” was to those of the sixties and seventies; and he was more successful. He, too, was a product of the club’s youth team who spent nineteen years in the first, making more than 700 appearances. He, too, was a whole-hearted defender, not above stepping beyond the bounds of the rules, whose dedication to the club’s cause won him an affection from his own supporters as strong as the distaste his aggressive tactics inspired in others. With fifteen first-class honours, he is the most successful captain the club’s history; but he and Harris are too similar to play together in this formation. With two attacking full-backs and the right-half holding the midfield, the left-half position needs a speedier, more skilful defender to cover for Harris; and the job goes to Terry’s old mentor, Marcel Desailly.

If this were a pan-European league instead of an exclusively English one, he’d have to play for Milan or Marseilles, but it isn’t. Signed in the same year that Terry broke into Chelsea’s first team, the two-time European Champions’ League winner and newly crowned World Cup winner taught Terry how to play his position on the left side of a central defensive pair. Nicknamed “The Rock,” Desailly had the strength, aerial ability and tactical intelligence which Terry would use to great effect. In addition, he was faster than Terry, and at least as skilled on the ball. Sweeping up alongside first Frank Leboeuf and then William Gallas, he secured the defence with his pace, positional play and expert organisation. He cut out danger before it appeared, and once he had the ball, he almost invariably used it constructively, starting attacks with his passes and occasionally finishing them with well-timed runs forward. He won only one major honour with Chelsea, leaving the club the summer before the championship-winning season of 2004-’05, but he is still one of the club’s greatest ever defenders. When it celebrated its centenary, its supporters voted both Terry and Desailly into their all-time greatest XI. But both Terry and Desailly were at their best on the left side, and in this team, I must choose between them. Individually, Terry might have the better case; but Desailly’s pace makes him the better partner for Harris, and his ability to advance into the midfield will add an extra dimension to the attack that a second stopper will not. When he does advance, Harris and Cole can cover for him; and when Cole advances, Desailly can do likewise.

7. Terry did not in fact wear any shirt number between 1 and 11 for Chelsea, although he did on several occasions for England. Instead, playing in the modern age of pre-assigned squad numbers, he chose to be given the Number 26. Why? So that in the dressing room he could sit next to Number 25.

Gianfranco Zola had arrived at Chelsea’s training ground in November 1996, and had impressed his new colleagues before he had kicked a ball competitively. Upon his arrival, they had held a free-kick competition between Dennis Wise, their club captain and designated dead-ball specialist, and the new playmaker signed from Parma, who had been hailed in Naples as the heir to Diego Maradona – by Maradona himself. A sock was hung from the crossbar and each man challenged to hit it. Wise managed in once in ten attempts, Zola in all ten.

The rest of England would soon be equally impressed, as he inspired his team to the FA Cup; and although he had arrived midway through the season, the FWA voted him its Footballer of the Year, his three-fifths of a season judged to be more valuable than a whole season from anyone else.

“A clever little so-and-so” was Alex Ferguson’s assessment after Chelsea’s new signing had danced his way through the Manchester United defence, and in subsequent encounters Ferguson would accord him football’s highest form of respect: Zola was the only opponent whom his team would habitually man-mark, although even that was no guarantee of success. Other teams would start to do the same, but the Italian international would not be foiled by such tactics. He had, after all, come from the home of catenaccio; and compared with the sophisticated sweeper systems of Serie A, the rigid 4-4-2 formations of the Premier League’s early years were to Zola as a Caesar Shift cipher to Alan Turing. If a central defender marked him, he would drop deep, or drift out to the wing to pull him out of position, before twisting his way past him as he turned back towards the goal. If a wide defender took the job, he would play inside, forcing his marker to leave the flank unattended and freeing up space for a cross. For six and a half seasons at Stamford Bridge, he was the principal creative force in a team which won six major honours, his repertoire of tricks earning him the nickname of “Magic Box.” In 312 games for Chelsea, he scored 80 goals, including the winner in the Cup Winners’ Cup final of 1998, and created chances for several more. He was voted the club’s Player of the Year twice, and its greatest-ever player in his last season at Stamford Bridge.

No Chelsea player has worn his Number 25 jersey since. Here, I’ve given him the Number 7, although the position it indicates is very much relative rather than absolute. He’ll have to do his fair share of defending in that position, but I don’t expect him to stay on the wing. He’ll play all over the park, interchanging with his fellow forwards as he and they see fit. The numbers are only numbers; and on each side of the attack, it should be difficult to discern which is the inside man and which is the outside. In combination with their overlapping full-backs, they’ll create the width they need with their movement.

8. Orchestrating that movement from the midfield is a man who knew as much as anyone about playing a roaming role. In November 1953, Chelsea manager Ted Drake took forty of his players to Wembley to watch the Hungarian national team inflict on England her first defeat to continental opposition on home soil. Whether or not Roy Bentley was among them, I do not know; but subsequent developments suggest that the Bristol-born playmaker-cum-striker had been taking notes. At a time when the typical British defender was accustomed to identifying the man he was marking by his position as printed in the match programme, or by the number on the back of his shirt, England’s stopper centre-half Harry Johnston found himself flummoxed by the positional play of Hungary’s deep centre-forward, Nandor Hidegkuti.

By then, Bentley was one of the best forwards in football, but he wasn’t too good to learn. Since being bought from Newcastle United in 1948, he had won international caps of his own at all three inside-forward positions, and at club level had proved himself capable of playing on the wing as well. But, copying Hidegkuti, he became better still, beginning to befuddle Football League half-backs as completely as Hidegkuti had perplexed Johnston. He destroyed defences designed for a W-M formation with his movements, meandering into the midfield or wandering out to the wing to pull them apart, then finding his fellow forwards, who filled the spaces he created, with well-placed passes, or dashing forward into a striker’s position to score himself. He finished the ’53-’54 season with 21 League goals, matching his personal best. In ’54-’55, his first full season in the Hidegkuti role, he went one better with 22 as Chelsea won the championship. He also won his final four international caps, all at inside-right, scoring three goals in a 3-2 win against Wales and one in each of his last three, which included a 3-1 win over West Germany’s World Champions. He left Chelsea in 1956 as the club’s all-time leading goal-scorer, with 150 scored in 367 games for the Pensioners, along with 9 goals in 12 for the England XI.

He won’t play centre-forward for this team, at least not officially, but never mind. In order to accommodate others, I’ve brought him back to his original inside-right position, relegating the hard-running Michael Essien to the status of substitute. Whatever the number on his back, he was a great player -a precise passer, a sharp shooter, and an excellent exploiter of space- and he is one of those who simply have to be included in a team such as this.

9. Even with Bentley positioned elsewhere, and with Vivian Woodward and Hughie Gallacher spoken for by Tottenham Hotspur and Newcastle United respectively, the task of selecting a centre-forward is enough to give one a headache. Peter Osgood, Kerry Dixon and Jimmy Hasselbaink all added lustre to Chelsea’s Number 9 shirt; Didier Drogba, wearing the squad number 15 or 11 but playing in a central striker’s position, may have been the greatest centre-forward the Pensioners ever had; and George Hildson, George Mills and Jack Cock all earned star status at Stamford Bridge before players were numbered at all. But I’ve decided to give this number to a different type of player.

With all the midfielders and strikers I’m attempting to accommodate, there’s space for only one true wing-forward. Ideally, we need one who can play on either side, and drop back into midfield if needed. Left-wingers Florent Malouda, Frank Blunstone and Bobby Tambling; and right-wingers Pat Nevin and Peter Brabrook; can consider themselves out of luck. With Willian, Eden Hazard, Arjen Robben, Salomon Kalou and Juan Mata still playing for other clubs, the job is contested by Joe Cole and Charlie Cooke, whose records set side by side suggest kindred spirits separated by time.

Both Cole and Cooke started their careers at other clubs, Cole at West Ham United and Cooke at Aberdeen and Dundee; both enjoying the greatest successes of their careers at Chelsea – Cooke over two spells spanning eleven years from 1966 to 1978, with a single season’s worth of games for Crystal Palace sandwiched in the middle, and Cole in one seven-year stretch from 2003 to 2010; and both ended up playing in their era’s incarnation of the North American Soccer League. In terms of playing style, they were equally similar. Each was more of a provider than a goal-scorer, Cooke netting 30 goals in 373 first-class games for the Pensioners, Cole scoring 39 in 282; and each was a tricky, versatile playmaker, capable of playing on either wing or in the middle. Cole’s Transfermarkt profile shows two roughly equally-sized spots, indicating playing time, at outside-right and outside-left, and a larger one in the centre. On the same website, Cooke is listed simply as a right-winger, but his shirt number history shows him to have played every position in the forward line, plus right-half. On team honours and international caps, Cole has the edge (7 to 2 and 46 to 14 respectively, counting only those won as a Chelsea player); although Cooke, playing in a less successful period for the club, was voted the Pensioners’ Player of the Year twice to Cole’s once. Nevertheless, I’ve decided to go with Cooke, his slightly greater versatility and significantly greater longevity outweighing Cole’s superior goal-scoring record and heavier collection of caps and medals.

Between 7 and 11, it would make as much sense to assign him one number as any other, and I’ve decided to give him the middlemost. No, centre-forward won’t be his usual position. Indeed, it will be the one position in the front five in which he will hardly ever find himself. But it will be his average position, more or less, as he moves from one wing to the other, attacking whichever looks the most vulnerable in the moment, in something approximating a lop-sided 4-3-3 formation. If he does this, the Intermediate Value Theorem means that he will have to occupy the position at some point in his wanderings, however briefly. With the centre-forward attacking down one side, the full-back on the other side can get forward to provide width on the other.

10. The centre-forward spot vacated by Cooke can be filled by wing-forwards playing narrow or by deeper-playing inside-forwards advancing through the middle. Roy Bentley will do that job from inside-right, Frank Lampard Jr from inside-left. Intelligent, industrious, and defensively disciplined, Lampard was a multi-functional midfield man, effective in withdrawn or in advanced positions, and as capable of winning the ball to start attacks as he was of finishing them, but it is his achievements as a goal-scorer that most strikingly set him apart from the competition.

John Giles’ description of him as a striker playing in a midfield position perhaps underestimates his all-around ability, but his statistical record is one of which most strikers would have been proud. Between his being singed from his father’s club, West Ham United, in 2001 and his transfer to New York City in 2014, he racked up a club record 212 goals for Chelsea in 648 games. His late runs into the penalty box, his laser-like long-range shooting and his expertise in dead-ball situations brought him more than ten in ten consecutive seasons from 2003 to 2013, including a five-year run from 2005 to 2010 in which he scored at least twenty in each campaign.

That run was preceded by a 2004-’05 season in which he scored 19 and led the Premier League in assists, including both goals in the 2-0 win against Bolton that clinched the club’s second league championship. It had been Jose Mourinho’s first season in charge of Chelsea, and during the pre-season the Portuguese coach had told his new inside-left “you’re the best player in the world, but you have to prove it by winning trophies.” Lampard, whose only major honour up to that point had been the 1999 Intertoto Cup, appeared to have taken his manager’s words to heart. He would go on to win thirteen over the next nine years, including three Premier League Championships, four FA Cups, and a European Champions’ League. Although the world of football at large never did agree with Mourinho’s assessment of him, 2005 saw him voted the world’s second-best player by the international sporting press, and into the inaugural World XI by his fellow players, while the Premier League and the FWA each named him the best player in England. He was named the FA Cup’s best player in 2007, 2009 and 2010; and the League Cup’s best in 2005 and 2007, all five awards coming after cup-winning campaigns.

One could argue that Alan Hudson was marginally more creative, but Lampard’s greater goal threat and longevity outweigh whatever advantages Hudson may have in that department. Lampard, who led the Premier League in assists three times himself, made more than three times as many appearances in the club’s colours, including all 38 Premier League matches in three consecutive seasons from 2002 to 2005, and scored more than fifteen times as many goals. He may not have been a success as manager; but with Zola at outside-right, Bentley at inside-right, and Jimmy Greaves counted as a Tottenham player, he takes the inside-left position in Chelsea’s all-time XI without serious competition.

11. Ahead of him on the left side of the attack is the team’s principal striker. For him, as for Zola on the right, outside-left is a relative term in this team’s total-football-type system. You may have inferred, from the fact I’ve given him Number 11, that I’ve picked a striker who wore that number at some point in his Chelsea career, and you’d be right. Three men who fit the description stand above the competition, and choosing between them is not easy.

Didier Drogba was given the Number 11 in 2005, after one season wearing the Number 15. He had not yet done enough to be voted into the club’s Centenary XI; but seven years later a poll conducted in Chelsea Magazine would have him voted its greatest ever player. By that time, he had won eleven major honours with the Pensioners and established a reputation as one of the best big-game players in soccer. A poacher in the penalty box and a long-range sniper outside it, he had scored 100 goals in 226 Premier League games, winning two Golden Boots. He had scored nine goals in nine cup finals, including at least one in each of his four FA Cup finals and three League Cup finals. In the 2012 European Champions’ League final, he had headed home a late leveller before scoring the decisive penalty-kick in the shoot-out that followed.

When his contract ran out that summer, it looked as though that final would be his last game for Chelsea. He spent the next two years in the Chinese and Turkish leagues, before Jose Mourinho brought him back to Stamford Bridge for one more season. In 2014-’15, he wasn’t the same frightening force he had been, but he played his part in another successful campaign, scoring 7 goals in 40 first-class games as the Pensioners won the Premier League and the League Cup again. His nine years in Chelsea blue brought him 164, the fourth-highest tally in the club’s history, from 381, along with 71 assists.

Drogba was unquestionably a great striker, and his hold-up play made him perfect for the two-wingers-one-striker systems in which he played; but he is not quite what this team needs. While I don’t expect the Number 11 to stay on the left wing, he still needs to be able to play there when needed. Drogba, in spite of his shirt number, offered little in the way of wing-play, or positional flexibility in general. For that, we’ll have to go back to the sixties and seventies – to two men who, in their careers at the club combined, won less than a quarter as many trophies as Drogba and played in only half as many finals; but who in their limited opportunities showed the same knack for scoring in big games.

Bobby Tambling, a winger-cum-striker who played at inside-right, inside-left, and outside-left, was not only a more versatile player than the Ivorian international but an even more prolific goal-scorer. His 202 goals in 370 games for the club, played between 1959 and 1970, not only beat Bentley’s previous record but remained a record of their own until Lampard surpassed him in 2013; and although some of those were scored in the Second Division, Tambling still comes out ahead in comparison if one limits oneself to top-division League matches, with 129 in 262 to Drogba’s 104 in 254. He was Chelsea’s leading scorer for five successive seasons in the sixties, scoring 35 in ’62-’63, as he became the youngest captain to lead a team to promotion in the history of English football. He scored four goals in the team’s last match of that season, a 7-0 win over Portsmouth that saw the Pensioners promoted on goal average. In September 1966, he went one better by scoring five, still a joint club record, in a 6-2 defeat of Aston Villa. He played and scored in the final of the 1965 League Cup, the only first-class club honour he ever won, and scored again in a losing effort in the 1967 FA Cup Final. He missed both games of the 1970 FA Cup Final, however, having played in only seven matches that season, before being transferred to Crystal Palace.

The emergence of younger strikers had seen Tambling eased out of the first XI, and his torch had been picked up by Peter Osgood. Osgood, born in Berkshire, had signed for Chelsea in February 1964, the month in which he turned seventeen, and had become a sensation with 30 goals in his first 20 games for the reserve team. He was handed his first-team debut in the League Cup in December and scored both goals in a 2-0 win against Workington.

Although he missed out on the final of that competition, and indeed did not make another appearance in the first team for the rest of the ’64-’65 season, ’65-’66 saw him cement his place. He got another chance in an Inter-City Fairs Cup match against AS Roma, a game so violent that it would become known as “the Battle of the Bridge.” Chelsea won 4-1, and Osgood emerged from the ordeal with his account in the manager’s mind in credit. He kept his place in the first team for the rest of the season, and finished the campaign with 11 goals in 48 matches. Four of those goals had come in four consecutive matches in January, each of which was decided by the odd goal in three. Like Tambling, he was a superb dribbler as well as an excellent shot, and one mazy run in the second of those matches, a televised cup-tie against Liverpool, prompted commentator Kenneth Wolstenholme to compare him with David Jack. In his next match, against Burnley, he scored after a sixty-yard dribble. “Osgood is good” was the cry from the Shed End, and Alf Ramsey agreed. The England manager picked him for his provisional 40-man squad ahead of the World Cup that summer, although he failed to make the final cut.

Four years later, after scoring 31 goals in the ’69-’70 season, including at least one in every round of the FA Cup from his team’s entry, he did. In February, he had finally been handed his first international cap; and after the season ended, Alf Ramsey took him to Mexico, although he found his playing time at the tournament limited to two appearances as a substitute. In each of the following two seasons, he again reached cup finals with Chelsea, scoring in both of them. He scored in both games as the 1971 European Cup Winners’ Cup Final went to a replay, in which the Blues beat Real Madrid 2-1, and in the 1972 League Cup Final as Stoke City won by the same score. He didn’t reach a final in ’72-’73, but did score 17 goals, including one that won the Match of the Day Goal of the Season award. In ’73-’74, over the protests of his club’s supporters, he was sold to Southampton, where he would win the FA Cup again in 1976.

He spent almost five years playing in the lower divisions, for Southampton and Norwich City, and for the North American Soccer League’s Philadelphia Fury, before returning to Stamford Bridge in December 1978 season, as Drogba would do decades later. Like Drogba’s, his comeback lasted a year, although it was considerably less successful. He played in ten games, scoring two goals, in the second half of the ’78-’79 season, in an ill-fated attempt to rescue the Pensioners from relegation, and in ’79-’80 he made only one appearance before retiring halfway through.

By the end, he had scored 150 goals for Chelsea, tying Roy Bentley’s tally, in 380 games. His goals-per-game ratio is slightly lower than Drogba’s, and significantly lower than Tambling’s, but at least some of that difference can be explained by the greater number of games he played in deeper positions. Whereas Drogba was almost exclusively a centre-forward, and Tambling was an inside-forward or outside-left, Osgood’s career in Chelsea blue saw him play not only every forward position except inside-right, but both wing-half positions as well. In ’68-’69, he managed to score 13 goals while playing predominantly as a right-half. Tambling and Drogba may have been better goal-scorers, just about, but Osgood’s ability to move around the pitch makes him the better fit for a team playing something akin to Total Football. The formation may be described loosely as a lopsided 4-3-3; but it’s a very fluid 4-3-3, capable of turning into almost anything from the classical 2-3-5 to a more modern 3-5-2. With Cole and Clarke taking turns to attack down the flanks, and Harris and Desailly capable of moving into midfield, this team could be said to have four defenders or none at all; and with Cooke switching wings, Osgood and Zola cutting infield and falling back, and Lampard and Bentley breaking into scoring positions at every opportunity, the distinction between midfielders and attackers among the front five is equally difficult. As much as anything else, it depends on your point of view.

Who should be trusted to turn this mishmash of multifunctional players into a team, and bring about the order underlying the apparent chaos? Carlo Ancelotti, Antonio Conte and Jose Mourinho are all still active at other clubs and therefore ineligible for this league; while Ted Drake the manager is rendered unavailable by Ted Drake the player, a backup striker in the Arsenal squad. With none of Chelsea’s four championship-winning managers available, we must turn instead to one of the club’s many cup-winners.

Roberto Di Matteo won the FA Cup and the European Champions’ League in 2012, but lasted only eight months in the manager’s job. Player-manager Ruud Gullit, who led Di Matteo and company to the FA Cup in 1997 with his “sexy football,” would be a good fit for these players; and his successor, Gianluca Vialli, won both domestic and continental honours in a similar style; but their spells in charge of Chelsea, like Di Matteo’s, were as short-lived as they were successful. For a combination of success and longevity, only two candidates are left.

Tommy Docherty, at first another player-manager, suffered relegation in his first full season in the job, but brought the club back into the First Division at the first attempt and spent the next four seasons challenging for cups and championships with a highly creative team, winning the League Cup in 1965 and reaching the FA Cup Final in 1967. Dave Sexton, who succeeded Docherty, also reached the finals of both domestic cup competitions, winning one and losing the other, and in addition won the European Cup Winners’ Cup in between. Neither manager, it could be claimed, achieved all he could with his team, and each found himself undone at a critical juncture by a falling-out with several of his own players; but in this they were no worse than Vialli, their closest competitor for the job. Choosing between them is close; but I’ve gone for Sexton, whose record is slightly superior. Docherty lasted approximately five and a half seasons in charge, reached two major finals and won one. Sexton, with several of the same players, won two out of three major finals in about seven years, and was never relegated. In ’74-’75, after he had been sacked two months into the season, the Pensioners were.

Next: Everton

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Robert Gregory
Robert Gregory
Read next: The Spanish Connection
Robert Gregory

Directionless nerd with a first class degree in Criminology and Economics and no clear idea of what to do with it.

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