IN six years as Manchester City manager, Pep Guardiola has never been bitten on the backside by allowing a player to leave.
So the potential sale of Raheem Sterling to Chelsea may be the biggest gamble of his Etihad reign.
For a man who demands risk-taking from his players, the Catalan has been extremely cautious in allowing key players to hop it.
Usually those at the core of Guardiola’s plans only depart when their elite playing days are over — such as Sergio Aguero, David Silva, Vinny Kompany, Yaya Toure and Fernandinho.
Edging out Joe Hart was a bold early shout which worked out well. Leroy Sane and Ferran Torres were two decent players in their early twenties who wanted to leave.
But there has been nothing with the potential to sting Guardiola quite like flogging Sterling.
The forward is 27 years old, with an excellent fitness record. He is a four-time title-winner who was Footballer of the Year in 2019, and would have been Player of the Tournament at last summer’s Euros had England won the penalty shootout in the final.
He has scored 109 Premier League goals. Among players who are not out-and-out strikers, only Frank Lampard, Steven Gerrard, Mo Salah and Sadio Mane have more.
Sterling is an A-lister — thrilling dribbler, outspoken campaigner, MBE and razor salesman.
Yet he has been gradually squeezed out at City over two summers. First, by the £100million arrival of Jack Grealish, who, like Sterling, prefers to start wide-left.
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And now, after a season in which Sterling often operated as a ‘false nine’, by the signings of two elite, young centre-forwards in Erling Haaland of Norway and Argentina’s Julian Alvarez.
City’s attacking style will change with those additions and Sterling, along with new Arsenal signing Gabriel Jesus, look like the two to make way.
Talks over a new contract for Sterling stalled last season and City would rather sell for close to £60million, even to rivals Chelsea, than allow him to enter the final year of his existing deal.
Sterling got restless late in the 2020-21 season when he was benched for City’s Champions League quarter-finals and semi-finals.
During his outstanding Euros campaign, he suggested he was happier with England than City.
And last term, despite 23 Premier League starts and 13 goals, Sterling found himself on the bench for both legs of the Champions League semi-finals against Real Madrid.
For the title-clinching victory over Aston Villa, Sterling was not introduced until the 56th minute, whereafter he was instrumental in overturning a 2-0 deficit.
Yet still Guardiola doesn’t seem to fancy him enough.
A man as diligent as the Catalan won’t have been fooled by the idea that Sterling simply misses too many chances – an accusation not backed up by statistical comparisons with other elite forwards.
Gareth Southgate – England’s most successful boss since Alf Ramsey, however maligned he is right now – has always sworn by Sterling, despite several high-class wide options, and clearly prefers him to Grealish.
So there is an air of disbelief – even among some City players – that Sterling is being allowed to go.
There have been no denials about the widely-reported story that Sterling has already spoken to Chelsea boss Thomas Tuchel.
This would be an illegal ‘tap-up’ had City had any qualms about allowing Sterling to join the Blues.
The move is also risky for Sterling – not only because of the infamous racist abuse he suffered at Stamford Bridge three and half years ago.
Chelsea are a club in flux, the team’s defence and the club’s hierarchy are undergoing complete overhaul, with new owner Todd Boehly currently opting for a jack-of-all-trades role rarely seen since dear old Ron Noades was in his pomp.
With Romelu Lukaku gone, and unlikely to be replaced like-for-like, Sterling might find himself operating centrally as often as he was at City.
And having played for Liverpool and City, what is there left for Sterling to achieve in English domestic football? Why not a move abroad, with Real Madrid and Barcelona long-term admirers?
It would be an intriguing move for Sterling and an impressive statement of intent from Boehly.
But for Guardiola, that infamous ‘over-thinker’, this might be a rare case of not thinking carefully enough.
ROO TO BOSS IT
THERE is a trend towards great former Prem players getting decent managerial jobs now — Patrick Vieira, Steven Gerrard, Frank Lampard and Vinny Kompany among them.
This tendency didn’t exist a few years ago and it is good news for Wayne Rooney, as he completes his coaching qualifications ahead of a likely move into top-flight management.
I visited Pride Park on Good Friday, to see Derby beat champions-elect Fulham just days before their own drop into League One.
The spirit in a young Rams team — struck by a massive points deduction and frequent sale of senior players — as well as strong home support, hinted that Rooney had created something special amid adversity.
Those who never imagined Rooney as a successful boss tend to be those who never met him.
The all-time record scorer for England and Manchester United may become the first to prove himself a true great as both a Prem manager and player.
WEBB’S SO WISE
HOWARD WEBB is not just a former World Cup final referee.
He is an intelligent, forward-thinking, media-savvy man, whose imminent appointment as England’s refereeing chief is exactly what our men in black need.
Under Webb’s leadership, referees might even be allowed to speak regularly in public again.
And then we might even know what the hell is going on with VAR.
JACK IS SUPER
DESPITE all the gay abandon of England’s positive approach to batting, one of the most pleasing aspects of the series whitewash of New Zealand has been the emergence of Jack Leach as a true Test-class spinner.
Until this weekend, Leach was best known as the bloke wiping sweat from his spectacles and scoring one scrambled run during the extraordinary last-wicket stand with Ben Stokes which won the 2019 Ashes Test at Headingley.
Now, under the captaincy of Stokes, Leach is finally flourishing in his day job, with a ten-wicket haul in Leeds.
Three years ago, Leach was likened here as Clark Kent to Stokes’ Superman. But England’s skipper will soon be giving his old mate a pair of underpants to wear over his whites.
ICONS’ END OF AN ERA
THIS summer might be a last chance to see three all-time greats of British sport — Lewis Hamilton, Andy Murray and Jimmy Anderson.
After seven world titles and being robbed of a record eighth, Hamilton, 37, is struggling for motivation ahead of this weekend’s British Grand Prix at Silverstone.
And his once-supreme Mercedes now resembles a rusty ringer out of Exchange and Mart.
At 35, Murray — Britain’s finest tennis player since the Second World War — has a metal hip and may struggle to make it back to Wimbledon next year.
As for Anderson, the most prolific seam bowler in Test cricket history, well he will turn 40 next month.
I once made the mistake of kicking off an interview with Anderson by assuming the following winter’s tour of Australia would be his swansong — and that was five years ago.
So I’m not going to rule out the possibility of Anderson playing Test cricket at 50. Or headlining Glastonbury at 80…