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Daily Football Briefing: Which club has had the worst transfer window in the Premier League era? 31 Aug 2021
It's the final day in one of the most remarkable transfer windows in history, which has seen Lionel Messi leave Barcelona for free, Harry Kane decide to remain at Tottenham following speculation he would move to Manchester City, Cristiano Ronaldo go back to Manchester United and Romelu Lukaku rejoin Chelsea for a cool £95m.But sometimes the top talent is not available — and clubs have to make do with what they can get.
Sometimes it can go badly wrong.Let The Athletic take you through some of the worst transfer windows we have seen in a — by no means exhaustive — list that will remind you of some shocking sales...(Surprise Surprise - who is the only manager they put in the pic!)
Manchester City will be fine without a new striker, but not signing one should still be deemed a failure

For those Manchester City supporters who lived through the bad times, of all that misery and all those relegations, there will be something laughable about the handwringing of recent days.
Missing out on England captain Harry Kane and five-times Ballon d’Or winner Cristiano Ronaldo? Talk about first-world problems. Imagine proposing such a “crisis” to those supporters back in 1998-99, when they lost to Lincoln City, Wycombe Wanderers and York City in the third tier before making it through the play-offs in nerve-shredding fashion, or even in 2006-07, when their last Premier League goal at the Etihad Stadium came on New Year’s Day.
They have scored ten times in their first two Premier League home games of this season. That’s as many as they scored at home in the whole of that miserable 2006-07 campaign (Georgios Samaras four, Joey Barton three, Bernardo Corradi two, Richard Dunne one). They have broken the British transfer record to sign Jack Grealish for £100 million, they are the bookmakers’ favourites to win what would be their fourth Premier League title in five seasons and second-favourites to win the Champions League. So, no centre-forward incoming? First-world problem.
But it is a problem nonetheless. If it wasn’t, Manchester City would not even have entertained the idea of signing a 36-year-old Ronaldo. The case for signing him, which was discussed extensively by Pep Guardiola and those above him, was based on a degree of desperation after accepting defeat in their efforts to wrench Kane from Tottenham Hotspur. And whether the truth is that they walked away from Ronaldo out of resignation once Manchester United showed up (“Never fancied him anyway”) or out of a sensible, cold-headed analysis of the pros and cons of such a deal, or somewhere in-between, the factors behind that desperation are still there. But it is a problem nonetheless. If it wasn’t, Manchester City would not even have entertained the idea of signing a 36-year-old Ronaldo.
“We can’t replace him. We cannot,” Guardiola said, fighting back the tears when he spoke to Sky Sports on the pitch among the ticker-tape and the celebrations at the end of last season. He was talking about Sergio Aguero, who was saying his goodbyes after a glorious decade in Manchester. Aguero’s father Leonel later accused Guardiola of lacking sincerity, but the emotions appeared genuine.
Guardiola was talking about the loss of Aguero the personality, Aguero the icon, Aguero the club’s all-time record goalscorer. But in purely technical terms, the Aguero of last season (559 minutes and four goals in the Premier League, increasingly troubled by injury as he approached his 33rd birthday in June) appeared entirely replaceable.
City have had years to prepare for the Aguero succession. This is a club where, behind the scenes at the City Football Academy, there is a constant, established, clear emphasis on long-term strategy. They had been planning for years in the expectation that Aguero would depart — or at very least would need to be replaced — when his contract expired in the summer of 2021. And yet, for a variety of reasons, they appear to be on the verge of drawing a blank.
Make no mistake. There are very few centre-forwards in world football who would measure up to the standards that Guardiola demands — not just in terms of goalscoring but in terms of linking play and, significantly, commitment to the type of pressing game that didn’t come naturally to Aguero. Guardiola felt Kane was the stand-out candidate. That he found himself opening up to the idea of signing Ronaldo, whose presses far less than Kane, Lionel Messi, Aguero and just about any centre-forward you could think of, speaks volumes.
The feeling persists that Ronaldo would not have been the right player for City. Yes, he would have guaranteed goals, as well as bringing Champions League-winning experience, but the trade-off would have been far greater than across Manchester at United, where the playing identity is less defined. (And again, imagine writing those words in previous decades.)
Then there was the wages issue.
Sources at the Etihad flagged concerns about that even while optimism about a deal for Ronaldo was growing on Wednesday and Thursday of last week. Like any club, City have a wage hierarchy, with Kevin De Bruyne at the top of it, but there are good reasons why they have tended to steer away from signing established, A-list stars since the early days of Sheikh Mansour’s ownership more than a decade ago. Kane would have represented a move away from that principle too, but he was a long-established target. Ronaldo would have represented a panic deal, a shotgun marriage of convenience. For both parties equally, it might be said.
Whatever the consequences of his return to Old Trafford (a first title challenge since Sir Alex Ferguson retired in the summer of 2013, perhaps, or a first trophy since the 2016-17 Europa League?), City and their supporters cannot allow themselves to be dragged into the convenient narrative that will seek to portray Ronaldo as the one that got away.
That was Kane, who was desperate to join them, only to be frustrated by the man Guardiola sneeringly referred to as “the big master of negotiation, Daniel Levy. He knows everything, and we couldn’t do it”. If there was a price, somewhere north of £140 million, at which Levy might have been tempted to do business on Kane, City didn’t get close to it.
It is certainly tempting to feel they should have prioritised Kane ahead of Grealish, but by now that is a moot point. And it’s amazing how many people, including some of those who are usually most critical of City’s spending, have criticised the club for not offering whatever it might have taken to get Levy to the negotiating table.
Alternatively, perhaps the one that got away was Romelu Lukaku.
The Belgium forward might not appear the most natural fit for a Guardiola team either, but the idea of incorporating his talent and goalscoring threat was discussed extensively within City’s recruitment department as they planned for this summer. They were content to leave Chelsea to tie up a £97.5 million deal with Inter Milan on August 13. With the benefit of two weeks’ hindsight, perhaps they would have pursued that option even if, again, the player’s preference was to reunite with a former club.
Or perhaps the one that really got away this summer was Messi.
It is easy to forget that this time last year, ahead of the delayed start to the new season, Messi was City’s obsession. Whether he was ever truly serious about leaving Barcelona back then is unclear, but he and his entourage gave the impression he was ready to swap blaugrana for sky blue. And when he didn’t follow that through, members of the City hierarchy were left feeling used, which is certainly one significant reason why they showed no interest in revisiting the Messi situation this summer.
As much as Ronaldo and Kane, will City regret letting Messi slip through their fingers? (Photo: Getty Images)
Might that — more than not offering Spurs another £50 million-plus for Kane, much more failing to beat United to Ronaldo — have been a misjudgement? Last summer, they largely dropped their interest in Kane to pursue the tantalising option of a deal for Messi, only to encounter frustration. This summer they went after Kane, which proved impossible, and passed up what really was perhaps a once-in-a-lifetime to sign Messi, who instead left Barcelona at the end of his contract to join Paris Saint-Germain. Again, with hindsight, that looks questionable.
Once more, there is a danger in falling into the trap of suggesting City could or, worse, should do these things at the drop of a hat. But if they were willing to consider paying what it took to sign a Ronaldo who turns 37 at mid-season from Juventus — as well as the initial €15 million transfer fee and the possibility of another €8 million further down the line, United are reported to have agreed to a contract worth up to £480,000 a week — then surely they would at least have considered trying to negotiate with Messi, who was on a free transfer, is two years younger than Ronaldo and was a far more obvious fit from a technical/tactical perspective.
Director of football Txiki Begiristain was, like Guardiola, convinced Messi would stay at Barcelona, as was just about everyone at the Nou Camp. When that situation unravelled due to the Catalan club’s struggle to meet La Liga’s financial regulations, City were putting the final touches to that record-breaking deal to sign Grealish from Aston Villa and continuing to play the waiting game with Kane. PSG reacted quickly, showing money-no-object urgency and paying whatever it took to get Messi.
At the time, City were comfortable with that outcome. Again, the wage issue is an important one. But if Messi was worth chasing a year ago, it is hard to avoid the feeling that this summer’s non-approach came down to either a) a misreading of the situation or b) a sense of wounded pride after last summer. Either conclusion would be surprising, given how expertly Begiristain and his team usually navigate the market.
(20 years as a Times football writer before selling his soul to The Athletic - Oliver Kay is another tragic example of the demise of integrity in journalism)
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