It was the cartoon, published on the Daily Telegraph website a few years ago, that probably demonstrated the perception at the time that the man in charge of Manchester United’s transfer business was straying dangerously close to getting the reputation of being a bit of a pushover.

Entitled “Manchester United and the Transfer Market” and published shortly after the arrival of Ángel Di María and Radamel Falcao, the cartoon showed the club’s executive vice‑chairman, Ed Woodward, walking into a convenience store called Costless and asking to be shown the “very finest” chocolate they had for sale before handing over £80 for a Mars Bar.

He returned to the same store a while later and the shopkeeper, sensing another easy kill, offered him a packet of wine gums for £100. Woodward offered the “far more realistic price of £95” and they started haggling.

Shopkeeper: “£98.” Woodward: “£99.” Shopkeeper: “£110.” Woodward: “£100.” Shopkeeper: “Deal!” Woodward (triumphantly): “Still got it …”

It’s an easy laugh. Yet it’s not entirely fair to portray Woodward as a soft touch and, if we think back to his first transfer window in the role, he never really got the credit he deserved for the way he faced down Wayne Rooney and refused, point-blank, to bend to the requirements of Chelsea and Roman Abramovich.

Chelsea, you might recall, had lodged two bids for Rooney after José Mourinho’s return to Stamford Bridge in the summer of 2013. The player was doing all he could to make the move happen and Mourinho was under the impression it was only a matter of time. Yet Woodward held firm. Bending to player power, he concluded, would be weak in the extreme. It wasn’t a question of money. It was a case of self-preservation, assessing the dangers and looking after his own club’s reputation. Chelsea’s £50m signing of Fernando Torres from Liverpool was seen throughout the sport as a shift in dynamic between the two clubs. Woodward decided his position was irreversible and that he could not risk United going the same way.

Most people would conclude that was the right decision when Rooney, at 27, was still capable of scoring 20 goals a season for the next three years. Yet it is also fair to say Woodward was under considerable pressure to change his mind. Rooney went to see him, making it clear he wanted to go, but it made no difference. And of course it was the sensible thing to do when the alternative, as Chelsea might yet find out with Nemanja Matic, risks a scenario where the selling club see a former player lift the Premier League trophy in another team’s ribbons.

Chelsea evidently thought they could take that risk, bearing in mind their favourable reaction when Mourinho, now their former manager, identified Matic as an ideal wearer of United’s colours and found out that his former club were happy to do business with his current one. Matic has fitted in seamlessly to his new team, immediately giving the impression his contribution to United’s season is going to be considerable, and it is easy to understand why throughout the sport there is an element of mystery why a club with Chelsea’s ambitions have been so obliging.

To put it into context, perhaps the best place to start is an interview last February in which Mourinho was asked whether it was possible in the Premier League for the top clubs to sign players from their leading rivals. “This is not Germany,” he pointed out. “In Germany, Bayern Munich starts winning the league in the summer. They go to Borussia Dortmund every year and buy their best player. One day they go there and [Robert] Lewandowski. The next year, they go there, Mario Götze. The next year, Mats Hummels.

“Do you think I can go to Tottenham Hotspur and bring two Tottenham players to kill Tottenham? I can’t. I cannot go to Arsenal and bring the two best Arsenal players. I cannot go to Chelsea and bring two of the players that I love very, very much. That time is over. That time of attacking your direct opponents in the country is over. You cannot attack your rivals that way any more.”

It turned out he was wrong, or at least partly wrong, given that one of his favourites from Chelsea is now exerting his influence in a red shirt. Mourinho seems as surprised as anyone and there may come a time when Chelsea have to concede that maybe Woodward had the right idea. Why help out the team that could be going head to head against you for the title? Why facilitate a club who would never dream of being so generous in return? And how much will the £40m transfer fee matter to a man of Abramovich’s wealth if Matic’s contribution for his new team helps to return the championship trophy to Old Trafford?

Arsenal were guilty of an even more reckless form of business when they allowed Robin van Persie to move to Old Trafford in 2012 and handed over a player who had just won the Professional Footballers’ Association Player of the Year award. They seemed quite happy with the money they received for the player – £22.5m, initially – but not so much when he scored 35 times the following season and Sir Alex Ferguson’s team won the league with four games to spare. For that, Arsenal received a £1.5m top-up payment. Who would you imagine was the happier?

United made a calculated risk of their own when Danny Welbeck went the other way during the Louis van Gaal era. Yet Welbeck was not a performer with Van Persie’s intuitive brilliance and there have been only a few other occasions – Mickaël Silvestre to Arsenal and Juan Sebastian Verón to Chelsea, being the notable ones – when the modern United have broken away from their position that it makes absolutely no sense to solve your rivals’ problems.

United even brought in lawyers in 2007 to prevent Gabriel Heinze from moving to Liverpool. Heinze had a written agreement that he could leave Old Trafford if a potential buyer offered £6m. He ended up employing Liverpool’s solicitors to act for him against his own club – an incredible story of politics, rivalry and legal manoeuvring – but it got him nowhere and Phil Chisnall remains the last player, in April 1964, to move from one club to the other, in the same week that BBC2 was flickering on to the nation’s black-and-white televisions for the first time.

The strange thing, perhaps, is that some of the other clubs with realistic aspirations of going for the title are nothing like as particular about who they do business with. Spurs, for one, have regularly pained their own supporters that way and Arsenal, similarly, have spent a number of years helping the Manchester clubs assemble title-winning sides.

For the reigning champions to risk the same, however, doesn’t make obvious sense. Matic might not have been an automatic starter after Tiémoué Bakayoko’s arrival from Monaco but the Serb has gone straight into United’s midfield and, at 29, could feasibly stay there for the next four years. It defies logic and the popular theory, namely that Abramovich apparently ticked off the deal after a personal request from the player, doesn’t make it any less perplexing. Very decent of him, you might think, but if the question is whether United would do the same in return then Rooney can probably provide the answer.

Costa blank when it comes to blame

It shouldn’t be a great surprise, if you have followed the pattern of Diego Costa’s career, that this is not the first time he has failed to report for duty after a summer of self-indulgence.

Costa was so out of shape when he turned up late for pre-season training one year at Atlético Madrid one of the journalists who covers the club, José David Palacio, recalls the player trying to strike a deal with the local media. “He tried to avoid the cameras as much as possible and insisted that we didn’t film his whole body,” Palacio says.

Costa had been awol for the first four days of training and was made to issue a public apology in which he initially blamed his mother’s cooking. “It was just a breakdown in communication. I lost my Spanish mobile and didn’t realise that the club don’t have my Brazilian number. Otherwise they could have called me on that. But I came back the minute they called and I’m really sorry this happened. Something seems to go wrong every year. Problems seem to seek me out.”

He is right. Problems do seek him out. Yet Costa seems to labour under the misapprehension that it is merely misfortune and, in that regard, one imagines it will be a considerable relief for Chelsea when they have finally removed one of the more tiring characters in the business from their payroll.

FA’s odd omission in Aluko inquiry

The FA’s decision to publish the barrister’s report relevant to the Eni Aluko “hush money” case detailed why the governing body had not upheld her complaints about an alleged racial remark and ruled there had been no wrongdoing by the England women’s team manager, Mark Sampson.

What it did not address was the well‑sourced claim that the mixed‑race player he was said to have left “distressed” during the China Cup in 2015 – Sampson was alleged to have asked her how many times she had been in trouble with the police – was not among the people to be interviewed in the wake of Aluko’s varied complaints.

It feels bizarre, yet there have been no denials from the FA. Can it really be true? Can there really have been an allegation of that nature and an investigation took place without actually speaking to the player in question?