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Bayern Munich and Man Utd are now miles apart - only the Bundesliga side can challenge for the Champions League after going all out for Harry Kane

Bayern Munich versus Manchester United was once a classic Champions League fixture. The two giants had never met in the European Cup era, but then played each other 11 times in the space of 16 years.

The most famous meeting is, of course, the 1999 Champions League final at Camp Nou when United turned a 1-0 defeat into a 2-1 win in the space of three minutes. But the 2009-10 quarter-final tie was also epic, with Bayern coming from behind in both legs to eventually go through through on away goals. The Bavarians also prevailed in the quarter-finals in 2000-01 and at the same stage in 2013-14, when David Moyes' United briefly led against Pep Guardiola's Bayern before a quick-fire turnaround.

However, Wednesday's match at the Allianz Arena is the first meeting between these European juggernauts in nine years. And the reason for the long gap is not down to chance. Bayern have reached the Champions League quarter-finals in each of the last 10 years, including four semi-finals and one final (which they won). United, however, have only reached the last eight once since then, and have failed to even qualify for the competition on four occasions. While the Red Devils last won a Premier League title in 2013, Sir Alex Ferguson's final year in charge, Bayern have won the last 11 Bundesliga crowns.

The two clubs' contrasting fortunes are no coincidence. While United have been run in a shambolic manner since Ferguson retired, Bayern are arguably the best run club in Europe. And it was thanks to their management that they were able to beat United to the biggest signing of the summer: Harry Kane.

The England captain was United's No.1 target towards the end of last season as he approached the final year of his contract with Tottenham. They had their reasons for not going through with it in the end, though, and have instead taken a punt on their long-term future by signing Rasmus Hojlund instead, as well as strengthening their squad in other areas.

But after making a woeful start to the season, losing three of their first five Premier League games for the first time ever as well as being afflicted by a never-ending list of off-field problems, the fact United missed out on Kane should give the club a pause for thought. A decade ago they would have done whatever it took to sign one of the best players in the world. Had Ferguson still been in charge and different owners at the helm, they would have pulled out all of the stops to sign Kane. They would have done what Bayern did.

They fact they did not, and that Kane did not push for a move to Old Trafford, shows how far they have fallen in comparison to the Bavarians. Not long ago United considered Bayern their equals, but now they are in almost a different league...

  • Erik ten Hag Manchester United Brighton 2022-23Getty Images

    Kane's United preference

    It was an open secret that Erik ten Hag was desperate to sign Kane to provide the finishing touches to the exciting project he was building last season. When United drew 2-2 at Tottenham in April, with Kane setting up Son Heung-min's late equaliser, Ten Hag was directly asked whether he wanted to sign the striker for United.

    Although he avoided naming Kane, his response was telling:"Everyone knows, it’s not a secret that over the whole season we have had a shortage of No.9s. With fewer players we have to cover many games, so we definitely need players in the frontline who strengthen the squad."

    Kane, who tried to join Manchester City in 2021, had already made it clear that he wanted to finally leave Tottenham in pursuit of trophies and was not going to sign a new deal with Spurs when his contract ran out in 2024. Spurs were running out of time to make money on their star player and risked losing him for free. This was United's time to strike, and they had two factors in their favour: Kane was keen to stay in England and break Alan Shearer's Premier League scoring record.

    There were also family reasons behind him staying in England over moving abroad, with his wife Kate pregnant with their fourth child. Ultimately the family factor did not prevent him from signing for Bayern, but the fact Kane's family have initially opted to remain in London over relocating to Munich suggests they would have preferred to stay in England.

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    Glazer and Arnold resist move

    Although Ten Hag was all in on Kane, his superiors were less certain. According to The Athletic, United chief executive Richard Arnold and co-owner Joel Glazer had their reservations about about what would have been a very costly move for a player who turned 30 in July.

    The club's scouts were also resistant to signing Kane, while sporting director John Murtough was wary of getting into a back-and-forth with Tottenham chairman Daniel Levy, who is regarded as the toughest negotiator in football. United had been stung by their long and futile pursuit of Frenkie De Jong from Barcelona the previous summer and they wanted to get their business done early and focus on a realistic target.

    As early as mid-June, they abandoned their pursuit of Kane and focused on getting Hojlund, who was 10 years younger and, at first glance, a cheaper option as Atalanta were always going to be easier to negotiate with than Tottenham.

    But United still ended up paying £64 milion ($79m) plus an additional £8m for a player with just one season in Europe's top five leagues. Levy, as expected, forced his hand in negotiations with Bayern and drove the price for Kane up to £86m ($106m) plus add-ons, taking the total fee to just shy of £100m ($123m).

    In the end, it was a difference of about £25m ($30m) between signing the potential of Hojlund or the world-class, proven quality and experience of Kane. United got no advantage in doing their business early either, as Hojlund arrived with a back injury and could not make his debut until almost a month after completing his signing.

    Ten Hag deemed him not ready to complete 90 minutes against Brighton on Saturday, provoking the fury of the Old Trafford crowd when he took the striker off for Anthony Martial. Kane, meanwhile, made his Bayern debut the very next day after sealing his move and has scored four goals in four Bundesliga appearances so far.

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    Kane gave off RVP vibes

    United's reservations about Kane's age and price tag were understandable, especially when you consider his history of ankle injuries. He may have only had two or three years in peak condition and then left for little or no resale value after taking huge wages. There was also concern that signing Kane, who reportedly has a salary of more than £400,000 ($495,000) per week, would upset United's wage structure and cause tension with other players.

    But Kane would have been worth it. One of Ferguson's last acts as United boss was to sign Robin van Persie from Arsenal in the summer of 2012. The Dutchman was 28 at the time and cost £24m ($29m), a huge fee at the time for a player also with one year left on his contract.

    But he was also the best striker in the Premier League then and had been top scorer the previous season. United knew exactly what they were getting and Van Persie fired them to the title with 26 goals, again collecting the Golden Boot. To tell the truth. it was his only good season with United as his previous injury problems then came back to haunt him.

    But no one at the club regrets signing Van Persie and no one would have regretted signing Kane. There must be plenty of regrets, though, about paying £85m ($105m) for Antony, who has only scored four Premier League goals for United and may never play for the club after facing serious accusations from three women.

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    Bayern put in the hard yards

    Bayern certainly felt Kane was worth the money and they do not normally pay over the odds for players. Former president Uli Hoeness used to describe the international transfer market as "madness", and their three previous biggest signings were Lucas Hernandez for €80m ($85m) in 2019, Matthijs De Ligt for €67m ($71m) in 2022 and Leroy Sane for €60m ($64m) in 2020.

    But, given the German champions had played most of the previous season without a centre-forward, they were prepared to break with their usual tendencies to get Kane. They began their pursuit before the end of last season, with coach Thomas Tuchel flying to London to meet with Kane at his house.

    Bayern directors also flew to London to hold face-to-face talks with Levy over the summer and were flexible with the chairman's demands after making an initial bid of £70m ($86m) which Tottenham rejected. Their determination meant they beat Real Madrid's bid of £60m ($74m) as well as an undisclosed offer from Paris Saint-Germain and a bid from unnamed club from Saudi Arabia. United, however, never tabled an offer for Kane.

    Tuchel, who has a way with words, could not hide his satisfaction when discussing the transfer on the eve of the clash with United. “It’s a big thing, we took the skipper of England out of England,” said the Bayern coach. "Anyone looking for a No. 9 would’ve been happy to have Harry in the team. He makes the team better and gives you what you want from a nine. I’m not sure what’s going on at other clubs, but we’re more than happy that he finally took the decision and came to make us better."

  • Harry Kane BayernFC Bayern

    Masters of money

    Bayern were able to do the deal for Kane which other top clubs backed away from it because they have been run so well over the years. Despite making only €100m from television income annually - United made £214m in 2022 - the Bavarians earned €665m in revenue last year, boosted by big-money deals from partners Allianz, Audi and adidas.

    That made them the sixth-richest club in Europe, according to the Deloitte Money League, with United ranked fourth on €688.6m. But unlike almost all of their competitors on the continent, Bayern have no net debt. According to their last accounts in March, United owe a total of £969.9m due to a combination of gross debt, a revolving credit facility and outstanding transfer payments. And that's before you take into account this summer's spending.

    Bayern also sell well. Despite signing Kane and the highly coveted South Korea centre-back Kim Min-jae from Napoli for around €50m, they ended the transfer window in profit thanks to the sales of Hernandez, Ryan Gravenberch, Marcel Sabitzer, Sadio Mane, Benjamin Pavard and Yann Sommer for a combined total of €173m.

    Contrast that with United, who spent €206m on new signings but earned just €55m on sales. The Red Devils also failed to move on unwanted players such as Harry Maguire, Scott McTominay and Jadon Sancho.

    Bayern, ultimately, were allowed to indulge themselves and sign Kane thanks to years of excellent management behind the scenes. United were unable to do so due to years of woeful management.

  • ONLY GERMANY Hasan Salihamidzic Uli Hoeness Karl Heinz Rummenigge FC Bayern 2021imago images

    Ex-players in key roles

    A big reason why Bayern have been so well run over the years is they have a long tradition of appointing very experienced people who know the game. Hoeness, who was president for 10 years between 2009 and 2019, was a former Bayern player who won three Bundesliga titles and three European Cups. Hoeness' former team-mate Karl-Heinz Rummenigge was the club's CEO for 19 years. His successor was legendary goalkeeper Oliver Kahn, who was removed from the post in May of this year.

    Former midfielder Hasan Salihamidzic, who won the Champions League with Bayern alongside Kahn in 2001, was sporting director for six years until he too was fired in May. For once. Bayern did not replace him with a club legend. Instead, they hired one of the best in the business, poaching Christoph Freund from Red Bull Salzburg. Among his many achievements with the Austrian side was to sign an 18-year-old Erling Haaland.

    Now contrast Bayern's boardroom expertise with United's. CEO Arnold is a former accountant who started working with the club as a commercial director. He rose through the ranks under predecessor Ed Woodward, who also had no football background, due to his skill at signing commercial deals. But he has no prior experience on the football side and now has to make huge football decisions, such as backing out of a move for Kane.

    Then there is director of football Murtough, who joined United in 2013 from Everton as an administrator and was another close ally of Woodward who had no background in playing or coaching football.

    Above Murtough and Arnold there is Joel and Avram Glazer, who have barely even been to Old Trafford for a match. With such a gulf in expertise and knowledge, it is little wonder that Bayern ended up signing Kane. And it's no wonder why these former rivals now appear to be worlds apart.