Will Mourinho show at Tottenham that he has learned from his mistakes?

Mark Ogden believes Tottenham have themselves a serial winner in new boss Jose Mourinho. (1:34)

He’s back. Eleven months have passed since Jose Mourinho was sacked by Manchester United and, in between, we got a couple of commercials for bookmakers, a global roadshow in multiple languages to remind us he was still special, some technical analysis in TV studios and talk of wanting to join a club with “structural empathy.” That’s your starting point. Those two words: “structural” and “empathy.” Will Mourinho get this at Tottenham now that he has replaced Mauricio Pochettino?

As far as structure is concerned, despite praising not just Tottenham’s “great structure” but the “dynamic of the structure” at his cheery unveiling to the press on Thursday, Mourinho will get what he had at Manchester United, where executive vice-chairman Ed Woodward held control, unless something radical happens in North London: He’ll be working for an owner who never speaks and sits an ocean away (Joe Lewis), plus a big boss in Daniel Levy who runs the club, micromanaging transfers and budgets. And not much else, in the sense that there is no Director of Football or Head of Recruitment to act as a buffer between the manager and the top.

As for empathy, suffice to say it’s not a word often associated with Levy, his new Woodward. Levy is routinely depicted as a shrewd, ruthless negotiator, relentlessly looking for value. It’s a neat contrast with the profligacy of his previous boss — whether it be Alexis Sanchez‘ paycheck or Romelu Lukaku‘s fee — but it’s also a different way of doing business.

Woodward is (or at least was when Mourinho was at Old Trafford) the guy who buys the priciest ingredients in an attempt to bake the best pie and then looks to grow it; Levy is the guy who doesn’t like to share his pie and looks after every single crumb.

But look at it another way: Perfect fits are exceedingly rare in the highest echelons of football. If you take over a team in mid-season, it’s usually going to be a club in distress. It will usually be in distress because your new employers made some very poor choices and you have to trust that they will make better decisions going forward.

There is no question here that while Mauricio Pochettino bears some of the responsibility for what went wrong at Tottenham — the most damning statistic: 25 points from 24 league games dating back to February — and was effectively waiting to leave since the summer, which no doubt hurt Spurs’ performance, fingers of blame have to be pointed upstairs.

It’s easy to be desensitised because it has been a running theme for so long, but it’s simply unconscionable for a club to find itself with four starters — Jan Vertonghen, Christian Eriksen and Toby Alderweireld — out of contract next summer and Danny Rose, who wants to leave, in contractual limbo. While it’s true that Pochettino made a point of pushing out various recruitment figures at the club (Franco Baldini and Paul Mitchell) to arrive at a situation where it was just him and Levy calling the shots, it’s equally true that the buck stops with Levy.

When a player is underperforming, you sell. When a player is running down his contract, you either sell or extend it. These are basic tenets of running a club. It’s what Spurs used to do very well — this is the club that got around £60 million ($80m) for Kevin Wimmer, Nabil Bentaleb, Benjamin Stambouli, Roberto Soldado and Paulinho — but it’s what they were seemingly incapable of doing over the summer. Offers came in for every one of the “Tottenham Four” named above but partly due to indecision (from both Levy and Pochettino), partly due to an incorrect belief that they could get more and partly due to disagreements on potential replacements, they all stuck around.

So this is what Mourinho inherits: Not much “structural empathy” there at all. He tiptoed around the contractual time bomb on Thursday, noting that “it is too early.”

“I have no time for individual cases,” he said. “I don’t know how I can influence or try to influence. Mr Levy did not have time to discuss this.”

Whether you buy this or not, it’s hard to imagine Mourinho walking into a situation where some $300m worth of talent (the minimum cost to replace them) could be walking away in the next few months without assurances of the grand plan. What’s the budget to replace them? Or do Spurs think they can persuade them extend their deals? Or is yet to be discussed in detail with Mourinho? Or — as some have mooted — is it all largely irrelevant because Lewis, having built a new stadium and enjoyed consistent top four finishes, is going to sell the club?

That last bit of speculation — and it is just speculation — would explain why Mourinho is so relaxed. He gets the club, he gets the stadium, he gets the academy and training ground (“So good it can’t be compared with any in football, just some NFL teams”), he gets London… but he doesn’t get Levy and the budget restrictions. Instead, he gets a hypothetical deep-pocketed new owner willing to make his dreams come true.

If that were the case, you too would be chilled out about taking over a team where four regulars have one foot out the door. Where Dele Alli is coming off a long injury and hasn’t yet returned to level he was before. Where Eric Dier, once a mainstay for club and country, has started seven league matches in 2019. Where Serge Aurier is his only serviceable right-back. Where injured goalkeeper and captain Hugo Lloris won’t be back until the New Year. And where there are only six clubs below them in the Premier League table.

Dysfunction above Mourinho, distress in the squad and a league position that leaves little margin for error, at least this season. On the flip side, there will be plenty of mitigating circumstances of the “he’ll need at least four transfer windows to sort it out” variety, like the overtures we heard when he was at Old Trafford.

Jose Mourinho explains he will make new mistakes at Tottenham and how he’s learned from previous failures.

Tottenham are in a situation screaming out for “rebuild” and “long game,” except that Mourinho’s past suggests this is not where he excels. We know how the United rebuild went (not well). His second Chelsea stint was more retooling than a rebuild. The bulk of his Real Madrid squad arrived the season before him.

In short, he’s the guy who jumps on the bike in the last few miles of a Tour de France stage, pedals furiously and gets you over the line first, not the guy who builds the bike from scratch and does the first 200 miles. And that’s before you get into his other character traits: The rows with other managers, the sniping about his own players, the moans about the club and the testosterone-filled “Special One” schtick that wore thin a long time ago.

But — and this is something we often forget — managers are human beings, not WWE characters. They evolve, they change, their storylines have an arc. It’s not set in stone that the Mourinho we’ll see at Tottenham Hotspur Stadium will be the guy who rocked up at the Bernabeu, Stamford Bridge and Old Trafford. He knows that he left his past three jobs under a huge cloud.

Likely this was part of the reason he sounded so humble on Thursday. Asked if Tottenham were getting a new and improved Jose, he sounded like a guy just back from a Tony Robbins self-help session.

“I think so. I believe so. I have to believe so,” he said. “I always thought that these eleven months [out of the game] were not a waste of time. These [were months] to think, to analyze, to prepare… I think you never lose your DNA, your identity, what you are [but] I had time to think about many things. I realized that during my career I made mistakes. I am not going to make the same mistakes. I am going to make new mistakes.”

“I am humble,” he added. “I am humble to enough to analyse my career, problems and solutions. The principle of the analysis was not to blame anyone else.”

If Mourinho is introspective enough to realise that he needs to change, if he’s intelligent enough to figure out how best to change while keeping what made him a great manager, if he’s virtuous enough to follow through on it, if he can go back to the shop floor and rediscover what made him excel with limited resources at Porto nearly two decades ago, and if Levy can regain his transfer mojo and install a better working relationship than what the Pochettino one had become, then it might just work.

But that’s a ton of “if.”

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