A curious hypothetical that’s been floating around the interwebs recently: Suppose that Manchester City finish fifth in the Premier League but then ride all the way to the Champions League final… where they meet Bayern Munich. How does Pep Guardiola prepare for that one knowing that losing the game is his only way of getting back into the competition next season?

Obviously that’s hardly a conundrum. His Bayern team would go out there to win and invariably they would do just that. But it is a solid indication that the job he’s taking on in Manchester is not exactly the open goal that people seem to think it is. Sure, he could have taken a job with some battler club and maybe he could have done something special and proved to the world what a genius he is. Or he could have fallen flat on his arse for the likes of Harry Redknapp to laugh and gloat about (love ya, ‘Arry!). But when you can have any job in the world, you tend to take the one with the biggest salary and the chance to work with your buddies. So what? We’d all have done the same thing.

The point is that after incredible success with Barcelona – and chasing that with a rampaging Bayern Munich team – moving to England in itself is a fresh challenge. Trying to form this unbalanced City team of injury prone stars and ex-Gunners back into the dominant force of the British Isles (as well as bringing that elusive continental success) is a far tougher gig than he’s being given credit for. Oh, City are still good. But for what they’ve done the last five years they should be superb and they absolutely are not that.

You want proof? How about Manchester City losing at home to their closest rivals, a team I’m going to (not so) affectionately refer to as *this* Manchester United team. Despite all the dramas with Louis Van Gaal and the club’s Ross and Rachel relationship with Jose Mourinho, it turns out that the pre-season favourite and the fumbling former giant really aren’t so far apart. In fact with only one win in their last six Premier League fixtures (and it was against Aston Villa, so it barely counts), City are just one point ahead of United and West Ham in fourth and their Champions League place for next season is teetering.

This isn’t a complete shock. Manuel Pellegrini doesn’t care about next season, he ain’t even gonna be there. His focus now is on taking this team as far as they can possibly go in the Champions League – and they’ve already gone further than the club has ever made it before. Their lack of progress in Europe has been a massive frustration for City. Pellegrini was meant to help that and now he’s been jettisoned for the most successful Champions League manager of the last two decades, but it isn’t too late for Manny. Should their league form suffer from that pursuit, well so be it. Clearly that wasn’t meant to extend to home derby losses but the point is their main focus is definitely elsewhere.

The UCL draw has already been kinder to them than they’re used to. Paris Saint Germain is no sitter, drawing Wolfsburg or Benfica would have been far better. Still, in PSG they get a team that’s in a similar state to them. They may cruise to the French title every season (they’ve already wrapped it up for this season) but zero Champions League semi-finals since 1995 puts a truckload of pressure on them as well. There’s more talent in that PSG squad but there are almost as many holes. Hey, Chelsea nearly beat them. Chelsea aren’t that good.

Although Chelsea did beat City 5-1 in the FA Cup. Just as City have also lost recently to Leicester City, Liverpool, Spurs and Man United. They’ve lost to Arsenal, Stoke and West Ham this season. People talk about how important it is to beat the teams around you and City now have Premier League losses to seven of the top nine. Bear in mind that they don’t get to play themselves – though some would argue they’ve been beaten by themselves more than they’ve been beaten by anyone else.

Against Manchester United, City manage 26 shots and only three were on target. Jesus Navas and Wilfried Bony were especially wasteful. Sergio Aguero looked dangerous but kept losing the ball. David Silva drifted in and out of the game, Yaya Toure looked lethargic again. Oh, and then we have Martin Demichelis.

Oh sweet Jesus, what can you say about Demichelis? The 35 year old was almost as welcome a name on the team sheet for Red Devils fans as Marouane Fellaini’s was off of it. Demichelis and Eli Mangala have played together once before in the PL and it was a 4-1 demolition at the hands of Liverpool, they were just as bad against United, albeit against a less punishing attacking team. Not that that stopped Marcus Rashford from gliding around Demichelis, riding a shocking attempt at a last-ditch tackle before slipping the ball past Joe Hart in goal for what would prove the winning goal.

But Demichelis’ night didn’t end there. No City outfielder had a worse passing percentage than Marty and while he did manage a few good tackles, he never looked anything close to comfortable when Rashford and Anthony Martial were running at him. For reference, those are two players whose combined age is only three years older than Demichelis’. Right at the end of the first half he should have conceded a penalty. Rashford slipped past him once more and a late thrust of the hips took him down, only for the ref to keep his whistle unwetted. A lucky break but he did his best to make up for that after HT when a terrible back pass was almost picked off by Martial. Joe Hart desperately slid to clear it but in doing so he hurt his calf and could be out for up to month. Nice one, Marty. He was subbed off for Wilfried Bony after 52 minutes, that’s a kick in the nuts. The fact that Demichelis was playing at all shows you the depth of what Pep has to deal with.

Bringing in Guardiola is a huge show of power for City and as such he’s gonna get every cent he wants to spend in the transfer market. For some reason, though, there are folks out there who think that money is everything in the transfer market. Those people aren’t thinking clearly. Mo’ money, mo’ problems, as they say. Here are City’s recent transfers:

Kevin De Bruyne (Wolfsburg) - £55.50m
Raheem Sterling (Liverpool) - £46.88m
Nicolas Otamendi (Valencia) - £33.45m
Fabian Delph (Aston Villa) - £8.63m
Patrick Roberts (Fulham) - £5.40m

So much money and still no solution. Delph’s transfer would never have happened were it not for the homegrown players rule. Same with Roberts, although that kid is one hell of a talent (probably a season or two away). De Bruyne and Sterling started off magnificently but Sterling has struggled recently and De Bruyne is injured. Those two facts are probably related. As for Otamendi, great player and a top defender, which addressed a massive need. Why was that such a need? That would be on account of Vincent Kompany’s constant injuries and the fact that the only defender they bought last season was Eliaquim Mangala. Look, when you bring young players into a new league you cannot expect them to be immediately impactful, they need time to settle and develop. Mangala is a fine player who has been poorly handled at City. He was great at the start of the season next to Kompany (when they didn’t concede a Premier League goal for the first 455 minutes of their season) and has not come close to that form again and you can blame that squarely on the inconsistency next to him. Chances are that of the five major signings that they made this season, four are gonna be remembered as hits (Sterling signed a five year contract – there shall be no official judging of him until that time’s up). Unfortunately it doesn’t cover up all the damage they did over the three seasons before that.

In 2011-12 they won the Premier League for the first time and in the most incredible fashion. Sergio Aguero was in his first season at the club, Yaya Toure, Edin Dzeko, Mario Balotelli, James Milner, Alex Kolarov and David Silva all in their second. They had a magnificent squad that wasn’t to be stopped, most of those players were key figures again in the 2013-14 triumph. Given that only Aguero and Silva are: A) Still at the club and B) Still at their peak, you can see why they’re having trouble now, given that these are the players they’ve signed between winning the title the first time and up until last season (excluding the irrelevants below £3m):

Jack Rodwell… now playing off the bench for Sunderland.
Scott Sinclair… getting relegated at Aston Villa.
Matija Nastasic… a solid young defender, now at Schalke. Traded in for Mangala.
Javi Garcia… one of the PL’s biggest busts, now at Zenit.
Martin Demichelis… see 3-5 paragraphs above.
Jesus Navas… still a solid contributor, very fast but awful finisher.
Alvaro Negredo… battling at Valencia, after scoring 23 goals in his one season at City – slumping hard in the back half of the campaign.
Stevan Jovetic… back in Italy with Inter after 11 goals in 39 games. Pretty much quit after Bony was signed.
Fernandinho… probably the best of them, one of the best holding mids in the PL, although one without a clear partner in crime.
Wilfried Bony… signed to play backup to Aguero with all the other strikers leaving for starting roles. Plays with all the confidence of a player who doesn’t know when his next game is coming.
Eliaquim Mangala… solid centre back who has had a few teething problems. Not a first XI guy yet.
Willy Caballero… backup keepers are always a balancing act. Seen as a weak option until he won them the League Cup shootout.
Fernando… a worse version of Fernandinho.

Yeah, so one of the richest clubs in the world, and those three seasons netted them a total of zero players that are among their first choice starters. De Bruyne, Sterling and Otamendi all suit that label but three years without improving the top end of that squad, no wonder they’re still over reliant on 32 year old Yaya (he could be so much more effective with another strong midfielder behind him). No wonder the defence shows cracks as soon as Kompany gets his next knock. No wonder the goals don’t flow when Aguero isn’t there. Manchester City are paying the price for some terrible transfer dealings and as we’re seeing, one good window can’t solve all that. The same thing happened to Liverpool post-Suarez.

Which is why Pep Guardiola isn’t going to be a simple fix. He can’t waltz in and sell half the squad without accepting that they’re in for a rebuilding period – look at Man Utd since the post-Moyes clear-out. But then at the same time, Pep sold Yaya when they were at Barcelona. He has a style of football that he encourages and it involves high pressing and quick passing. He adapted that with Bayern to be more direct, which better suited guys like Arjen Robben, but it was still the same core formula. He’ll be taking that to City because you don’t sign Pep Guardiola without that expectation. Guys like Sergio Aguero and David Silva are gonna love it, while guys like Bony, Navas, Toure and all those aging fullbacks… not so much.

Somehow Guardiola has to fashion a squad of champions from that while also negotiating the financial fair play stipulations.

One cause for optimism is the rise of Kelechi Iheanacho this season. Nine goals so far, the Nigerian teenager is the first guy to break through from the academy at City probably since Micah Richards. They’ve spent millions and millions of pounds on their academy. It’s something that they desperately want to be known for. In Pep Guardiola they have a manager who isn’t afraid to blood the kids and their pool of ‘Elite Development’ players is as strong as it gets. Okay, maybe Chelsea’s haul of prospects edges them (the lost generation…) but if you spend that much money on development then you are going to see a result. Of the team that was pumped by Chelsea in the Cup, you can pencil in the likes of Manu Garcia, Bersant Celina, David Faupala, Brandon Barker, Cameron Humphreys-Grant and Tosin Adarabioyo as players with a chance of sitting in on the fringes of first team football, not to mention current loanees like Pat Roberts, Jason Denayer and Enes Unal who should all be near that conversation already.

They’re gonna have to be, because Pep Guardiola is not winning the Champions League with Martin Demichelis, that’s for damn sure. After that derby display he might not even be in the Champions League.