Todd Boehly's wild £300m spending spree suggests he does not understand our game

Roman Abramovich's first encounter with English football nearly 20 years ago was on the night I drove him to Old Trafford.

My friend Pini Zahavi had offered me one of his executive box seats for Manchester United's Champions League quarter-final against Real Madrid. I decided against going to the match, in which the Brazilian Ronaldo starred and United won 4-3, but agreed to drive him and some friends over from Manchester Airport anyway.

One of them was Abramovich, who sat in my passenger seat and mistook me for the chauffeur. It was when someone put him right, in the conversation which was being conducted in Hebrew from the back seat, that he stopped staring out of the left window and actually turned around to acknowledge me.

Abramovich went on to be a hugely successful football club owner but on his first day at Chelsea, a few months after our encounter, he surrounded himself with so-called experts who knew nothing about football. He wasted a lot of money because of it.

His successor, the American Todd Boehly, seems to be making the same mistakes. In his hurry and enthusiasm to get Chelsea supporters onside, he has just spent the thick end of £300million in the summer transfer market, appearing to do all the business himself. I do hope I'm wrong in that assessment.

Unless you have a bottomless pit, the money they have spent on Marc Cucurella makes no sense, considering Chelsea already had Marcos Alonso, Ben Chilwell and, at a push, Reece James in the same position.

Is Cucurella that much of an upgrade on them? I don't think so. Chelsea only seem to have taken him because Manchester City wanted him.

I get that they needed centre backs because of Antonio Rudiger and Andreas Christensen going and having 37-year-old Thiago Silva, an age when your game can fall off a cliff inside a month. But £70million for Wesley Fofana? At 21, he only brings potential.

The upside to signing Pierre-Emerick Aubameyang on deadline day is that Chelsea now have a striker who has scored goals in the Premier League, something notoriously hard to find.

The downside is that he's 33 and has a dodgy gene somewhere. Mikel Arteta did very well for Arsenal, and for his own longevity as manager, by getting Aubameyang out of the building and seems to have found an upgrade in Gabriel Jesus.

If you want to indulge Aubameyang, then you risk heading down the same road as Arsenal did with that fool Mesut Ozil, who got in his armchair the minute Arsene Wenger put him on a ridiculously inflated salary.

Boehly certainly seems convinced he knows what he's doing, even though Marina Granovskaia and Petr Cech, who provided the football knowledge for Abramovich, have had enough and are off.

He is the latest in a long line of wealthy individuals to come into football thinking the game is easy. So maybe he'll prove the utter folly of thinking he can understand it. Go and get Alex Ferguson out of retirement, send him to manage LA Dodgers and ask him to put a valuation on baseball stars playing at other clubs, with a view to deciding which ones he might buy. It would be impossible.

Chelsea are not the only ones who have been spending in this way. Around £2billion has been laid out by our 20 top-flight clubs this summer. Manchester United have spent more than ever before. Yes, of course, this is madness, but I do understand why we've reached this level.

We live in a generation where everything has to be 'today', not 'tomorrow'. A generation where football's popularity transcends anything we have known.

The pressure on the big teams to deliver now, not tomorrow, has never been greater.

In an ideal world, you buy players at the right age, knowing they are only going to get better over five, six, seven or eight years. But that has all gone now.

The rest of football just look at us and shake their heads. If you're United, Liverpool and Chelsea you're paying the Premier League premium and a big club premium. It's a double whammy.

European clubs just lick their lips when an English club phones to inquire about a player.

It generally takes new owners such as Boehly, who think they know it all, a couple of years to realise they actually don't, by which time they've spent hundreds of millions of pounds on bang-average players because they've been listening to the wrong advisers.

It took Abramovich four months to admit he assumed I'd been the chauffeur that afternoon.

I asked him straight out when my Blackburn team went to Chelsea and drew 2-2. He looked slightly sheepish. And he didn't tip me, by the way.

Fofana has thrown his toys out of the pram at two clubs now - best of luck to Chelsea if Real Madrid come calling

I can understand where a player is coming from when he deliberately becomes a pain in the arse if a club is reluctant to sell him.

That's how I was at Middlesbrough when they rejected Liverpool's first bid for me in 1978, though I never refused to play. It wasn't a saga. I ended up being a record English transfer fee between two clubs at the time, in a deal worth £352,000. All sides benefited from the deal.

It is a very different situation with Wesley Fofana's refusal to train with Leicester to secure a move to Chelsea. Brendan Rodgers and Leicester are entitled to feel aggrieved because they gave him a new five-year contract in March, even before he'd returned from a broken leg sustained in pre-season.

Within five months, he's upsetting everyone and he wants to leave. He did the same thing to get a move to Leicester from Saint-Etienne. So here we have a player who, before he's even 22, has thrown his toys out at two clubs.

Good luck to Chelsea if Real Madrid come calling.

Why I rejected the man I now spend Monday morning's vigorously debating

One of the individuals I'm spending Monday mornings with might have been my boss had things worked out differently.

I met Simon Jordan in Marbella in the summer of 2006. He wanted to explore the idea of me becoming manager at Crystal Palace, who he owned at the time. I liked him but I'd not long been sacked by Newcastle, an experience which told me I was finished with management.

Simon was intelligent enough to see that. He didn't push things when I said that Palace was not for me. Now, we spend three hours debating football with Jim White on the talkSPORT mid-morning show.

There's a surprising amount that Simon and I see the same way. The business side of the game, the rights and wrongs of how players behave. We are a little bit apart on how managers behave and how they speak to the press. There will be fireworks, as we will disagree. But Simon argues his corner and knows his mind. I respect that.

Winks will come back a better human being - and player - for his time in Italy

I am pleased to see that Harry Winks, a very gifted midfielder, has headed on loan to my old team Sampdoria from Tottenham.

In many ways, I would like to have spent more than the two years I did at that excellent club. Italy was a great place to be a midfielder in the 1980s because there wasn't the same intense pressing as in England.

It won't be the same now for Winks because everyone presses these days. But he can go there both for the life experience and the football experience. He should soak it all up. He will come back a better human being and a better player.