Greatest transfer windows of all time, which club can trump Madrid's summer 2009 window?

[Fortitude]

Topic for discussion on a plate:

By the end of this season, Benzema will be 2nd all time Madrid top scorer and he's already their all time assist leader.

Pretty cool if you think about it from Madrid's standpoint.

They signed Benzema and Ronaldo the same summer. Fast forward to 2022. 4 UCL wins later.

Benzema all time assist leader, Ronaldo second.
Ronaldo all time leading scorer, Benzema second.

What incredible signings !

Has to go down as one of the best transfer windows of all time.

And to think if we got to hang on to Ronaldo and sign Benzema like SAF planned it could have been us.

It's got to be the best transfer window a club has ever had, surely?

I put forth Milan's Van Basten - Gullit acquisition as a challenger, but that Madrid pairing have them beat in every aspect, really and we're talking about magnitude at this end of the market: players that are legion and part of the fabric of their clubs. So, even on that score, who enters the discussion? Can what Madrid did that summer be matched, let alone beat by anyone else?

It was sickening to sell them Ronaldo for £80m at the time when we should have been pushing for a lot more, and in hindsight, they easily, easily got the better end of the deal.

 

[RoyH1]

I think it’s unmatched. 2 of their two top scorers of all time plus Xabi Alonso. Kaká didn’t pan out for them though

 

[BenitoSTARR]

Topic for discussion on a plate:


It's got to be the best transfer window a club has ever had, surely?

I put forth Milan's Van Basten - Gullit acquisition as a challenger, but that Madrid pairing have them beat in every aspect, really and we're talking about magnitude at this end of the market: players that are legion and part of the fabric of their clubs. So, even on that score, who enters the discussion? Can what Madrid did that summer be matched, let alone beat by anyone else?

It was sickening to sell them Ronaldo for £80m at the time when we should have been pushing for a lot more, and in hindsight, they easily, easily got the better end of the deal.

I’d say certainly the best in a very long time in terms of signing absolute quality for a sustained period.

I do agree it’s such a shame we never signed Benzema when we had the small chance to. I remember him first bursting onto the scene and being so impressed by his play for a then 20/21 year old would have been a great player for us too under Sir Alex.

We got a world record fee and so I don’t think we got a bad deal at all but we invested that money so poorly in the squad that it’s hard to look back and say it was worth it. But as we all know we got one more season out of Ronaldo than we could have got.

That window looking back though sealed our fate as no longer a giant in Europe. Lost Ronaldo and Tevez and didn’t bring in players of the requisite quality like Ribery, Robben, Sneijder, Eto’o, Villa, Benzema, Ibrahimovic, D.Silva, Aguero all of whom with a bit more of a push were possible movers.

 

[Neil_Buchanan]

We should have told Madrid that they can only have Ronaldo if they leave Benzema to us, him and Rooney together would have been spectacular.

 

[Invictus]

From memory, Madrid signed both Alfredo Di Stéfano and Paco Gento in 1953. That would be the greatest transfer sequence in club history (and consequently of all time, for any team), because as good as Cristiano and Benzema have been, they never truly matched, let alone eclipsed, the legacies and accomplishments of the primordial gods. Di Stéfano finished his career as maybe the greatest player in football history, guided Madrid to a level that no one thought was possible, was the club's highest scorer by a considerable distance at this time of his retirement, the highest scorer in European Cups, the highest scorer in La Liga, and on and on; and Gento was his near-perfect partner in crime, as well as the bridge to the Ye-yé generation — winning a record 6 European Cups and a record 12 La Liga titles in total, while setting the record for appearances and scoring the most goals after Di Stéfano and Puskás.

P.S. Of course, I might be misremembering the order of events — which would invalidate the entire argument.

 

[Morty_]

Ronaldo and Benzema are the big 2 from that transfer window, no doubt, and they also signed Xabi Alonso who was very good for them as well.

Kaka was a flop though, but overall, it was an amazing transfer window.

Not quite on the same level, but the money Liverpool got for Coutinho was very well spent, to say the least.

 

[JPRouve]

Due to Longevity the Benzema-Ronaldo duo beats any other examples but in 2001 Juventus signed Nedved, Buffon and Thuram which in terms of quality is exceptional.

 

[PoTMS]

Manchester United - Summer 2022

Rice, Kane and Webster. Only the £250m.

 

[led_scholes]

2009 was also when Bayern bought Robben and Inter Snjeider right? Coincidentally, from Real too. Also, Toure and Barry to City, Silva to Milan.

Was that the summer of "no value in the market"?

 

[Iker Quesadillas]

Real Madrid summer 2013 wasn't half-bad. It's the one that actually got the trophies to start rolling.

 

[ThierryFabregas]

I mean it's government backed financial doping. Isn't 70m in 2009 like 300m today footballistically? And you're buying a player who's obviously a generational talent.

 

[ti vu]

Don't remind Perez or he's gonna Mpabbe, Dembele and Lahaand this summer on cheap.

 

[Gio]

Topic for discussion on a plate:


It's got to be the best transfer window a club has ever had, surely?

I put forth Milan's Van Basten - Gullit acquisition as a challenger, but that Madrid pairing have them beat in every aspect, really and we're talking about magnitude at this end of the market: players that are legion and part of the fabric of their clubs. So, even on that score, who enters the discussion? Can what Madrid did that summer be matched, let alone beat by anyone else?

It was sickening to sell them Ronaldo for £80m at the time when we should have been pushing for a lot more, and in hindsight, they easily, easily got the better end of the deal.

I think it's closer than that. In the 5 years after they were signed, Van Basten won 3 Ballon D'Ors and Gullit won 1. As much as I rate Benzema, he's never even been in a conversation for a Ballon D'Or until now. And there's probably some era-specific context to those signings. There was less room for error in a transfer window in 1987. With only 3 foreigners allowed, clubs could not afford to make a single mistake in the market. Van Basten and Gullit were perfect signings because they both fitted into Sacchi's hard-working and collective ethos, while also elevating the whole team with their quality from the front, filling a quality gap that the Italian players could not meet. All of that said Benzema and Ronaldo win out for longevity given their overall contributions for several years after, comparatively, injury affected or ended the careers of the Dutch duo.

Just an aside on those assist stats in the OP - I'm not sure how back they go to actually be 'all-time'. But roughly speaking Di Stefano played 400 games for Real and was estimated to assist around 0.4 assists per game in his career, which would put him around par with Benzema's current total of 160 or so in 600 games.

 

[Lentwood]

I mean it's government backed financial doping. Isn't 70m in 2009 like 300m today footballistically? And you're buying a player who's obviously a generational talent.

Don't start this on here

The concept of transfer inflation goes well over people's heads. £70m is loads because it's 44 Eric Cantona's, but it's also a bargain because it's only half a Coutinho.

 

[the_cliff]

I think it's closer than that. In the 5 years after they were signed, Van Basten won 3 Ballon D'Ors and Gullit won 1. As much as I rate Benzema, he's never even been in a conversation for a Ballon D'Or until now. And there's probably some era-specific context to those signings. There was less room for error in a transfer window in 1987. With only 3 foreigners allowed, clubs could not afford to make a single mistake in the market. Van Basten and Gullit were perfect signings because they both fitted into Sacchi's hard-working and collective ethos, while also elevating the whole team with their quality from the front, filling a quality gap that the Italian players could not meet. All of that said Benzema and Ronaldo win out for longevity given their overall contributions for several years after, comparatively, injury affected or ended the careers of the Dutch duo.

Just an aside on those assist stats in the OP - I'm not sure how back they go to actually be 'all-time'. But roughly speaking Di Stefano played 400 games for Real and was estimated to assist around 0.4 assists per game in his career, which would put him around par with Benzema's current total of 160 or so in 600 games.

Of course assists has only been statistically recorded recently, the source I used has Benzema first, Ronaldo second and Figo third (There was also no mention of Di Stefano and players of his time as they probably don't have statistical data). I was also speaking more in terms of records and numbers, to sign 2 players the same season and fast forward 13 years later for them both to be in your top 3 assists/goals all time is incredible, especially for a team as big as Real Madrid.

I'm not sure it's been done before (in recent history) and I'm pretty sure it might not be done again.

 

[NoLogo]

I don't think this could ever be matched, not with todays transfer prices, they bought 3 Ballon D'Or winners in one transfer window. Don't think that will ever happen again.

 

[AndySmith1990]

Manchester United - Summer 2022

Rice, Kane and Webster. Only the £250m.

Summer 2023
we need to get rid of all the shite Poch signed last summer

 

[Luke1995]

In terms of results, Inter's 2009 one could very well top Madrid's own.

Sneijder and Eto'o were absolutely a big part of their treble. Also Lucio, Pandev and Diego Milito played their part.

Obviously when you consider Ronaldo's and Benzema's longevity, Madrid had the better window overall, but looking at that 2009-2010 season, Inter''s smartness was great.

 

[cyberman]

Isn’t Ronaldo both all time CL goal scorer and most assists?

 

[jm99]

2009 was also when Bayern bought Robben and Inter Snjeider right? Coincidentally, from Real too. Also, Toure and Barry to City, Silva to Milan.

Was that the summer of "no value in the market"?

I've never been so frustrated with a transfer decision we've made as I was at taking a straight £80m for Ronaldo, when Madrid had robben, sneijder and Van Der vaart that they wanted rid of and could have used as part exchange. Then to sign obertan, Valencia and Owen

 

[Dancfc]

I think Liverpool in 2018 has to be there or there abouts.

They went to a good team with flaws holding them back in crucial areas to plugging those holes practically overnight which turned them from top 4 scrapers to a late 90s points team.

 

[RacingClub]

Chelsea 2004/05 Drogba, Cech, Robben, Carvalho and Ferreira (Tiago and Kezman to a lesser extent) has to be be up there with the most transformative windows.

 

[Red the Bear]

Psg transfer has Obviously been a disaster by now but it could funnily enough change in the future, say Messi has a last hurray sort of performance the next season and both ashraf and donoroma turn out to be great future investments ( ashraf has already been) and wjnaldom going back to his best, not that I think they will but it's still a possibility.

Also it's nice to remember that real's transfer window didn't work out the first season and was kinda of a disappointment (Ronaldo scored less than what you expect of him , benzema was meh and kaka always injured) so there's always time for it to change.

Also I don't think we'll ever see one ever again as the prices have simply gone too out of control to ever pull that sort of madness ever again ( that Ronaldo might as well go for 300 mil in today's market)

 

[Red the Bear]

Summer 2023
we need to get rid of all the shite Poch signed last summer

Who's the third one?

 

[Varun]

Madrid may top that this year if they get Haaland and Mbappe both

 

[Red the Bear]

Madrid may top that this year if they get Haaland and Mbappe both

They won't as neither will be willing to play second man to the other.

 

[Bondi77]

1992 was the best one I can remember.

 

[Lay]

In terms of results, Inter's 2009 one could very well top Madrid's own.

Sneijder and Eto'o were absolutely a big part of their treble. Also Lucio, Pandev and Diego Milito played their part.

Obviously when you consider Ronaldo's and Benzema's longevity, Madrid had the better window overall, but looking at that 2009-2010 season, Inter''s smartness was great.

Good shout. Won the UCL immediately

 

[1988]

Topic for discussion on a plate:


It's got to be the best transfer window a club has ever had, surely?

I put forth Milan's Van Basten - Gullit acquisition as a challenger, but that Madrid pairing have them beat in every aspect, really and we're talking about magnitude at this end of the market: players that are legion and part of the fabric of their clubs. So, even on that score, who enters the discussion? Can what Madrid did that summer be matched, let alone beat by anyone else?

It was sickening to sell them Ronaldo for £80m at the time when we should have been pushing for a lot more, and in hindsight, they easily, easily got the better end of the deal.

You can't leave Xabi Alonso out. Phenomenal player.

 

[the_cliff]

Could be up there with the greatest strike partnership of all time as well. Some of the goals here are incredible. The chemistry between them, the movement, the technical ability, the finishing.

 

[giorno]

In terms of results, Inter's 2009 one could very well top Madrid's own.

Sneijder and Eto'o were absolutely a big part of their treble. Also Lucio, Pandev and Diego Milito played their part.

This is kind of funny

"Modric and Bale were absolutely a big part of real madrid's 3 CL. Oh yeah, and i guess Cristiano and Sergio Ramos were good too"

 

[B20]

John Aldridge, Ray Houghton, Peter Beardsley and John Barnes has to be up there for English clubs.

 

[Luke1995]

This is kind of funny

"Modric and Bale were absolutely a big part of real madrid's 3 CL. Oh yeah, and i guess Cristiano and Sergio Ramos were good too"

Well, I was talking about players Inter signed in the 2009 summer window.

 

[giorno]

Well, I was talking about players Inter signed in the 2009 summer window.

Which includes Lucio, Milito and Thiago Motta. Pandev came in the winter window

 

[Josh 76]

John Aldridge, Ray Houghton, Peter Beardsley and John Barnes has to be up there for English clubs.

Good shout

 

[desertegil]

What about worst transfer windows?

In Liverpool's 2010 summer window Roy Hodgson signed Paul Konchesky, Christian Poulsen, Raul Meireles, Joe Cole and Milan Jovanovic for the first team.

The following summer Cole was loaned to Lille and the rest were sold for a loss.

 

[B20]

What about worst transfer windows?

In Liverpool's 2010 summer window Roy Hodgson signed Paul Konchesky, Christian Poulsen, Raul Meireles, Joe Cole and Milan Jovanovic for the first team.

The following summer Cole was loaned to Lille and the rest were sold for a loss.

We also signed Hodgson. And had g&h. And purslow.

Genuinely the darkest days of the club.

 

[donkeyfish]

What about worst transfer windows?

In Liverpool's 2010 summer window Roy Hodgson signed Paul Konchesky, Christian Poulsen, Raul Meireles, Joe Cole and Milan Jovanovic for the first team.

The following summer Cole was loaned to Lille and the rest were sold for a loss.

 

[GhastlyHun]

We also signed Hodgson. And had g&h. And purslow.

Genuinely the darkest days of the club.

Weird to think how close (releative to Pool's great PL drought) this happened to the arrival of the Kloppsiah

 

[Dave Smith]

I think the Milan Van Basten-Gulliet one was the best, or at least the best duo. Real's CR7/Benz one is up their for best longevity but I think as a duo, they weren't quite ad transformative as VB/Ruud, even if they went on to have much longer careers. That said, I am not great with transfer pre-mid 80's.

As for the PL, I would say that the three best at pushing a team forward where:

Blackburn 92: Shearer, Le Saux, Sherwood, Berg

Chelsea 05: Cech, Robben, Carvalho, Drogba

City 10: Yaya, Silva, Dzeko, Boatang, Kolarov