PloKoon13
I don't like that kind of talk
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Giving it some thought, this is harder to answer than I initially expected.
The notoriously expensive (in contemporary context) disasters often have caveats; Torres scored a decisive goal in the Europa League Final, and was part of our first Champions League-winning squad, and not to mention scored that goal against Barcelona. Kepa was also part of a Europa League-winning side, and has provided a number of memorable moments in penalty shoot-outs (including one against Tottenham in a League Cup semi). Most of the egregiously overpriced squad players who turned out to be sh*te didn't actually impact the squad all that negatively and barely presented a drop in the ocean financially or in terms of overall negative impact. (Veron, Drinkwater, Rahman, etc.) Even Shevchenko scored that belter against Tottenham!
The world in which we have existed for the past two decades has made it hard for an individual signing to be all that harmful. Should Tiemoué Bakayoko and Danny Drinkwater prove to be 70 million pounds' worth of idiot, an über-wealthy club can simply spend a further 90 million pounds on Jorginho and Mateo Kovačić the following summer and immediately rectify the problem. What does it matter if Juan Cuadrado doesn't work out straight away when six months later you can go out and buy Pedro Rodriguez? After our two worst transfer windows in recent memory we've finished 10th and 5th; on each occasion, the following season we have qualified for the Champions' League and won a major trophy.
While it is tempting to shrug and simply pick five expensive players I don't like, I think the most harmful transfers would have to come from before a time in which we have so much money that potential negative impact is almost entirely mitigated. I'm in my thirties so have only ever known a Chelsea in the top flight, and even as a kid we were in a position to sign Chris Sutton for £10m, realise he's sh*t, sign Ballon d'Or winner George Weah on loan in January to cover the remainder of the season, win the FA Cup and finish in the quarter-finals of the Champions' League, then spend £15m on Jimmy Floyd Hasselbaink the following summer. Realistically the answer to this question came during a time when the stakes were far higher, and the club wasn't in a position to simply spend their way out of trouble, i.e. before I was born.
The notoriously expensive (in contemporary context) disasters often have caveats; Torres scored a decisive goal in the Europa League Final, and was part of our first Champions League-winning squad, and not to mention scored that goal against Barcelona. Kepa was also part of a Europa League-winning side, and has provided a number of memorable moments in penalty shoot-outs (including one against Tottenham in a League Cup semi). Most of the egregiously overpriced squad players who turned out to be sh*te didn't actually impact the squad all that negatively and barely presented a drop in the ocean financially or in terms of overall negative impact. (Veron, Drinkwater, Rahman, etc.) Even Shevchenko scored that belter against Tottenham!
The world in which we have existed for the past two decades has made it hard for an individual signing to be all that harmful. Should Tiemoué Bakayoko and Danny Drinkwater prove to be 70 million pounds' worth of idiot, an über-wealthy club can simply spend a further 90 million pounds on Jorginho and Mateo Kovačić the following summer and immediately rectify the problem. What does it matter if Juan Cuadrado doesn't work out straight away when six months later you can go out and buy Pedro Rodriguez? After our two worst transfer windows in recent memory we've finished 10th and 5th; on each occasion, the following season we have qualified for the Champions' League and won a major trophy.
While it is tempting to shrug and simply pick five expensive players I don't like, I think the most harmful transfers would have to come from before a time in which we have so much money that potential negative impact is almost entirely mitigated. I'm in my thirties so have only ever known a Chelsea in the top flight, and even as a kid we were in a position to sign Chris Sutton for £10m, realise he's sh*t, sign Ballon d'Or winner George Weah on loan in January to cover the remainder of the season, win the FA Cup and finish in the quarter-finals of the Champions' League, then spend £15m on Jimmy Floyd Hasselbaink the following summer. Realistically the answer to this question came during a time when the stakes were far higher, and the club wasn't in a position to simply spend their way out of trouble, i.e. before I was born.
(source: Athletic)
