7 hours ago, Backbiter said:

I'd have Sterling ahead of Garnacho and Sutton. Nothing personal, but just a very bad signing at crazy wages. Agree with your top two.

7 hours ago, Backbiter said:

I'd have Sterling ahead of Garnacho and Sutton. Nothing personal, but just a very bad signing at crazy wages. Agree with your top two.

Fair. Though Sterling has not seemed to cause any issues, or been a jacka$$

47 minutes ago, axman2526 said:

Fair. Though Sterling has not seemed to cause any issues, or been a jacka$$

He hasn't, which is why I said there's nothing personal in my ranking him so high on my list of all-time bad buys, but he was a terrible signing on account of the fee, his wages and his contribution.

On 04/04/2026 at 09:26, C3blue said:

Kepa, world record fee? How the f**k did that happen.

We dicked around with Courtois at the end of 2017/18, instead of moving to secure Alisson in Jan 2018. Then instead of punting him at the start of the transfer window, we held out until the end and had to sign Kepa at his release clause.

11 hours ago, Backbiter said:

I'd have Sterling ahead of Garnacho and Sutton. Nothing personal, but just a very bad signing at crazy wages. Agree with your top two.

Still think it's just too soon on Garnacho given his age. The crazy wages are an issue, but at least we did not sign Sancho from them. in football, what looks like crazy wages today may not seem that crazy tomorrow. 😅

1. Lukaku

2. Kepa

3. Sheva

4. Torres

5. Bakayoko

6. Kk

7. Sterling

8. Mudryk

9. Nkunku

10. Morata

11. Cudrado

12. Disasi

13. AvB (though a coach deserves to be here)

14. Pulisic

On 28/03/2026 at 17:41, Timmy Elms said:

In no particular order. Fleck, Fleck, Fleck, Fleck, Fleck, Fleck, Fleck and Fleck

That’ll be Fleck then!😀

In no order.

Sutton,

Lukaku,

Kepa,

Drinkwater

Mudryk.

Bogarde

Bolareouz

Bakayoko

Sutton

Marin

Pre prem

Mitchell

Mayes

Liningstone

Docherty

Fleck

17 hours ago, PloKoon13 said:

I'd say Kepa but it has been slightly mitigated by later inflicting him upon Arsenal. Makes Bobby Sánchez look like Lev Yashin.

This and it is not even close. Some mention Lukaku n Sterling, these two didn't workout but they were clearly good players.

Kepa on the other hand feel more like a scam.

I’ll admit when we signed Brian Laudrup in the summer of 1998. He’d be a brilliant player for us.

And when we bought Lukaku the second time. I thought he’d be a great signing and score a lot goals.

The lack of Torres and Shevchenko high up on these lists is so surprising. I can't decide whether it's because time heals all wounds, or whether it's because our transfer business somehow got worse after they left!

My top 5:

1. Torres - Firstly, it derailed the Ancelotti years after we had fought hard to be a force again, and secondly the fallout clearly led Abramovich to reduce spending and investment. The biggest issue, however, was the opportunity cost - by signing Torres we missed on on Sergio Aguero, who we were also in for at the time and could have easily beaten City to.
   

2. Shevchenko - our first 'reality check' under Roman. Shevchenko's failure was seismic because it made us look vulnerable again as a club and it made Jose Mourinho look like he'd lost his magic touch. Shevchenko's transfer was the catalyst behind a lot of things that eroded the club: the rift with Mourinho, the departure of Robben, the introduction of the 'death of football' midfield and the struggle between boardroom, manager and players that never really healed until Sarri/Lampard/Tuchel. It was a cultural mess that the club hadn't really seen since Vialli had the rug pulled out from under him.
   

3. Shaun Wright-Phillips - a high-profile vanity project that fanned the flames of media resentment even more. The money spent on him was massive at the time (equivalent to a 80m+ signing now). He added nothing to the team and couldn't handle the pressure of such an environment.
   

4. Tiemoue Bakoyoko - Reading the thread at the time, I remember thinking that Monaco's golden generation was similar to the 1995 A**x team; we could pay top money for a world-beater (Mbappe, Fabinho, Silva) or try be clever and sign the Jari Litmanen of that bunch for cheap. The club outdid all my expectations by paying top dollar for the worst player in that team. Again, it wasn't just the money but the fact that his failures left Conte's plans in a heap after Matic's loss of form and eventual departure, and arguably contributed to Kante's burnout and recurrent injury. Just never looked nor acted like a top-flight footballer from day 1.
   

5. Bogarde - but not for the money. It was the damage to the club and to its reputation that followed that hurt more. Vialli later claimed he had no knowledge of the transfer and it was entirely done by Colin Hutchinson. It's possible that he had already lost the dressing room by that pre-season. Bogarde became synonymous with Chelsea waste, but I think history has been harsher on him than it has on the club.

You’ve all forgotten about the legendary Mineiro who’s now plying his skills in an amateur Australian league playing against former socceram gold years and What Did You Do Yesterday? presenter Max Rushden.

22 minutes ago, Munkunku said:

You’ve all forgotten about the legendary Mineiro who’s now plying his skills in an amateur Australian league playing against former socceram gold years and What Did You Do Yesterday? presenter Max Rushden.

Actually, he's coaching

13 hours ago, SydneyChelsea said:

We dicked around with Courtois at the end of 2017/18, instead of moving to secure Alisson in Jan 2018. Then instead of punting him at the start of the transfer window, we held out until the end and had to sign Kepa at his release clause.

Other keepers were available, surely.

12 hours ago, SydneyChelsea said:

Actually, he's coaching

That article is three years old & he’s only playing amateur football, he can do both.

4 hours ago, Munkunku said:

That article is three years old & he’s only playing amateur football, he can do both.

I forgot to mention that Max Rushden is considered some sort of top-tier sports presenter god over here, for some reason. Truly a meeting of the mediocre

10 hours ago, Backbiter said:

Other keepers were available, surely.

Donnarumma would surely have been the preferred option were it not for his agent at the time being Mino Raiola, whom the club basically banned in 2017 after the Lukaku saga.

Another problem was that most of the top-tier of keepers at the time had just completed their moves. IMO we should have gone for Jan Oblak as a straight swap, since we were never getting a huge fee for Courtois and he just wanted to move to Madrid so probably would have preferred returning to Atletico.

26 minutes ago, SydneyChelsea said:

I forgot to mention that Max Rushden is considered some sort of top-tier sports presenter god over here, for some reason. Truly a meeting of the mediocre

Donnarumma would surely have been the preferred option were it not for his agent at the time being Mino Raiola, whom the club basically banned in 2017 after the Lukaku saga.

Another problem was that most of the top-tier of keepers at the time had just completed their moves. IMO we should have gone for Jan Oblak as a straight swap, since we were never getting a huge fee for Courtois and he just wanted to move to Madrid so probably would have preferred returning to Atletico.

Kepa was basically sarri signing, he was recommended by Reina to sarri

1 hour ago, Bob stark said:

Kepa was basically sarri signing, he was recommended by Reina to sarri

Reina recommended Sarri to Kepa, not the other way around

6 hours ago, SydneyChelsea said:

I forgot to mention that Max Rushden is considered some sort of top-tier sports presenter god over here, for some reason. Truly a meeting of the mediocre

Max is a broadcasting legend and I won’t hear a bad word against him.

4 hours ago, Munkunku said:

Max is a broadcasting legend and I won’t hear a bad word against him.

Max is a nice, affable chappie with one big black mark against him.

On 06/04/2026 at 09:38, AndyDowsleftflank said:

1: Paul Winstanley

2: Laurence Stewart

3: Ben Roberts

4: Sam Jewell

5: Joe Shields

Was going to say exactly the smae. Blue Co are our worst signings. set the club back decades.

21 hours ago, bluelightening said:

Was going to say exactly the smae. Blue Co are our worst signings. set the club back decades.

Unfortunately, yes

1. Nicolas Jackson - almost £40 for a donkey of a player, that we are lumped with on along term contract. Sex pest. petulant. utterly rubbish at football. atrocious human being and an even worse footballer.

2. Lukaku - purchased for close to £100m, and didnt want to play for us

3. Kepa - purchased for £71m, loaned out, sold for a token fee

4. Bakyoko - winner of worst performance ever (think it was that first half against watford?) - signed for £40m, let go on a free. Terrible player.

5. Mudryk - Big bucks, almost always useless, social media scandals. drugs.

Lukaku for me was very disappointing, I don't think he ever wanted to stay here.

Torres I think had a mental breakdown, though he secured us a champions league final in the Nou Camp.

Shevchencko, the most shocking thing was seeing him play for Ukraine after he look finished with us.

Batshuyai most frustrating.

Fleck.

Pier Luigi Casirgahi - injured much too quickly.

Gael Kakuta - looked so skilful early on yet did not deliver.

.

On 08/02/2022 at 08:01, PloKoon13 said:

Haha I saw this out of the context of the post you were replying to and wondered 'why does this guy hate left-backs so much?'

In my opinion Zhirkov and Luis were both legitimately good for us, in fact in the case of the latter there were quite a few shouts to drop Ivanovic for him and move Azpilicueta to right-back. Zhirkov had the misfortune of his competition being the best left-back on the planet (Ashley Cole) and Florent Malouda in the form of his life. If I remember right he did have a brief spell in centre midfield in Ancelotti's second season when everyone bar a recently-signed and misfiring Ramires and the only sane man Mikel were injured.

On 08/02/2022 at 08:01, PloKoon13 said:

Haha I saw this out of the context of the post you were replying to and wondered 'why does this guy hate left-backs so much?'

In my opinion Zhirkov and Luis were both legitimately good for us, in fact in the case of the latter there were quite a few shouts to drop Ivanovic for him and move Azpilicueta to right-back. Zhirkov had the misfortune of his competition being the best left-back on the planet (Ashley Cole) and Florent Malouda in the form of his life. If I remember right he did have a brief spell in centre midfield in Ancelotti's second season when everyone bar a recently-signed and misfiring Ramires and the only sane man Mikel were injured.

On 08/02/2022 at 01:15, Brigadeiro Mk II said:

5. Zhirkov (I'm not even sure if he was signed as a LB or a left winger, but oh well)

4. Del Horno

3. Kennedy

2. Filipe Luis

1. Baba Rahman

We try...

Also, from the lot of useless signings shout-out to my countryman Mineiro! What a player! (He was really good at São Paulo, but I guess the same can be said about Baka in Monaco?)

You know i liked Kennedy but sadly he was not good enough and now we only sign players who are Kennedys.