The most painful transfers out of THFC

[Spurslove]

We're all excited about the current situation with players coming in, but which are the transfers out of the club down the years which have hurt us most (apart from the most obvious one with you-know-who joining you-know-who of course...)?

For me, Sheringham and then Berbatov going to United hit me really hard.
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[Monkey boy]

Klinsmann hurt me bad as i was still young and then Sheringham following not long after but the Bale one was on a whole other level. Having been pipped to 4th place by them lot and then losing our only shining light in an otherwise dull team it felt like we'd be stuck for mid table mediocrity for the next decade.

Also Berbatov to Utd was a kick in the nuts just because it seemed that Utd could and would just swoop in and take our players at will. Fergie meeting him at the airport and making a point of shaking his hand as if presenting him to the media when the deal had not even been completed made me very angry.

 

[Geyzer Soze]

Berbatov, Modric, Bale and of course Bongani Khumalo were the heartbreaks for me

 

[kursaal]

Archibald, Hoddle and Waddle were the ones that first broke my heart. Then Gazza and lastly Bale.

 

[Tucker]

Ginola. He didn’t want to leave, but that misery guts Graham wanted him gone.

 

[Nine while nine]

David Pleat has done a lot of wonderful things for Tottenham, but his treatment of Graham Roberts was a fucking disgrace and I was gutted when he went to Rangers. As our enthusiasm for Romero shows, we do love a player with a bit of steel to him, and Graham certainly had that.

 

[Chris Finch]

Weirdly Keane going to Liverpool. Berbatov was obvious he was off that summer and it was just a matter of where so wasn't as annoyed and I was thinking get the money in, spend it on a partner with Robbie (who had been excellent that season) and we'll be fine.

 

[littlewilly]

Souness.

 

[Spartanspurs]

Dele was a painful one. Everyone knew it was the best move for everyone but it was still a painful goodbye. Felt like the end of the Poch era to me as well for some reason, despite him moving on long before.

 

[0-Tibsy-0]

Ginola, Campbell, Sheringham...

The Carrick transfer pissed me off.

Bale and Modric were upsetting but you know no one really says no to Madrid.

More recently - loved Lamela and Dele but understood the reasons.

Not a transfer - but throwing Poch and Jol leaving in to the mix. Both of those going were very upsetting - there was a real affinity there.

 

[SpringHeeledJim]

Keane to Liverpool was awful. That one really hurt at the time

 

[Spursmatty87]

Klinsmann- I was devastated. Nothings hit me as much as that.

Ginola- just because it didn’t make sense and we didn’t buy a replacement and ended up with leonardson playing instead ?

 

[Cavehillspur]

I think Keane to Liverpool, Bale to Madrid and Carrick to United annoyed me the more than any others.

 

[arthurgrimsdell]

Jimmy Greaves. My formative years ended with that hellish announcement. Once something that bad happens any favourites leaving are merely a disappointment. I quite liked Martin Peters but he was no compensation.

 

[Oh Teddy Teddy]

I know he could barely last 65 minutes, but VDV was ditched by Villas Boas far too quickly. Think he had more to give for us but could just be he was a stout fan favourite.

 

[Rocksuperstar]

Teemu

I'd also say Andros Townsend as well - because of social media, for the first time, we got to see someone who had, literally, grown up at the club as a child having to leave the training ground for the last time and it hurt, I felt bad for him. Glad he's gone on to do well for himself.

 

[beats1]

It always felt like if we could kept a signing or two and invested it would have catapulted us

imagine Dembélé playing next to Modric and Parker/VDV

Van Der Vaart was painful as it was so unnecessary and it was shit by AVB, thank fuck his fan club dispersed

 

[rightwayup]

Hoddle for me was awful. Thought he would never leave, then when he was going hoped that he would change his mind. Still get emotional seeing that goal against Oxford.

 

[popstar7]

Seeing the back page of the Sun or the Mirror announcing Waddle’s transfer to Marseille. Huge money at the time but that didn’t really soften the blow.

 

[cjsimba]

VDV for me. Gone far too soon.