5. Peter Crouch
Considering that Spurs would eventually pay £10m to bring Peter Crouch back to White Hart Lane in 2009, it’s fair to say that the club made a mistake in letting him leave on the cheap when still a youngster.

Crouch was sold to QPR in 2000 for just £60,000. Within four seasons he was playing in the Premier League for Southampton and winning the first of 42 England caps. Thankfully the club more than got their money’s worth after paying an eight-figure sum to re-sign the striker, with Crouch scoring the vital goal at the Etihad which clinched Champions League qualification in 2009-10, before eventually being sold to Stoke for another £10m fee.

4. Iago Falque
The Spanish winger had enough talent to have spells at Real Madrid, Barcelona and Juventus as a youth player, before Tottenham signed Falque on a season-long loan in 2011, that was eventually made permanent when the club paid Juve €1m.

Falque would make a total of just eleven appearances for Spurs before being sold to Genoa for £3.5m in 2014, off the back of a successful loan spell at Rayo Vallecano. Yet while the club made a modest profit, you can’t help feel that Falque could have become a much more valuable asset had he been given more of a chance. Over the last four seasons in Serie A playing for Genoa, Roma and Torino, Falque has scored 21 goals in 59 league games.

3. Jermain Defoe
After Jermain Defoe only scored one goal in 14 Premier League appearances in 2013-14, he was sold for £6m to the MLS outfit Toronto. While it didn’t seem a bad fee for an ageing player, the signs were there to suggest that Defoe still has something left in the tank.

After all, the England striker had scored ten goals in 22 appearances in all competitions and after scoring twelve in 21 for Toronto, returned to the Premier League for Sunderland. In two and a half seasons Defoe would score 37 goals for the struggling club, before signing for Bournemouth this season. During a period in which Spurs have struggled to find cover for Harry Kane, you do wonder if Defoe could have been that man.


2. Teddy Sheringham
In an article published by Betway, journalist Adam Drury pondered what former Premier League strikers would be valued at in the modern transfer market. Based on the 31-year old Olivier Giroud’s £18m transfer to Chelsea in January 2018, Drury estimated that Teddy Sheringham would have been worth £20m at the same age.

Unfortunately, when Spurs sold the 31-year old Sheringham in 1997, it was for a fee of just £3.5m. Manchester United had baulked at the original valuation of £6m, citing the player’s age, so master negotiator Alan Sugar reduced the price and replaced Sheringham with the 30-year old Les Ferdinand… for £6m. You’re the one that should have been fired Alan.

1. Graeme Souness
When still a teenager, Graeme Souness told Bill Nicholson that he should be playing for the first team as he was the best player at the club. Nicholson disagreed and Souness was sold to Middlesbrough for £30,000 in 1972, having only played one game for Tottenham.

Souness could be accused of arrogance, but he had the talent to back it up. In 1978 he was sold to Liverpool for £350,000 and in seven seasons at Anfield won five league titles, three League Cups and three European cups. The deep-lying midfielder is arguably Liverpool’s greatest ever player and certainly the biggest talent that Spurs let slip through their fingers.



  1. Typo on Sheringham when he left he was 31 not 21. I believe that he also wanted a longer contract than the club were prepared to offer.

    Graeme Souness was seen as a trouble maker. He said he was homesick for Edinburgh – so went to Middlesborough! As time proved he did have a bit of an attitude on him, a bit of arrogance, but what a player. Part of the generation that made Bill Nick decide to quit – too soon.

    The real loss was Crouchy, who was sold too soon and too cheap.

    Things have changed a bit since then. Five “clangers” in 46 years looks good on paper, but like all clubs we let some other good ones go too.

    It is the duffers that we bought who were more frustrating!

  2. Players Spurs sold too soon? 1) Graeme Souness (Bill Nick’s biggest ever mistake). 2) Pat Jennings (Inexplicably not offered a new contract and sold to Arsenal when still in his prime) 3) Glenn Hoddle (Clashed with David Pleat and decided to leave/was sold, also while still in his prime). 4) Chris Waddle (Sold for financial reasons, in the prime of his career, after Irving Scholar bankrupted the club – ditto Paul Gascoigne, but we had the best of Gazza). 5) David Ginola (Sold by George Graham, despite being the best player at the club).

  3. Souness was only the last and worst of quite a few transfer blunders made by Bill Nicholson, from dud buys like Laurie Brown and David Jenkins from Arsenal, to ill-judged sales like Weller and Possee to Milwall, and Mullery back to Fulham within weeks of the UEFA Cup win to which he’d contributed so much. Towards the end of his tenure he seemed to have lost his nerve completely, with no big signings between Coates in ’71 and Conn in ’74, and the apparently successful youth policy which produced two FA Youth Cups in the early ’70s hardly plugged the gap, as our relegation in ’77 (after a very near miss in ’75) proved.
    His achievements at Tottenham in his early years were undeniably great, but it’s sadly just as undeniable that he left the club in a sorry state, with almost the whole of the team of stars which won a series of cups between 1967 and 1973 reaching their sell-by date without adequate replacements being found, his own awareness of the scale of the problem probably being as much a factor in his resignation as the general (and justified) disillusionment with modern football and modern footballers which was the accepted reason at the time. What he’d have made of football 2018 style, God only knows.

  4. Souness was NOT the bindipper’s best player ever. Dagleish, Ian Rush, Alan Hansen were all superior and more influential.
    Glenn Hoddle, Dave Mackay and Pat Jennings were our biggest sell on blunders

  5. Fully agree with CheshuntBoy

    I often think of that great 1960s/70s era.

    What about Jimmy Greaves ?
    One bad game vs Crystal Palace in the F.A. Cup in Jan 1970 and he and Gilzean were dropped.
    Jimmy was 29 at the time. The Clubs record goal scorer and voted the most popular Spurs player ever !!

    Before we knew it Nicholson bought Marin Peters from West Ham for 200,000 with Greaves thrown in.
    Peters was good but he was no Jimmy Greaves !

    The sale of Dave Mackay to Derby for 5,000 in 1968 was a poor decision. Mackay went on to captain Derby to the old Div 1 title. He put Spurs to the sword in a 8-2 victory at the Baseball Ground.

    Bobby Smith ( transferred to Brighton in 1964 ) and Cliff Jones ( to Fulham in 1968 ) had still something to contribute and I still think Martin Chivers was let go too soon.

    Jimmy Robertson to Arsenal in exchange for David Jenkins was totally bizarre. Jenkins only played 15 games and was shipped out.

  6. Thank you for a fine article and to the others for their contributions. Educational for me.
    You don’t sell folks like Greaves or Jones or Hoddle. You figure a way they can retire from the club.

    In the modern era, one can only wonder – what if – the most poignant 2 words in Spurs lexicon – Bale and Modric were the pillars of a team as a young Poch built DESK around them.

  7. The worst players bought by Spurs were: David Jenkins, Laurie Brown, Victor Janssen, N’Jie, Ben Alnwick, David Bentley, Nicola Berti, John Bostock, Jason Cundy, Gilberto, Helder Postiga, Bongani Khumalo, Oyvind Leonhardsen, Mbulelo Mabizela, Steven Pienaar, Grzegorz Rasiak, Serhiy Rebrov, Rohan Ricketts, Rodrigo Defendi, Moussa Saib, Benjamin Stambouli, Kazuyuki Toda and Paolo Tramezzani

    • David Jackson, how could you omit Venables inept chum from your list of bad buys ? The infamous Terrence William Fenwick. Gotta be the worst signing EVER.

  8. David Jackson, how could you omit Venables inept chum from your list of bad buys ? The infamous Terrence William Fenwick. Gotta be the worst signing EVER.


This site uses Akismet to reduce spam. Learn how your comment data is processed.