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.