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Tottenham allowed a number of young players to leave the club in the summer transfer window, as Roberto De Zerbi put his own stamp on the squad he inherited.
The biggest departure was that of Luka Vuskovic to Brighton, for £50million having never played a game for Spurs. He is making waves with the Seagulls, proving the transfer decision wrong, but he is not the only one making Tottenham rue their outgoing summer business.
Former Tottenham forward Will Lankshear has had an outstanding start to the new season. The 21-year-old, who spent last season on loan at Oxford United, left Spurs on a permanent deal in the summer and signed for Championship promotion-chasers Middlesbrough.
He penned a five-year contract at the Riverside Stadium with Boro paying an initial fee of £10million, which could rise to a club-record £20m if various performance-related add-ons are met.
Since his move to Boro, Lankshear has been in inspired form, netting an impressive 13 goals in 13 Championship appearances this season, and he is the division's top scorer by quite a distance.
Lankshear netted on his debut in a 1-0 win against Wrexham in the Carabao Cup back in August, and hasn't looked back since. He followed that up with a brace in a 2-1 comeback success at home to Lincoln City and has helped spearhead an excellent start to the campaign for Boro.
A 3-0 win against Charlton Athletic - a game in which Lankshear scored twice - on Saturday ensured Kim Hellberg's side remained top of the Championship after winning eight and drawing four of their opening 13 matches. They sit two points ahead of second-place Swansea City.
There is no doubt that Tottenham made a mistake by selling Lankshear, but it's all well and good saying that now with hindsight. Last season, he showed glimpses during his time at Oxford, where he scored 11 times in 44 matches, but he was nowhere near consistent enough.
Part of that was down to Oxford struggling and not creating enough chances, but it didn't feel as though Lankshear did enough at times, whether that be in front of goal or with his all-round game.
However, Lankshear appears to have turned it up a notch at Boro this season and is the complete package. He can drop in and help link the build-up, but then spin in behind with his athleticism and be a poacher inside the box, where he has scored the vast majority of his goals this season.
Indeed, 11 of his 13 league goals for Boro have come in the 18-yard area. But Lankshear did find the net from a rare long-range strike against Charlton, with some comparing him to Tottenham legend and now-Ballon d'Or winner Harry Kane.
Picking the ball up just outside the box, Lankshear took three touches before bending the ball with his weaker left foot into the far top corner. It was a fine finish from the England Under 21s international and some Tottenham fans are calling for the club to bring him back.
Although Tottenham don't have a buy-back clause inserted into his Boro contract, they have a 20 per cent sell-on fee and hold matching rights. Therefore, if Boro accept a future offer for Lankshear from another club, Tottenham must be notified and has the right to match that bid.
Regardless, Tottenham should have kept Lankshear and now need to attempt to bring him back to the club in January. He would be an upgrade on Dominic Solanke, and although he is unproven in the Premier League, and he would start for Roberto De Zerbi's side right now.
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Spurs are desperate for someone of his capabilities to lead the line and put the ball in the back of the net, and Lankshear would be able to do both. He is the best forward in the EFL by a long shot and would be pushing the top 10 in the Premier League if he got the chance.
Tottenham did some great work in the summer transfer window, buying talent to strengthen the squad and selling several unwanted players, but getting rid of Lankshear was their biggest mistake.
Solanke is Tottenham's only recognised senior striker at the club and he has endured a woeful start to the season, scoring once in nine league matches. A number of other players, including Omar Marmoush, can be used through the middle, but Solanke has been preferred.
Due to his recent form, Lankshear would be a considerable upgrade on Solanke and even if it takes £50m, Tottenham should re-sign him during the winter transfer window. Fifteen goals in 16 matches, regardless of the division, are numbers that cannot be sniffed at.