Tottenham Hotspur got to the end of the summer transfer window having achieved plenty of positive things but that doesn’t mean they won’t have regrets.
The club’s managing director of football Fabio Paratici officially began work on July 1 and since that point has overseen the appointment of Nuno Espirito Santo as head coach and plenty of ins and outs at the north London outfit.
Tottenham brought Pierluigi Gollini, Bryan Gil, Cristian Romero, Pape Matar Sarr and Emerson Royal through the door.
Out the door and off the wage bill went Erik Lamela, Toby Alderweireld, Joe Hart, Juan Foyth, Moussa Sissoko, Serge Aurier, Danny Rose and Paulo Gazzaniga among others as Paratici oversaw a squad rebuild.
They also held on to Harry Kane and tied Son Heung-min down to a big new four-year contract.
Here are five things though that Spurs might have regretted when the transfer window closed this week:
Moving quicker on Martinez
Spurs thought they had agreed a big deal in principle, more than 60m euros plus add-ons, with cash-strapped Inter Milan for striker Lautaro Martinez only for the Italian side to receive a much bigger offer from Chelsea for Romelu Lukaku.
Inter did not want to – or in the end need to – sell both of their star strikers and they agreed on the bigger deal for Lukaku to leave Spurs disappointed.
Tottenham have a habit of deciding to make their best move for a player too late – just think of the debacle around trying to sign Jack Grealish from Aston Villa.
The intention was always to play Martinez up front with Harry Kane and the thought of the Argentine partnered with the England captain is a mouth-watering one.
You can’t help but wonder what would have happened if Spurs had just moved that little bit sooner. Inter’s financial woes were common knowledge long before.
One type of player that has been lacking for a while in Spurs’ squad is that Cristian Eriksen replacement, a playmaker who does his work in playing killer balls through to the strikers from an advanced position.
Tanguy Ndombele and Giovani Lo Celso play naturally more deeper but both can take on the role, while Dele Alli is more of a suddenly arriving in the box man than a creative player.
Gil could develop into the role while Lucas can also act as a number 10 if required.
However, nobody ticks all of the boxes like the Dane did in his pomp and if Spurs struggle for creativity in the months ahead they may look back to the decision not to move for an advanced playmaker and regret it.
Getting bigger fees
This is really a minor regret – maybe more so one for chairman Daniel Levy than the fans.
Spurs managed to finally get a lot of players out the door and off the wage books.
However, it was a case of players kept too long or simply a lack of interest in them for too many windows and their values had plummeted.
Foyth was the most lucrative departure and even the 15m euros agreed in his option to buy following his loan at Villarreal was pretty low after the event with his performances for the Spanish side, as their season ended with the Europa League trophy.
Most of the others departed for nothing or for nominal fees.
Ultimately the club’s wage structure will benefit but having a bit more in the bank to use towards new incoming players would have been a help.
Signing a back-up striker
When it became clear that signing a top drawer striker to play alongside Kane wasn’t going to happen, as both the avenues for Martinez and Fiorentina’s Dusan Vlahovic closed, Espirito Santo and Paratici made it clear that they did not see a back-up striker as a priority.
Espirito Santo sees Son as being comfortable playing up front, particularly in a front three or in a pair, and would not be concerned about playing the South Korean star up front in Kane’s absence as he did early in the season.
There is also 17-year-old Dane Scarlett, who is learning his trade under Espirito Santo and alongside Kane and Son and he will continue to get minutes here and there, primarily in cup competitions, but he has also been on the bench for two of the three Premier League matches so far.
However, there still seems to be a hole in the squad for a back-up striker.
It’s difficult to find someone willing to play second fiddle to one of the world’s best strikers and it’s been something Spurs have struggled with.
However, they managed it with Carlos Vinicius last season and the Brazilian, now on loan at PSV, brought 10 goals to the table and allowed Kane to have a rest in the cup games.
Having Kane or Son as the options means that unless Scarlett suddenly develops with huge strides then either Son or Kane will always have to be present in every game and that’s not ideal.
Both Espirto Santo and Paratici are big fans of Adama Traore.
The Portuguese worked with the Spanish winger at Wolves and the Italian attempted to sign him while he was at Juventus with a bid of more than £50m.
While Tottenham have an abundance of wingers, Espirito Santo believes Traore, with his strength and pace, brings something unique.
The problem is that Wolves’ valuation of the player, who has two years left on his contract, is believed to be around the £50m mark.
Spurs were not willing to reach that valuation and while it’s hard to argue that, particularly with his lack of end product, Traore is worth that sort of money, there will be some regret that Paratici could not deliver the head coach a player he would have loved.
Source by Football London