Fabio Paratici has been working closely with his old club Juventus in an attempt to save Tottenham's transfer window with moves that will benefit Antonio Conte but raise some questions.
Paratici worked for the Turin club for 11 years and Spurs chairman Daniel Levy coveted the 49-year-old for around half of that before finally getting his man last summer as Tottenham's managing director of football, a far wider role than previous sporting directors at the north London outfit.
Since arriving, the Italian has been evaluating every single department within the football side of the club, given autonomy from Levy to make the necessary changes to raise the levels within Spurs to something approaching those he left at Juventus.
One of those areas that football.london understands has been given an increased budget is Tottenham's scouting department, with a flood of new scouts set to be hired for not only first team work but also for the club's academy, to increase the number of gifted young starlets Spurs produce from within.
In the mean time, the expectation, certainly from the fans, was that Paratici with his vast network of communication with agents and contacts at clubs across the world would bring talent aplenty through the door to improve the squad.
However, after missing out publicly to Barcelona and Liverpool having held talks to sign Adama Traore and bid for Luis Diaz this week, the Italian, who has been back in his homeland this week, has returned to what he knows and his old employers for some assistance with two players who will improve Tottenham's squad.
Juventus' versatile 21-year-old Dejan Kulusevski is set to fly to the UK today in order to undergo his medical at Hotspur Way and complete the formalities ahead of signing for Spurs on Monday's deadline day.
The deal is expected to be a loan one but with an option to buy for £33m, which becomes an obligation if certain criteria are met.
The Swede is a player Paratici has high hopes for and has previously enquired with the Turin club about.
The young midfielder came through the Atalanta academy set-up after moving to Italy as a 16-year-old and shone during two loan spells with Parma, once from Atalanta and again after Paratici took him to Juventus in 2019.
Kulusevski scored 10 goals and provided nine assists in 39 games for Parma and was named Serie A's young player of the year in the 2019/20 season, before adding another seven goals and seven assists in his first campaign for Juventus last year.
This season the Swede has found opportunities harder to come by with two goals and three assists in 27 appearances for the Turin side so far this term, more than half of those coming off the bench in a variety of positions. He has scored twice in his past five matches though, with recent goals against Roma and Cagliari in Serie A.
Spurs are also believed to be closing in on another deal for a Juventus player, 24-year-old central midfielder Rodrigo Bentancur.
The Uruguayan was taken to the Old Lady by Paratici in 2017 after becoming a young star at Boca Juniors in Argentina.
Bentancur helped Juventus to two Serie A titles as he continued to adapt to Italian football before becoming a key figure in the centre of the pitch for their third title win in the 2019/20 season.
He started most of the club's matches last season as they finished fourth, but has found himself in and out of the team this term with Juventus currently sitting fifth under Massimiliano Allegri.
Aston Villa have also been involved in talks for the South American, but are understood to have pulled out of these with the player's preference believed to be a reunion with Paratici and Spurs are trying to tie up a permanent deal for him.
football.london understands that Paratici has also held talks this month with the representatives of another Juventus midfielder in Weston McKennie about a potential move.
Paratici remains a big admirer of the 23-year-old USA international, who he took to Juventus from Schalke in 2020, but a switch this month was deemed unlikely.
The versatile Texan, who can play either as a box to box midfielder, a defensive one or on the right or left of midfield, has been starting regularly for Juventus this season and Allegri is not believed to be keen on losing the American midway through the campaign.
Kulusevski and Bentancur would go some way to ticking the boxes decided upon in Paratici and Levy's squad evaluation and transfer meeting with head coach Antonio Conte earlier this month.
It was decided to go for right wing-back and an attacker, while Conte also asked for a central midfielder. A left-sided centre-back is also on the wanted list but was expected to be pushed until the summer, unless an opportunity rose late on with players leaving the club.
Kulusevski, a player Arsenal have also been looking at this month, can play naturally as a right winger but also up front if needed or as a central attacking midfielder.
He could help give some thrust to Spurs' attacking attempts while also providing another option alongside Harry Kane up front. Conte is believed to have wanted Inter Milan to sign the Swede during his time in Italy.
Bentancur will provide further competition in the centre of the park for Pierre-Emile Hojbjerg, Oliver Skipp and Harry Winks and he can also play on the right or left of a midfield three, giving Conte more options to play with a 3-5-2.
Not primarily known as a creator, the Uruguayan can chip in with the attacking efforts, recording eight assists in Serie A in the 2019/20 season when Juventus last swept to the title. He also collects yellow cards with his aggression in the centre of the park.
Paratici is believed to have enquired about other Juventus players and going back to raid his old club can be seen from two different sides when it comes to the Spurs transfer chief's methods.
On one hand, the moves makes sense as he rates these players highly, knows them inside out and whether they will suit both Conte and the Premier League plus their strengths and weaknesses, so scouting is not particularly required.
In what is seen as the most difficult of the two transfer windows, both will add to Tottenham's squad and give their head coach more options, something he has asked for.
Those more cynical might suggest that with an entire month of a transfer window plus the pre-planning for it, Paratici has simply had to return to his old club in the final days, helping them out with players he signed for them in the first place that they don't want any more.
Both players still have plenty of contract time left at Juventus and the Italian club will let both go for more than they originally paid for them if all of the terms are met.
There is an irony also that the funds for Paratici's old club will go towards helping them offset their signing of Fiorentina striker Dusan Vlahovic, a player Spurs' managing director of football wanted to sign last summer, although the flip side to that suggestion is that the Serbian's extra wages and transfer fee put pressure on his old club to part with a couple of players he liked, thus presenting an opportunity for Tottenham.
Spurs are looking to do more before the window closes in a frantic final 36 hours.
While links to Brighton midfielder Yves Bissouma and wing-back Djed Spence, on loan from Middlesbrough at Nottingham Forest, have been played down, Paratici is trying to bring in further faces before the window shuts.
Barcelona's Ousmane Dembele is one of a number of players offered to Spurs in recent days, although the 24-year-old's wages plus his numerous injury problems in recent seasons raise question marks over that deal being done unless the north London club believe in the final hours that the Frenchman is still worth taking a chance on.
After missing out on Traore, who was to be converted by Conte, Paratici will also try to bring in another right wing-back, particularly if Matt Doherty heads out of the exit door, and will continue to explore any late opportunities for a natural striker to join the squad should any arise.
That exit door at Hotspur Way could be a busy one if all of the players Conte has deemed expendable head through it.
Spurs are working on deals to send Tanguy Ndombele, Giovani Lo Celso and Dele Alli to other clubs before Monday's deadline.
They also have strong interest from Ajax in Steven Bergwijn and from a couple of Spanish clubs, including Valencia, in Bryan Gil.
Both would be slightly odd deals if completed, with Conte liking the 24-year-old Dutchman Bergwijn and repeatedly stating he was not keen on losing him, even before his match-winning heroics at Leicester.
Gil, just 20, was only signed for Tottenham six months ago by Paratici as one of the most exciting young talents in Spain and to ship him back there on loan so quickly, while helping him get minutes, will not aid his adaption to the English league and culture.
Centre-back Joe Rodon is also keen on a move out of Spurs, on loan or permanently, to get game time and there are some suggestions that if, as expected, Newcastle can prise Dan Burn away from Brighton then the south coast club could make a late enquiry for Rodon.
The Spurs players returned to Hotspur Way on Sunday following their six days off granted by Conte during the winter break and they are believed to have returned to a double training session to start the preparations for next weekend's FA Cup tie against Brighton.
All eyes will be on new faces though. Transfer deadline day always brings plenty of activity and Tottenham could be one of the busiest sides in the country on Monday.
