Daniel Levy faces a pivotal summer as Tottenham prepare for the 2021/22 season.
With Jose Mourinho's future right at the top of the chairman's list at present given the team's dreadful run of form this year, he also has calls to make over a number of his playing squad.
Discussions need to take place over those who will soon be in the final year of their contract, with the club also needing to make a final decision over whether or not loan duo Gareth Bale and Carlos Vinicius return for next season.
In the case of the latter, Spurs may in fact find themselves in an all too familiar position if they elect against signing the Brazilian on a permanent deal form Benfica.
Joining the club on a season-long loan deal in October as the club finally ended their long search for a striker to play second fiddle to Harry Kane, Vinicius has caught the eye with ten goals and three assists form his 24 games in all competitions.
While many may point to the fact that nine of his strikes have come in cup competition, the 26-year-old has more than done the job he was brought into the club to do.
One negative to the loan move so far has been the striker's lack of action in the Premier League after playing 303 minutes across nine games, although that was always going to be the case with Kane only ever out of the team when injured.
The terms of the loan agreement between the clubs does allow Tottenham to buy Vinicius at the end of the season for a fee of around £36million.
However, that is a price Levy will be looking to drive right down if they do decide to make the striker's move permanent.
Quite what fee Benfica will accept for Vinicius remains to be seen, but Spurs ideally need to save a lot of money in a summer where cash isn't going to be freely available due to the limited revenue coming into the club over the past 12 months.
Right now Tottenham have a striker in Vinicius on their hands who has proved he can score regularly and is willing to be second choice behind Kane.
Given very few strikers are prepared to move to north London knowing their game time will be extremely limited with the England captain the first name on the teamsheet, it's rather hard to find a man who can not only score but is also happy at the club despite a lack of Premier League minutes.
Amid some reports stating that Tottenham will not be taking up their option to buy the Brazilian, Vinicius' future has been a talking point back in Portugal, with Benfica needing someone to help lighten the load on Haris Seferovic.
Speaking to Portuguese publication Record, Luis Neves, the man who scouted the frontman, believes he can still be an important figure for Benfica if he does return to Lisbon next season.
“Vinícius is tremendously aggressive, especially against centre-backs, when he’s the other way around; he’s quick to attack from depth; he hits hard on goal; he has midfield qualities there; he’s very strong in looking for the ball,” he said, as reported by Sport Witness.
“[Jorge] Jesus is, for me, the best coach within the four lines of our country. I have a tremendous admiration for him. But attention, he’s very demanding, if a player doesn’t give the best… for some reason he had scored goals in the previous season and didn’t stay for this current one.
“It’s also certain that there’s no-one better than Jesus to polish this player, to give him even more shine and to make him a better player than what he already is. Jesus will make him score goals. If Jesus wants, we have another Vinicius in a year.”
Struggling in the past to find the perfect second striker to compete with Kane following Vincent Janssen's woes and Fernando Llorente's decision to part for regular first-team football elsewhere, Tottenham ideally don't want to be in the same boat as in years gone by once again ahead of next season.
Perhaps not worth paying the £36m to make his move permanent, Levy will have to work his magic to bring the price the right down in his bid to get his team a bargain.
In a year when Spurs need to make key changes to their squad given their form this campaign, as well as talk about a possible exit for Kane, one thing they cannot afford to do again is go into 2021/22 without a second out-and-out striker.
It has proved incredibly costly in the past and Tottenham must do everything to ensure that scenario isn't repeated all over again.
