All you need to know: Tottenham's Transfer Window Rundown

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For the majority of Spurs fans, the 2023/2024 season can surely be considered a success. There were inconsistencies at times, but Ange Postecoglou brought with him a dogmatic, entertaining style of play that players and fans alike bought in on.

Spurs had been crying out for a bit of flair, and it feels like they have hit the jackpot with the Australian.

The Jose-Nuno-Conte (insert Mason multiple times) trauma seems such a long way away now - Spurs fans are truly loving Big Ange instead. Optimism like this hasn’t circulated around the club since the earlier days of the Mauricio Pochettino era.

The similarities are there between Poch and Postecoglou too. Both inherited slightly ageing and certainly underwhelming squads.

Furthermore, both also finished fifth in their first season at the club, scoring 64 and 66 points respectively. Pochettino managed to challenge for the league twice whilst at Spurs, could Postecoglou do the same?

The players seem to think so. Earlier this week James Maddison said the squad were looking to “make history” this season. It is clear they believe in the vision Postecoglou has set out at Tottenham.

But simply replacing the man in the dugout will not bring success, personnel must also change. Often the most frustrating thing for fans was seeing the players unable to perform the, admittedly tactically complex, demands of Postecoglou.

The team doesn’t feel like it is totally his just yet. Of course there have been moments. The first 10 games of last season where Spurs picked up 26 points out of a possible 30, arguably came too soon, with the team never going close to recreating such form later in the season.

Injuries hurt the team badly last season too. A period in late 2023 where both Cristian Romero and Micky van de Ven were out saw Spurs start matches with no recognised centre backs. James Maddison spent prolonged periods out the side, whilst Richarlison struggled to maintain consistent fitness.

The spine of the team never felt particularly settled, with the gap in quality from the starting XI to the reinforcements being glaringly obvious.

But the signs are there, and now Spurs must push on in the transfer market. It has been said that Spurs are in a very healthy position with regard to FFP and profit and sustainability rules, and would therefore be on hand to spend big this summer. So far, it hasn’t quite gone that way.

The need to rebuild

The biggest compliment you can pay to Daniel Levy is that since the chaos of Conte, he has made a sustained effort to bring back the joy of Tottenham that so many fans associate with the club.

All of a sudden, Spurs have began to assemble one of the most exciting young squads in Europe.

There has been big restructuring too. Scott Munn has arrived as chief football operator, Johan Lange as a technical director from Aston Villa, and it has been widely reported the club consult Fabio Paratici on a regular basis despite his football ban.

During this time, the club managed to move on many of the players who had reached their peak at the club long ago. Eric Dier was moved on to Bayern Munich in January, Pierre-Emile Hojberg left the club this week in a move to Marseille, and Tanguy Ndombele had his contract terminated at the start of the summer.

What could still happen in this transfer window?

The defence is certainly an area where it feels that Tottenham need to improve. They shipped 61 goals last season and looked fragile throughout. The club did well to recruit the services of Romanian centre back Radu Dragusin in January, but there are still issues at full back.

With Emerson Royal there are huge question marks when it comes to his suitability within the squad. The Brazilian has had a tough time at Spurs.

Initially signed as a defensive right-back under Nuno, converted to a make-shift attacking wingback under Conte, before finally being asked to transform into an inverted full-back under Ange.

Throughout his spells under the above three managers, Royal has shown that he is uncomfortable on the ball and simply doesn’t have the technical ability required.

Spurs will struggle to recoup the £25 million fee paid for him in 2021, but there is genuine interest surrounding his signature, with both AC Milan and Galatasaray circling.

A similar situation concerns Sergio Reguilon. Spurs will struggle to get back even half of the £30 million they spent on him. Despite having no potential suitors currently, the Spaniard impressed at Manchester United last season and having been left in England to pursue a move, there is little chance he will be at the club next season.

At the start of the summer, the club had been linked with Monaco right-back, Vanderson. However after Djed Spence’s impressive start to pre-season, it looks like there could be a future at Tottenham for him after all, and with European football next season squad depth could be crucial.

The midfield

Midfield is a tricky area for Spurs. Although this is a position where there seems to be good depth (Yves Bissouma, Pape Sarr and Rodrigo Bentancur are three quality players fighting for two midfield places), it felt like an all action, box-to-box destroyer in midfield was going to be signed.

Of course there is still time; the departure of Hojberg combined with the fact that Postecoglou clearly doesn’t fancy Oliver Skipp as an option means that no doubt Spurs will be sniffing around the market.

However, this is one of the most sought after positions in modern football and, at this time, any player Spurs do go after will come at a heavy premium.

Tottenham chose not to pursue a deal for Amadou Onana, who has now signed for Aston Villa. His technical profile, physical frame and the fact he is still only 22 would make you think he would have slotted seamlessly into the side.

Of course with Villa, Champions League football was likely a factor in his decision to head to the Midlands, and Postecoglou himself has stated many times that he is not interested in players solely motivated by the Champions League games.

Spurs have been heavily linked with Jacob Ramsey from Villa too, in a deal that would potentially see Giovanni Lo Celso heading the other way.

Ramsey isn’t quite a lone ‘6’, but he would be a welcome addition to the squad, bringing bags of energy and having a high ceiling.

Chelsea’s Conor Gallagher has also been heavily linked with a move to Tottenham over the last two seasons and has just one year left on his deal.

For Lo Celso, his time at Spurs should be ending this summer. His injury record is poor and it is another move, similar to Ndombele, that just hasn’t worked out.

However, there has been signing that Tottenham have managed to get over the line. 18 year old Archie Gray was signed for 40 million pounds from Leeds United this month. Gray is versatile and can play both midfield and at right-back, but has also featured as a centre back this pre-season.

With Gray what is most striking is his resistance to the press. He first caught the national eye in an FA Cup fixture against Chelsea this season, effortlessly controlling the game.

Leeds fans reckon they have lost a superstar, and hopefully Spurs fan will get to see plenty of Gray during the Europa League campaign if not the Premier League.

Questions over Spurs firepower: Werner not the long term answer

It is well known that Postecoglou’s style relies on his wingers having an intense directness to their play, as well as being imperious in the 1v1 duels with dribbles and take-ons. The wide areas are crucial when playing inverted full-backs, and it was the side's weakest area last season with Dejan Kulusevski in particular struggling at times.

Brennan Johnson came in and performed well, especially in terms of output when playing on the right hand side. His place in the side seems assured next season; he was a big investment and will only improve.

The left wing is trickier. Both Son and Richarlison played the role to a decent level last season, but it wasn’t until Timo Werner arrived that there was real consistency there in terms of a starting name.

Werner is not the answer long term. His extended loan is a win-win for Spurs, but the club needs to be looking to spend big in this area.

This is a key area that Spurs will look to strengthen on, and this week, Postecoglou said “what we [Tottenham] started with at the start of the summer is still there”, suggesting that their targets are still available and are being worked on.

The strongest rumour has been 18 year old Rennes wonderkid Desire Doue. A week or so ago it looked like Spurs might have a clear run at the Frenchman, but with heavy interest from PSG and Bayern Munich, it is hard to see how his head wouldn’t be turned.

The biggest name out there linked with Tottenham is Eberechi Eze.

The Crystal Palace forward has a £60 million release clause and is signed to CAA Base Agency, who represent Spurs’ Maddison, Son, Sarr and Pedro Porro.

Eze would be the dream signing: dynamic, skillful and a joy to watch - there is no Tottenham fan who would say no to this one. Of course that means Palace would be equally desperate to keep hold of their man - especially after selling Michael Olise to Bayern Munich.

It might be optimistic, but if Levy and Spurs are ready to pay the big up-front fee Palace are demanding then this should be a relatively straightforward one to pull off.

Pedro Neto is another name rumoured to be under consideration. His pace is frightening and he is without doubt one of the best 1v1 dribblers in the league. Against him is his injury record, the forward missed five months of the campaign last year with two separate hamstring issues.

Set to be confirmed as signed is Yan Min-hyuk, an 18 year old South Korean winger. Having only played professionally for a few months, he will join in January 2025, with an exciting and quickly growing reputation.

The Richarlison question

Richarlison seemed a sure fit when he was signed from Everton in 2022, but it has just never got going for him.

There are two ways of looking at this one.

The first is that Spurs probably overpaid quite heavily with Richarlison at £60 million, his injury record is not the most flattering, and even when he was scoring it sometimes looked a bit square peg in round hole-ish.

The Brazilian can be petulant at times, making him reckless or sometimes simply anonymous during a game. There has not been much concrete interest in Richarlison other than tenuous links to Saudi Arabia, but if a team from the Saudi Pro League was to come in and offer even £40 million, then it is something Tottenham would have to surely consider.

The second is that last season was such an improvement on the first, that Richarlison deserves another season at it. On balance, he played the role to the best level last of anyone season. Unlike Son he is a natural striker, and his scintillating form on either side of Christmas gave us all a glimpse at what we could have.

But does Richarlison provide enough for a team that says they want to "create history"? Goals are gold. Arsenal have found out the hard way, back to back, what the value of guaranteed goal output is in a title race that is usually decided by such fine margins.

Options could include Ivan Toney, who is the name that has been touted most, along with Sporting Lisbon’s Viktor Gyokeres. Toney would be the likelier of the two; he has one year left on his deal and has been publicly speaking of his desire to challenge himself at a higher level.

His specific style is not particularly suited to Ange-ball as he is not great in the press, but the idea of starting the season with a Toney plus Richarlison is a lovely one - however wishful that might be.

Though it is hard to see another striker coming in if Richarlison does not depart.

Looking forward

There is no bedlam just yet at Spurs. The board have earned trust from the fans with the acquisitions they have made in recent years, but the clock is certainly ticking.

Of course no deal is easy, but Tottenham will be shooting themselves in the foot if they choose to delay all of their big business until the season starts. Spurs fans saw last year, with Maddison, just how positive a pre-season can be for a player to hit the ground running.

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