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Emerson Royal has returned to Brazilian football, a year after Tottenham Hotspur sold him to AC Milan, and the details of the transfer clearly show that Daniel Levy pulled off a masterclass.

It is fair to say that most Tottenham fans were not unhappy to see the back of Emerson Royal, who left Spurs to join Milan in a €15m (£13m) deal last year.

After the right-back had made just a few appearances for the Rossoneri, pundits already concluded that Milan paid too much to Tottenham for Emerson.

That proved to be right, with the Brazilian struggling to prove his value at the San Siro. Emerson came in for a lot of criticism in Italy, and Milan have now cut their losses on the defender.

AC Milan accept a big loss on Emerson after Brazil return

According to Globo Esporte, the former Tottenham man has now sealed a move to Flamengo in a deal worth €9m (£7.8m), which means that Milan have taken a £5.2m hit on the £13m they paid to Spurs just 12 months ago. The deal has since been given Fabrizio Romano’s ‘here we go’ seal of approval.

The outlet explains that Emerson was initially close to joining Turkish side Besiktas on loan, with the Rossoneri preferring to loan the full-back out rather than taking a massive hit on him.

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However, Flamengo then arrived with a permanent offer for the 26-year-old, which was attractive to both Milan and the player.

While Tottenham Hotspur’s decision to pay €30m (£26.1m) for Emerson in 2021 looks extremely poor, there is no doubt that the North London side got a very good deal when they sold him last summer.

Tottenham could take a hit from Emerson Royal’s switch to Flamengo

Globo Esporte reveal that Emerson was initially intent on remaining in Europe, but Flamengo managed to change his mind with the project they presented to the 26-year-old.

The outlet notes that the player’s quick departure from Milan is not good news for Tottenham, as this move rules out the prospect of Spurs getting any add-ons from the Italian side for Emerson.

However, given how poorly things were going for the full-back in Serie A, it is fair to say that he was not going to meet the criteria for any performance-related add-ons anyway.

Tottenham fans are starting to get restless as transfer activity slows down, but here is why the silence may not be a cause for concern.

The Premier League season is now less than a month away, and for Tottenham Hotspur, it is just two proper new signings – or should I say two new faces that fans would instantly recognise as additions.

Tottenham have technically signed four new players and spent over £100million in the process, having paid £21million for Kevin Danso, £29.5million for Mathys Tel, £5million for Kota Takai and £55million for Mohammed Kudus.

However, for a side that finished 17th last season, one would have expected Tottenham to be getting deals done right, left and centre in a bid to ensure a significantly better campaign next term.

That appeared to be the case, as after the club went big on Kudus, reports quickly emerged that Spurs had activated Morgan Gibbs-White’s £60million release clause, with a medical expected within 24 hours – it was an exciting few hours for Tottenham fans, who were beginning to see some ambition from their club.

Well, the Gibbs-White deal has since been delayed, and two weeks have now passed without any further additions. Spurs fans may have every reason to be anxious, but the transfer patterns under the current regime suggest otherwise. Here is why.

Big six transfer activity highlights why Tottenham fans are uneasy

At the start of the transfer window, we noted that with the slow pace at which Tottenham were operating, they risked being left behind in the race for the top six.

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Not long after that observation, Tottenham completed deals for Mohammed Kudus and Kota Takai, followed swiftly by the Morgan Gibbs-White development.

At present, however, frustration is brewing among Spurs fans due to the lack of activity in the window, a frustration only amplified by the speed and scale at which rival clubs are strengthening.

Manchester City, Liverpool, Manchester United, Arsenal and Chelsea have all been aggressive in the market – signing top players early, ensuring they integrate with the squad well before the season begins, and reducing the usual adaptation period that comes with such arrivals.

Chelsea, Liverpool, Arsenal and Manchester City will be among the Champions League participants next season, and their spending patterns suggest a clear intent to retain that status. For Tottenham, who only qualified through the back door, there is a valid concern about how they can keep up – especially given the need for significant reinforcements.

Tottenham transfer silence fits Johan Lange’s past patterns

Despite the concern, it is not yet time to hit the panic button, because this sort of slow, quiet window has become quite familiar since Johan Lange took charge of Tottenham’s transfer strategy.

Under Fabio Paratici, fans often had an idea of the club’s primary targets even before a deal was completed – perhaps a key reason why the Italian is still fondly remembered by many in north London.

Since Lange’s appointment, however, Spurs’ transfer activity has become more controlled, with fewer leaks and an increasing number of surprise deals.

This summer is a case in point. Tottenham were widely linked with Antoine Semenyo, Eberechi Eze and Bryan Mbeumo – players tipped to be the main targets.

Yet it was not until talks with West Ham United reached an advanced stage that reports linking Mohammed Kudus to Tottenham began to surface.

Kota Takai was barely mentioned in the rumour mill before his move became public knowledge, and the same was true for Morgan Gibbs-White.

Let us also not forget the club’s move for Wilson Odobert last summer, which came out of the blue and caught many by surprise.

This is how Lange operates, and it will likely remain the theme this summer – meaning fans may need to stay patient, as Tottenham’s approach may still deliver a few shock signings before the window closes.

Of course, there is a fair debate to be had about whether this is the most effective approach, especially when rival clubs appear to be getting business done quickly and efficiently.

Tottenham Hotspur’s hopes of securing one of their main transfer targets of the summer window have taken a significant blow.

Spurs moved to sign Mohammed Kudus from West Ham United earlier this month had looked as if they were about to complete a surprise deal.

It seemed like it came from out of nowhere when news broke that Tottenham had triggered Morgan Gibbs-White’s £60m transfer release clause and a medical had been booked at Hotspur Way.

In a remarkable turn of affairs, Forest filed a complaint to the Premier League over Tottenham’s approach for Gibbs-White which put the brakes on the switch to North London.

Tottenham target Morgan Gibbs-White signs new deal with Nottingham Forest

In a huge blow to Tottenham’s summer transfer plans, David Ornstein has revealed in a piece for The Athletic that Gibbs-White has now agreed a new contract with Nottingham Forest until 2028.

A new contract would be expected to remove the current £60m release clause and significantly increase the valuation.

The England international had two years left to run on his existing deal at the City Ground and having also been considered by Manchester City earlier this summer, will now remain with Nuno Espirito Santo’s side.

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Tottenham fans will be hugely frustrated by the news and feel that the last fortnight of their pursuit of Gibbs-White has been a complete waste of time.

Tottenham once again are in a transfer mess

News of Gibbs-White’s new contract is a massive setback and an embarrasing one for Thomas Frank’s outfit.

With Tottenham having also looked to have passed up any interest in Crystal Palace’s Eberechi Eze, who is nearing a switch to Arsenal, it looks as if they will have to go back to the drawing board.

Tottenham are moving quickly to secure one of Italy’s most promising young defenders, with a report now suggesting an official bid could be imminent.

For most parts of the summer window, there had been talks about whether Tottenham Hotspur would keep hold of one of their best defenders – Cristian Romero.

Romero had been attracting interest from Spanish side Atletico Madrid and even Real Madrid, but those links have since cooled off, with reports claiming Diego Simeone’s side have moved on to other targets.

Still, Tottenham have been linked with more centre-backs, including Illia Zarbanyi, although Fabrizio Romano has tipped Paris Saint-Germain as the main suitors.

Tottenham interested in Giovanni Leoni transfer move

The links to centre-backs continue, as a fresh report from Caughtoffside now claims that Tottenham are close to making an official move for 18-year-old centre-back Giovanni Leoni.

The defender currently plies his trade at Serie A club Parma, where he featured 17 times in the Italian first division, scoring one goal and keeping three clean sheets.

It is understood that Tottenham are the ones leading the chase for the Italy Under-19 international, with the report stating that Spurs view the youngster as a cornerstone for their future defensive setup.

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Tottenham, however, are not the only ones in the Premier League showing interest in the centre-back. It has also been revealed that Newcastle United are keen on the 18-year-old, and they too are said to be close to making an official move for Giovanni Leoni.

Parma sets price tag for Giovanni Leoni

With interest in the 18-year-old rife, it is stated that Parma have set a €30–40 million (£25.3m–£33.7m) price tag for their in-demand talent, and they are not looking to accept offers below that.

The defender is also catching the eye of Italian giants, including Juventus, AC Milan, Inter Milan, Napoli, and Bologna, who are said to also be tracking Leoni as part of their long-term squad planning.

Spurs, of course, are not ones to be shy to splash the cash on youngsters with huge potential, as we saw last summer with Archie Gray, where Tottenham paid £40 million to lure him to the Tottenham Hotspur Stadium.

It would be interesting to see how things pan out with Leoni in the coming weeks, as it is claimed that his name is expected to dominate transfer talks.

Tottenham and Daniel Levy could soon announce multiple commercial deals, which could significantly boost the club’s revenue over the coming years.

Tottenham have spent more aggressively this summer than many people expected them to, particularly after Daniel Levy issued a warning back in March about the Spurs’ unsustainable spending.

Some see this as evidence that ENIC might have invested some money into Tottenham, although the Lilywhites have not made any official announcement on the matter.

Other journalists have discussed the possibility that Spurs expect to sell a minority stake in the club to a third party, with discussions over a potential takeover thought to have been held over recent months.

Tottenham set to be boosted by commercial deals

However, Football Insider have now explained that Tottenham’s financial muscle may not have come via equity, but rather through commercial agreements.

The report claims that Spurs are now in talks over multiple commercial deals after making new hires to help maximise the club’s commercial potential.

The outlet says that the growing influence of the Tottenham Hotspur Stadium has strengthened the club’s global appeal to sponsors in recent years.

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Daniel Levy and co are now aiming to capitalise on these commercial opportunities and hope to tie up multiple new sponsorship deals.

Tottenham in talks over stadium naming rights deal

Football Insider add that apart from these commercial deals, Tottenham are also holding talks over a lucrative stadium naming rights deal for their stadium.

The outlet claims that Levy is currently holding out for a deal worth in excess of £20m per year for the naming rights of the stadium.

Tottenham’s hopes of offloading an experienced star have received a blow as Juventus, who were previously keen on the player, have now decided against signing him.

Tottenham have completed three signings so far this summer and would have added another player in Morgan Gibbs-White, but his move to Spurs has been held up by controversial circumstances.

However, the Lilywhites have not managed to shift any of their deadwood as of yet, with the likes of Manor Solomon, Bryan Gil and others still at the club.

Additionally, it has been reported over recent weeks that Tottenham are working to find a buyer for Yves Bissouma, who has only one year left on his contract.

Several Italian outlets had previously claimed that Juventus are eyeing a move for Bissouma after hearing that he is surplus to requirements at Spurs.

Juventus are no longer expected to land Yves Bissouma

It had previously been alleged that Juve’s general manager, Damien Comolli, could use his relationship with Daniel Levy to land Bissouma, with the Frenchman having previously served as Tottenham’s director of football.

However, a new report in Gazzetta dello Sport has claimed that the Bianconeri are now not expected to make a move for the Spurs star.

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This is because they only have one non-EU spot remaining in their squad, and that is expected to be filled by Nahuel Molina, who is on the verge of moving to the Turin club from Atletico Madrid.

As a result, the idea of signing Bissouma from Tottenham Hotspur is ‘furthest away’, with the Serie A club instead expected to turn to options such as Fulham’s Sander Berge.

Why Tottenham need to get rid of Yves Bissouma swiftly

It has been claimed by Alasdair Gold and others that Tottenham want to offload a midfielder before they can sign a number six.

Juventus cooling their interest in the Mali international may thus delay the Lilywhites’ pursuit of a defensive midfielder.

A Premier League centre-back, who has been on Tottenham’s radar for a while, is thought to be on the verge of signing a new contract.

Even though Cristian Romero now looks likely to stay at Tottenham, various centre-backs continue to be linked with a move to N17.

That includes a pacy French centre-back, who has been on Spurs’ radar from the start of the calendar year, according to some sources.

It was previously claimed that Tottenham had an offer of just over £20m turned down for Burnley centre-back Maxime Esteve in January.

The 23-year-old was one of the best defenders on show in the Championship last term, and he played a key role in the Clarets’ promotion, which Scott Parker’s men secured mainly thanks to their solid defence.

Tottenham receive Maxime Esteve transfer blow

Despite Burnley’s promotion, some reports have claimed over recent weeks that Tottenham could try again to raid Turf Moor for Esteve, who is thought to be valued by the Clarets at £50m.

However, Sky Sports journalist Lyall Thomas has now revealed that the newly promoted side have moved to protect their star man’s value amidst the interest that he is generating.

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According to Thomas, Esteve is now on the verge of signing a new long-term deal at Burnley, which could end Tottenham Hotspur’s chances of swooping for the former Montpellier man this summer.

Which other centre-backs are Spurs looking at?

According to various outlets, Tottenham continue to remain interested in Marc Guehi, who Crystal Palace are ready to listen to offers for.

Some sources have suggested that Spurs are ready to spend big on Bournemouth’s Illia Zabarnyi, while it has also been claimed that the Lilywhites have held talks over a deal for Genoa’s Koni De Winter.

Tottenham Hotspur will accept a cut-price fee from LAFC for Heung-min Son this summer as the Major League Soccer club steps up their pursuit of the Spurs captain.

It emerged a couple of days ago that LAFC are stepping up their pursuit of Heung-min Son and are determined to get him through the door this summer.

Since then, the situation has developed rapidly, with Son alleged to have held talks with the American club over a summer transfer.

On Thursday, it was reported that LAFC had launched their opening offer for the Spurs captain, although it is unclear how much their bid is worth.

Tottenham set new Heung-min Son asking price

The Sun have now become the latest outlet to report on LAFC’s approach for Son, and they claim that the Lilywhites do not want big money for the forward, who is now into the final year of his contract.

The outlet says that Tottenham Hotspur will consider selling the South Korean if the MLS side make a £15m bid, with the North Londoners hoping to collect £15m-£20m for their star man this summer.

However, it is made clear that it is the forward who will make the final decision on whether to make the move across the pond, with the player not ruling out staying at Tottenham and fighting for his place under Thomas Frank.

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The outlet adds that Son is currently involved in discussions with all parties over his future.

Son will not leave Spurs within the next two weeks

Even if the forward greenlights a move to the United States, he will not be making the move within the next couple of weeks.

This is because Tottenham are contractually obliged to include Son in their pre-season trip to South Korea, where they take on Newcastle United in a friendly.

Mathys Tel has now shared what he did ahead of his permanent move to Tottenham Hotspur to get an understanding of how Thomas Frank will set the team up.

Tel became Tottenham’s first signing of the Thomas Frank era, with the Lilywhites paying £30m to land him permanently from Bayern Munich.

The North Londoners saw enough to take a punt on the 20-year-old, even though he only scored three goals in 20 appearances for the club in his loan spell during the second half of last season.

The forward did show glimpses of his quality last season, and Spurs fans will take heart from Tel’s impressive showing in the European Under-21 Championship, and hope that he can replicate those performances in a Tottenham shirt.

Mathys Tel did not speak to Thomas Frank before Tottenham move

The fact that Ange Postecoglou had been replaced did not deter the Frenchman from agreeing to a move to N17, and interestingly, the forward has revealed that he did not even speak to Frank before making the switch.

However, Tel admitted that he watched videos of Brentford matches to gain an understanding of how Frank will set Tottenham Hotspur up.

When asked if he spoke to the Danish coach before greenlighting a permanent move to N17, the 20-year-old told Sky Sports: “No, but I watched some games last year of Brentford, I just watched to get [an idea of] how they play.”

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Thomas Frank is excited about Tel’s potential at Spurs

The new Spurs head coach might not have spoken to the forward prior to his transfer, but the former Brentford boss certainly approved his arrival.

We know this because following the forward’s permanent switch, Frank said he is very excited about Tel’s arrival, and admitted that he is keen to work with the forward to improve his all-around game.

As the speculation linking Kobbie Mainoo with a move to Tottenham Hotspur gathers steam, the midfielder may have already hinted at what he feels about the North London side.

We know that Tottenham are looking to add another central midfielder to their squad, and many different players have been mooted as targets for the Lilywhites over the last few weeks.

The likes of Joao Palhinha, Douglas Luiz and Joao Gomes have been linked with a move to N17, but over recent days, a new name has also been mentioned by various reports.

Some journalists have claimed that Kobbie Mainoo is on Tottenham’s radar as Man United continue to struggle to reach an agreement with the midfielder over a new contract.

Kobbie Mainoo’s Instagram post suggests he has a soft spot for Tottenham

According to some sources, Mainoo is emerging as a realistic target for Spurs, particularly as he is keen to get regular football ahead of a World Cup year, which he might not under Rubem Amorim at Old Trafford.

It turns out that the 20-year-old hinted at the start of the summer that he had a soft spot for Tottenham Hotspur as a kid.

Back in April, Kobbie Mainoo posted an image of himself as a child wearing a retro Spurs shirt.

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Mainoo was celebrating his 20th birthday and posted an old image on his Instagram wearing Tottenham’s third kit from the 1995-96 season.

Spurs are pushing ahead with talks over experienced midfielder

Over recent days, a number of outlets have claimed that Spurs are holding talks with Bayern Munich over a deal for Joao Palhinha, who Thomas Frank is said to be a fan of.

Palhinha is reportedly available for €25m (£21.6m) this summer as Vincent Kompany has deemed him surplus to requirements at the Allianz Arena.