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If the waffling on Ange Postecoglou's future is any indication, Tottenham and, specifically, chairman Daniel Levy aren't exactly great at making difficult decisions quickly and sticking to them. Tottenham's indeciveness with their Europa League-winning manager threatens to put them irrecoverably behind the curve on the transfer market, with Spurs already set to lose out on top target Rayan Cherki to Manchester City.

What Tottenham can't continue to do is be complacent with key decisions, such as their manager's future or capitalizing on signing top young players. They have a decision to make with a top young player currently in their squad, loan signing Mathys Tel, this summer, and they can't afford to mess this one up, too.

Tel did enough on his six-month loan to Tottenham to merit a long-term stay with Spurs, and his actions on and off the pitch are those of a young man very much wanting to be a part of the long-term future of this team.

Tottenham hold about a 45 million pound option to buy on Tel's contract, and they could potentially ngotiate that down to less. Now, Sky Sports Germany's Florian Plettenberg is reporting another possibility in the Tel case for Tottenham and that is another loan deal for the 2025/26 season with an option to buy at the end of that.

Waiting a year comes with more risk for Tottenham

A decision point is coming soon, and, per Plettenberg, as Bayern Munich sporting director Max Eberl continues his "intense" negotiations with Tottenham and Tel alike, the Bavarians clearly prefer a permanent sale, even if another loan is possible.

For Tottenham, kicking the can down the road on Tel for one more year isn't necessarily a bad idea, because, like with the Timo Werner repeat loan, it can give them some more intel on the player and another year sample size to decide if they want Tel permanently or not.

But that intel comes at a price. A loan deal with an option to buy next season may set Spurs back another 45 million pounds with less leeway to negotiate down, whereas Bayern's desire to sell to raise funds this year leaves it easier for Tottenham to get a discount potentially closer to even 30 million pounds.

Remember, too, the possibility of choice in Tel's and Bayern's cases. As Tottenham are realizing with Johnny Cardoso, whom Spurs had a 25 million euro release clause over, the player can always choose against them if given the chance. Right now, Tel is choosing Tottenham. Who is to say that if he plays so extaordinarily well in 2025/26 that he still wants Tottenham under a new manager? And who is to say that Bayern don't change their minds if Tel plays that well and are able to convince him to return in 2026?

There's a lot of conjecture and uncertainty in the background if Tottenham wait on Tel and leave it up to a decision point in 2026. Whereas if Tottenham are sold - or, at least, sold enough - on Tel in 2025, they might as well capitalize on the 20-year-old's potential now and take a minor gamble, negotiating down the fee with Bayern. If the Cardoso case has taught Spurs anything, it's to leave absolutely nothing to chance in the pursuit of fine young talent.

It's anyone's guess as to what Tottenham do with Ange Postecoglou this summer, as the second-year manager is at a crossroads after helping Spurs win the Europa League for the first time in 41 years while also finishing a worst-ever 17th in the Premier League.

As time trudges on without a real judgment on Postecoglou's future, the chances of the former Celtic boss remaining in North London increase. The managerial musical chairs in Serie A has already yielded a couple of big hires - Max Allegri to AC Milan and Gian Piero Gasperini to Roma - and there could still be a third that leads to Spurs missing out on another top manager.

While Tottenham have, per a report from The Sun's Tom Barclay, reached out with interest in Inter Milan manager Simone Inzaghi, they have not yet decided on Big Ange's future and have thus not really pursued Inzaghi hard.

Tottenham aren't looking hard enough at top managers

For the most part, the main manager names that come up in their search are those in the mid-table of the Premier League like Thomas Frank of Brentford, Andoni Iraola at Bournemouth, and Fulham's Marco Silva. All decent managers but none with the kind of track record that Tottenham are aiming for, which is competitiveness at the upper echelon of the Champions League.

Inzaghi has been to two Champions League Finals in the last three years, leading the Nerazzurri back to those heights for the first time in more than a decade when Jose Mourinho became the first and only manager to win a treble with a Serie A club.

Yet all of that may be a moot point, because as brilliant of a tactician as Inzaghi is, Tottenham seem to have so little interest in hiring him that he seems poised to pick a totally different option on Tuesday. Fabrizio Romano reports that this is the date that one of the most highly-regarded managers in world football will decide his future, and he is between staying at Inter Milan and joining Al-Hilal ahead of the Club World Cup for a fat paycheck.

Now, Tuesday is all about Inzaghi choosing to stay at Inter or hit the open market, so he isn't necessarily going to Al-Hilal and his interest in the Saudi Arabia giants is plausible but debatable at this juncture.

The real issue is, why aren't Tottenham more interested? Why isn't Fab tweeting about Tottenham being highly interested in Inzaghi, as interested as Al-Hilal? A lot of that is probably down to the fact that Spurs are legitimately undecided on Postecoglou and may be swayed by public endorsements from key figures in the locker room like James Maddison and Lucas Bergvall.

When Tottenham agreed to sell Giovani Lo Celso last summer, they received a special deal from Real Betis, who granted Spurs the opportunity to sign one of the best United States internationals and one of the better young box-to-box midfielders in the world at a reduced price.

Spurs were granted a special release clause to sign Betis center midfielder Johnny Cardoso for the summer 2025 transfer window only. For a fee of just 25 million euros, Tottenham would be able to sign a 23-year-old talent worth at least double that amount of money, offering a solution at what has become a major area of weakness for Spurs.

Instead, it looks like Tottenham won't get the opportunity to sign Cardoso at all. After rumblings that Cardoso isn't interested in leaving Betis this summer at all, thus totally nullifying Tottenham's clause, it appears that the narrative has shifted to Cardoso not wanting to leave LaLiga.

Johnny Cardoso doesn't want a Tottenham transfer

According to a report from GiveMeSport's Tom Bogert, an expert on the USMNT, Atletico Madrid, as expected, are now the leaders in the Cardoso transfer battle. They are expected to sign him this summer for 30 million euros, and, now, even Tottenham feel that the player is more interested in staying in the Spanish league than jumping ship to the English Premiership.

It's a transfer blow that Tottenham need to acknowledge at this point and effectively scrap Cardoso off their board. With the special clause Betis gave Spurs after the Lo Celso sale, Cardoso's situation feels like a loss, as if a player were taken away from Tottenham since Cardoso seemed like such an easy signing to make.

But Cardoso's situation is a sobering reminder that not only is nothing for certain in football, but, also, that Spurs have fallen in stock with this 17th-placed finish despite a Europa League title win. Tottenham need to cherish young players like Mathys Tel who want to join them and remember that they have now fallen behind clubs like Atletico Madrid in the transfer pecking order for talents like Cardoso who have already arrived on the big stage.

Tottenham need to look for more underrated box-to-box alternatives, and while those players will be more expensive than 25 million euros, they could be better and more dynamic players than the slightly overrated Cardoso. Players like Lamine Camara have had better seasons with less hype, and it's time for Spurs to look at Cardoso as an opportunity that has passed and move on.

Tottenham may have won the Europa League for the first time in nearly 40 years, but their 17th-placed finish across a 38-game Premier League season speaks more to their profound issues as a squad and their inability to consistently compete with teams at the highest professional level.

For Spurs, the key will be prioritizing areas of weakness so that they can invest their limited funds wisely and focus on positions that need to be upgraded the most for the Premier League and now Champions League campaigns ahead in 2025/26.

Chiefly, Spurs should be looking at new midfield help, specifically a defensive midfielder who can control games, playmake from deep, and screen the team defensively from counterattacks. The biggest problem Tottenham had, especially in the Premier League against teams with a higher technical and athletic level than the Europa League, was getting overrun in midfield.

Tottenham need game-changers in attack

There were too many games in which Tottenham were already losers from the get-go because they had no control. A defenive midfielder should be their biggest priority, especially in view of how London rivals Chelsea and Arsenal have prioritized this position big-time with major signings like Martin Zubimendi, Declan Rice, Moises Caicedo, and Enzo Fernandez.

Next up, Tottenham need difference-makers in their team. They already have one of the Premier League's best creators and No. 10's in James Maddison, who delivered nine goals and seven assists for Spurs last season to tie Son Heung-min as the team's leader in goal contributions.

Everywhere else, though, Spurs have needs. Dominic Solanke is better than his nine Premier League goals show, but even the biggest Solanke homers can't argue that he's living up to his 65 million pound billing. Richarlison is likely on the way out after another sub-standard, injury-plagued year, so a young and affordable striker to replace Richarlison and compete with Solanke should be one of chairman Daniel Levy's priorities.

Along with a striker, Tottenham should sign a left winger. Preferably, that would be Mathys Tel, who is the exact profile Spurs should be looking for. Tel is a 20-year-old player with game-changing creative, dribbling, and goal-scoring qualities who can step in for Son Heung-min when necessary and eventually replace him.

Spurs already have adequate cover on the right wing between Dejan Kulusevski and leading scorer Brennan Johnson, providing two very different profiles there. And then there is young gem Mikey Moore. But on the left, Tottenham can't afford to go into the 2025/26 season with just Son as an option, given how his play tailed off in the second half of the season due to injury. They have to bring in another difference-maker on the left wing, with Tel being a tailor-made option.

Tottenham Hotspur are going to be making some difficult decisions this summer in the transfer window, clearing out players who no longer have a long-term future at the club and making upgrades in order to compete at the Champions League level again in 2025/26.

Many of those changes are expected to occur in the middle of the park, as Tottenham were overrun in many games in the Premier League, finishing the season in a historically poor 17th place. Spurs need more control in the middle of the park and more technical quality.

Although he is a decent player, Rodrigo Bentancur has been speculated by fans as one of a number of veteran players who could be headed out of the squad as sellable assets who may not have the quality necessary to be top players in the Premier League.

Could Spurs be calling Rodrigo Bentancur 'captain'?

But Spurs seemingly aren't in agreement with those doubters in the fanbase. According to a report from TBR Football's Graeme Bailey and Jamie Brown, Tottenham are very high on Bentancur. Not only are they prepared to give him a contract extension, instead of selling him, but they are also even considering making him their captain.

Whereas Tottenham are ready to send Yves Bissouma packing after a(nother) disappointing season, Bentancur is set to be rewarded. The 27-year-old former Juventus midfielder has been an asset to Spurs since joining, and he recently stepped up his performances big-time when the club needed it in the Europa League knockout stages, occasionally dominating the competition.

Spurs need to continue to see more of that from Bentancur, who hasn't convinced the entire fanbase that he has the creativity or athleticism to beat the best midfielders in the league among the top-five teams. But against mid-level competition in the Europa League, Bentancur stood out defensively and with his quality of passing and positioning.

There are absolutely better midfielders out there than Bentancur, but he's also clearly one of the better players on the team right now. Spurs can't completely blow everything up and get rid of every veteran presence, especially not someone who has been playing well for years in Bentancur. Eventually, Spurs may have to find someone better than Bentancur as they aim higher and higher, but, even then, he should always have a spot as a role player.

Captain is a stretch and Bentancur shouldn't get too rich of a raise, but the Uruguayan international showed when Tottenham needed him the most this season that they can count on him to deliver.

Tottenham Hotspur are taking an approach on the transfer market in which they focus on signing young talents with superstar potential. They added Lucas Bergvall, Archie Gray, and Wilson Odobert last season to bolster their midfield and attack, and then they acquired Mathys Tel on the wing this winter as a loan signing from Bayern Munich with an option to buy.

But Spurs don't need to just sign players from outside to build a young nucleus that can win more trophies than this season's Europa League. They have some serious homegrown talents, and one of their biggest gems is Mikey Moore, who had a brief breakout moment during this season's Europa League tournament.

Moore is so talented that Borussia Dortmund, known for developing great young players, are showing a keen interest in the 17-year-old winger. Tottenham have so many reasons to keep Moore, and with the player getting new representation, Spurs have to put their money where their mouth is and pay the young man.

Tottenham are serious about keeping Mikey Moore

According to a report from TBR Football's Graeme Bailey and Jamie Brown, Tottenham have already begun contract talks with Moore over a new deal and have a plan in place to sign the 17-year-old to a long-term contract before he turns 18 this August. They aim to have that deal signed, sealed, and delivered before that date, securing the future of one of their biggest young talents before any clubs like Dortmund get the idea of stealing him away.

It's an important step for Tottenham and Daniel Levy to make. They've already lost on so many high-upside young gems on the transfer market that you could only imagine the embarrassment and the blow it would be if Tottenham were to lose a homegrown player like Moore and watch him shine with someone else in European football.

Tottenham are clearly as high on Moore as the fans are, and it should only be a matter of time, months at most, before Spurs fans get word of a new deal for the English winger. After they already secured Lucas Bergvall to a new deal, Moore has become the new focus for the club when it comes to a player deserving of a long-term extension that keeps him at the Tottenham Hotspur Stadium for the long haul. Moore is one of those players who has the potential to be special, and Spurs need to keep a few of those in order to push further in the Premier League than they ever have before.

If the biggest task for Tottenham Hotspur as June begins is to figure out the future of manager Ange Postecoglou, then the second-biggest task is definitely to figure out the future of star center back Cristian Romero.

Just a few weeks ago, it appeared to be a foregone conclusion that Romero would be leaving Tottenham, as Atletico Madrid were in hot pursuit of the 26-year-old central defender and had apparently even agreed to a deal with him. That obviously wasn't the case, and after his crucial performances in must-win Europa League knockout games, Romero has become someone Spurs fans desperately want the club to keep.

After giving an interview a month ago in which he said he dreams of a move to LaLiga, "Cuti" struck a completely different tone and had a more positive and Spurs-centric outlook when discussing what lies ahead for him.

Cristian Romero didn't commit to Tottenham

In an interview with Los Edul, the Argentinian international stated, “I’m happy. They make me feel like an important player. I’m going to give my best until the last day I’m here.”

On the one hand, that's a nice thing to say about Tottenham and seems to go hand-in-hand with the renewed optimism that the 2024/25 Europa League Player of the Tournament will remain with Spurs for the 2025/26 season and beyond.

But cynically, perhaps, it doesn't mean that Tottenham are out of the woods yet. Because Romero said that he's currently "happy" and feels "important" but will give his best until his "last day". He didn't say that he's "staying" or that his "last day" will be "years" from now.

Romero is playing a more political game than he did a month ago when the vice captain starting going on about dreaming of LaLiga at a time when Tottenham needed focus. He's smartly leaving the door to his future open while saying positive things about Spurs so fans don't get the wrong idea, but he's also not getting anyone's hopes up by committing to Tottenham.

Of course, part of that has to do with the fact that Romero doesn't 100 percent control his own destiny. What if Atletico or Real Madrid send Tottenham an offer they can't refuse? What if Daniel Levy sees the dollar signs on the transfer market again and makes another dumb decision to sell an important player for less than what they are worth to Tottenham?

As much as Spurs fans may want to take an overwhelmingly positive message away from what Romero is saying, nothing changes with that quote. Because Romero may secretely think that his "last day" with Spurs already happened and his Europa League Final performance against Manchester United was that example of him fighting until the end. Hopefully, that's not the case, but when it comes to Tottenham, it pays to be at least a little bit cynical.

Tottenham appear to be targeting playmaking stars in the summer 2025 transfer window in order to add more attacking juice to a team that didn't have a single player with double-digit assists and just one, Brennan Johnson, with at least 10 goals.

For the most part, their search has focused on young up-and-comers like Rayan Cherki of Lyon and even RB Leipzig's underrated Xavi Simons, but Tottenham are also looking at big names in the Premier League in the prime of their careers like Crystal Palace's Eberechi Eze.

And it looks like Tottenham fans can add another one to the list. According to a report from talkSPORT's Alex Crook and Ben Jacobs, Tottenham are among the Premier League clubs that have enquired Chelsea with an interest in attacking midfielder Christopher Nkunku. Spurs are said to be the English side most concretely interested in the Frenchman, and while the player has been linked with moves outside of the Premier League, he is reportedly open to staying in England, too.

Tottenham could sign a former Ballon d'Or candidate

Nkunku has been shopped by Chelsea since the winter transfer window, as he has clearly not figured into Enzo Maresca's plans. Maresca has improved the Blues markedly this season, taking them from the Premier League's biggest disappointment back to the Champions League, and Chelsea also won a notable trophy, beating Real Betis 4-1 to take home the Conference League honors.

The 27-year-old joined Chelsea in 2023 from RB Leipzig for 60 million euros, which was actually significantly below his market value. Nkunku was so good in Leipzig that he not only led the team to their first major trophy with a DFB Pokal victory in 2022, but he was also the Bundesliga Player of the Season above the likes of Bayern Munich legend Robert Lewandowski.

A legitimate Ballon d'Or candidate in Germany, Nkunku has been a disaster in England due to a bevy of injuries and an inability to get into the starting lineup under a revolving door of coaches who don't seem to value him. When he does play, Nkunku has shown that he is at the level of a Premier League playmaker with his athleticism, creativity, and high footballing IQ.

In the Bundesliga, Nkunku could do it all, and if the price is right, he could be a strong signing for Tottenham as a secondary playmaking option to James Maddison with the additional versatility to start on either wing or even as a center forward, which was arguably his strongest position in Leipzig.

While Nkunku isn't without his flaws and has both a concerning injury record and a poor 2024/25 campaign on his docket, he could be a low-risk, high-upside signing with the additional benefit of giving Tottenham some bragging rights over Chelsea.

Tottenham Hotspur didn't have a single player register 10 assists in the 2024/25 Premier League season, and only Brennan Johnson scored double-digit goals for the Europa League champions. Spurs were the most profoundly disappointing team in the Premier League last season, finishing 17th in a historically putrid campaign.

Needless to say, Tottenham are going to need to sign some difference-makers to bolster their sagging attack. Even if Son Heung-min bounces back next season at the age of 33, Spurs are going to need more star power to supplement veterans Son, James Maddison, and Dominic Solanke up top.

Lyon playmaker Rayan Cherki has become a dream target for Spurs in the attack, because he is exactly the kind of player they need. Cherki can create something out of nothing, he has immense skill, he's been productive for a historic team a top-five league for a few years now, and, most of all to Daniel Levy, he is ludicrously cheap with a laughable 22.5 million euro release clause.

Rayan Cherki is an elite club's top target

The problem for Tottenham is all the big boys in the Premier League are after Cherki, and it looks like Manchester City are ramping up their pursuit of the uber-talented Frenchman. According to a report from Fabrizio Romano, Man City have now made contacts to begin talks to sign Cherki, and he is one of their top two targets at the No. 10 position alongside Nottingham Forest star Morgan Gibbs-White.

Manchester City have endless resources financially and the most highly-regarded manager in world football in Pep Guardiola. They are also out for revenge after a poor, by their lofty standards, 2024/25 Premier League season. Guardiola usually gets who he wants, and Cherki has that extra quality the Citizens are looking for.

So if Tottenham don't move quickly, they could be left holding the bag yet again, missing out on another transformative young star. Spurs are in a tough spot since nobody quite knows who will be coaching them next season, but it's safe to say that any coach worth their salt would be over the moon about working with a 21-year-old left-footed wide playmaker coming off a season with 12 goals and 19 assists between the Premier League and Europa League.

There's no shame to losing out to Manchester City in the transfer market, but there's no glory in it either. And Spurs fans are tired of watching Daniel Levy and the club's board room constantly take the complacent approach with slam-dunk young stars on the market.

Tottenham will mostly be after midfield talent and attacking difference-makers in the summer 2025 transfer market as they look to improve their squad significantly from finishing a lowly 17th in the Premier League.

Despite those being their biggest priorities in the transfer window, Tottenham are also expected to go after a top center back, especially if they are not able to keep star man Cristian Romero. Although Romero's chances of staying in Tottenham have increased over the past couple of weeks, there is no guarantee the Argentinian international stays in North London.

Crystal Palace star Marc Guehi, fresh off his own big title win, has widely been considered Tottenham's dream transfer target in defense, especially after they already tried to sign the Eagles star last summer for a cool 70 million euros

Tottenham are under pressure now

Tottenham are expected to be back in for Guehi if they lose out on Romero this summer, but they just got some stiff competition for him. Despite already agreeing to terms with top free agent center back Jonathan Tah from Bayer Leverkusen (and the German national team), Bayern Munich have begun talks with Guehi for a summer transfer, per a report from Paul O'Keefe, via Spurs Connect.

Bayern need defensive reinforcements after a disappointing 2024/25 campaign. Despite winning the Bundesliga again, Bayern were far from their best in Europe and had to run Kim Min-jae in to the ground due to a lack of options. One of those options was former Tottenham backup Eric Dier, who just joined Monaco for the 2025/26 season. So you can see how Guehi would be an attractive target to them, especially since they have already benefited greatly from another former Palace star in right winger Michael Olise.

Die Roten's interest in Guehi is another sign for Daniel Levy and Tottenham to get serious. Spurs are behind the eight ball with their biggest targets on the transfer market, such as Lyon playmaker Rayan Cherki, because they are still waiting to make a decision on Ange Postecoglou as their manager.

Tottenham don't have to act now with Guehi, and they still may not necessarily need him if they are able to keep Romero, as Kevin Danso is a great third center back to have behind Romero and Micky van de Ven. But if Romero starts talking to clubs besides Atletico Madrid that can pay Spurs more, Guehi is the only one who looks 100 percent capable of replacing the 26-year-old standout.