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Tottenham Hotspur face an unusual decision that reflects the contrast of emotions as the curtain falls on their rollercoaster season.

What's next for Ange Postecoglou? Will he stay, or will he go?

Heung-min Son, who deservedly lifted the Europa League trophy into the Bilbao sky, has made his stance crystal clear.

"He won the trophy. Nobody did it, so," Son said, according to Alasdair Gold of football.london. "It's not up to me or the players, but we just have to look at the facts, at the fact that we haven't won in 17 years, today is the day we finally won it. It's the manager who wins the trophy. So we see what's going to happen."

Son delivered a message directed straight at Daniel Levy, who faces arguably the most challenging decision of his tenure.

Postecoglou's Spurs delivered a historically poor Premier League performance, with the team entering the final weekend in a battle to lift themselves out of 17th. But it's contrasted by a night in Bilbao that will live for eternity, with Spurs fans rewarded for enduring the gloomiest storm in recent memory and finally reaching the other side to experience the rainbow.

Is it a false dawn that requires a managerial shift or a historical turning point that can lead Tottenham into an exciting new era under Ange?

Daniel Levy should listen to Heung-min Son about Ange Postecoglou's future

It almost makes no sense to retain a manager who, in another season, may have sent Tottenham into the Championship with a pathetic 38 points from 37 games.

But how can Levy fire a manager who just delivered Tottenham's proudest moment in over four decades?

How can Levy fire a coach whom the players adore? Son went to bat for Postecoglou after the game, despite being relegated to the bench at kickoff, and it was clear by the emotional postgame moments Ange shared with his players that they love him.

If there's one way to quickly deflate the locker room after such a monumental achievement, it's to send the man behind it packing.

It truly makes no sense to retain a manager who took a Spurs team with Champions League aspirations into a near-relegation scrap. But that's the beautiful paradox they find themselves in. Ange's to-do list included clinching Champions League football and winning a trophy.

He checked both boxes with Wednesday's gutsy win over Manchester United.

Spurs cycled through "proven winners" like Jose Mourinho and Antonio Conte. They won nothing. It was Postecoglou, the manager they settled on after an exhausting and frustrating search, who brought silverware back to N17.

The league table doesn't lie, but nor does the emotion, joy, and relief shared after the most important Tottenham win for generations.

Retaining Ange makes zero sense, but it also makes complete sense. Son is right — Spurs should roll the dice and keep the coach who made this happen.

Tottenham Hotspur clash with Manchester United in the UEFA Europa League final on Wednesday (May 21). Ange Postecoglou is on the cusp of becoming the first manager since Keith Burkinshaw in 1984 to guide the Lilywhites to a European trophy.

It's one of the most important games in both clubs' recent history, with a chance to win silverware at stake and qualification for next season's UEFA Champions League. If the two Premier League sides' encounter is anything like most of their last scraps, we're in for a treat.

Tottenham vs Man United past results in the last 10 meetings

Here is how this season's Europa League finalists have squared off in each of their last ten meetings.

Tottenham 1-0 Manchester United - Premier League (February 16, 2025)

James Maddison grabbed the only goal of the game in the 13th minute to ease the pressure on Postecoglou amid a concerning start to 2025. It was just the second time this season that Spurs had won back to back games and it came at home against an extremely wasteful United side.

Tottenham 4-3 Manchester United - Carabao Cup (December 19, 2024)

This seven-goal thriller is what many hope will ensue when the two sides meet in San Mames this week. It was a game that had everything including stunning strikes, goalkeeper howlers and nearly a remarkable comeback.

Dominic Solanke (15', 54'), Dejan Klusevski (46') and Son Heung-Min (88') were on target for Spurs. The Red Devils hit back through Joshua Zirkzee (63'), Amad (70') and Jonny Evans (90+4').

Manchester United 0-3 Tottenham - Premier League (September 29, 2024)

Tottenham's thrashing of United in September gave fans optimism that Postecoglou's men would be right up there come the end of the season. It turned out to be a red herring as their fallen opponents were there for the taking.

Nevertheless, it was one of the Lilywhites' best performances this season with Brennan Johnson (3'), Dejan Kulusevski (47') and Dominic Solanke (77'). Of course all the talk coming out of the game was Bruno Fernandes' sending off.

Manchester United 2-2 Tottenham - Premier League (January 14, 2024)

The last time United managed to come away with at least a draw was back in January 2024 and Spurs probably merited all three points. Rasmus Hojlund (3') had stolen a lead only for Richarlison (19') to equalise.

Marcus Rashford, whose loan spell at Aston Villa means he will miss the Europa League final, put the hosts back in front (40'). But Rodrigo Bentancur (46') came to the fore as Ange's troops settled on a draw.

Tottenham 2-0 Manchester United - Premier League (August 19, 2023)

Another Spurs win and this was one to celebrate amid Postecoglou overseeing his first home game with the club. It was a well deserved and dominant victory which saw Pape Matar Sarr score his first league goal (49') before Lisandro Martinez's late own goal (83').

Tottenham 2-2 Manchester United - Premier League (April 27, 2023)

Son Heung-Min's late 79th equaliser ensured Ryan Mason's first game back in caretaker charge finished honors even. The Lilywhites pulled off a comeback draw courtesy of Pedro Porro's 56th-minute lifeline strike after his side had fallen behind to goals from Jadon Sancho (7') and Marcus Rashford (44').

Manchester United 2-0 Tottenham - Premier League (October 19, 2022)

The last time United beat Spurs was nearly three years ago and only five of the players that started that game remain with the club. Fred opened the scoring in the 47th minute before Bruno Fernandes made it two 22 minutes later.

Manchester United 3-2 Tottenham - Premier League (March 12, 2022)

Another entertaining affair between two of English football's fallen giants came in early 2022 when Cristiano Ronaldo made history. The Portuguese forward hit a hat-trick (12', 38', 81') to be recognised by FIFA as world football's all-time top scorer.

Spurs had replied through Harry Kane (35' P) and Harry Maguire's own goal (72') but Ronaldo conjured up brilliance. At least he can't have a say in the final in Bilbao.

Tottenham 0-3 Manchester United - Premier League (October 30, 2021)

The tide has turned over the years in meetings between the two clubs as United were on a four-game winning streak from April 2021 to October 2022. Their biggest result came in late October 2021 when Cristiano Ronaldo (39'), Edinson Cavani (64') and Marcus Rashford (86') struck in a 3-0 away win.

Tottenham 1-3 Manchester United - Premier League (April 11, 2021)

Son Heung-Min's opener (40') was in vain as United surged to another victory on the Lilywhites' stomping ground. Fred (57'), Edinson Cavani (79') and Mason Greenwood (90+6') helped Ole Gunnar Solskjaer come away with all three points.

There was already so much riding on Tottenham Hotspur's shot at ending their 17-year trophy drought, but Fabrizio Romano has thrown in another curveball.

Spurs meet Manchester United in Wednesday's Europa League final.

Beyond the desperation to win their first trophy since the Juande Ramos era and Ange Postecoglou potentially coaching for his job, Tottenham's performance could determine Cristian Romero's future with the club, as Wednesday's victors will also qualify for next season's Champions League.

"His contract at the moment is not even close to being extended. This is why the situation of Cuti Romero could be one to watch," Romano said on the Here We Go podcast. "In this case, I think Champions League football could have an impact on the future of the player. Let's see if Tottenham will be in the Champions League next season or not. This is going to be important."

Romero's future remains a major question mark, and it feels that for Tottenham to have any chance of retaining the World Cup-winning defender, they must get past Man United and secure Champions League qualification.

Tottenham need to beat Man United in Europa League final to avoid losing Cristian Romero this summer

Spurs' rumored interest in Crystal Palace defender Marc Guehi is no coincidence. He would fill the void left by Romero, but wrestling the England international away from the new FA Cup champions won't be easy.

As Romano said, there has been interest from Spain in Romero. That's a potential hint at the speculation about Atletico Madrid.

To some extent, Tottenham hold the cards — Romero remains under contract for two more seasons.

However, if his heart is away from N17 and he has no interest in extending the deal, Spurs need to make a move now while they can demand top-of-the-market money. If nothing else, Daniel Levy must ensure Tottenham receive a massive transfer fee to reinvest into their depleted squad.

Spurs fans have accepted that Romero may push for his exit. A loss to Man United and an impending European competition-less season would likely seal his fate.

But if Spurs can remove the "It's only Tottenham" tag and take down Man United in Bilbao, maybe, just maybe, the prospect of Champions League football could make a new contract look a little sweeter for Romero.

A loss on Wednesday, and Levy may need to pick up the phone to Palace about Guehi.

Tottenham manager Ange Postecoglou has induced many eye rolls around the grounds during the 2024/25 season, because he has an awful lot to say for a manager who is currently commanding Spurs to a historically poor 17th-placed finish in the Premier League - a feat so pathetic that it seemed impossible even during the darkest ages of Spurs sides past.

Postecoglou is hanging his hat on a Europa League Final appearance against Manchester United, which, while a big deal, is not yet a trophy won. Nor have Tottenham been truly tested in the tournament, beating an Omar Marmoush-deprived Eintracht Frankfurt in the quarterfinals and minnows Bodo Glimt in the semis.

Yet as David Ornstein and other top English transfer journalists weigh in with consistently pessimistic updates regarding Postecoglou's future, likening him to Erik ten Hag for Manchester United last season, Big Ange can't help but be his biggest fan and bang his own drum, portraying the false calmness that only a man more obsessed with the word "mate" than tactics can.

Ange Postecoglou has a point behind the madness

In his latest media faux pas, Postecoglou, as relayed by journalist Chris Wheatley, is claiming that his "future is assured", "My future is assured, mate. I wouldn't be the first person who changes jobs. I've got a beautiful family, a great life. I'll keep on winning trophies until I finish - wherever that is. Don't worry about my future."

Although Postecoglou obviously has a point about living a good life with his family and still competing for trophies even without Spurs, the point is so obvious that it's almost nauseating. Of course a millionaire is going to enjoy his life. And of course, Postecoglou should. But to say his future is "assured" in the wider context that everyone is discussing his future as it pretains to the Tottenham job is quite absurd.

Postecoglou's job is far from assured, and his ability to compete for trophies higher than the level of the Europa League is even less assured. At the same time, Postecoglou's bizarre claim to job security has two kernels of truth in it.

The first is, again, the obvious one, and that is that Postecoglou can be personally and professionally successful without Tottenham Hotspur, with the professional success necessitating perhaps a less ambitious definition of what success in football means.

But the second is more concrete, and that is that Postecoglou can be the manager who delivers a major trophy to Tottenham by winning the Europa League on Wednesday. For all the inane press conferences, horrible losses, atrocious tactics, misuse of young talents, and general quackery that has gone on at the Tottenham Hotspur Stadium this past 12 months or so, Postecoglou can lay claim to an honor above what his peers achieved with Spurs. And that, along with his success in his personal life, has to be respected, even by the staunchest of his critics.

It's the hope that gets you. Tottenham Hotspur fans know this better than anyone.

Having already lost James Maddison and Dejan Kulusevski ahead of Wednesday's Europa League final against Manchester United, Spurs fans clung to hope of a surprise Lucas Bergvall return.

Tottenham boss Ange Postecoglou shut that down once and for all.

"Lucas isn't available. Pretty much the same as we were as of last week," Postecoglou told reporters on Tuesday.

He couldn't let us dream for one more day?

Bergvall is dealing with an ankle injury that is expected to end his season, although recent rumblings provided fans with a glimmer of hope. It never felt realistic, but nor did winning the Europa League while finishing 17th in the Premier League.

Spurs fans had their theories. Many observed that the social media team had notably "hidden" Bergvall during their videos from Bilbao, which other fan-filmed videos showed the 19-year-old playmaker appear to move comfortably without a walking boot.

Bergvall's absence creates a major problem for Spurs ahead of their biggest game since reaching the Champions League final six years ago.

Where does the attacking creativity come from? If not Bergvall, there was Maddison. Failing that, they had Kulusevski. All three playmakers will sit on the sidelines on Wednesday night.

Ange Postecoglou must find a creative solution to Lucas Bergvall's absence in Europa League final

It's fitting that Tottenham's most important game captures the gloomy forecast fans have dealt with all season. Only Spurs could lose all three players at a position so vital before their biggest game.

Ange has a decision to make.

Does he play it safe with a midfield trio of Pape Mate Sarr, Rodrigo Bentancur, and Yves Bissouma? Or does he dare to dream?

To Dare Is To Do, right? Ange hasn't ruled out moving Pedro Porro into an advanced role, which is the kind of boom-or-bust experiment best reserved for the preseason and not a European final. Does he roll the dice with the inexperience of Wilson Odobert or Mikey Moore?

At this point, an unpredictable cup-final gamble feels better than taking the cautious route against a United team that, for all its faults, knows how to win the big one.

After all, Ange is a risk-taker. He has stayed true to his all-out-attack formula, even when his resilience to maintain a high line with nine players versus Chelsea resulted in derby-day embarrassment.

In what is likely his final game as Spurs boss, Postecoglou faces an all-too-familiar injury crisis and is left with a tough decision. Ange boldly promised a trophy in his second season, but to get there, he may need to roll the dice once more.

Bergvall isn't coming to save Tottenham. Ange must dare to dream one final time.

In less than 24 hours, Tottenham will battle Manchester United in Bilbao in the Europa League Final with both a spot in next season's Champions League and a whole lot of bragging rights on the line. Spurs are coming into this game hobbled with James Maddison, Lucas Bergvall, and Dejan Kulusevski all out for the season to dwindle down the team's creativity and ball progression in the attacking midfield.

There were some rumblings that, by some miracle, Spurs could have one of Maddison or Bergvall available, with many fans holding onto the Swedish international's return as a potential game-changer against Manchester United.

That, of course, isn't happening, as much as diehard football fans love to delude themselves into dream land. The Daily Mail's Nathan Salt relayed his observation that neither Maddison nor Bergvall were present at the training on the day before the Europa League Final, essentially ruling them out of the Manchester United clash.

Tottenham will have one key midfielder healthy

However, in a positive twist, a previously questionable player was available, effectively confirming his availability. Young center midfielder Pape Sarr suffered an injury after 53 hard-fought minutes against Aston Villa in a 2-0 Premier League loss a couple of days ago, calling his status into question for Wednesday night's do-or-die fixture.

Sarr is part of the Tottenham group training ahead of the game, and with three midfielders already ruled out, Spurs will need the 22-year-old Senegalese international to be at his best. He's the most dynamic box-to-box midfielder in the side with Bergvall out, and he and Rodrigo Bentancur will likely be the double pivot of choice behind, potentially, the unproven Wilson Odobert as a high-risk, high-reward No. 10 replacement for Maddison.

The defensive work and running Sarr provides will be crucial for Tottenham if they want to secure this major piece of silverware against another fallen Premier League giant. Sarr has to be as close to 100 percent healthy as possible, so the fact that he is able to practice with his teammates is an important sign.

Tottenham have suffered more than enough bad injury news as of late, so getting confirmed word that Sarr is healthy enough to practice and in a good position to play a significant role against Manchester United is the right kind of injury news for Spurs. Sarr has his ups and downs, but the young No. 8 is definitely an asset to this current Tottenham squad. It's good to see he is out there.

Ange Postecoglou's days at Tottenham Hotspur should be limited, even if he wins the Europa League this week. If he wasn't already, he'll be sweating at the club's imminent arrival, Fabio Paratici.

Ange Postecoglou is coming towards the end of his second season at Tottenham Hotspur. All season long, he's reiterated the fact that he's always successful in his second season. It remains to be seen whether this trend will ring true again at Spurs, as they play in the Europa League final this week.

That said, the damage appears to be done at Tottenham. While any club would take winning the Europa League, it doesn't paper over the obvious cracks. Spurs could finish as low as 17th, their current position, in the Premier League. This is simply inexcusable, even with other trophies.

This season, it's been excuse after excuse. A large section of the Tottenham fanbase is sick to the core of Ange blaming everything except himself and his players.

Look, winning European silverware would be a great end to Ange Postecoglou's short stay. Beating Man United in the process would secure the Aussie's place in the club's history books. But is he the right man for the long-term future? It doesn't seem like it.

Ange Postecoglou should be sweating at Tottenham's imminent arrival

According to a report by Tom Barclay of The Sun, Fabio Paratici's arrival at Tottenham Hotspur is "imminent" and one of his first jobs at the North London outfit will be to replace Ange Postecoglou with a new manager.

The report states that Tottenham are now considering Francesco Farioli of Ajax as their new manager. The Italian has recently decided to leave Ajax, leaving his future in question. The Tottenham opening appears to have happened at the right time.

Of course, other options are also being considered by Tottenham. With the North London side actively dabbling in the manager's market, there are a number of options creeping up. Long story short, Farioli can join the growing list of potential Ange successors.

It may seem harsh for Ange Postecoglou to be shown the door after potentially lifting a European title. However, the truth is that he's lucky to have made it this far. It would be a welcome parting gift, but not a get out of jail free card.

So, if Ange Postecoglou harbored any hopes of keeping hold of his Tottenham job, then the arrival of Paratici won't be welcome news to him.

Although Tottenham Hotspur spent a combined 125 million pounds on strikers Richarlison and Dominic Solanke in the previous two summer transfer windows, the forwards have combined for just 12 goals and 4 assists during the 2024/25 Premier League season, which is just one more goal and one more assist than younger winger Brennan Johnson.

Simply put, Tottenham need more production from their strikers, and with Richarlison edging closer towards a move back to Everton, there could be an opening for Tottenham to make a smart signing at the striker position.

Unfortunately, it looks like Spurs may be behind the eight ball for the cheapest option, which is Lille free agent Jonathan David, who looks like the best available free agent in the summer 2025 transfer window at any position.

Antonio Conte is racking up the wins in Napoli

According to a new report from Football Insider's Pete O'Rourke, Napoli are currently the best-placed club to sign David, edging out Tottenham and West Ham right now. O'Rourke feels that Napoli are pushing the hardest of any of the clubs to sign David, so Tottenham could lose out on David to the favorites to become Serie A champions and former manager Antonio Conte.

Napoli have one of the biggest names at striker in Europe in Romelu Lukaku, as well as young Italian talent Giacomo Raspadori. But David can be a great partner and, later, successor to Lukaku, helping make sure Napoli can remain competitive in Serie A and the Champions League next season.

Right now, Napoli are a much better side than Tottenham, and, as an additional slap in the face to Spurs, are better-coached with Conte at the helm. In classic Conte fashion, the iconic Italian coach is already feuding with Napoli ownership, so his own future in Europe's most romantic city is uncertain. However, Conte could beat out Tottenham in one last stroke of adding insult to Spurs by convincing David to join the potential Serie A champions.

If David is off the table, Tottenham would then likely turn closer to Serie A for their next striker, where Napoli's rivals Juventus have a great market opportunity of their own in Serbian international Dusan Vlahovic, who is just waiting for a club to rescue him from Turin.

David's transfer saga is far from over, and Napoli have clearly not won the race yet. Plenty of clubs are involved in the sweepstakes, and Tottenham should be among them dialing the phone, working hard to bring the Canadian international to North London. But they have to face the fact that with a possible title-winning team in a top-five league heavily interested, Spurs are the underdogs.

Tottenham are 17th in the Premier League and know that they need to make sweeping changes to their squad in the summer 2025 transfer market, but in order to bring in players capable of taking the team back to the top five of the Premier League, they are going to have to sell some notable names this summer.

The most mentioned in transfer rumblings at this early stage before the market even officially opens on June 1 are center back Cristian Romero, who is wanted highly by Spanish giants Atletico Madrid, and striker Richarlison, who has been linked with a return to Everton.

Since Richarlison's 60 million pound transfer to Tottenham in 2022, the Brazilian international's stock has fallen. He's had trouble staying healthy, and while he has scored some goals in limited action when healthy, his overall impact on matches has been minimal.

Everton love Richarlison more than Tottenham do

Richarlison is expendable to Tottenham, whereas at Everton, he was an actual hero who carried the team from a scoring perspective while making things happen out of nothing. Without Richarlison, Everton would have been relegated, and you can tell that there is so much mutual respect between player and club.

That respect and love has never wavered, and Everton fans clearly want Richarlison back. In the farewell match at Goodison Park, Everton supporters could be heard chanting, “He’s Brazilian, he only cost £50 million, and we think he’s f—– brilliant, Richarlison!” They were singing to the tune of the Oasis hit "She's Electric".

The way Everton supporters yearned for Richarlison in an important game in the club's history only fans the flames of the transfer rumors linking the 28-year-old with a move back to the Merseyside. With Tottenham kicking around the idea of signing some big names at striker like Juventus's fallen star Dusan Vlahovic and Ange Postecoglou praising Dominic Solanke as someone to build the team around, Richarlison fulls further and further out of the picture at the Tottenham Hotspur Stadium.

There's more of a bond between Richarlison and Everton than Richarlison and Tottenham, to the point where Spurs are starting to see the player as more of a sellable asset than someone who will help the team on the pitch next season. It's a bit harsh, but Richarlison may be a better fit for the Toffees and would improve significantly in his confidence as one of the stars of that team as opposed to a forgotten role player in North London.

Tottenham manager Ange Postecoglou's days are numbered at the club, because the results in the Premier League have been so poor that there's a pervasive belief among journalists covering the league that even a Europa League triumph won't be enough for Big Ange to save his job.

For the most part, Tottenham are focused on managers within the Premier League who have achieved greater success than Spurs this season at clubs with smaller budgets. Fulham's Marco Silva, Bournemouth's Andoni Iraola, Brentford's Thomas Frank, and FA Cup winner Oliver Glasner of Crystal Palace are all high-profile manager targets for Spurs.

But there have been coaches outside of the Premier League generating interest, too. Tottenham have been linked with Scott Parker and even Dortmund's Niko Kovac, who rescued BVB from missing out on the Champions League. These options are largely underwhelming, but there is one new name worth thinking about who isn't obviously linked to Spurs.

Tottenham can't just focus on the biggest names

On Saturday, Lens manager Will Still made it official and stepped down as manager of the overperforming Ligue 1 club, per Fabrizio Romano, in order to be closer to his partner who has a serious medical illness. Still is expected to take a job in England, and Southampton, set to be relegated from the Premier League, have reportedly held talks with the 32-year-old coach.

Although Tottenham should be prioritizing big names with experienced track records who can right the ship, it's not really realistic for Spurs to do that. Of the available managers with links to Tottenham, Glasner is the only one with a clear record of top-level success as a Europa League winner with Eintracht Frankfurt and an FA Cup winner with Palace, but he's hardly proven at the absolute top level; his resume isn't all that much more convincing than Kovac's.

But resume isn't everything. Ideas and results compared to situation are. Still was exceptional at Reims and Lens, somehow improving Lens's results in the 2024/25 season despite the fact that they sold four of their most important players, including phenom center backs Kevin Danso (to Tottenham) and Abdukodir Khusanov (to Manchester City).

Still shouldn't necessarily jump the line as an immediate favorite for the Tottenham job, but Spurs should at least consider him an option, given what he has done in Ligue 1 for two clubs in getting them to outperform expectations. Perhaps he's ready for a step up from Lens to Spurs, like Danso, rather than an arguable major step down to Southampton. It's hard to argue that Still isn't a better manager candidate for Spurs than Scott Parker, after all.