Why Do Elite Managers Keep Failing at Tottenham?

As the Tottenham Hotspur Stadium gears up for a season-defining Europa League semi-final, Ange Postecoglou will likely be aware that his job security as manager, which is hanging by a thread as things stand, will become incredibly tenuous if his side don't beat Bodo/Glimt this evening.

⏳ pic.twitter.com/3H7NKChNdY

— Tottenham Hotspur (@SpursOfficial) May 1, 2025

Yet it's only eighteen months ago that Ange-ball was the pride of the Lilywhites and that the Australian talisman could do no wrong in the eyes of Spurs fans.

Elsewhere in Tottenham's recent history is the better-forgotten reigns of Jose Mourinho and Antonio Conte, neither of whom need their pedigree explaining - but context's sake, they have thirteen league titles, nine domestic cups and a Champions League victory between them.

It feels like Spurs have tried every type of manager: from the proven entity and cult hero of Mourinho to the emerging innovator in Postecoglou. Yet success has continued to evade Tottenham at every turn.

As a result of this, it's no surprise that pressure has mounted on owner Daniel Levy. But what is it about his planning (or lack of) that has led to perpetual failure at Tottenham?

One Game Away

Before diving into the patterns behind Spurs' struggles, it is important to understand the unique situations surrounding each of their recent long-term managers (if two years is considered 'long') over the past five years.

Mourinho's appointment in November 2019 was met with mixed emotions from Tottenham fans. On one hand, the Portuguese had the ability to instill unto the club a 'winning mentality'. To others, he felt like a square peg in a round hole.

What didn't help his cause was the fact the Special One was appointed just twelve hours after Mauricio Pochettino was sacked. Spurs were fourteenth at the time, but faith in Pochettino was still strong amongst fans, and they had reached their first Champions League final just months before!

The appointment of Mourinho was clearly a 'win-now' move from Levy - a complete U-turn on the long-term project that Pochettino had committed five years to.

So when Tottenham exited the Champions League in the last sixteen and went out of the FA Cup in the Fifth Round in 2019/20, Levy's choice to appoint the former Chelsea manager was seriously questioned.

What is the biggest question around Mourinho's time at Tottenham though, is the bizarre timing of his sacking. He had guided Tottenham to a League Cup final - yet was sacked six days before he had the chance to end their trophy drought. This is the same Mourinho who has won fourteen out of nineteen cup finals in his career.

He was one game away from being the man who brought silverware back to North London, but he never got the chance to do so.

Self-Destruction

Antonio Conte's arrival in November 2021 (after the uninspiring reign of Nuno Espírito Santo) was the last straw for many Tottenham fans. His arrival was met with cautious optimism - he was a serial winner. Equally, he was ex-Chelsea and had a proclivity for outbursts. But his clear identity and track record meant many fans were willing to give him a chance.

For a while, it worked. He dragged Spurs to a top-four finish in 2021/22, overhauling Arsenal late in the season. The football wasn’t always pretty, but it was efficient — and it got results. Son Heung-min shared the Premier League Golden Boot under Conte’s guidance, and Harry Kane remained prolific.

But by his second season, the mood had soured. The football was increasingly stale, the squad looked worn out, and performances were wildly inconsistent. Behind the scenes, tensions were simmering. Conte had grown visibly frustrated with the club’s recruitment model and perceived lack of ambition. He was often cryptic in his press conferences — until March 2023, when he exploded.

After a 3-3 draw away to Southampton, Conte launched into a now-infamous tirade. He labelled his players “selfish,” accused them of lacking professionalism, and suggested that the culture of underachievement at Tottenham stretched back years. “They don't play for something important,” he said, in what felt like a direct attack on both the squad and the club hierarchy. “They don’t want to play under pressure. They don’t want to play under stress.”

In saying these things, Conte effectively sacked himself. Many interpreted the rant as a calculated act of self-sabotage; a way to force the club’s hand. Sure enough, he was gone just over a week later, his contract terminated by mutual consent during the March international break.

His time at Tottenham ultimately ended in implosion — not because of one bad result, but because he made his position untenable in spectacular fashion.

Europa League Or Bust

Postecoglou’s arrival to North London brought a refreshing change in tone. He was somewhat of an unproven entity, but quickly became popular amongst fans for his refreshing, attacking playstyle. It was like Tottenham had taken the Mourinho and Conte-shaped blinkers off, and feelgood football was back.

Spurs started the 2023/24 season in electrifying fashion, sitting top of the Premier League after ten games, and winning hearts with their fluid attacking play. The atmosphere around the club shifted, with fans backing their new manager and his vision for a long-term project. Postecoglou had earned the affection of the supporters, many of whom were finally excited by Spurs’ prospects.

They inevitably tailed off towards the end of the season and ended up finishing fifth, but the feeling of optimism remained.

Yet as the 2024/25 season has unfolded, Postecoglou's unyielding belief in his footballing philosophy began to test the patience of fans. The results became inconsistent, and then they became consistently poor. They are now at genuine risk of finishing as low as seventeenth in the league, and the Ange-ball fire looks to have burnt out.

Which brings us to this evening, and if Postecoglou is to reignite any of that flame, a convincing performance and result is absolutely imperative.

The Common Denominator

As each manager has failed, the fault for Tottenham's decline has got closer and closer to Levy's door. Fans have protested against his ownership: slating his recruitment, consistency in messaging, lack of investment, culture and patience.

The lack of investment is arguably the most damning element of fans' arguments. Each of Mourinho, Conte and Postecoglou were tasked with winning trophies, but not presented with the infrastructure, recruitment or transfer funds to make a serious challenge for a trophy. They have essentially fought with one arm tied up.

Yet every time, Levy has managed to find fault in the manager, rather than his own process. There hasn't been a change in transfer policy or tangible increase in investment.

🚨⚪️: Tottenham's management has invested £122 million in the club since 2001.

Aston Villa's management has invested £600 million in the club since 2018. https://t.co/PlN3oCxu4H

— Tottenham Transfer News (@Bergvallisking) April 28, 2025

Coinciding with this is a major lack of long-term planning at Tottenham. Mourinho replaced Pochettino in the middle of a crisis, while Conte was appointed after Nuno’s failed stint. Postecoglou, though promising, was thrust into a turbulent situation without full support. It has felt like constant firefighting rather than proactivity.

The cultural problem is one Levy probably shouldn't take full accountability for. Conte's explosion over the weakness of the players may have been out of turn, but he wasn't necessarily wrong. It has been Spurs' chronic instability, lack of board support and pressure for a quick fix that has led to failure after failure. The managers simply haven't been setup to win.