Glenn Hoddle’s biggest career regret will cut even deeper with Tottenham fans today

Glenn Hoddle’s past comments about Tottenham Hotspur still ring true to this day, with the club continuing to struggle in the transfer market.

Many Tottenham Hotspur fans will point to the club’s higher-ups as the reason for the Lilywhites’ struggles in recent seasons.

Spurs find themselves currently in the relegation zone following their latest defeat at the hands of Sunderland and are now at risk of becoming a Championship side next campaign.

However, many fans will point out that the relegation scrap could well have been avoided had Spurs dipped into their cash reserves and strengthened their squad during the winter window.

Glenn Hoddle reflects on his biggest Tottenham regret

In January, Tottenham only signed Conor Gallagher and Souza, spending a net of £15 million as Brennan Johnson was sold for £35 million, the same fee they paid for Gallagher.

The club’s director, Johan Lange, explained that Spurs opted against spending heavily because they did not want to make any panic buys.

However, those decisions are set to come back to haunt them, with the squad struggling through an injury crisis and now on the verge of losing their Premier League status, one they have held for 48 years.

But these challenges are not new at the club. In an interview with The Guardian in 2021, Tottenham legend Glenn Hoddle reflected on his struggles to build any meaningful relationship with majority owner Joe Lewis, while also highlighting the limited investment during his tenure.

Reflecting on that period and why it remains a major regret, he said: “No. I’ve never met Joe Lewis. Never even had a phone call. Never had a conversation with him and Spurs were always my club. That was the happiest I should have been but it was probably the most disgruntled I felt – at Tottenham.

“It was such a shame because I wanted it so much. I wanted to build a side to win the league like we did at Monaco. That was one of my big regrets but the money was not there.”

Spurs spending contrasted as Glenn Hoddle reveals missed transfer chance

Spurs, who were 12 points clear of the bottom three back on matchday 19, have now lost that cushion to West Ham United, who leapfrogged them in gameweek 32 after their 4-0 win over Wolves.

The Hammers, whose relegation fate looked sealed at the time, have fought their way out of danger, having spent a significant amount bolstering their squad in the winter window.

In January alone, Nuno’s men splashed the cash, completing six transfers, with new signing Taty Castellanos’ brace helping the London side secure their victory over Wolves.

Hoddle also revealed he could have signed both Fernando Morientes of Real Madrid and Samuel Eto’o from Mallorca for just £12 million in 2003, but claimed Joe Lewis and Daniel Levy were too slow to act. Reflecting on the missed opportunity, he said: “That hurt me big time.”

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