Tottenham: Beware Harry Kane, this is what happens when Daniel Levy plays hardball

Tottenham may not have a fearsome reputation on the pitch at present, but in the boardroom they have it in bucketloads.

Chairman Daniel Levy is infamous for being one of the most formidable and toughest transfer negotiators in the game - and anyone who has an experience of going toe-to-toe with him will likely have an interesting story to tell.

Spurs have been forced to sell some of their best players over the years, but not without a final throw of the dice from Levy to get the upper hand. The 59-year-old, renowned for a last-minute dash on Deadline Day - has played down talk of his ability to secure a good deal and insists he only wants what is best for Tottenham.

Well, that will surely be put to the test this summer when the vultures start circling for Harry Kane, who has told the club he wants to be sold after growing frustrated by a lack of progress in north London.

With Manchester City, Manchester United and Chelsea thought to be weighing up a £150million bid for the England captain, Levy will be pulling out all the stops to convince his star striker to commit to the club. And with three years still left on Kane's deal, the negotiating power is on Levy's side of the table.

But should Kane make it clear he is unhappy and force a move through, Levy could be forced to get in touch with his old methods of driving the hardest of deals.

As Kane prepares for a likely showdown with the Spurs chief, Sportsmail looks back on some famous encounters with Levy and how he left a few managers pulling their hair out in the process.

Sir Alex: Berbatov talks were more painful than my hip replacement

Legendary former Manchester United boss Sir Alex Ferguson has been there and seen it all - for 26 years he presided over numerous transfers both in and out of Old Trafford, but rarely came across a man like Levy.

In 2008 his club went in pursuit of another in-demand Tottenham forward - the Bulgarian Dimitar Berbatov, who would go on to join for £30.75m on Deadline Day. But it wasn't without a tough fight, as Levy tried to squeeze every penny out of United when their rivals City joined the chase.

'Daniel Levy, chairman of Tottenham, nailed us to the flagpole in 2008 when he took us all the way to the last day for the transfer window before agreeing terms for Dimitar Berbatov,' Sir Alex recalled in his autobiography Leading.

'When we got wind of the fact that Levy was trying to sell Berbatov to Manchester City, we stuck in our oar, chartered a plane and flew the player to Manchester, agreeing on terms with the player and, as I thought, a transfer fee with the club.

'Then Levy came back to us and said he needed Fraizer Campbell, one of our young strikers, as part of the deal. David Gill demurred so Levy then upped Berbatov's transfer fee a little.

'Finally, in order to get the deal over the line, and to add insult to injury, we sent Campbell on loan and paid the increased fee.

'We were up until midnight signing and faxing papers to make sure all the paperwork went through before the deadline expired.

'That whole experience was more painful than my hip replacement!'

The Scot admitted his respect for Levy for defending Tottenham's interests during talks, as he eventually landed the striker who would go on to score 56 goals for his United side.

'You can't discuss both sides of the issue with Daniel,' he added. 'It's about him, and Tottenham, nothing more, which is no bad thing from his club's perspective.'

United can expect similar hardship should they test the waters for Kane.

'Very difficult' Carrick negotiations 'went on for ages'

Just two years earlier Sir Alex had another face-off with Levy - this time over star midfielder Michael Carrick.

Carrick - who went on to make nearly 450 appearances for the Red Devils and became a club icon during his 12 years at Old Trafford - signed in 2006, but not without causing a few sleepless nights for United chiefs.

'I must say negotiations were very difficult and went on for ages,' Sir Alex told MUTV while reflecting on his career.

'I always remember I thought it was done and [former chief executive] David Gill phoned me on the golf course to say they want more. Typical [Spurs chairman] Daniel Levy!

'It was very hard to negotiate but, at the end of the day, we got it through and, ever since he joined us, he's had a fantastic career.'

Having only cost Spurs £2.75m to sign him from West Ham, United paid £18.6m to get him to Old Trafford. At the time of Carrick's arrival, Ferguson joked about the length of negotiations and admitted he was simply pleased to get it finalised.

'I think we may have ended up paying two pence more than I would have liked,' he said. 'But no more. Negotiations are always like this. Eventually, you get to a point where both sides may be unhappy but you shake hands and get on with it. That's where we got to with this one.'

Modric 'resented' Levy over failed Chelsea move

Softening the blow of Berbatov's move to United, Luka Modric arrived in the same window and went on to become a fan favourite.

The Croatian wizard put in some sensational displays in midfield for Spurs to help them secure a first ever passage into the UEFA Champions League in 2009-10, but Chelsea soon came calling for him - lining up a bid of £40m.

Despite the midfielder meeting Blues owner Roman Abramovich on his yacht in Nice, Levy stood firm to block the move - adamant he would not sell to a direct Premier League rival.

Modric made his desire to leave public and clashed with the Spurs chief, who rejected a number of Chelsea advances and leaving the player frustrated after claiming he 'broke promises'.

'Chelsea kept coming back with improved offers after Levy's every rejection. All of this aggravated me,' he wrote in Luka Modric: My Autobiography.

'Despite all the turbulence, I always had a good relationship with Levy. He was the one who brought me to Tottenham – for a record fee in the club's history. That only showed how highly he thought of me.

'However, I resented him because on a couple of occasions he had promised to let me move to a bigger club and then broke his promise. For me, one's promise and one's word are more important than anything.

'I had proven myself as a player. I didn't know where I would go from Tottenham. I didn't know if and when Levy would agree to sell me. But I was convinced it was time to move on, to a new and bigger challenge.'

In the end Modric can be grateful that his move to Chelsea was thwarted - as he would go on to join Real Madrid in 2012, where he would win four Champions League trophies and two LaLiga titles.

Levy discussions were 'the hardest I've ever had to undergo', says Lyon chief

Of all the stories about Daniel Levy's dealings, the tale of Lyon chief Jean-Michel Aulas' negotiations with him are perhaps the most telling.

Spurs were looking to sign goalkeeper Hugo Lloris in 2012, but it went all the way to the wire on Deadline Day as Aulas accused Levy of moving the goalposts, saying 'agreements had not been respected'.

France captain Lloris went on to sign for Tottenham in a £12m deal, but Aulas reflected on 'very, very difficult' talks with Levy that were 'the hardest I have ever had to undergo' in his career in football.

'We have had people speaking all night with Daniel Levy,' he said. 'He talks a lot and goes back on what we've agreed in writing.

'The things as they were at 5am were not the same at 10am. Agreements have not at all been respected. We've done what we can. Hugo has been troubled by the difficulty in these negotiations.

'It's been very, very difficult. I've got 25 years of experience as a president of a club and it's our 16th participation in a European competition in a row. But this is very rare in the football world.

'The negotiation with the Tottenham directors has been the hardest I have ever had to undergo in these 25 years.

'We had email exchanges which have been contradicted, so that's made it very complicated. It's difficult.

'The Tottenham board's theory is to explain that the economic market is very hard and so we have to get used to renegotiating.'

Lloris has since become one of Tottenham's longest-serving players, becoming their club captain and leading them to a Champions League final in 2019 after playing 371 games overall.

Refusing to back down to Real Madrid over Bale

Gareth Bale became the latest star name to emerge at Tottenham, and as a result, top teams from around Europe emerged to take him off their hands.

Just like Modric, Levy was unwilling to do business with a team in the same league despite Manchester United showing huge interest - and just like Modric, Real Madrid became the front runners.

Madrid chief Florentino Perez had stumped up £85m - a then world record fee that would eventually be accepted, but wanted to pay it over installments over three years  - something Levy would not entertain.

Levy stood his ground and made it clear Spurs would only sell on their terms. He had become infuriated with Madrid's conduct in accidentally advertising Bale shirts on the club's website before an agreement had been reached, while they had also set up a stage for his unveiling at the Bernabeu.

The Spurs supremo also tried to insist that striker Alvaro Morata be part of the negotiations for Bale. However, just a wonderkid at the time, Madrid were unable to throw him into a cash-plus player deal.

Getting £17m for Eriksen with six months left

When faced with losing one of his best players in Christian Eriksen on a free transfer, Levy was always going to pull out every weapon in his arsenal to rake in some cash for a player who had become one of the hottest talents in Europe.

At the start of the 2019-20 season, Eriksen had made it clear he had no plans to sign a new deal at Spurs amid interest from Real Madrid, and later said he wanted to 'try something new'.

After interest from Los Blancos waned, Inter Milan became the favourites to seal a move for the Dane - and with six months left on his deal, they were hoping to strike a bargain.

But Levy negotiated hard with his Serie A counterparts, going back and forth with the club after they had initially stumped up just £11m. Levy valued him at closer to £20m but ended up settling at £17m - not a bad price for a player who would have been available for free at the end of the season.

He had made it clear to Eriksen that Spurs were willing to match whatever Inter Milan were paying the midfielder to spell out to him that his reason for leaving wasn't motivated by money.

He told the Dane in the club's All or Nothing documentary on Amazon: 'I said to Jose [Mourinho], and I just want to make this clear now, from Tottenham's viewpoint I've always been consistent here, we don't want you to go.

'From a financial viewpoint, I've always said to you whatever another club is offering we'd do exactly the same, so there can be no doubt in your mind that your reason for leaving isn't a financial one.'

Digging his heels in over Dele Alli

Once one of the first names on the teamsheet, Alli quickly found himself out of favour under Jose Mourinho after failing to impress him in training and receiving a rebuke from his boss for his displays on the pitch.

He was heavily linked with a move to PSG last summer and in the January transfer window just gone - where he would have joined his former manager Mauricio Pochettino in Paris, but Levy pulled the plug on the deal.

PSG submitted a number of loan bids for the outcast midfielder but were left frustrated by Spurs' reluctance to sanction the move.

Despite Mourinho happy to let Alli leave so long as a replacement came in - and the player keen to move too - Levy dug his heels in, wanting more squad depth with Spurs still in four competitions at the time.

He had explored a shock move to bring Eriksen back to north London, but when that deal failed to materialise he decided to force an unhappy Alli to stay put.