Tottenham Hotspur chairman Daniel Levy tends not to take holidays in August, at least not at the end of the month. A notorious tough negotiator, Levy demands, and usually gets, top dollar when it comes to selling his players. He is also superb at signing players on value deals, a habit that looks likely to continue just days before Spurs kick off their Premier League season with a tough fixture at Newcastle United.

That’s certainly what happened last season, when Levy was haggling to get the best price in buying Scott Parker, in a £5.5m deal that was concluded on August 31. A few days earlier, Spurs had brought in Emmanuel Adebayor on loan, though the striker was not allowed to make his debut until after Spurs had played Manchester City, his parent club. One year earlier, Levy signed Rafael van der Vaart for a bargain £8m in a deal that went through after 6pm on the August 31 deadline, but was permitted after technical problems were traced on Spurs’s computer systems. Last season ended on May 13, and over three months later, Levy is still waiting to conclude his business.

It’s impossible to know how those deals affected Spurs’s results in the first few games of last season. Spurs lost to Manchester City (1-5) and Manchester United (0-3), before Parker and Adebayor helped turn the season around. Would they have won those matches with Parker and Adebayor in the side? Unlikely, I would say.

The season before, Spurs drew with Manchester City (0-0), beat Stoke (2-1) and lost at home to Wigan (0-1) before Van der Vaart came in. That summer, Levy had a successful selling month, making a combined £18m on the deals that took Peter Crouch and Wilson Palacios to Stoke, and £5m from Jamie O’Hara’s move to Wolves.

This summer has also been a successful one, at least in some ways, from a selling point of view. Levy sold Steven Pienaar back to Everton for £4.5m, making a profit of £1.5m on a player bought 18 months ago; he sold Vedran Corluka to Lokomotiv Moscow for £5.5m, four years after signing him for the same fee (when he was, arguably, a better player); and he sold Niko Kranjcar, amazingly, for £5.5m, making a profit of £4m.

It was Kranjcar who gave an insight into Levy’s methods when he recently told Croatian newspaper Sportske Novosti that he was reneging on a promise made last summer to sell Luka Modric to Real Madrid. “I know that the chairman talked to him face-to-face last autumn. He promised Luka he would let him go,” Kranjcar said. “They held me back for two years, until finally my new club paid what they were asking. Not a pound less. That is their specialty: they set unreasonably high transfer demands, but the absurd thing is they always get what they ask for.”

The Modric saga has caused a bottle-neck in Spurs’s transfer strategy so far and the frustrating thing is that everyone concerned wants the deal to happen. Madrid wants Modric; Modric wants to go; Spurs coach Andre Villas-Boas said over a month ago that he expects Modric to leave. And it looked like Levy would keep him at the club until the price was right. In a week that Portsmouth look likely to go into liquidation, his stance is admirable – and you won’t catch many Spurs fans criticising the man at the top. But Thursday’s reports from Spain suggest that Levy has blinked first, and will let him leave this weekend for £23m, which could rise to £28m in bonuses. That’s far less than the £40m he turned down from Chelsea 12 months ago.

Will Levy’s game of brinkmanship affect results? Spurs travel to Newcastle with Jermain Defoe and Harry Kane as their two striking options, Emmanuel Adebayor still waiting to join (a hold-up, by all accounts, that is not Spurs’s fault) and talks still ongoing with Internacional over Leandro Damiao. Their second game is home to West Bromwich Albion, and while it’s one thing to be six points off the pace after facing both Manchester clubs, it’s another to be playing catch-up if refusing to blink first causes points to be dropped at home against beatable opposition.

The question becomes one of putting a financial value on points. Between season 2004-05 and 2010-11, Spurs’s annual budget spend (on wages, amortisation and other expenses) was an average of £115.7m. In that period, the team won 406 league points, an average of 58 per season. Each point, then, came at an average cost of £1.99m. This is a simplified calculation, of course, and the figures are a little skewed by that final season (the club spend was £170.7m for 62 points), but it’s a rough guide for a club of Spurs’s level (Manchester City’s spend per point will be far greater, while that of Stoke, or Fulham, far less, of course).

The greatest example of his brinkmanship came in August 2008, when he refused to lower his £30.75m valuation of Dimitar Berbatov. Manchester United completed the deal late on August 31, sending Fraizer Campbell on loan to Spurs to cover their depleted strike-force (Robbie Keane had also been sold that summer). By then, Spurs had already lost to Middlesbrough and Sunderland and the side struggled to recover from Levy’s late machinations: after eight games the team was bottom of the table with two points and coach Juande Ramos was fired.

Villas-Boas has a similar profile to Ramos – both are serious-looking tacticians known for their high-tempo attacking styles, who replaced popular ‘cheeky chappies’ (in Ramos’s case, Martin Jol) – and at this rate, both are suffering the same frustrations with their boss’s obsession with getting a deal.

Sometimes waiting for that extra million can cost you dear. It appears that Levy has now realised that, and has met his match in Florentino Perez. Without Modric, Spurs can bring in more new players, something Villas-Boas would have liked to happen ten weeks ago.