This is another of those summers when Daniel Levy, Tottenham Hotspur's combative chairman, may have confused football with a high-stakes poker marathon in which brinkmanship is the finest of all life's thrills.

Spurs fans must view their boardroom warrior with ambivalence. On the one hand he jabs at Chelsea with a pitch-fork to keep Luka Modric at White Hart Lane. But on another reading, Tottenham's transfer strategies look needlessly protracted and ego-driven, to the detriment of the team.

One sure thought is that Arsenal's followers would like a Levy in their midst. In the transfer trade, all agree that the Gunners are too slow and tentative in pursuit of major targets. The late, cut-price lunge for Bolton's Gary Cahill, for instance, would have been better timed when the transfer window opened. Set against Arsenal's vacillation and high-wage phobia, Levy is The Terminator next door, driving up the price of Tottenham players coveted by other clubs and smashing down the fees demanded by sellers.

Where money meets machismo, sparks are bound to fly. But there are risks in having a chairman who behaves as if he has spent too long battling it out with cowboy-booted poker-meisters in Las Vegas. The first is instability. The habit of dragging out deals to the final hours leaves players and management staff unsure what the starting XI will be until dawn breaks on 1 September. Spurs have already shipped a 3-0 loss to Manchester United and are in a state of flux as Manchester City descend on London on Sunday.

The signing of Emmanuel Adebayor on loan is a minor flourish for Levy to lay before the crowd. But it remains a loan, and Adebayor's attitude is open to doubt. If he uses his stay in N17 to earn a move to a top-five club on the continent then he will need to dazzle, to Tottenham's benefit. A deal of this kind, though, is only a temporary solution to Harry Redknapp's hunt for a top-tier centre-forward, which stretched, this week, to a reported £11m bid for the Brazilian striker Leandro Damião.

For a club so adamant that Modric would be staying, Spurs have done a fine job of measuring up replacements. Joe Cole, Lassana Diarra and Scott Parker have all been coveted by Harry Redknapp, who has also signed Iago Falqué, a young attacking midfielder, on a season-long loan from Juventus. There is a pattern of Redknapp seeking a new midfield formula to ameliorate the loss of Modric, while Levy goes about telling Chelsea to get stuffed.

The backdrop is Spurs settling into a Europa League group place alongside Rubin Kazan, PAOK Salonika and Shamrock Rovers. After last season's great Champions League adventure, Tottenham were out-gunned by City and demoted back to Europe's junior competition. With the acquisitions of Sergio Agüero and Samir Nasri, City are unquestionably stronger, while Spurs are still unsure what their personnel list will be. So Sunday's game, coming six days after the United result, will offer a guide to the success or otherwise of Levy's rhino-skinned negotiating style.

Positives still abound. Spurs have managed to hang on to Gareth Bale, their most dynamic player, and appear strong on the youth-development front. Kyle Walker, at right-back, is a prospect, and Jake Livermore has caught the eye of Fabio Capello, the England coach. Against Hearts in midweek, six academy graduates played a part, including the debutants Harry Kane, Tom Carroll, Ryan Fredericks and Jake Nicholson. Andros Townsend is another with promise.

At the front end, though, Spurs need a route back into the Champions League qualifying places, and in that respect a little less posturing might help. Levy could point out that Rafael van der Vaart arrived on a midnight train at the end of the last summer's transfer window and enhanced the side. Brinkmanship isn't always synonymous with chaos, yet Spurs are high on the list of top clubs with issues to resolve.

Liverpool moved sharply for Stewart Downing, Jordan Henderson and Charlie Adam; City identified targets and swooped, even if the Nasri deal was spun out by Arsenal; United picked up Phil Jones, David de Gea and Ashley Young without fuss. The pursuit of Modric by Chelsea is in no way Tottenham's fault, but their summer has looked like one long struggle to hang on to a star player while shuffling contingency plans in case he leaves.

Redknapp, as we know, trades on instinct. He knows Cole and Diarra from previous incarnations and is always looking to fold pure talent into his mix. But the urges of a born scout run up against the granite business ethic of a chairman who appears to derive as much pleasure from negotiating as he does from the action on the pitch. Even the Tottenham relocation – Olympic Stadium or Northumberland Park? – has become a battlefield.

Offered a price for one of his players, Levy has been known to say: "You'll have to go north [with the amount]". Nothing wrong with that, in a world of chancers, as long as results don't go south.

British tennis could use brutal Dutch clarity

Britain's athletes are about to learn that the London Olympics last a year, not 17 days, because the World Championships in Daegu are cast as giant preview and audition for next summer's Games. The 66 GB runners, throwers and jumpers in South Korea have entered a new phase of scrutiny that the more sensitive among them could find exhausting.

While the British public take a renewed interest in track and field, at least for a week or so, there will be no nannying from Charles van Commenee, the forthright and uncompromising head coach. "When we're at the London Games, people will consider it a success or failure based on the number of medals won and lost," he said in Daegu. "They will not say we had a great transport system or that the stadiums looked quite nice."

There is nowhere to hide with this Dutch martinet. The brutal clarity of his thinking is precisely what's missing in another British sport. Tennis.