If the Tottenham chairman genuinely plans to build a team capable for the league title, he must stand firm against Abramovich and retain his best players.
Spurs's stand on Modric to deny Chelsea is sign of their ambition
When Roman Abramovich, wearing a beaming grin and displaying all the grace expected of a Russian oligarch, bought Chelsea eight years ago, he ushered in an era of vertiginous transfer fees.
Lost amid the big-name signings in the summer of 2003 - among them Hernan Crespo, Adrian Mutu and Claude Makelele - was a Scottish goalkeeper who transferred from Tottenham Hotspur to Chelsea for a meagre £500,000 (Dh2.93 million).
Neil Sullivan's role in the Chelsea revolution was limited - he made only four appearances - but his transfer is significant in that it was the first and remains the only time Abramovich managed to successfully strike a deal with Daniel Levy, the chairman of London rivals Spurs, without the threat of legal action.
The two men met for the first time two months before the Russian acquired Chelsea for £150m. Abramovich asked as to the availability of the north London club. Levy quoted the billionaire a deliberately high price to end any interest.
With no formal offer on the table, the Tottenham chairman was able to dismiss the approach out of hand without having to put it to the board.
With the exception of the Sullivan transfer, Abramovich has never since relied on negotiations involving the club's chief decision maker - it is little wonder the loathing between the two clubs is as strong as ever.
In 2004, Frank Arnesen, the renowned Danish scout, was employed as Tottenham's director of football. In his first year in the role, the man credited with discovering the Brazilian striker Ronaldo and Dutchmen Jaap Stam and Arjen Robben, secured Spurs the signatures of, among others, Michael Carrick, Tom Huddlestone, Michael Dawson and Aaron Lennon, all of whom have gone on to become England internationals.
However Arnesen, just 12 months after joining Spurs, was suspended by his club following an alleged illegal approach by Chelsea. Abramovich, in bypassing Levy, was able to convince Arnesen to request a move to Stamford Bridge.
But when the Dane was photographed aboard his prospective employer's yacht, Levy's tapping-up claims were reinforced and he threatened to file a complaint to the Premier League. Chelsea eventually agreed to pay a "significant" sum of compensation, believed to be in the region of £8m to £10m.
Despite dismissing Arnesen at the end of the most recent season, Abramovich's willingness to pay compensatory fees to secure his staff has obviously not diminished. Chelsea activated a €15m (Dh79.1m) buyout clause in the contract of Andres Villas-Boas, the former Porto manager, on Tuesday, but it is their pursuit of Levy's latest prize asset, Luka Modric, that smacks of similarities.
Last week, after refusing to consider a £22m bid for Modric, Tottenham issued a strongly worded statement that intimated they believed Chelsea were deliberately trying to unsettle the Croatian midfielder - much in the same way they did six years ago in their courting of Arnesen.
"We made our stance on this issue abundantly clear in writing to Chelsea," Levy said. "They chose to ignore it and then subsequently made the offer public."
Modric signed a six-year extension only last summer yet was quoted by an English newspaper as saying "Chelsea are a big club with an ambitious owner" and that "I want to leave Tottenham".
Levy responded by announcing Modric as "not for sale at any price" and behind closed doors, threats have been made that he will report Chelsea to the Premier League if they return with an improved bid.
Levy's stance is admirable. Having graduated with a first-class degree from Cambridge University, he is clearly no fool and is renowned in football circles for driving the hardest of hard bargains.
Critics often cite the transfers of Carrick and Dimitar Berbatov to Manchester United as Levy's willingness to capitalise on his investment at the detriment of his club, but the Modric situation will prove such naysayers wrong.
Such a strong statement means were he to relent, not only would it send an apocalyptic message to the rest of the Spurs squad, but it would also prove his own position at the helm wholly untenable.
Spurs have shown in recent seasons they can go toe-to-toe with Chelsea on the football pitch, now Levy must prove he can go toe-to-toe with Abramovich in the boardroom, without buckling to a lucrative compensation package.
If the Tottenham chairman genuinely plans to build a team capable of challenging for the league title, he must stand firm against Abramovich once again, he must retain his best players and he must strengthen his squad to show Modric that the north London club he is contracted to for the next five years has its own "ambitious owner".
With Modric expected to backtrack on his recent comments in a statement set for release later this week, Levy's hand will be strengthened and the most significant transfer of recent times directly involving the two clubs will remain a Scottish goalkeeper.