Mauricio Pochettino insists he enjoys working with Daniel Levy despite the Tottenham chairman's long-earned reputation.
Manchester United great Alex Ferguson infamously described doing business with Levy as "more painful than my hip replacement" after he signed Dimitar Berbatov for Spurs in September 2008.
That was the last time the two clubs, who meet at Wembley on Sunday, did business – a situation many expect to change over the coming months, with Pochettino reportedly sought as the long-term successor to Jose Mourinho at Old Trafford.
Spurs are 10 points ahead of United in the Premier League table despite not spending during the previous transfer window.
Pochettino has suggested over recent weeks that his club need to show greater ambition in the market but maintains his relationship with Levy is not a stressful one.
Responding to a question about Ferguson's observations, the he told reporters: "For me, it's the opposite. For me, if there was one person that was easy to do business with, it was Daniel.
"Historically, other [Spurs] managers were the opponent of Daniel, they always fight with him! I think it’s only me maybe that has a good relationship with him."
Pochettino signed a new five-year contract at Spurs last May, the terms of which are likely to be of interest to United and Real Madrid, and he feels that negotiation was a tougher on Levy than himself.
"For me, it was not difficult, I think it was more difficult for him than me," he said. "It was difficult because I am the manager and he cannot upset me.
"If we are talking about extending a contract or giving me more money, you need to be careful.
"With agents, you can talk very openly and say anything you want and the agent will manage the situation.
"But when you are talking directly to your manager, you need to be careful because one word can change the negotiation or change your mind.
"For him, that was new and it was tough every time he needed to talk to me."
Pochettino added: "For me, I negotiate harder when I am talking about my staff. They deserve a lot of credit.
"I am tougher when I talk about them because I feel a massive responsibility when I talk about them because they depend on me."
|Wozniacki enjoyed status as defending champion in Melbourne|
|Solskjaer backs Mourinho to return to football´s big time|
|Murray to miss Open 13 Marseille|
|Solskjaer´s United turnaround no easy task, says Hughton|
|The big Friday Premier League quiz|
|How James Harden´s 2018-19 numbers compare to his MVP campaign|
|It´s insane! - Tsitsipas excited to face ´legend´ Federer|
|Sharapova ends Wozniacki title defence|
|American teen Anisimova sends records tumbling at Aus Open|
|Lakers survive Ball´s gaffe to beat Thunder in OT|
|Federer expects ´athletic´ and ´attacking´ Tsitsipas clash|
|Alcacer is fit and available – Favre|
|Fantastic Federer breezes past Fritz|
|Pogba happy with Man United approach under Solskjaer|
|Mickelson leads Desert Classic, ties career-low with 12-under 60|
|Warriors´ Durant on Curry: He´s a once-in-a-generation, once-in-a-lifetime talent|
|Patriots owner says Brady is greatest player, not just quarterback, of all time|
|Inglis to retire from representative duty this year, NRL in 2020|
|Is Beal better without Wall? Wizards star says it´s ´absolutely nonsense´|
|Rockets C Capela undergoes thumb surgery, expected back after All-Star break|
|This Week in U.S. Sports: Irving apologises, Machado´s agent isn´t happy|
|Knicks in woeful shape, but 2019 could still be bright in New York|
|Valverde not worried about Levante´s Copa appeal|
|Nowell an option for England at flanker, reveals Jones|
|Pellegrini: Arnautovic available for the right price|
|Knicks throw away 19-point lead and lose on last-second goaltending call|
|Tebow invited back to Mets´ major league spring training|
|Canelo and Jacobs agree unification fight|
|Barcelona 3 Levante 0 (4-2 agg): Dembele at the double as Barca advance|
|Levante to lodge complaint over Barcelona Copa selection|
|Kanter´s London absence ´very unfortunate´, says NBA commissioner|
|NBA could swap London for Paris in 2020|
|Spurs coach Popovich uncertain if he will return next season|
|Pistons´ Griffin fined for verbal abuse of official|
|Everton do not have financial conditions to enter transfer market - Silva|
|Andy Cole joins Sol Campbell´s coaching staff at Macclesfield|
|Atletico confirm Saul has thigh injury|
|Wood replaces injured Stone in England squad|
|Lebanon 4 North Korea 1: Disciplinary record cruelly denies Radulovic´s men|
|Saudi Arabia 0 Qatar 2: In-form Ali bags brace as Qatar top group|
|Robertson signs new Liverpool deal|
|Vunipola backs Farrell to thrive in solo leadership role|
|People don´t know what´s going on behind the scenes - Mourinho defends United stint|
|Indefatigable Muguruza knocks out Konta at 3:12am|
|Serena coasts, difficulties for Halep and Muguruza´s marathon|
|Lowry retains Abu Dhabi lead|
|Djokovic battles past Tsonga, young guns flourish|
|Louisville airport to be renamed in Muhammad Ali´s honour|
|Emery not thinking about Ozil speculation|
|Sri Lanka hopeful over Kusal Mendis finger injury|
|Oman 3 Turkmenistan 1: Last-gasp Al-Musallami guarantees progression|
|Emery wants Cech to end career ´in a good moment´|
|Japan 2 Uzbekistan 1: Shiotani stunner seals comeback and top spot|
|Calhanoglu deal ´financially impossible´ for Leipzig|
|Not seen at Aus Open since Nadal, Djokovic and Murray in 2009 – ´Next Gen´ make move|
|Martial: Solskjaer lets me express myself|
|Djokovic sees off Tsonga to reach third round|
|Returning Cousins calls Warriors ´the most hated team in sports´|
|Halep injury ´nothing dangerous´|
|Warner picks up elbow injury in Bangladesh|
|Mkhitaryan returning to Arsenal training next week|
|Leeds United pounce for Real Madrid goalkeeper Casilla|
|Watson lights up Gabba before power cut forces abandonment|
|Superb Serena blows Bouchard away|
|Tevez, Hulk, Oscar, Lavezzi - how the CSL stars Dembele is following to China fared|
|Thiem retires from Australian Open|
|Osaka ´not telling´ when it comes to injury niggle|
|Fabinho enjoying Klopp´s management style|
|Halep battles past Kenin in Melbourne|
|Hartley to miss England´s Six Nations opener|