Mauricio Pochettino can envisage spending the rest of his career at Tottenham but admits he would be interested to hear whether Arsene Wenger regrets spending so long at a club operating with financial constraints after a stadium build.
Wenger consistently kept Arsenal in the top four after the Emirates Stadium opened in 2006, but couldn't add to his trio of Premier League titles. And, although he won the FA Cup in 2014, 2015 and 2017 he was a divisive figure among Gunners fans until his departure in 2018.
Pochettino is now in charge of a north London club that is set to move into a new home and struggling to compete with their rivals in the transfer market, and he can see parallels, having himself secured three successive top-three finishes while receiving criticism for a lack of silverware.
"I have massive, huge respect for Arsene Wenger because when you talk about 22 years in charge of a club like Arsenal and all that happened in that period, you need to be so good -- not only a fantastic coach but a great human being to display the values you have," said Pochettino.
"It's amazing. That is why it's a little bit sad the way he finished in his club. All that Arsene Wenger gave for Arsenal, to finish in the way he finished, yes, it was a completely unfair.
"For me, it's an amazing recognition about his work. Only I hope, if I have one day the opportunity to talk with him, to ask, 'Was it worth it to do?' I don't know what he would say.
"It's true that we work and we know the reality of all that happens inside, and we cannot expect that the people live the same reality or have the same knowledge about what happens inside.
"I hope, or I wish, maybe to be here 20 years and decide to leave or to finish my career here. But I don't know because I need to ask him, if one day I have the possibility, if he's so happy in the way that he finished.
"I don't believe [so]. What I saw from my point of view, it was so unfair how the people treated him and talked. But we'll see."
Pochettino said earlier on Monday that Tottenham will need to invest more in their squad if they want to win trophies.
However, he insists he does not wish for the kind of funds that Tuesday's opponents Chelsea are able to spend. And, although Spurs may end a second successive transfer window without any signings, he believes the club is heading for greatness.
"No, it's not my dream to have this type of money," he said. "Of course, it's going to help you but it's not my dream to have this money here.
"The only way the people think is about money. That's going to help but at the moment I'm happy. Maybe I think in advance. Today, the club is doing what the club needs to do and I'm so happy to be here and helping the club, and it's so clear, the project.
"It's true the people are so impatient [and want to] win titles, but it's going to arrive. I can see in the future Tottenham winning trophies. I don't know if it's with us or without, in one year or in five years. But all the basis and foundation is one day to start to win titles and be like another club, so successful.
"It's difficult for the people because they're talking about today, today, today. But the vision of the future is that Tottenham are going to be one of the most exciting clubs in the world, not only in England.
"Today I'm so focused here and want to help the club to achieve what the club wants, and to be in the history because we're helping the club to finish all the facilities, and maybe we can win in that way. It would be fantastic. I'm so happy to be here. I'm so happy to work in that project."