The Italian is a proven winner who demands that his employers back him in the transfer market, while Tottenham are prudent under-achievers…
The boos that greeted the full-time whistle at Tottenham Hotspur Stadium on Wednesday night were unsurprising.
The home fans had just watched a team that had fought so hard to qualify for the Champions League bow out with a whimper. It was undeniably demoralising.
Against a far-from-vintage AC Milan side, they had managed just two shots on target, the first of which had only arrived after an hour of play.
The fans' fury was perfectly understandable, then, their show of dissatisfaction totally justified.
However, it was the air of resignation that had preceded the conclusion of the contest which was truly indicative of the sorry situation Spurs now find themselves in.
When the board was held up signalling six minutes of injury time, there was no collective roar of encouragement, just an eerie silence. THAT was the surprising aspect of Spurs' last-16 exit.
The fans had accepted their team's fate. There was no defiance, no hope, just an air of acceptance of the inevitability of defeat.
They had essentially already given up on their team, and their coach. And they might argue, with a certain degree of validity, because he has long since given up on the club.
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Why Conte took the job
Antonio Conte and Tottenham were always an odd match. The Italian is one of the game's winners. Spurs are most definitely not.
From Conte's perspective, though, that lack of success was part of their appeal. As he declared after taking the job, he has never been afraid of a challenge.
"Having a one percent chance to win is enough for me," he told Sportweek back in November 2021.
"I've never taken charge of teams that had won the year before. I have always rebuilt [clubs] during my career. Juventus had finished seventh, Chelsea 10th, Inter fourth.
"But I know it will take some patience this time."
However, Conte's own patience arguably began to wear thin after his very first transfer window in north London.
It was at that time that he realised that Daniel Levy's recruitment strategy didn't match his own.
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The first cracks appear
âWhat happened in January was not easy," he lamented in an interview with . "We lost four players. Four important players for Tottenham, and we brought in only two.
âSo even just in terms of numbers, rather than reinforce the squad, we on paper weakened it.
"(Rodrigo) Bentancur and (Dejan) Kulusevski are ideal prospects for Tottenham, because Tottenham are seeking young players they can develop and grow, not players who are ready.
"That is the issue. It is inevitable that if you want to grow quicker and if you want to be competitive more rapidly, you need players with a lot of experience, because they also raise the experience level of the overall team.
"But I repeat, I have realised now that this is the vision of the club."
Which begs an obvious question: why was Conte only realising that then? Had it not been made clear to him during his first talks with Tottenham?
Also, was he completely unaware of Levy's modus operandi?
Spurs have never been among the European game's biggest spenders, after all.
They once went three windows without buying a player â and that was at a time when Mauricio Pochettino was proving that he deserved a bigger backing in the transfer market.
It's difficult, then, to comprehend what exactly Conte was expecting from Levy in terms of investment in the squad.
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A 'sh*t' season
Conte could, of course, argue that Spurs should have signed all of his preferred transfer targets last summer, after almost miraculously securing a place in this season's Champions League.
However, it's not as if his squad wasn't strengthened.
Spurs spent âŹ170 million last summer â more than all but three teams (Chelsea, Manchester United and West Ham) across Europe's 'Big 5' leagues, including Barcelona, Paris Saint-Germain, Manchester City, Newcastle and, most damningly of all, Arsenal.
Indeed, it's hard for Conte to put on the poor mouth when the north London rivals Spurs pipped to fourth place last season are now top of the Premier League table.
Again, there is a counter-argument, that Arsenal have only been playing in the Europa League, whereas Spurs, until Wednesday night at least, were in the Champions League, where there is next-to-no room for rotation, particularly with a squad that Conte believes is as shallow as Tottenham's.
He's also claimed that Djed Spence was a club signing but that doesn't explain why his most expensive acquisition, Richarlison, is now so frustrated by his lack of game time that he has labelled his season "sh*t".
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'A dagger to our hearts'
The situation is still somewhat salvageable, of course, as qualification for the Champions League would still be a hugely significant achievement for a club of Spurs' stature.
But there appears to be little hope of Conte and Spurs saving a marriage that appeared doomed to end in divorce right from the start.
Spurs fans crave silverware, having failed to win a trophy since 2008, yet Conte openly admitted that the only competitions that really counted in his eyes were the Premier League and the Champions League.
Which is obviously why Spurs didn't start their strongest side in the FA Cup fifth-round clash with Sheffield United.
Conte obviously wasn't on the bench that night, as he was still recovering from gallbladder surgery.
However, he clearly picked the team and the insipid 1-0 defeat at Bramall Lane precipitated the start of a slump that has effectively signalled the end of his tenure, because it was followed by a damaging loss at Wolves and then the tame European exit which has provoked an awful lot of introspection in North London.
As Harry Kane told Standard Sport, "If you go through [to the quarter-finals of the FA Cup], you take that momentum into the league game [at Wolves] and this game [against Milan].
"But I feel like that loss last week [at Sheffield United] put a dagger in our hearts and, as you can see, we haven't really recovered from that."
Kane added that while qualifying for next season's Champions League is now Spurs' sole objective, fourth place is still "not enough for this club".
Conte would obviously beg to differ, arguing that it is the best Spurs can hope to achieve given their resources â which obviously only serves to highlight the crucial divergence in opinion on Tottenham's targets.