When Daniel Levy's near-25-year reign as executive chairman of Tottenham Hotspur concluded earlier this month, some may have wondered why a large proportion of the fanbase were in such a celebratrory mood.
Spurs have blossomed into a commercial juggernaut under Levy's watch, with his off-field utopia facilitating impressive self-sufficiency while so many others succumb to money trouble. Well, unless you're funded by a Russian oligarch or a Middle Eastern state.
Levy did plenty of good for this football club, and doubtless deserved his flowers in the aftermath of his tenure, but his legacy remains confused as a result of his inability, at crucial junctures, to give several of the managers he hired the best chance of success by delivering them the players they demanded.
While a canny operator for much of his tenure, Levy's hard-nosed negotiating style grated on plenty, and there were many times when a lack of assertion, or erroneous penny-pinching, cost Spurs a superstar.
Here are five of the best players that Spurs almost signed but cruelly slipped from their grasp.
1. João Moutinho
I just had to include this. From memory, this was my first experience of gut-wrenching transfer heartbreak.
This was a time when Fabrizio Romano wasn't a timeline protagonist, with social media in its infancy. It was the summer of 2012 and, if the Aryans had their way, missing out on João Moutinho wouldn't have mattered all that much.
Spurs looked set to complete the signing of the elegant Portuguese midfielder on Deadline Day, with André Villas-Boas, new to the role, desperate to replace Luka Modrić after the Croatian star departed for Real Madrid earlier in the window.
Moutinho had the makings of an impressive coup for Villas-Boas, with the midfielder keen on the move to north London. A record-fee was agreed with Porto, and the club worked tirelessly to get the deal over the line, even earning an extension after the deadline to ensure Moutinho put pen to paper.
However, a third-party owner of Moutinho's economic rights scuppered the move, with the Premier League forbidding third-party player ownership and Spurs not having enough time late in the day to fix the issue. Mousa Dembélé's arrival in the window meant things worked out okay at White Hart Lane, just not for Villas-Boas.
2. Rivaldo
Moutinho was very good all the way up until his twilight with Wolves, but he wasn't a bona fide superstar.
On the contrary, Brazilian forward Rivaldo is one of the most iconic figures to ever play the sport. He perhaps wasn't venerated to the degree that long-time international teammates Ronaldinho and Ronaldo were, but that shouldn't detract from his indisputable legacy.
Rivaldo was on the wrong side of his apex when the opportunity arose for Spurs to sign him as a free agent in 2002, and it would've been nothing short of remarkable had the club pulled this one off. They finished ninth in the Premier League the season prior, and weren't exactly a lucrative draw for a player of the Brazilian's standing.
However, then-manager Glenn Hoddle revealed that we were "so close" to landing Rivaldo, who instead opted to sign a three-year deal with Milan and explained his decision in a letter to Hoddle, which the boss certainly appreciated. A tenth-place finish beckoned in 2002/03, while the Rossoneri went on to win the Champions League and Coppa Italia.
Probably a wise move, to be fair.
3. Eden Hazard
My Dad was telling me all sorts of things regarding this 'Eden Hazard' fella, a name he was definitely mispronouncing, at the start of 2012.
The Belgian starlet had lit up Ligue 1 with Lille, and looked set for a big move. Spurs, however, were keen to jump ahead of the rest, supposedly securing a pre-contract agreement with the electric winger.
Unlike the Spurs side Rivaldo opted against joining, Hazard had the opportunity to complement a Lilywhite outfit that may well have put up a stiffer fight for the Premier League title had Levy handed Harry Redknapp just a little bit more than Ryan Nelsen and Louis Saha in the January transfer window.
We were so good to watch, and Hazard would've been the perfect succession plan for Gareth Bale, who's ascent to superstardom was complete the following season. The Belgian admitted he was tempted by Redknapp's north London project, but Chelsea's unthinkable Champions League success in Munich thrust us out of UEFA's premier club competition, and Hazard instead took his talents to SW6 as opposed to N17.
4. Paulo Dybala
I'm sure there are a few supporters that heave at the mention of La Joya.
Tottenham had been defeated in the 2019 Champions League final, and there was a sense that Mauricio Pochettino's team, our best of modern times, had embarked on their last hurrah. Poch spoke of a "painful rebuild" that had to be overseen, and Spurs' window of excitement returned them Tanguy Ndombélé, Giovani Lo Celso and the highly-rated Ryan Sessegnon.
It looked like the club were ready to shift to the next level, and they'd seemingly saved their best work for the very end when we came in for Juventus' Paulo Dybala.
The low-sock donning playmaker was an undisputed star; the sort you never thought would wind up in N17. However, there was a genuine chance for Spurs to land him late in that summer transfer window, with the club agreeing a fee with the Old Lady worth just shy of £65m. Never before have I woke up for a Deadline Day so excited. It felt like Christmas morning.
But, as many of us came to learn during this period of promise but eventual heartbreak, we weren't allowed nice things. A debacle over the player's image rights, whatever they are, meant the deal fell through.
5. Bruno Fernandes
There was initial transfer frustration in the 2019 summer window over Bruno Fernandes, who has just celebrated his 200th Premier League appearance by scoring his 100th Manchester United goal. Thank God he wasn't playing in last season's Europa League final...
While Fernandes isn't unanimously adored, his talent is doubtless appreciated. Had we struck a deal with Sporting CP off the back of our Champions League final defeat, the whole Dybala thing wouldn't have happened and, who knows, perhaps Pochettino is still in the job, with Fernandes leading the Argentine's rebuild of pain in unison with Harry Kane and Son Heung-min by contributing to multiple Premier League title successes.
Alas, some vintage Levy haggling compromised the deal, and there were reports of Fernandes, who had his heart set on a move to the Premier League, being reduced to tears when he heard that his proposed move had fallen through.
There are conflicting reports as to why exactly the transfer didn't materialise, but most suggest that the two clubs failed to settle upon a payment structure that suited both parties.