Tottenham Hotspur's trophy drought sits at an agonising seventeen years.
For a club of their stature, it has become an easy stick for rival fans to beat them with.
The fact Crystal Palace, Leicester City, Swansea City and even Wigan Athletic have won major trophies in that time has rubbed extra salt into the wounds.
It's not to say Tottenham haven't had chances to add silverware as they've accrued four runners-up medals since their 2008 League Cup triumph over rivals Chelsea.
Ange Postecoglou's side will look to avoid increasing the runners-up medal tally to five when they take on Manchester United in the Europa League final in Bilbao on Wednesday.
Purely on reputation, it would be billed as a heavyweight clash and in many respects, it still is.
But both sides have floundered in the Premier League this term as Postecoglou and Ruben Amorim have set embarrassing new lows throughout.
Yet Wednesday gives the two managers one final chance to make something out of an otherwise-dismal campaign for their respective sides.
It goes without saying what a victory in Bilbao would do for Tottenham.
However, speaking on talkSPORT's Trans Euro Express, journalist Andy Brassell does not believe a win for Postecoglou's side would trump the significance of a similar result for United.
"It feels to me, actually, that winning this game is more important for United," Brassell said.
"I can see the route to Spurs getting better quite quickly. Even if there are problems at the club, even if I have doubts over the coach, I don't think they're a million miles away from being able to improve.
"For United, I think they've got so much work to do, an incredible amount of work to do.
"I don't even know if Amorim is going to be the person to do it, because it's clear he's getting more and more frustrated.
"But they need this Champions League, they need the money, they need to be able to pull players of repute because that squad needs one heck of a turnover."
One factor in Postecoglou's favour is he is yet to lose to United since he took over as Tottenham boss.
The Australian boasts four victories and one draw against the Red Devils in all competitions, with their latest encounter ending in a 1-0 win for Tottenham.
However, Postecoglou will enter Wednesday's final with a serious midfield conundrum on his hands.
Postecoglou appears to have found success using a double pivot in midfield, where Yves Bissouma and Rodrigo Bentancur are expected to feature against United.
But questions remain regarding who will fill the void as the attacking midfielder.
James Maddison and Lucas Bergvall will play no part, nor will Dejan Kulusevski who had been earmarked for an advanced midfield role but has since undergone knee surgery.
Pape Matar Sarr is an option, although he is more comfortable in a less attacking role.
Wilson Odobert showed promise in the position during Tottenham's 2-0 loss against Aston Villa last Friday, but he is far more accustomed to life on the wing.
Brassell believed Sarr to be 'the safest bet', even if he has high praise for Odobert.
"I think if you wind back to AZ in the last 16, I thought Odobert was brilliant in the second leg," Brassell said.
"But I just think sticking him in a position that's not out wide, I think is a bit of a risk.
"Sarr's ability to break into the box gives you something else to play with as well.
"I don't think there's any right answer and I don't think there's an enormous amount of options, which I guess feeds into the Postecolgou narrative of how hard done by he's been this season."
Regardless of who gets the nod, they will have an almighty task in limiting the effectiveness of their opposite number, Bruno Fernandes.
The Portuguese star has been an ever-present for United this season and one of their few shining lights, having accrued an impressive 19 goals and 19 assists from 55 appearances in all competitions.
Put simply, Spurs do not have a player available who can turn a contest on its head quite like Fernandes.
It is the reason why Brassell feels slightly inclined to favour the Red Devils to land silverware for a third season on the bounce as he explained the unique situation behind Fernandes' success at Old Trafford.
"If that's why I'm going to lean slightly towards Manchester United, that would be why," Brassell said.
"I don't think it's impossible for Tottenham, at all. But I think the Bruno Fernandes factor is huge.
"United have not dragged him down in the way they have dragged others down.
"But why Bruno Fernandes works so well for Manchester United is because he likes to run a team.
"Because they didn't really have a plan or a strategy when he came in, and the plan was to let Bruno run the team, he got to play exactly how he was playing at Sporting before. There was no tactical nuance to it.
"That's what he's done for most of the time he's been there, which is why he's been exceptionally successful."
Yet for all of Fernandes' evident brilliance, Postecoglou has found a way to nullify him on five separate occasions.
If he can do it for a sixth, the Australian's claim he 'always' wins things in his second season may very well remain blissfully intact.
Man United and Spurs legends give Europa League final verdict
Former Manchester United defender John O'Shea knows a thing or two about what it takes to win silverware.
After all, the Irishman picked up an impressive 14 trophies in his time at Old Trafford.
Yet O'Shea believes the importance of securing Champions League qualification may outweigh the value of a trophy for United, especially given the riches associated with a spot in Europe's marquee club competition.
"Not only do you win a European trophy, which the club has been synonymous with, but it's the build-up for what it leads up to for next season," O'Shea told talkSPORT.
"Listen, it won' t be a feel-good factor, far from it, from either team's point of view. But when you win silverware, it's huge for any club.
"You can argue the different tournaments, but that's the tournament you're in. You get Champions League qualification from it, you do all you can to win it."
O'Shea added victory on Wednesday would 'be a crumb of comfort' for United's suffering supporters, but was also not oblivious to the fact there's 'lots of work to do' going forward.
His international teammate Paul McShane, who came through United's academy and now coaches the Red Devils' Under-15s, echoed a similar sentiment.
"With the season that the first team has had, it's been poor. There's no denying that." McShane told talkSPORT.
"There's a chance to resurrect it a little bit with the game on Wednesday.
"Spurs are in a similar situation, so it's going to be a very interesting game. It's big for the club, it's big financially."
McShane even claimed United may have 'hit rock bottom', but felt it was a necessary pain to endure in order to progress.
"It's been a crazy season," McShane said.
"No-one expected the team to finish as low as they have. It's clear to see there's a few issues and it needs sorting.
"I think you have to hit rock bottom before you go up again. I'm guessing this is pretty much rock bottom for the club.
"But there is a chance, there's a European final and the fans will be excited about it. They'll be desperate for any bit of success now."
Wayne Routledge, who was on Tottenham's books from 2005 to 2008, was reluctant to lean one way or the other regarding who he thought would win Wednesday's final.
However, the 40-year-old pointed out how a spot in the Champions League for United would be 'huge'.
"I think they both need it to be honest, to save their season," Routledge told talkSPORT.
"I think it's pretty evident a trophy might paper over some cracks. I think it's very difficult to say which team needs it more."
Routledge added: "I think you have to look at the other side of it. Manchester United will be in the middle of a massive rebuild.
"To be playing Champions League will be huge for them. May the best team win."