The two most expensive signings in Manchester United's history both came when there was no Champions League football to offer at Old Trafford and if the club pursues Harry Kane this summer it will make it a hat-trick of mega deals at a time when the club was out of Europe's elite.
It's been a United strategy to splash the cash when their stock has fallen in recent years but the £89million capture of Paul Pogba in 2016 and the £80million spent to sign Harry Maguire three years later hardly fall into the category of money well spent.
On both occasions, United improved enough the following season to return to the Champions League and it probably says a lot about the attraction of playing for the club that one season away from Europe's top table wasn't seen then as a deal-breaker.
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Part of that is a feeling that an absence from the Champions League is only ever temporary for United, but presuming they don't find a run of form that has looked beyond them all season they are about to finish outside the top four in the Premier League for the fifth time in nine seasons.
At some point, a manager will be appointed by United that will get things right, but then Pogba would have thought that was the case in 2016 and he's coming to the realisation that six years in his prime have produced a League Cup and a Europa League. That would have felt unthinkable when he joined the club, but then so much that has happened in the last nine years has been unfathomable.
In that summer of 2016 United signed players from Juventus, Paris St-Germain, Borussia Dortmund and Villarreal, so the status of the club as being part of Europe's elite was clear. This is a club that markets itself as being one of the biggest two or three in the world and that stature still held then.
Now, however, it is nine years since United won a really significant trophy. They've reached the last eight of the Champions League twice in nine seasons and for players in their early 20s there is little memory of this ever being a club that competed with Manchester City, never mind Real Madrid and Bayern Munich.
So this summer, presuming it is a window where United can only offer Thursday nights in Europe's more low-key cities next season, will be a sign of whether that pulling power that remained strong in 2016 is still there and perhaps Kane will be the litmus test of that.
Kane wanted to leave Tottenham last summer and has made no secret of his desire to play in the Champions League.
“I want to be playing in the biggest games, the biggest moments. This season I’m sitting there watching the Champions League and watching the English teams doing amazing, and those are the games I want to be involved in," he told Gary Neville on The Overlap last May.
“So, I’m definitely in a moment in my career where I have to reflect and see where I’m at, and have a good, honest conversation with the chairman [Daniel Levy].
“I hope we can have that conversation and I’m sure he’ll want to set out a plan, but ultimately it’s going to be down to me and how I feel, and what’s going to be the best for me in my career.”
Kane wanted to join Manchester City last year but found a deal impossible to do, now the Blues have switched their sights to signing Erling Haaland from Borussia Dortmund.
That has limited Kane's options and domestically United might be the only suitors for the 28-year-old, but a lot will depend on what happens over the next two months.
It seems very unlikely that United will be able to offer Champions League football next season, so if he wants to come to Old Trafford the striker will be accepting that competing in those "biggest games" won't happen until after he's turned 30 in the summer of 2023.
Arsenal are favourites to finish fourth at the moment, but Tottenham are a point ahead of United and under Antonio Conte might still fancy their own chances of securing what has looked an unlikely Champions League berth for most of the season. If that happens Kane will have to decide between next season in the Champions League with Tottenham or, in the hope of United, more regular contributions to the knockout stages over the long-term if they start to get things right this summer.
Whoever gets the United job this summer will have something of a rebuild to do, a process that won't be easy without the riches of the attraction of the Champions League, but whether or not they prove attractive to players like Kane will signal how much progress they can make.
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