The last time Manchester United missed out on Champions League qualification they signed players from Leicester City, Crystal Palace and Swansea. The time before that they raided Paris Saint-Germain, Juventus, Borussia Dortmund and Villarreal.
The discrepancy in ambition showed the difference between Jose Mourinho and Ole Gunnar Solskjaer, but Mourinho's grand approach had fallen short and Solskjaer was performing what Ed Woodward labelled a "cultural reset", which looking back seems to be a way of describing a window that resulted in United signing players that simply weren't good enough for the club.
Of the 2019 intake, Harry Maguire remains captain, but that status should be reconsidered in the summer and the 29-year-old is probably worth half of his £80million price tag three years on. He's had a poor season and needs to focus on salvaging his own Old Trafford career than leading a group of players struggling to pull in the same direction.
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Daniel James arrived in that window and while his sale to Leeds United last summer turned a £10m profit he only really looked like he might make the grade at United for his first month at the club.
The domestic treble of signings was completed by Aaron Wan-Bissaka, a £45m right-back who would barely fetch £20m on recent evidence, finds himself relegated to reserve and is still struggling to show any sign of an attacking game good enough for the highest level.
United's 2019 was about signing young, hungry, domestic players, but being young and determined doesn't equate to being of the requisite quality. They jumped three places the following season but finished on the same number of points, so any improvement was the result of weakening standards elsewhere.
The spending spree in 2016 didn't bring immediate league improvement, with United dropping from fifth to sixth, but they won the League Cup and Europa League and did finish second the following season.
Zlatan Ibrahimovic arrived on a free transfer as a short-term shot in the arm and was hugely successful, both on the pitch and in raising standards. Paul Pogba was the marquee signing and while his six years at the club have generally been disappointing, the fact United could sign him when out of the Champions League was a sign of their pulling power and he's been failed by the club as much as he's failed those around him.
The four new arrivals were completed by Eric Bailly and Henrikh Mkhitaryan. Bailly is still at United but injuries have wrecked any chance he had of establishing himself as a first-team regular. Mkhitaryan had his moments before moving to Arsenal and 13 goals in 63 games wasn't a disastrous record.
After Arsenal's win at Aston Villa on Saturday it seems United are heading for another season outside of the Champions League. They now trail Mikel Arteta's side by four points and the Gunners still have a game in hand, while United must also travel to the Emirates.
It's a disastrous season to find themselves ostracised from Europe's leading competition given something of a rebuild is again required this summer, with at least four players likely to leave when their contracts expire and more potentially being sold. Attracting players is generally tougher without the Champions League to offer and United's budget will be hit without the money that competition generates.
But 2016 proves that elite players can still be signed and this is what United must be aiming for. The idea of that reset in 2019 might have sounded like good management-speak but three years on only one of those players is still in the team and he's been clinging on by his fingernails.
So United must show the ambition of six years ago under whoever their new manager is. Next year will mark a decade without a title challenge and signing players from mid-table Premier League clubs or the Championship isn't going to bring an end to that.
The one worry for United is that the scaled-back approach in 2019 might also have been a result of their diminishing attraction. In 2016 they were still one of the world's biggest clubs, as they prepare for a fifth season in 10 outside of Europe's elite it's getting harder to continue pushing that myth and today's generation of players aged 25 and under have little or no recollection of this ever being a successful football club.
United must aim high this summer and in doing so they will find out just how attractive the name of Manchester United is.
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