Ole Gunnar Solskjaer made a splash in the transfer market in his first summer in charge of the club. Harry Maguire, Aaron Wan-Bissaka and Daniel James were signed for a combined fee of £145million and they were the faces that would define his tenure.
Three years later and Solskjaer has been sacked, James departed for Leeds before joining Fulham, Wan-Bissaka is currently up for sale at Old Trafford and Maguire has confirmed suspicions that he wasn't good enough to be known as the world's most expensive defender. The fee that Leicester received for Maguire was not the player's fault but it has inevitably followed him around.
Solskjaer's first three signings as permanent manager felt like positive business in the summer of 2019 and most supporters would suggest that is now laughable, with the benefit of hindsight. James was a limited winger, Wan-Bissaka has been a failed signing and Maguire is now a fourth-choice centre-back, with Erik ten Hag seemingly demoting his club captain this season.
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Wan-Bissaka was told in the summer that he could leave the club. It's difficult to imagine that United will recoup most of the £50m fee he commanded and it's telling that even Solskjaer wanted to sign Kieran Trippier in the final months of his premiership.
It's obvious the money that was invested in Solskjaer's first signings in 2019 could have been better spent and any manager's first summer transfer window is their most important, as it lays the foundation for success, or ultimately for failure.
A manager's first window is an opportunity to mould the team into their vision and to sign players who align with their philosophy. In an impatient industry, it can make or break a manager's reign and Ten Hag would have been aware of that this summer.
Are you happy with United's transfer business? Have your say on the season so far in our big survey here and below.
Ten Hag inherited a side that was devoid of confidence and that had just finished with the lowest points in the Premier League in the club's history and that also placed greater importance than usual on making sure the right personnel were signed.
The club bankrolled six new signings in the summer, bringing Tyrell Malacia, Lisandro Martinez, Christian Eriksen, Antony, Casemiro and Martin Dubravka to Old Trafford, and United spent over a total of £200million in the market on those arrivals.
There have been two months since the transfer window closed and, although conclusions should be made on a full season's evidence, it seems like the business that Ten Hag made in his first summer was excellent, with the money shrewdly invested.
Although the correct signings were eventually made, that doesn't mean the summer was not a circus. United looked foolish chasing Barcelona's Frenkie de Jong, while the summer nadir was the club's short-lived embarrassing interest in Marko Arnautovic.
The majority of the players that United signed in the summer were recommended by Ten Hag and football director John Murtough, who is responsible for first-team recruitment, merely completed the deals, which is obviously a dangerous strategy, as there is no framework in place to ensure recruitment is aligned with the club's long-term vision.
If the season had continued as it began against Brighton and Brentford, Ten Hag could theoretically have been sacked by late September and United would have been stuck with players his replacement might not have wanted, for example.
The most successful clubs give power to the manager but not to the extent that Ten Hag was given this summer and It's obvious why clubs need to have continuity with their recruitment, as players tend to outlast the managers that sign them.
However, fortunately for Murtough, the signings Ten Hag made this summer are delivering and that has saved him from the spotlight and scrutiny. The appointment of the Dutchman, which was Murtough's biggest decision yet, has also seemed a wise one.
It was a gamble for the summer's transfer strategy to be so reliant on Ten Hag, but the United boss' signings have improved the team and some have become undroppable, like Lisandro Martinez and Christian Eriksen, who are perhaps the signings of the summer.
Casemiro has also been a world-class addition - he is the defensive midfielder that was desperately needed - and Antony clearly has a bright future, but Martinez and Eriksen have played more games and it's easy to see why Ten Hag rates them so highly.
It could be suggested that the Brazilian pair are undroppable and there would obviously be merit in that, but it feels like that status has been reserved for just Martinez and Eriksen so far, who are currently competing for club's the Player of the Season award.
United gambled with their recruitment strategy in the summer but the signings have made a brilliant start.
It already seems like it will be remembered as a better window than summer 2019.
Are you happy with United's transfer business? Have your say on the season so far in our big survey here and below.
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