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Had Benjamin Sesko chosen to sign for Newcastle United rather than Manchester United this summer, then the wheels might have been greased for Alexander Isak to get his dream move to Liverpool.
And as the $100 million (£74 million) Slovenian stepped up to take a penalty at Blundell Park on Wednesday, he would have been forgiven for wondering whether he had made the right call. Sesko scored, but another summer signing, Bryan Mbuemo, missed, and Manchester United exited the Carabao Cup on penalties to a League Two team before Liverpool had even entered.
As a side in European competition this season, Liverpool only made the draw for the third round. The Reds will take on Southampton at Anfield in around a month — and Ruben Amorim will go back to the drawing board.
The image of Amorim desperately playing around with his tactics board in the driving rain in the second half, with his side needing to come from two goals down, might well become an iconic image in future years.
Manchester United's manager has a win percentage of just 38 per cent across all competitions (a figure that drops to 24 per cent in the Premier League). This summer, Amorim has spent big — but the major issues remain.
Goalkeeper Andre Onana looked like a fourth-tier player — not Grimsby's heroes — as he flapped at a cross and was beaten for the second time. On the first goal, he should have done better with a shot that was near his foot.
Amorim's insistence on playing with a back three — even against a team three divisions below — looks outdated. No modern, attacking and front-footed team plays with a trio of center-backs and Manchester United doesn't even have three good ones.
Though he has added quality in the form of Mbuemo and Matheus Cunha in attack, they mean Bruno Fernandes has been forced out of position. And Manchester United still has no proper wing-backs, which are crucial to the 3-4-3 system.
That rigidity and unwillingness to move away from a back three is exactly why Liverpool steered clear when it was looking for a new head coach and settled on Arne Slot — an inspired decision that has already brought home one Premier League title.
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Amorim is a good coach but he is working in an environment that is dysfunctional. Manchester United's recruitment this summer has been fine, but nothing more, and hasn't really addressed its biggest issues.
And don't forget, it is only a few months ago that Jim Ratcliffe was pleading poverty as he signed off on more cuts. Those who brutally lost their jobs after decades of service were probably hoping that money wouldn't simply be wasted.
Though Liverpool made the right call in not moving for Amorim, as highly rated as he was at Sporting, it isn't really the Portuguese's fault. He has not been perfect — and appearing to hide away while his players took their spot kicks wasn't a good look.
Really, though, Manchester United needs a lot more changes behind the scenes and a complete overhaul of its playing staff. If losing 1-0 at home to Arsenal being dressed up as some kind of victory wasn't evidence enough, this new low at Grimsby should be.
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