The England man has posted a photo of himself on social media with former United teammate, Memphis Depay.
It was a poignant reminder of a budding bromance that promised to make both players United legends before a sliding doors moment altered what looked to be the course of history.
Depay joined United in June 2015 and seemed to find an instant and almost telepathic understanding with Shaw as the pair marauded down Uniteds left wing.
The 2015/16 season started incredibly brightly for the Red Devils and Memphis looked to be one of the clubs most promising signings, scoring goals and providing assists in virtually every early match.
But on September 15th, in the opening match of the Champions League group stage against PSV Eindhovem, Shaw suffered a horrific double leg break after he was caught by Héctor Moreno.
It was an injury that clearly rocked the team and Memphis in particular, whose form fell apart without Shaw behind him.
He went on to only play 29 games that season and four the next, before he left for Lyon in Ligue 1.
Memphis has subsequently carved out a decent career for himself but many wonder what might have been at United had that cruel injury to his teammate not have occurred.
Having got to the final of Euro 24, Shaw is holidaying late and may not be back in time to join up with his current teammates for the US tour.
However, manager Erik ten Hag will be hoping there is enough time to get his left back match fit for the Charity Shield against Manchester City on the 10th August and for the Premier League opener against Fulham six days later.
Shaw will certainly be hoping that the injury nightmares he had in 2015 and those that kept him sidelined for much of last season are now behind him as he strives to do for Uniteds current left wingers, Marcus Rashford and Alejandro Garnacho, what he did so briefly for Depay nine years ago.
Red Billy is the managing editor of The Peoples Person, author of three books and totally obsessed with football''s transfer market. Billy still insists Matteo Darmian and Alex Telles could have made it at United given half a chance.
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