The England international had spent his whole career with the Gunners, minus a loan spell at Bournemouth, and after a bright start as a youngster saw injury curtail his development.
With time on his side, the Hammers would have no doubt been hoping he could put his dreadful record of problems behind him and start a new and successful chapter in east London.
They would not have been expecting to see the now-28-year-old play just eight games all season, injury once again striking him down as he underwent ankle surgery.
There is no doubting he was a risky capture and so far that gamble, which includes him signing a three-year deal with wages of £100,000-a-week [Spotrac], has not paid off.
Football.London report that the West Ham board held reservations over his previous issues and wanted to hand the former Gunner a one-year deal in order to protect themselves from the worst, but it was manager Manuel Pellegrini who overruled the senior figures and got him a longer contract.
If he had been on that one-year deal, would he still be at the London Stadium this summer? Quite possibly not and so Wilshere owes his boss a hefty amount for having that faith in him.
With added competition in Pablo Fornals, the England ace is going to find it tougher than ever to repay that faith and you have to wonder whether Pellegrini is regretting his decision too, with those £100,000-a-week wages a hefty drain on resources in east London.
Remaining fully fit and playing to the best of his capabilities has got to be Wilshere’s priority. Failure to do so reflects not just badly on him but on his manager too.