Moyes spent 11 years with the Toffeemen before being offered the chance to succeed Sir Alex Ferguson last summer.
Having hauled Everton back amongst the Premier League's most consistent clubs, finishing ahead of Liverpool in his final two seasons, and guided them into the Champions League, to an FA Cup final and semi-final despite working with a meagre budget, the Scot's place in the club's folklore should have been secure.
Yet Moyes angered many Everton fans, if not by returning for Marouane Fellaini and Leighton Baines, then offering what was perceived was a paltry sum.
A joint £28million bid was branded "insulting" by the Merseyside outfit.
And though Fellaini eventually made the move on deadline day for £27.5million, Baines remained, with Everton rejecting Moyes' final advances in the hours before the transfer window shut.
Kenwright was unhappy at United's conduct and many Everton fans voiced their opposition to Moyes.
But the Red Devils chief insisted his long-time chairman should have known what was coming - because he told him.
"Once I got the United job I discussed it with Bill near enough immediately," said Moyes.
"I said that there would be some players I would be interested in.
"Bill was well aware of it but obviously it was always going to be a difficult thing when it actually came to it."
In hindsight, Moyes recognises the situation might have been handled differently by all parties, which is just as well given it appears his interest in Baines remains.
"There were bits of it I would have liked to have done better but there were also bits of it as a whole I think could have been done better," he said.
"That is football. I speak with Bill Kenwright regularly. We both knew that this would happen but it is never that easy.
"But time moves on as well.
"Life is too short to hold any grudges.
"I had a great working relationship with Bill and the board of directors there and that is the way it remains."
That Fellaini has done little to justify becoming the fourth most expensive player in United history has eased the angst felt amongst the Everton faithful.
Handicapped by a wrist injury that will eventually require surgery, the Belgium midfielder has struggled to make an impact at Old Trafford.
He is yet to score for his new club and failed to start either the midweek Champions League hammering of Bayer Leverkusen or Sunday's draw with Tottenham even though Michael Carrick has been sidelined by an Achilles problem.
Fellaini could come into contention to face his former club though as Phil Jones has been ruled out through suspension, reducing Moyes' options even further.
"Marouane's probably going through the same settling-in process as most players who join Manchester United," said Moyes.
"Obviously there'll be some players who hit the ground running and can go straight in.
"But then there are others for whom it takes quite a little bit of time to settle in and there's been quite a few here."