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Paul Scally admitted Andy Hessenthaler’s future was virtually sealed once the final whistle went at Northampton in the penultimate game of the season.
The Gills chairman (pictured) demanded promotion at the start of the season but a draw at Northampton meant they missed out for a second season running.
Mr Scally finally delivered the news to Hessenthaler on Tuesday that he was being replaced as manager and his contract was being terminated.
"It was a day that I was thinking about four or five days before and it troubled me over the weekend," said Mr Scally.
"I pretty much knew I had to do it after the Northampton game but I was trying to think of ways not to do it but ultimately it had to be done."
The two men met at Priestfield on Tuesday where Mr Scally delivered the news to his manager and friend.
Mr Scally said: "We had a nice chat for a couple of hours and Hessy is that good a friend he understood anyway and it wasn’t as bad as I thought it was going to be."
The team assembled by Hessenthaler contained some big players at League 2 level but they never performed on a consistent basis. Mr Scally, however, wasn’t about to attack the players who he will be relying on next season to win promotion.
He said: "There is an old saying that players get managers the sack but in fairness to the players, they are a good bunch and there are no bad apples in the camp."
Was your mind made up about Andy Hessenthaler after Gillingham failed to beat Northampton? Have your say below.