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Jay Saunders is locking horns with former Gillingham manager Justin Edinburgh this weekend.
Edinburgh, sacked by Gills last season, returns to Kent when his new club Leyton Orient visit the Gallagher in an all-ticket match on Saturday.
He is rebuilding his reputation after a brief spell at Northampton also ended in his dismissal.
After Tranmere, Orient are the biggest club in the National League but arrive just one place outside the drop zone.
Stones boss Saunders had dealings with Edinburgh during his time at Gills and expects the former Spurs left-back to lead the O’s up the table.
Saunders said: “I spoke to Justin a few times, just about players and stuff and he came across well.
“As I got to know him, he lost his job, so it was a tricky one. I’m sure he’ll do a good job at Orient.
“He’s got good experience at this level. He took Newport County up and, let’s be honest, Orient have got money.
“They can sign good players, they’ve got good players and if he goes in there and adds two or three in the right areas, I’m sure they’ll start climbing.
“They’re a massive club and shouldn’t be at this level but they are and they need someone to sort things out.”
Maidstone are 11th, four points outside the play-offs with a game in hand.
They face four games in 10 days, with Orient followed by Dover away on Boxing Day, the televised trip to Aldershot on December 30 and the return game with Whites on New Year’s Day.