The duo made the same trip up from Portsmouth last summer to sign up for the big rebuild at Wigan.
And both proved to be integral parts of a promotion-winning campaign under Leam Richardson, who himself joined Latics from Pompey in 2017.
Having achieved what proved to be out of reach at Fratton Park, Naylor is delighted at the way things have turned out.
"I said to Jack before the Shrewsbury game: 'Right, let's go and do this, we both deserve it'," he said.
"We gave everything to make it happen the previous two years at Portsmouth, and unfortunately it wasn't enough.
"But it's great to be able to do it alongside Jack, he deserves it more than anyone, he's a great lad."
Naylor's story is even more remarkable given he was hours away from joining his hometown club Mansfield in League Two before Latics made their move.
And while a move 'home' would have suited friends and family, a League One title winners' medal vindicated his decision to relocate to the north west.
"This is why I chose Wigan," he said. "I could see the ambition of the club, and where they wanted to go.
"It's the best decision I've ever made, and myself, my family and my team-mates, we're all over the moon."
Naylor was a central figure in the victory celebrations that took the players straight from Shrewsbury to King Street for a now-traditional knees-up with the fans.
"It was a good night to be fair," smiled the 30-year-old.
"I spent all night standing next to the DJ, helping him mix the tunes up, and it was great to be able to mingle with the fans.
"Obviously they've been with us through the bad times and good, and it was nice to share that with them."