The former Celtic full-back was capable of the long ball that seemed to touch the very hem of heaven before descending on the unwary fan, sometimes in the same stadium.
He had, of course, his merits and his admirers will point out he won two SPL titles and a Scottish Cup with Celtic. Naylor was also part of a side that reached the knockout stage of the Champions League and played a part in two dramatic matches against AC Milan.
His career may be at a low ebb with Naylor admitting he was "currently unemployed" but he can console himself with the truism that fortunes change quickly in football. After all, when the Englishman signed for Celtic in August Wolverhampton Wanderers took £600,000 and Charlie Mulgrew in compensation. Naylor searches for a club while Mulgrew, now an established Scotland player, is certain to start in the San Siro.
Naylor, at 33, remains upbeat, with prospects of employment in the Midlands and a belief that Celtic can gain a point in Milan. His career with Celtic includes the defeat in Milan in the knockout stages of the Champions League in March 2007 when a Kaka goal in extra-time won the tie. He will have better memories of a match against Milan in October of the same year when Celtic defeated the Italians 2-1, although he conceded the penalty that allowed the visitors to score.
Naylor is routinely enthusiastic about the atmosphere on a Champions League night at Parkhead but he speaks with the added experience of having sampled it as a fan. He was at Celtic Park in November when the Scottish champions defeated Barcelona.
"It was memorable, a really good experience. I am glad I did it," said Naylor, who admitted he was off his seat for most of the match.
"When you are playing you are trying to concentrate on the game first and foremost. It is not quite that you are oblivious but you are concentrating on what you are trying to do. When I was in the crowd it was just mental, it was madness."
He believes players can be intimidated by an atmosphere, adding: "It is very hostile in Milan but I do not think the San Siro is on a par with Celtic Park. Celtic Park is a one-off, the fans are amazing and you do not get that anywhere else."
Naylor, of course, played with Neil Lennon, now the Celtic manager, and the full-back said it was no surprise the Northern Irishman graduated into management.
"He was made to be a manager," said Naylor who was in Glasgow to make the draw for the second round of the William Hill Scottish Cup.
"I could see it happening while he was still playing. There was only one direction he was going to go - into management. It just so happened he fell on his feet at Celtic."
He added: "He's totally transformed the team - there are only a few players left from when I was here and that wasn't that long ago. He's done an amazing job. He analysed things in different ways and he had that outlook where you thought he had everything to go into management. He'd worked under great managers and taken different things from them and carried it on."
Naylor shared a dressing-room with Lennon and was diplomatic about the Northern Irishman's reputation for expressing an opinion, saying: "Yes, he said his piece and people respected that and they still do now."
He was optimistic on Celtic's prospects tomorrow night. "I fancy a draw, I really do," he said. "I think they'll get something over there."