Stuart Byrne feels John Caulfield and Cork City never appeared comfortable being at the top end of the League of Ireland table.
Caulfield's reign came to an end this week and it did yield a league title and two FAI Cups.
But ex-Shelbourne midfield Stuey believes the manager didn't quite embrace their lofty status in the same way Stephen Kenny did for Dundalk.
"When you look back at Cork and their rise at the top, it happened extremely quickly," he said.
"Kenny embraced it"
"At the time, they were the only club putting pressure on Dundalk. That happened very, very quickly for him and for the club.
"Obviously, they didn't expect that to happen. But they found themselves in a scenario where they were going head-to-head with Dundalk for the last 4-5 years.
"It was just a situation that they had to take on board and deal with. Because the competition coming from [below], you have to be critical of Shamrock Rovers, Pats, Derry and the other clubs. They just weren't at the races.
"So Cork found themselves in this scenario very, very quickly. I've always felt they were never comfortable there.
"And I always felt he (Caulfield) was never comfortable there. When you look at the likes of Stephen Kenny... his maiden season, they ran Pats all the way to the title.
"They fell off just at the end and finished second. Dundalk subsequently went on and won the league the next year.
"I think the difference between Stephen and John is that Stephen was comfortable in that scenario. He embraced it and said, 'You know what? We are the best team in the league and we're going to push on. We want to do well in Europe'. And he wanted to accentuate the positive.
"My issue with John is I don't think he was ever comfortable being at the top and being expected to push for league titles. I always felt he had a difficulty with that."