The Gorgie side were beset by off-field problems under then owner Vladimir Romanov’s ruinous reign when the defender left Tynecastle for Wolves in a £2.5 million switch in January 2009.
Berra was also the skipper in his final campaign before embarking on a fresh challenge south of the border and on one occasion he had the unenviable task of telling his team-mates they would not receive their wages on time.
The Scotland internationalist also witnessed other bizarre situations, such as Romanov and striker Roman Bednar trading punches in an impromptu boxing match.
However, current owner Ann Budge has the club back on track with the help of supporters group the Foundation of Hearts, and Berra, who returned to Hearts from Ipswich in May, insists the stability on and off the pitch is a far cry from what he left behind.
He said: “There were a lot of good times under Romanov, but also a lot of bad times.
“When I was captain and we weren’t getting paid on time, I had to tell the players, although we always did get paid.
“At the time I was quite young so I didn’t maybe grasp how crucial it was for certain players. Lucky enough, in the back of my head I knew I would be moving at one point.
“When I look back now it’s probably made me a stronger character as well. It’s not nice at the time, I left when the s*** really did hit the fan.
“I remember that (the boxing match). I met Romanov a few times and he was fine with me. He didn’t punch me.
“But Ann is really straight down the middle, she is honest with you and that’s all you can ask. She won’t punch you.
“Everyone respects her and she’s done a great job and hopefully can take this club on to bigger and better things.
“It’s different now. Ann is first class in how she represents the club, what she’s done for the club and how she is around the players as well.
“The club has come back bigger and stronger now, the new stand is getting built and we’re signing some quality players and hopefully we can have a good season.”
Lithuanian businessman Romanov was rarely seen at Tynecastle and Berra says he has a much closer working relationship with Budge, so much so that he dealt directly with the successful businesswoman during his contract negotiations.
He added: “I was basically e-mailing back and forth to her. I think she would admit that I was a dream in contract negotiations. I wasn’t needy or high maintenance.
“I wanted to come back and I was happy with what I got. I think both parties were happy that I signed. I’ve got a good relationship with her and long may that continue.”
A symbol of the club’s progress under Budge is the ongoing construction of the new £12 m main stand at Tynecastle.
The players will get a close-up view on the redevelopment when Ian Cathro’s side host English Premier League side Newcastle United in a glamour friendly tomorrow evening.
Berra added: “I’m really looking forward to the experience of playing in front of the new stand, even if it’s not quite ready yet.
“With the glass front it looks great and I’m sure opposition players will be looking forward to playing at Tynecastle but we have to make sure they don’t enjoy it on the pitch.
“Hearts are getting bigger and better, with the redevelopment of the stadium, the additions to the squad and we have a really good manager with a great support staff.”
Meanwhile, head coach Cathro has denied being interested in the Norwich City and Northern Ireland goalkeeper Michael McGovern.
He said: “People spot patterns and think we’re going to sign every Northern Ireland player now. It’s untrue.
“There’s nothing in it and we can move on.”