Liverpool owner John W. Henry claims the Premier League club is still paying the price for the financial turmoil that engulfed it during the chaotic regime of Tom Hicks and George Gillett.
Henry and his Fenway Sports Group bought Liverpool from fellow Americans Hicks and Gillett nearly two years ago and the club are still no closer to recapturing their glory days of the 1970s and 1980s.
The Reds finished eighth in the Premier League last season -- their worst final position for 18 years -- and principal owner Henry is convinced the financial problems which almost forced the club into administration, have set Liverpool back years.
"The best analogy is that you can't turn an ocean liner around like you can turn a speedboat," Henry told British media ahead of the new season this weekend.
"You could say it was a bigger challenge than (when we bought) the Boston Red Sox.
"Looking back at the very first day, I was trying to make a point then about how much of a challenge it was going to be because of the issues we inherited.
"We had a lack of depth in the squad and some really high payrolls. We also had issues with the age of the players and so forth.
"We knew it was going to be very difficult. (Liverpool chairman) Tom (Werner) and I went for a long walk and we had to make the decision, 'Are we going to buy Liverpool?'
"We had to decide whether we really wanted to take this on, as we knew this was a huge challenge. A much larger challenge than any supporter could know.
"We had done due diligence and looked at how the situation was financially, with the player contracts and the youth system. The further we went into it, the more sobered we were."
When Henry and his fellow investors bought the Boston Red Sox baseball team, they were faced with the same problem that now confronts them at Anfield.
The Red Sox were historically seen as a big club but had been unable to keep up with the spending power of their arch rivals the New York Yankees.
Under Henry's guidance, the Red Sox reversed that trend and enjoyed considerable success. Now he hopes to repeat the trick with Liverpool after years in Manchester United's shadow.
"When you look back from this vantage point: the rivalry between Liverpool and Manchester United -- Liverpool isn't holding up its side of the rivalry," he said.
"That is the way it was with the Red Sox and the Yankees. The Yankees were just completely dominant when we arrived in Boston 11 years ago. We knew we could never be on an equal footing financially with The Yankees.
"But we had to do everything in our power to get on a level footing with them on the playing field. That was a tremendous challenge. As we started to close the gap, they built a new stadium. That was a quantum leap forward.
"This is an even bigger challenge."
Henry knows it will take time to catch up with big spenders like United, Manchester City and Chelsea, especially since the club has been out of the lucrative Champions League for three years.
But, despite Henry's desire for financial stability, Liverpool have still spent Â£25 million ($39 million) on Fabio Borini and Joe Allen since appointing new manager Brendan Rodgers in the close-season and chairman Werner believes they are finally on the road to recovery.
"We feel that we have work to do. We feel that we are behind but we are on it," Werner said.
"Do we feel that it is possible to get on a level with (the top European) clubs? Absolutely. We can close that gap and compete at the very highest level. Absolutely."