John W Henry has admitted that Liverpool are still paying an enormous price for the failings of their previous owners.
The Fenway Sports Group (FSG), founded by Henry and Tom Werner, bought Liverpool for £300 million from Tom Hicks and George Gillett in October 2010.
But when Henry and Werner conducted due diligence on the club before the takeover, they had serious doubts as to whether they were doing the right thing.
The stewardship of Hicks and Gillett had left Liverpool in such financial difficulties that administration was a possibility.
Principal owner Henry and chairman Werner have stabilised the club off the pitch, although the only trophy that has come the Reds' way since they took over was last season's League Cup.
Henry feels that Liverpool have lagged behind long-time rivals Manchester United for too long, and warns that closing that gap will be a big job for FSG - bigger than the one they faced trying to match the New York Yankees in Major League Baseball when they bought the Boston Red Sox in 2002.
"The best analogy is that you can't turn an ocean liner around like you can turn a speedboat," Henry told the Liverpool Echo. "When you look at the rivalry between Liverpool and Manchester United, Liverpool isn't holding up its side of the rivalry.
"That is the way it was with the Red Sox and the New York Yankees. The Yankees were just completely dominant when we arrived. 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. You could say Liverpool is an even bigger challenge than the Red Sox. Looking back at the day we bought Liverpool, 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.
"Tom 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 because 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."
Henry and Werner have brought money into the club with a series of lucrative commercial deals, with Liverpool just starting a six-year £25million per season deal with kit supplier Warrior Sports, and further partnerships signed with American car manufacturer Chevrolet and airline Garuda Indonesia.
"I think that we knew from the very beginning that it was important to increase commercial revenues," Werner said. "People have talked about this idea of virtuous circles. The stronger we are commercially, the stronger this club can be. I think we have made great strides."