Liverpool owners Fenway Sports Group (FSG) "underestimated how poor the playing quality of the squad was" before buying the club in 2010.
The admission was made by Edward Weiss, FSG's former general counsel, when giving evidence as part of the legal battle between Mill Financial, Royal Bank of Scotland and former co-owner George Gillett at the Supreme Court in New York.
Mill Financial believes "secret letters" and "clandestine activities" saw it incur "substantial damages" during FSG's takeover of the Premier League club. Mill also lent Gillet $70m in 2008 and claims that gave it a 50 percent state in Liverpool, and that it is due proceeds from the sale to FSG.
Weiss also said FSG did not realise players such as Fernando Torres and Pepe Reina were already past their prime, and only attended one game as part of "due diligence" before buying the club.
"We ended up losing quite a bit of money in our first couple of years and we had to make even more considerable investment in the playing squad than we had estimated as we went through the bidding process," Weiss said, as reported by the Liverpool Echo.
"So, you know, like trying to catch a knife falling off the table, you're not sure where before it's hit the ground you've caught it.
"You know, I think we underestimated how poor the playing quality of the squad was, and frankly, we underestimated how difficult it was going to be to stabilise the asset.
"We were overconfident in assuming that many of the things that we had done in Boston [Red Sox] at Fenway would translate naturally to the Premier League and they just didn't all translate.
"I mean, we obviously did some due diligence on the playing squad during this process before we closed on the transaction in the middle of October of 2010. What we came to know was that the playing squad was poor.
"We were sitting at the time we closed on the transaction for the club in 17th place is my recollection which is one spot above the relegation line.
"And while we had a few top players like Steven Gerrard, other players like Fernando Torres and Pepe Reina were probably beyond their primes, and Javier Mascherano was not even on the team.
"In due diligence we attended one match. The one we saw was less than thrilling. It was a near no match."