Mark Lawrenson has argued that Liverpool will find this transfer window to be particularly difficult with the side still suffering the effects of the ownership of Tom Hicks and George Gilette.
When Fenway Sports Group came in and bought the Reds in 2010, the side were in serious trouble as a result of the debts built up during the previous owners' tenure.
The club have since spent big in transfer windows, particularly under Kenny Dalglish who outlayed over £100m on new talent in his first year in charge of the club, but FSG have since insisted they must budget effectively in order to build a side capable of long term success.
And Lawrenson believes that the recent loaning of Pepe Reina to Napoli is a sign that the side are trying to cut costs wherever they can.
"It's a real catch 22 situation for FSG," he said in the Liverpool Daily Post. "They are striving for fourth place to get those revenues increased by Champions League football, but they might need to buy a couple of £25m players to do that - money they might not necessarily want to spend given it's no guarantee of a top-four finish.
"Clearly, Napoli haven't got the money to sign Reina permanently. But by allowing him out on loan, Liverpool are telling Reina his time at the club is over.
"I wouldn't be surprised if he had been unofficially available for transfer or loan for quite some time."
Lawrenson believes that even though FSG came into the fray three years ago, the financial issues of Hicks and Gilllett is still filtering through the club as Liverpool attempt to recover.
He explained: "If the manner of Pepe Reina's departure has demonstrated anything, it's that Liverpool are still paying the price for the reign of Tom Hicks and George Gillett.
"Brendan Rodgers was refreshingly honest in admitting financial forces were a significant reason for Reina being allowed to rejoin former manager Rafael Benitez at Napoli on a season-long loan.
"Reina is one of Liverpool's top earners, and the club's owners, Fenway Sports Group, were keen to take such a strain off the wage bill, not least for somebody the wrong side of 30."
Liverpool have so far signed four players this summer including a replacement keeper for Reina in the form of Simon Mignolet.
The side have been clear over having a tight budget this season but with the likes of Arsenal, Chelsea and Tottenham to compete with as well as the Manchester clubs they will indeed be facing an uphill battle in their mission for Champions League qualification.