Former Liverpool CEO Rick Parry has claimed the club almost signed Dani Alves in 2006.
The Brazil full-back, who looks set to join Manchester City from Juventus this summer, was a target for the Reds under Rafael Benitez.
He told BBC Radio Merseyside: “We had the deal — finally, after enormous complications — tied up for Dani Alves and then the decision was should we buy two players or should we spend all of that on a full-back?
“Dani Alves was not the player then that he is now, but he always looked like he would be a great player.
“Would he have been a better signing than [Jermaine] Pennant and [Peter] Crouch, for example? Probably yes, but it’s easy with hindsight.”
Parry explained that because Liverpool did not have the same clout as a club like Chelsea in the transfer market they had been “trying to be smarter.”
He added: “Looking back, if I could do anything different, it would be to focus on buying one [player] at a time rather than having to buy five or six every season.”