"I thought the £30m I got for Rio Ferdinand for them might be enough. It doesn't seem like it. So, I don't know what has gone on, I really don't."
O'Leary still has associates in the Yorkshire area and believes they will get back on the right track with former Chelsea chief executive Trevor Birch's appointment.
He added: "I think their new chief executive is an excellent choice. I've got a lot of time for him and I think he will do it. They might not be able to make many signings on the field, but off it they have just made a great one.
"I think he possesses all the right attributes to turn Leeds around. In my opinion, they've got one of the best men for the job."