The answer is, I honestly don't. Frankly, I'm baffled, as they seem to be in as good a position as an large NYC-based agency could be in these days.
They've got a strong DM and Interactive division (OgilvyOne) that's actually in the same building.
Which should be pretty significant-- many of their big agency competitors only have one part of that equation, e.g. a strong direct division (Y&R and Wunderman ) or a strong interactive arm (DDB and Tribal). And while Ogilvy's two halves may be more integrated on paper than they are in reality, they at least give integration lip service, which is more than several of their competitors do.
On top of that, they actually do some good work and they've got lots of smart and talented people working there, notably in account management.
So what gives?
Two theories I've heard bandied about, which may have some degree of truth to them are:
A. The whole Shona Seifert mess, while downplayed by people in the ad business, may scare off perspective clients more than anyone realizes. (For those of you who are unfamiliar with it. Shona Seifert was the former president of Ogilvy who is serving (has served?) an 18-month prison term (along with the former CFO) for doctoring time sheets while Ogilvy was working on the ONDCP account.)
B. Ogilvy's senior management team isn't exactly warm and cuddly. Several of them are also somewhere close to 7 feet tall. Combine the physical intimidation factor with the very white, very old school/old money feeling of the place and you can see how perspective clients could be left feeling kinda cold.
Now there's a third theory, which is the one I'm prone to subscribe to: bad timing and bad luck. Sometimes the ducks just don't line up. And while there's probably some degree of truth to the first two theories, I think bad karma may be at work here.