David Boies, one of the country's leading litigators, is getting some bad press over his involvement in the Harvey Weinstein matter. I guess even the biggest machers put their pants on one leg at a time.

Actress Rose McGowan is one of the many who have recently accused Weinstein of sexual improprieties ranging from unwanted advances to sexual assault. Fearing that McGowan's story was being looked into and might gain enough traction to lead to a story in the New York Times, Boies, apparently as an accommodation to his long-standing client Weinstein, hired a group of former Israeli intelligence officers to get dirt on McGowan, including obtaining a copy of a book she was writing about the affair.

The contract Boies signed with the intel group specifically listed as one if its objectives avoiding a Times story in any shape or form. If successful, the firm would get a hefty bonus, about 150 percent of the contract base price. The rub came when the contract became public and one of Boies' other clients, the New York Times, fired him and his firm, alleging a conflict and calling his conduct reprehensible.

Boies' problems reflect that state of affairs.

It does not appear that Boies' firm had a direct conflict, as it was not simultaneously handling matters for Weinstein and the Times in which either client was adverse to the other. Nor was there a “material limitation” conflict in which either client claimed that Boies' work on his/its behalf was materially limited by his responsibilities to the other by virtue of their status as a present or former client or a “third party” or because of Boies' own self-interest.

To the extent that Boies' firm did a conflict check at all, that's probably where it ended. The rules allow us to represent competitors as long as we don't represent both sides in a particular matter. No conflict, no disqualification—and more work for the firm.

What seems to have ticked off the Times was a perception that by undertaking a representation, here supervising an investigation designed to derail a Times investigation and prevent the publication of a damning article, Boies evinced inexcusable disloyalty to it. Though perhaps not rising to the level of an actual conflict (the ethics solons are not unanimous on the issue), Boies' conduct fell into a gray area in which the fiduciary duty of loyalty present in an attorney-client relationship requires us to avoid situations in which advancing one client's interests might harm another client.

What makes these cases hard is that the duty—and the perception of breaching that duty—may be as much intuitive as quantifiable. It's not something that can be easily doped out by staff using a conflicts-checking system, nor would it necessarily be readily apparent to a partner or firm risk manager reviewing the new matter memo.

Boies defended his conduct several ways. First, he claimed there were no adverse interests at play, since his investigation on behalf of Weinstein was really just looking for the truth, and the Times certainly would not want to print something that was not true. Unfortunately, the contract with the spies made it pretty clear the goal was preventing an article, not making sure it was factually accurate.

He also claimed that he had no idea how sneaky the intel guys were going to be in ferreting out dirt on McGowan. Again, the contract puts that to lie, as it speaks of using human engineering, avatars and other tools which pretty much sound like spycraft. The operative detailed to the project is identified using only a first name which is in quotes, “Anna.” Maybe I've read too much John LeCarre, but that sounds like an alias.

The bottom line here is that clients, even sophisticated ones like the Times, don't limit their conflicts analyses to the four corners of the rules. If a lawyer is scheming against them, they're going to react badly. Even if their disciplinary grievance fails, their economic revenge may be painful. As our Supreme Court said in 1964 in a case called Rottner, “(w)hen a client engages the services of a lawyer in a given piece of business he is entitled to feel that, until that business is finally disposed of in some manner, he has the undivided loyalty of the one upon whom he looks as his advocate and his champion.”