Ethics experts have a warning for David Boies, the man who represented both the New York Times and ran Harvey Weinstein’s oppo-research activities. If the Gray Lady makes good on its threat against the high-powered Democratic attorney, NBC News reports, Boies Schiller may have serious trouble ahead. One Stanford law professor wondered how Boies rationalized a campaign of oppo research on another of his clients:

“I think it’s inappropriate for a lawyer to hire oppositional research on a current client; isn’t that what this is in essence?” asked Deborah Rhodes, a Stanford Law professor and legal ethics expert.

Another ethics specialist has broader issues with Boies’ conduct. He engaged intelligence operatives who were perpetrating frauds to collect information on alleged victims and others, and in some cases propagating misinformation. Regardless of whether the target of those operations included Boies’ own clients, that’s a line attorneys can’t cross, Washington University professor Kathleen Clark tells NBC, especially when it doesn’t involve any litigation:

“One of the problems is the investigator hired was engaged in deception and developed an elaborate ruse to mislead a woman who apparently was allegedly raped by Weinstein,” Clark said. “The private investigator was essentially engaging in a fraudulent scheme and lawyers are not permitted to engage in fraud.”

Clark said legal “work product” doctrine, allowing attorneys to shield reports or research in anticipation of litigation from discovery, would not necessarily apply in this instance.

“The contract that Boies signed seemed to assert that it had something to do with litigation support services but that same contract identifies an objective that had nothing to do with the litigation,” she said.

The Atlantic also takes a close look at the ethics of spying on your own client for another client and concludes … that’s bad, mm-kay? Their expert reminds readers that contractors for law firms have to abide by the same ethical guidelines as the attorneys themselves. The New York State Bar has something to say about that as well:

Stephen Gillers, a New York University law professor who focuses on legal ethics, said it’s not unusual for law firms to hire private investigators, especially for corporations and wealthy clients. But he noted that firms are obligated to ensure those investigators abide by the same ethical boundaries as the lawyers themselves. “Most prominently, a lawyer cannot contact an opposing client whom he knows is represented by counsel,” Gillers pointed out. “You can’t go talk to an opponent. You have to go through his lawyer.” …

The New York State Bar Association’s rules of professional conduct instruct lawyers and law firms to “[not] engage in any conduct involving dishonesty, fraud, deceit, or misrepresentation.” Those rules also forbid lawyers from taking adverse action against a current client by negotiating against them or representing an opponent in litigation. But state disciplinary bodies, which are often underfunded, typically only enforce these rules against the worst offenders in the legal community, Gillers said.

Instead, law firms usually try to avoid conflict-of-interest situations because of the potential financial impact. “They worry about losing the client who is the target of the adverse conduct,” he explained. “They worry about losing the client they represented when they shouldn’t be representing that client. They worry about losing their fee.” The fear of lawsuits also acts as a deterrent. “Firms worry about civil liability, malpractice liability, breach-of-fiduciary-duty liability, they worry about disqualification from a matter,” Gillers said. “And they worry about adverse publicity.”

Will Boies Schiller face any disciplinary action for their alleged ethics violations? Any member of the bar can file a complaint about this, and one can bet that Boies has been around long enough to have irked someone enough into filing one. Whether they take any action against Boies is another matter. Boies is well connected, and his firm has a long and impressive track record, which includes several Supreme Court cases. As Gillers notes, they don’t have a lot of resources, and they may feel more obligated to pursue cases where legal incompetence puts clients’ lives and liberty at risk rather than tackling Boies. However, the high profile of the Weinstein scandal and the outrage over Boies Schiller’s role in silencing victims might be enough to force the bar to allocate some of its limited resources to a review of Boies actions.

Regardless of what the bar does, the New York Times has other attorneys, and it’s all but certain that a few of them will be in contact with Boies Schiller in the near future. The Gray Lady fired Boies yesterday, and what they fire at him next may end up costing Boies and his partners a lot of money and even more embarrassment. Don’t be surprised if this ends in another non-disclosure agreement and a sudden desire from Boies to spend more time with his family.