Whitey Bulger was recently convicted of a wide range of charges, including money laundering, and a Boston news team has asked an interesting question: did the lawyer who helped Bulger close the real estate deals that facilitated the money laundering engage in any misconduct?
I was interviewed for the story and said that the answer essentially turns on what Bulger's real estate lawyer knew and when he knew it. (You can watch the video here and read the transcript here.) That seems like the easy answer under Massachusetts Rule 1.2 and the predecessor to the Rule that would have been in effect at the time.
Somewhat suprisingly, Bulger's real estate lawyer (who performed the work decades ago) agreed to be interviewed for the story and expressed some regrets about his work for Bulger. The lawyer said he thought at the time that the deals were "legal," but he also noted that he had some "fear" of Bulger.
These remarks raise a number of interesting issues. First, I'm not sure it was a great idea for Bulger's old lawyer to share these thoughts on television. But putting aside the wisdom of it, do you think any of the information disclosed in the interview is covered by Rule 1.6? It's notable that the lawyer (rightly) refused to answer any questions about the specific transactions he handled for Bulger, so the answer is not entirely clear. And even if the answer is yes, might the comments be justified on the grounds that the lawyer was being accused of potential misconduct?
Second, there is an empirical question here that is hard to answer in hindsight: could a reasonable lawyer at the time of the real estate closings have believed the transactions were "legal"? The reporter makes reference to a source who said the transactions were, in fact, questionable at the time, but the ethics issue turns on what Whitey Bulger's lawyer actually knew.
Third, and perhaps most interestingly, assuming for the sake of argument that no reasonable lawyer could have believed the real estate deals were legitimate, could the lawyer's "fear" offer a defense against discipline? Are there are any disciplinary cases in which lawyers have successfully defended themselves against alleged misconduct on the grounds that they were acting out of fear of their clients?