To: the prosecution. With love, the Defendant’s lawyer.

89 years ago today, almost to the minute, seven men were murdered in Chicago’s Lincoln Park neighborhood.  The incident became known as the Saint Valentine’s Day Massacre. Al Capone is widely regarded as the criminal mastermind behind the killings.

As bar counsel, I’m intrigued by one aspect of the events that led to Capone’s conviction and incarceration.  My intrigue lies in the so-called Mattingly Letter.  It’s a letter that Capone’s tax lawyer provided to treasury agents and that was eventually used against Capone at trial.

Douglas Linder is a professor at the University of Missouri-Kansas City School of Law. He has a website dedicated to Famous Trials.  Among others, Professor Linder has written on the trial of Al Capone.

Per Professor Linder, as of 1929, Capone had never filed a federal income tax return.  So, the Department of Treasury launched an investigation into whether Capone had committed income tax evasion.

Lawrence Mattingly was Capone’s tax lawyer. In April 1930, Mattingly agreed to let “revenue agents” interview Capone.  The transcript of the interview is here.  Here’s an excerpt of what would become a key segment:

  • Revenue Agent RALPH HERRICK: I think it is only fair to say that any statements which are made here, which could be used against you, probably would be used.
  • LAWRENCE MATTINGLY, Capone’s tax lawyer: Insofar as Mr. Capone can answer any questions without admitting his liability to criminal action, he is here to cooperate with you and work with you.
  • HERRICK: What records have you of your income, Mr. Capone-do you keep any records?
  • CAPONE: No, I never did,
  • HERRICK: Any checking accounts?
  • CAPONE: No, sir.
  • HERRICK: How long, Mr. Capone, have you enjoyed a large income?
  • CAPONE: I never had much of an income.
  • HERRICK: I will state it a little differently-an income that might be taxable?
  • CAPONE: I would rather let my lawyer answer that question.
  • MATTINGLY: Well, I’ll tell you. Prior to 1926, John Torrio, who happens to be a client of mine, was the employer of Mr. Capone, and up to that point it is my impression that Mr. Capone’s income wasn’t there. He was in the position of an employee, pure and simple. That is the information I get from Mr. Torrio and Mr. Capone.

A few months later, Mattingly met again with federal agents.  As the meeting ended, he provided the agents with this letter.  Mattingly opened the letter by stating:

  • “The following statement is made without prejudice to the rights of the above-mentioned taxpayer in any proceedings that may be instituted against him. The facts stated are upon information and belief only.”

He closed by conceding:

  • “I am of the opinion that his taxable income for the years 1925 and 1926 might fairly be fixed at not to exceed $26,000 and $40,000 respectively and for the years 1928 and 1929 not to exceed $100,000 per year.”

Several months later, a grand jury indicted Capone.

Eventually, Capone and the government reached a plea agreement under which Capone would’ve served 2.5 years.  A judge rejected the plea, stating:

  • “The parties to a criminal case may not stipulate as to the judgment to be entered. It is time for somebody to impress upon the defendant that it is utterly impossible to bargain with a Federal Court.”

As trial neared, the government obtained information establishing that Capone had likely bribed a significant portion of the jury pool.  The prosecution team notified the judge. Per Professor Linder, here’s what happened next:

  • “Judge Wilkerson took his seat at the bench and looked out over the packed courtroom. He called the bailiff to the bench. ‘Judge Edwards has another trial commencing today,’ he told the bailiff. ‘Go to his courtroom and bring me his entire panel of jurors; take my entire panel to Judge Edwards.'”

At trial, the government sought to introduce the Mattingly Letter through the agent to whom Attorney Mattingly had delivered it.  The defense objected.  The court admitted the letter as proof that Capone had made certain statements, albeit not as proof of those statements.  (yeah, right.)  A transcript of the testimony surrounding the letter’s admission is here.

The prosecution referred to the letter during its closing argument.  That portion of the summation, which I found enthralling, is here.  Here’s my favorite part:

Referring to Attorney Mattingly, the prosecutor argued:

  • “He had tried to get the revenue agents to say that the admission would not be used against his client; now, in the letter, Mattingly is saying it himself. The letter says, “‘his statement is made without prejudice to the taxpayer in any criminal action that may be instituted against him.'”

The prosecutor continued:

  •  “Suppose a speeder, when stopped by an officer, should say; ‘I am telling you this without prejudice, officer; I don’t want it used against me; but I was going 50 miles an hour.’ Suppose a gambler could tack a little sign on a roulette, ‘This device is not to be used as evidence against me.’ Suppose a murderer could put a sign on his gun, “This weapon is not to be used as evidence against me.’ What a refuge for criminals that would be! And yet, that is what we have here, ‘I am telling you this, but it is not to be used against me.’ “

In the end, Capone was convicted and sentenced to 11 years in prison.  Admissions from his own tax attorney appear to have played a significant role in the conviction.

Competence.  Client confidences.  You be the judge.


An intriguing aside: one of the government’s key informants in the Capone investigation was Eddie O’Hare.  O’Hare held the patent for the mechanical rabbit that lures greyhounds around a race track. He also ran dog tracks for Capone.  Eddie was murdered shortly before Capone was released from prison.

The intriguing aside?  Eddie’s son, Edward, was a naval pilot. He was the Navy’s first “flying ace” and the first member of the Navy to receive the Medal of Honor in World War II. He was shot down in combat in 1943 and never found.  Chicago’s O’Hare Airport is named for him.



ABA Journal Provides Cybersecurity Tips

Rules 1.1 and 1.6 operate to impose a duty to act competently to safeguard information relating to the representation of a client.  The duty includes taking reasonable steps to protect against the unauthorized or inadvertent disclosure of (or access to) electronically stored client data.

In 2018, the ABA Journal will publish a year-long series on cybersecurity.  Last month, and as part of the series, the ABA Journal posted 5 cybersecurity steps you should already be taking.  I recommend it.  A quick summary:

  1. Check to see if you’ve been pwned.
  2. Consider a password manager.
  3. Improve the strength of your passwords.
  4. Use 2-factor (or multi-factor) authentication.
  5. Encrypt your devices.

Again, read the post.  It’s not long, and the tips are as simple as they are valuable.

Finally, don’t forget that the Vermont Bar Association is offering its first ever Tech Day on May 16.  It’s shaping up to be a fantastic CLE.


Concerns over Client Confidences Spur ABA to Oppose Bill in Senate Judiciary

Later today, the Senate Judiciary Committee will hold a hearing related to S.1454, the True Incorporation Transparency for Law Enforcement (“TITLE”) Act.  TITLE is an anti-money laundering bill.  Per the text, the Act’s purpose is:

  • “to ensure that persons who form corporations in the United States disclose the beneficial owners of those corporations, in order to prevent the formation of corporations with hidden owners, stop the misuse of United States corporations by wrongdoers, and assist law enforcement in detecting, preventing, and punishing terrorism, money laundering, tax evasion, and other criminal and civil misconduct involving United States corporations, and for other purposes.”

Last week, the ABA issued a press release announcing that ABA President Hilarie Bass sent a letter to the Senate Judiciary Committee in which she expressed concerns over provisions in the proposed legislation.

The letter is here.  The ABA Journal has the full story here.

Initially, President Bass expressed concern that TITLE “would improperly subject many lawyers and law firms to the anti-money laundering (AML) and suspicious activity reporting (SAR) requirements of the” Bank Secrecy Act.”  She argued that “[t]his would undermine the attorney-client privilege, the confidential lawyer-client relationship, and traditional state court regulation of the legal profession.”

Citing Rule 1.6 of the ABA Model Rules of Professional Conduct, and equivalent state rules, President Bass submitted that:

  • “Such aggressive reporting requirements may be appropriate for banks or certain other financial institutions, but requiring lawyers to report confidential client information to the government—under penalty of harsh civil and criminal sanctions—is plainly inconsistent with their ethical duties and obligations established by the state supreme courts that license, regulate, and discipline
    lawyers. These requirements would also seriously undermine the attorney-client privilege, the confidential lawyer-client relationship, and the right to effective legal representation by discouraging full and candid communications between clients and their lawyers.”

President Bass went on to cite other concerns, including “costly, and unworkable new regulatory burdens on small businesses, their agents who help them form corporations or LLCs, and the states.”

Might be something to keep an eye on to the extent that your practice includes business formation and advice to business entities.

Image result for senate judiciary committee


File Retention: How long?

Yesterday, I urged lawyers to resolve to deliver the file.  The post links to ABA Formal Opinion 471, an opinion that addresses the question “what is the file?”

A Twitter follower noted that natural follow-up to yesterday’s blog is one that addresses file retention.  How long must a lawyer keep a closed file?

It’s a common question.  To paraphrase another Irish guy, it’s not uncommon for me to hear a frustrated lawyer say something like:

  • I can’t believe the files in here.  I can’t close my eyes and make them disappear!  How long? How long must I sing this song? How long? How lonnnnnnnggggg……?

I’ll cut to the chase: I don’t have a good answer for you.  I’ll do my best.  But, I won’t be offended if you finish this post frustrated that you still haven’t found what you’re looking for.

Again, as I stressed yesterday, Rule 1.16(d) makes it clear that the duty to deliver the file kicks in upon the termination of the representation.  Delivering it moots the question of how long to keep it.  Of course, you’d be well-served to keep a copy for yourself, if only to defend against a potential disciplinary complaint or malpractice claim.

Once delivered, the only retention requirement in the rules appears in Rule 1.15(a)(1): records of funds & property must be maintained for 6 years from the termination of a representation.  The file is client property.  Thus, some jurisdictions have interpreted the rule to require lawyers to maintain a record of what happened to client files.  Even if not affirmatively required by the rule, keeping a disposition log is a good idea.

Now the hard part: what about the file that, for whatever reason, isn’t delivered upon the termination of the representation?

That’s a question that we haven’t answered.

Twenty years ago, the VBA’s Professional Responsibility Committee issued advisory opinion 97-08.  Here’s the synopsis:

  • “A lawyer must exercise discretion in determining the necessary length of time for the subsequent retention or disposition of a client’s file. The contents of certain files may indicate the need for a longer retention period than do the contents of files of similar age based on their relevance and materiality to situations which may foreseeably arise. Moreover, in disposing of a client’s files, a lawyer should protect the confidentiality of its contents. If possible, notice may be given the client as to the date of disposition, affording the client the opportunity to take possession of all
    or part of the material in the file.”

The VBA Opinion is consistent with the general consensus that “it depends.”  Three years ago, the Kentucky Bar Association’s Legal Ethics Opinion 15-01,  noted that the prevailing view is that a reasonable period to retain a file is between 5 and 10 years.

I understand that one-size doesn’t fit all and that, with closed client files, “it depends.”  Still, I’d like to provide relief to lawyers who’ve run out of physical & electronic storage space, or who simply can’t afford to maintain it any longer.

As I mentioned yesterday, I’ve asked the Professional Responsibility Board to consider a rule that would define “the file.”  The same rule would authorize lawyers to destroy files after 6 years, subject to certain exceptions.  The rule that the Board is considering is quite similar to this rule that was proposed last year in Massachusetts.

Until then, here are two things that I think are critical:

  1. If you haven’t already done so, build a retention policy into your standard representation agreement; and,
  2. Check with your carrier before destroying or disposing of a closed file.

Aside: real estate lawyers, #2 includes checking with your title insurer.

Finally, and as critical as the two thoughts expressed above, whether you pick a 6, 7, or 10-year retention policy, remember that there are some things that should never be destroyed, or that should be retained beyond your standard retention period.  Some (non-exhaustive) examples:

  • documents provided by the client;
  • anything that it’s reasonable to conclude the client might need;
  • files with original wills, deeds, trust documents, and estate planning documents;
  • criminal files;
  • files with pre-nups,
  • files for clients who had young children when support & custody were finalized;
  • files for which the statute of limitations on malpractice has yet to run;
  • files in which the client was a minor, and will remain a minor beyond the expiration of your file retention period;
  • adoption files;
  • Corporate books & records.

This list goes on.

I don’t want to make this blog too long.  If you have questions about file retention, call me.  If you want me to come meet with you and others at your firm, I will.  Until then, a few closing thoughts:

  • generally, it’s okay to store closed files electronically;
  • when disposing of or destroying files, do so in a manner that competently maintains the confidentiality of the client’s information.

Some other resources:

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Thaw Bound? Protect client data at the border.

The VBA’s Young Lawyers Division Thaw is this weekend.  It’s shaping up to be as terrific as usual, and there’s still time to register.

Undoubtedly, many of you rely on mobile devices to practice law.  Reminder: as a lawyer, you have a duty to take reasonable precautions to protect against the disclosure of client information during a border crossing.

I’ve posted three blogs on this topic.  The most recent was Crossing the Border? Consider Bringing Only What You Need.  The post includes a link to (and summary of) the NYC Bar Association’s advisory opinion 2017-5.  The opinion, which is here, addresses an attorney’s duties with respect to protecting client information before, during, and after a border search.  The ABA Journal also reported the advisory opinion.

The post and links might be worth reviewing.

For more, and thanks to a tip from Attorney Caryn Waxman, check out Jeff Richardson’s latest post on his iPhoneJD blog: New Customs and Border Protection policy on searching attorney iPhones.  The post focuses on the “new procedures that a border patrol agent must use when confronted with data protected by the attorney-client privilege or work product.”  Note: the duty to protect client data at the border is NOT limited to data on Apple devices.

If you’re going to Montreal, have a great time!  But, before leaving, consider how important it really is to have client data with you for the weekend.






#2 in 2017: Hey Lawyers! STFU!

Maybe 2017 will go down as the year that we resolved (for once and for all) that “public record” does not equal “generally known.”


I’m counting down this blog’s most-read posts of 2017.  So far:

Now, coming in at #2 is my post on client confidences: Hey Lawyers! STFU!  It’s a post in which I gently reminded lawyers that things like “but it wasn’t privileged” or “but it’s public record” are not exceptions to:

  • Rule 1.6’s prohibition against disclosing information related to a representation;
  • Rule 1.9(c)(1)’s prohibition against using information related to the representation of a former client to the former client’s disadvantage; or,
  • Rule 1.9(c)(2)’s prohibition against revealing information related to the representation of a former client.

After I posted the STFU blog, I followed up with this post on the “generally known” exception in Rule 1.9(c)(1). Read together, the two posts are best summarized by Thomas Edison:

“You will have many opportunities
to keep your mouth shut.
You should take advantage
of everyone of them.”
Thomas Edison


Can’t keep quiet? Try harder.

“You will have many opportunities
to keep your mouth shut.
You should take advantage
of everyone of them.”
Thomas Edison

I’ve blogged often on client confidences.  Today’s title is the kinder & gentler version of October’s Hey Lawyers! STFU!!!  

Last week, the ABA’s Standing Committee on Ethics and Professional Responsibility issued Formal Opinion 479: The “Generally Known Exception to Former-Client Confidentiality.”   The ABA Journal’s story on the opinion is here.

Before I share (precious few) thoughts from the new advisory opinion, here’s a quick refresher:

  • Rule 1.6 prohibits a lawyer from disclosing information relating to the representation of a client;
  • Rule 1.9(c) extends the prohibition to “former clients;” and,
  • Rule 1.9(c)(1) states that a lawyer “shall not . . . use information relating to the representation to the disadvantage of a former client except as these rules would permit, or when the information has become generally known.” (emphasis added).

As I mentioned in Hey Lawyers! STFU!!!:

  1. The rules do not permit a lawyer to use information to the disadvantage of a former client merely because the information is “public record.”
  2. Information that is “public record” is not necessarily “generally known.”

So, what is “generally known?”  That’s where the ABA Opinion comes in.

First, however, let’s pause for quick public service announcement:

  • if you’re looking for guidance on when it’s ok to use a former client’s information to the former’s client disadvantage, well, think about that for a moment.

Now, back to our regularly scheduled blog.

The formal opinion analyzes the issues far better than I could.  (plus, I’m late for a lunch meeting) So, I’ll leave you with its conclusion.

  • “A lawyer may use information that is generally known to a former client’s disadvantage without the former client’s informed consent. Information is generally known within the meaning of Model Rule 1.9(c)(1) if it is widely recognized by members of the public in the relevant geographic area or it is widely recognized in the former client’s industry, profession, or trade. For information to be generally known it must previously have been revealed by some source other than the lawyer or the lawyer’s agents. Information that is publicly available is not necessarily generally known. “

As always, let’s be careful out there.

Be Quiet

Tech Competence: Tips and a Conference

As Olivia might sing, let’s get techical, techical.

Last week, the Professional Responsibility Board voted to recommend a series of amendments to the Vermont Rules of Professional Conduct.  The package will be forwarded to the Supreme Court for publication for comment.

Rule 1.1 requires lawyers to provide clients with competent representation.  Among other things, the Board will recommend that the Court amend Comment [6] to Rule 1.1 so as to add language that is highlighted & underlined:

  • “To maintain the requisite knowledge and skill, a lawyer should keep abreast of changes in the law and its practice, including the benefits and risks associated with relevant technology, engage in continuing study and education and comply with all continuing legal education requirements to which the lawyer is subject.”

As of September 2017, 28 states have adopted the amendment.

If you’re concerned about tech competence, fear not!

  • On May 16, 2018, the Vermont Bar Association will present its inaugural Tech Day. Save the date! It’s scheduled to take place at the Sheraton-Burlington and will include several practical seminars.
  • Yesterday, Robert Ambrogi’s LawSites blog posted tips related to tech security, including a suggestion to consider client portals.

Finally, I’ve blogged often on this topic.  Related posts include:



Client Confidences: Again, it’s the simple things.

Rules 1.1 and 1.6 impose a duty to act competently to safeguard against the inadvertent or unauthorized disclosure of information related to the representation of a client.  I’ve blogged often on encryption, cloud storage, and other tech issues that impact the duty.

But I’ve also blogged that the most recent sanctions involving Rule 1.6 have nothing to do with hackers or technology.  As I wrote:

“To wit: the last three sanctions for violations of Rule 1.6 in Vermont were imposed:

My guess is that far more lawyers have put information related to a representation at risk by leaving files or computers in restaurants or airport waiting areas than by sending unencrypted emails or storing information in the cloud.”

The lesson: don’t forget about the “simple” steps you can take to safeguard against the inadvertent disclosure of client information.

Indeed, over the past few months, simple steps may have allowed various lawyers to stay out of the news. For example, the lawyer for the President who could’ve used his “inside voice” at lunch. Or the Big Law lawyer who could’ve disabled autocomplete . . . and avoided sending confidential information to The Wall Street Journal.

Here’s the latest simple step to take to guard against disclosing confidential information: don’t give job applicants confidential information as part of the interview process.

As reported by the Legal Profession Blog and the ABA Journal, a Massachusetts lawyer was sanctioned for providing job applicants with confidential client information.  It appears as if the lawyer wanted to assess applicants’ writing skills and asked for memos based on actual cases being handled by the firm.


Again, yes, issues related to the electronic transmission & storage of client information can be daunting.  But it’s often the failure to use simple common sense that leads to a violation of Rule 1.6


Related posts:



Comment Period on Proposed Sex Rule Closes on December 18

In October, the Supreme Court published for comment proposed amendments to Rules 1.7 and 1.8 of the Vermont Rules of Professional Conduct.  The comment period closes on December 18.

The Court published the proposed rule upon the recommendation of the Professional Responsibility Board.  31 states specifically prohibit client-lawyer sexual relationships. Vermont does not.  At least 18 of Vermont’s other licensed professions have adopted rules that specifically ban sexual relationships between a licensee and a client, patient, or person with whom the licensee has a professional relationship.

The Board’s position is that the imbalance of power inherent in the professional relationship between lawyer and client necessitates an absolute ban on a sexual relationship between the two. The Board supports a “bright-line” rule that recognizes the serious risk to a client’s interest in receiving candid, competent, and conflict-free legal advice that is presented when the professional relationship turns sexual.

A quick summary:

  • Proposed Rule 1.8(j) adds a specific prohibition on sexual relations between a lawyer and client unless a consensual sexual relationship existed when the client-lawyer relationship commenced.
  • Proposed Comment [17] to Rule 1.8 clarifies that the rule applies to all sexual relationships formed after the commencement of the professional client-lawyer relationship, including consensual sexual relationships and sexual relationships in which there is no prejudice to the client’s interests in the matter that is the subject of the professional relationship. In such instances, a lawyer would have to withdraw from continued representation.  See, Rule 1.16(a)(1).
  • Proposed Comment [18] provides guidance on sexual relationships that pre-date the commencement of the client-lawyer relationship.
  • If adopted, the conflict created by Rule 1.8(j) is personal and not imputed to other lawyers in the firm.  See, Rule 1.8(k); Rule 1.10(a).

Comments can be emailed to me at

For further reading, here are my previous posts on the issue: