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.


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