Connecticut: Ex-New Haven Police Chief Who Said He “Turned to Gambling” Pleads No Contest

Former New Haven Police Chief Karl Jacobson pleaded no contest on October 23, 2026, to one count of first-degree larceny, in a case that began with missing police money and led investigators to his sports betting.

Under the plea agreement, Jacobson faces one to four years in prison, his attorney said, according to NBC Connecticut. Sentencing is scheduled for January 29, 2027, in state Superior Court in New Haven.

What the court record shows

Jacobson entered a no-contest plea, known as nolo contendere, without admitting or denying responsibility. He waived a trial on that count and accepted the court’s authority to impose punishment.

The state’s online court docket (docket NNH-CR26-0264750-T), checked by Game Empress on October 26 with data current as of October 24, lists that plea on a count with an offense date of January 1, 2024.

A second count, dated December 23, 2025, still shows a not-guilty plea; that listing does not show how prosecutors will ultimately resolve that count. The case has also been referred to adult probation ahead of sentencing.

The charge is a Class B felony, according to the docket, and WTNH reported a range of one to 20 years in prison for it. The one-to-four-year figure is the range under his plea agreement, according to his attorney.

“I turned to gambling”

The case came to light on January 5, when three assistant chiefs confronted Jacobson about money missing from the department’s confidential informant fund. He retired the same day. WTNH reported that he admitted to taking $10,000.

“I have a problem,” he told them, according to a February state police affidavit quoted by the New Haven Independent. “I fix my alcohol problem. I turned to gambling.”

That admission led to search warrants covering his betting between January 2025 and January 2026 on several platforms, including DraftKings and FanDuel, WTNH reported.

Investigators reported more than $4.4 million in wagers and more than $4.2 million in winnings over the period, leaving a net loss of approximately $214,365. The wagering total should not be confused with the amount stolen. None of the reports reviewed accuses the betting companies of wrongdoing.

After his arrest, a judge ordered Jacobson not to gamble online or visit any casinos while the case is pending, News 12 reported.

How the reported theft total grew

That arrest came in February, and with it, prosecutors’ first account of the missing money. The Connecticut Division of Criminal Justice said $81,500 was unaccounted for or misappropriated from the department’s Narcotic Enforcement Program Fund, which pays confidential informants, between January 1, 2024, and January 5, 2026.

Prosecutors said another $4,000 was taken through two checks from the Police Activity League Fund in late December 2025. Checks from both funds reached his personal checking account, investigators said.

The figure has since grown. On the day of the plea, Mayor Justin Elicker said the state’s attorney had determined that Jacobson stole $178,000 in city funds since 2019, the Independent reported. Jacobson became chief in 2022, so the state’s figure reaches back to before he led the department.

The final restitution amount has not yet been determined. The docket lists January 14, 2027, as his next court date. The Independent reported that a restitution hearing is scheduled that day to determine the amount he must repay. Elicker said the state will likely seek the full $178,000.

What the plea could mean for his pension

The plea also brings his pension back into view. According to his retirement paperwork, Jacobson was set to receive about $10,361 a month, or $124,332 a year, WFSB reported in January. At the time, Elicker said the city had no legal authority to withhold or remove it.

In March, the city’s Police and Fire Pension Fund board rejected Jacobson’s application to classify his pension as a service-connected disability pension. He was already receiving an age-annuity retirement benefit, the Independent reported.

A guilty or no-contest plea can change that picture. Under Connecticut law, when a municipal employee enters such a plea to a crime related to their office, including felonious theft from a municipality, the attorney general must ask a Superior Court judge to revoke or reduce the person’s pension.

The judge weighs the severity of the crime, the money lost and the public trust involved, and can direct part of a reduced pension to an innocent spouse or dependents.

In a September 30, 2026, statement, the attorney general’s office said it had brought 32 pension cases since the law took effect in 2008. Among 30 litigated cases, 12 resulted in pension revocation, 10 in partial reductions and eight in no reduction or revocation.

A pension reduction or revocation requires a separate court decision; it does not happen automatically following a criminal plea. The reports reviewed for this article do not say whether the attorney general plans to act in Jacobson’s case.

The city’s response

“No one is above the law and that includes the chief of police,” Elicker said in a statement after the plea. He said new policies and protocols are now in place to make sure money for the department’s confidential informant program is properly safeguarded.

The case is not the only one in Connecticut this month with a gambling thread. On October 19, a Wolcott man pleaded guilty after moving investors’ crypto to Stake.com, where federal prosecutors say he lost it, and a former strip club owner was sentenced to 16 months in a case in which prosecutors said club cash paid for casino trips.

Until sentencing, Jacobson remains free on a $150,000 bond.