The former police chief of New Haven, Conn., was arrested on Friday and accused of embezzling money from city coffers as he placed millions of dollars of bets through two online gambling sites.
The former chief, Karl R. Jacobson, was charged with two counts of larceny on Friday, accused of embezzling as much as $85,500, investigators said. The majority of money came from a fund to pay confidential informants in drug cases, according to prosecutors.
A 15-year-veteran of the police force, Mr. Jacobson rose to become chief in 2022. The mayor of New Haven, Justin Elicker, said in January that Mr. Jacobson had admitted to misusing public funds and stealing from the city. The mayor said he had placed Mr. Jacobson on administrative leave. Instead, the police chief retired that day.
News of Mr. Jacobson’s resignation triggered interest from investigators with the Connecticut Department of Consumer Protection Gaming Division, investigators said. The agency sent search warrants to three platforms in the state: DraftKings, FanDuel and Fanatics.
It has never been easier to place a bet in America. Websites focus on sports betting, casinos offer traditional games like slot machines on your phone and so-called prediction markets, which are loosely regulated, allow people to bet on pretty much anything.
As early as 2019, Mr. Jacobson began dipping into the fund meant to pay informants, according to an application for an arrest warrant, eventually taking as much as $81,500 from it. He later embezzled two checks totaling $4,000 from the New Haven Police Activity League, in December.
Between January 2025 and January 2026, Mr. Jacobson’s accounts on DraftKings and FanDuel show that he wagered about $4.46 million, according to prosecutors. Over that period, Mr. Jacobson recorded a net loss of $214,365, investigators said.
Mr. Jacobson’s arrest was first reported by news media in Connecticut.
According to an arrest warrant application, some of the people directly reporting to him noticed Mr. Jacobson behaving strangely. One lieutenant reported that when he requested funds to pay informants, the former chief gave him $2,000. Then, Mr. Jacobson took back $1,000, and left the lieutenant an I.O.U., according to the application. However, Mr. Jacobson never returned the money, they said.
In a secretly recorded meeting, when the chiefs confronted Mr. Jacobson in January, he “admitted to spending too much money on gambling,” and said that he was seeking help and a loan and that he intended to replace the funds. He told them he had only taken tens of thousands of dollars, the chiefs said, and when he was asked how long it had been going on, he responded, “Not long, just the month,” according to the application.
Mr. Jacobson pleaded with them to allow him to replace the money, the chiefs told an investigator, and to “fix the logbook, and then retire.” He told them he was the only one stealing, they said.
“Chief Jacobson stated that he was embarrassed and asked them for an opportunity to avoid potentially going to jail and losing his pension for misusing government funds,” according to the application.
When the chiefs asked about Mr. Jacobson’s gambling, he said it had gotten worse over the “past couple of months,” and that he had done it “on the app.”
In the recording of the conversation, the investigator said, Mr. Jacobson admitted to having a problem.
“I fix my alcohol problem. I turned to gambling,” he says, according to the application. “I don’t know why it just got worse recently.”
Sheelagh McNeill contributed research.
Hurubie Meko is a Times reporter covering criminal justice in New York, with a focus on the Manhattan district attorney’s office and state courts.
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