Share 
What started as questions about missing informant money has turned into one of the most jaw-dropping stories to come out of Connecticut this year. According to a newly released arrest warrant affidavit, former Police Chief Karl Jacobson allegedly wagered more than $4.4 million on sports betting apps in 2025, ultimately losing just over $214,000.
State police say that while those losses were piling up, money went missing from city-controlled accounts. Jacobson now faces two counts of first-degree larceny tied to $85,500 in allegedly misappropriated funds from 2024 and 2025.
Secret recording triggers investigation
The affidavit outlines how the concerns first surfaced. In late December, a lieutenant noticed that money set aside for confidential informants had not been distributed as usual. At one point, Jacobson allegedly handed over informant funds but then reclaimed part of the cash, leaving behind a handwritten IOU.
Acting Chief David Zannelli and two assistant chiefs confronted Jacobson in early January. According to the warrant, Zannelli secretly recorded the conversation due to concerns about potential retaliation.
When asked directly whether he had a gambling problem, Jacobson reportedly acknowledged he had spent too much money.
At one point during the exchange, he tapped his cellphone on the table and said the gambling was happening “on the app.” Those apps were DraftKings and FanDuel, two of Connecticut’s approved online sports betting platforms. Investigators also confirmed he held an account with Fanatics.
FBI audit reveals missing informant cash
An FBI forensic accountant was brought in to compare Jacobson’s personal bank records with the city’s Narcotic Enforcement Program account. In 2025 alone, Jacobson allegedly cashed 14 checks of $5,000 each, totaling $70,000. Only $23,000 of that amount was documented by expenditure reports, leaving $47,000 unaccounted for.
Investigators also flagged $4,000 taken from the Police Activity League fund in 2025. That money was later returned, according to the warrant, though it was initially deposited into Jacobson’s personal account. Roughly $34,500 in additional withdrawals from 2024 remain unexplained.
Altogether, authorities say $85,500 across two years is either unaccounted for or misappropriated. Records show that at least $14,000 of those funds moved through Jacobson’s personal checking account before being transferred to betting platforms.
1,366 Transactions: Inside the betting logs
The online sports betting records are the most striking element of the case. Jacobson is alleged to have wagered $4,464,884.26 on DraftKings and FanDuel between Jan. 1, 2025, and Jan. 5, 2026. He received $4,250,518.52 in payouts during that time, resulting in a net loss of $214,365.74.
Over roughly one year, he moved $373,855 from his checking account to those betting apps in 1,366 separate transactions, according to bank records. Investigators also learned that since 2019, he had been withdrawing an average of $5,000 per month from the informant fund account he controlled.
Bond set at $150,000 as legal battle begins
Jacobson turned himself in at the state police barracks in Montville, accompanied by his attorney, and was released on $150,000 bond. His next court appearance is scheduled in New Haven. His lawyer stressed that an arrest is not proof of guilt and urged the public to keep an open mind.
Meanwhile, according to the original story reported by the New Haven Independent, investigators have expanded search warrants to review financial records going back further. What began as a discrepancy in informant payments has evolved into a case defined by millions in online wagers and a detailed financial paper trail.
