By Jonathan D. Cohen
(Opinion) On Friday, state police released an arrest warrant affidavit for former New Haven Police Chief Karl Jacobson. Over the course of 2024 and 2025, Jacobson is alleged to have misappropriated $85,500 of police funds; a continued investigation will assess the possibility that his malfeasance may date back to 2019.
It may be easy to see Jacobson as another public official caught with his hand in the till. The affidavit, though, makes clear that his alleged theft was to feed a gambling habit. While Jacobson did not explicitly say he was addicted to gambling, he did reportedly confess to colleagues that he “spent too much on gambling” and that he has “sought help” related to his betting. Whether he was technically addicted or not, Jacobson’s case is reflective of the dynamics of problem gambling and a symptom of the costs of Connecticut’s all-in bet on legalized betting.
Addiction has always accompanied gambling. Sports betting is no exception. Athletes and fans are attracted to the competitive aspect of gambling, convinced they can leverage their knowledge of sports into easy cash. When—not if—they start to lose, these same gamblers insist a few more bets will let them win it all back.
Americans were already getting addicted to gambling when it was confined to Las Vegas, tribal casinos, corner bookies, and odd corners of the internet. Then came a 2018 Supreme Court ruling that allowed states to legalize sports betting. As Karl Jacobson learned firsthand, gambling today is fully mobile. When an assistant chief told Jacobson that he had never seen Jacobson gambling, Jacobson tapped his cellphone and said, “It’s on the app.”
The version of sports gambling available on cellphones in Connecticut and 31 other states is more dangerous than any version of gambling available in the past. These are sleek apps with an endless menu of betting options, a slew of push notifications and promo offers, and basically no limits on how much someone can wager from the comfort of their couch, or their office at police headquarters.
This complicates the simple story of a corrupt public official. Sports betting today is designed to be enticing and is easy to become addictive. No wonder that, over the course of 2025 alone, Jacobson made over 1,300 deposits into gambling accounts, betting $3.1 million on FanDuel (net loss: $158,000) and $1.3 million on DraftKings (net loss: $55,500).
It is understandable why someone might withhold any sympathy for Jacobson. He allegedly misappropriated city funds! The chief law enforcement officer! The person in charge of arresting people for stealing was … stealing! How hard can it be to just not gamble?
Jacobson at some point made the choice to gamble. He downloaded the FanDuel and DraftKings apps on his phone and he began to bet, likely with his own money. We do not yet know when he began misappropriating funds and how that aligns with the nature of his trouble with gambling.
But, assuming it was only after he developed some sort of gambling problem that Jacobson began betting with money that was not his, then he was not choosing to gamble anymore than someone addicted to drugs is choosing to get high. This is not to excuse his behavior or downplay his alleged crimes. But the American Psychiatric Association places gambling in the same category as tobacco and alcohol when it comes to addiction. Gambling can rewire bettors’ brain chemistry to the extent that they cannot stop, and will not until they get treatment, get caught, or until the money is all gone.
Based on the affidavit, Jacobson may have been particularly vulnerable for a gambling problem. “I fix my alcohol problem. I turned to gambling,” he told the city’s three assistant police chiefs. He is hardly alone in this respect. Someone recovering from another addiction, like alcohol, or living with a mental health disorder, such as PTSD or bi-polar, is at heightened risk for problem gambling.
Jacobson’s experience also speaks to what makes gambling a uniquely insidious addiction. Someone with a drinking problem cannot reasonably convince themselves that their next shot is going to cure them of their alcoholism. But someone with a gambling problem can hold out hope that if they hit their next parlay they can wipe out all their debt from gambling and start fresh. So, the deeper a gambler falls into the hole, the more likely they are to just keep digging.
As one of just seven states to legalize both online sports betting and online casino games, Connecticut is at the forefront of legalized gambling in America. But the rush for state revenue five years ago overlooked how uniquely dangerous this version of gambling is. The state—and the nation—is just beginning to reckon with the consequences, from athletes getting caught trying to bet on their own performance to teenagers exposed to gambling advertising.
I have written elsewhere about the kinds of reforms states should make to their sports betting framework to reduce potential harm. One proposal that would have helped Jacobson is an affordability constraint, a measure to flag if someone is betting beyond their means, for example if a police chief with a salary of approximately $180,000 is gambling $4.4 million over the course of a single year.
Where gambling goes, gambling addiction follows. People with addictions will do anything to feed their dependence on betting. Locally, Karl Jacobson may be the first prominent Connecticut official who commits financial crimes because of online sports gambling. But he won’t be the last.