WEBVTT 1 00:00:05.839 --> 00:00:11.740 It's getting dark outside. 2 00:00:11.759 --> 00:00:16.719 Tapes from the Dark Side contains descriptions of violence and sexuality. 3 00:00:17.160 --> 00:00:20.100 Listener discretion is advised. 4 00:00:27.339 --> 00:00:31.390 Almost nobody writes checks anymore. It would probably take you 5 00:00:31.429 --> 00:00:34.070 a minute to find your checkbook right now. I know 6 00:00:34.109 --> 00:00:37.520 it would for me. There's a whole generation that has 7 00:00:37.619 --> 00:00:40.950 never filled one out, never will, and would have to 8 00:00:40.990 --> 00:00:45.229 be taught. The date here, the amount there, sign here. 9 00:00:46.250 --> 00:00:49.710 And even though it's essentially an antique, it's an antique 10 00:00:49.789 --> 00:00:54.320 with function. On every check, there's one place, the lower 11 00:00:54.359 --> 00:00:57.259 left corner, where you write what the money was for. 12 00:00:58.140 --> 00:01:01.460 It doesn't get filled out every time. The bank doesn't 13 00:01:01.500 --> 00:01:04.969 even read that line. It changes nothing about where the 14 00:01:05.010 --> 00:01:08.769 money goes. It's there mostly for the person writing the 15 00:01:08.849 --> 00:01:14.629 check or the person receiving it. It's called the memo line. 16 00:01:20.200 --> 00:01:23.319 Two checks were drawn on an account belonging to the 17 00:01:23.379 --> 00:01:28.939 Police Activity League of New Haven, PAL. It's a non-profit 18 00:01:29.019 --> 00:01:33.459 the police department runs for kids. funded by donations, a 19 00:01:33.500 --> 00:01:37.799 few grants, and small automatic deductions out of the paychecks 20 00:01:37.859 --> 00:01:42.200 of New Haven's own police officers. Together, the two checks 21 00:01:42.359 --> 00:01:46.849 came out to $ 4, 000. The memo line on the first check, 22 00:01:47.810 --> 00:01:52.790 toy giveaway. The memo line on the second check, toy drive. 23 00:01:53.450 --> 00:01:58.280 Both were deposited into the personal checking account of Carl Jacobson. 24 00:01:59.049 --> 00:02:02.150 I know about these checks because they're described in a 25 00:02:02.170 --> 00:02:07.319 10-page document, an arrest warrant affidavit written by a Connecticut 26 00:02:07.359 --> 00:02:12.960 State Police Lieutenant in February of 2026. In Connecticut, that 27 00:02:13.039 --> 00:02:16.680 document goes public almost as fast as the cuffs go on. 28 00:02:17.379 --> 00:02:20.370 Most of what you're about to hear tonight comes out 29 00:02:20.389 --> 00:02:24.430 of those 10 pages. 10 pages for a year like his, 30 00:02:25.289 --> 00:02:28.699 it's not a lot of paper. The apps kept a 31 00:02:28.740 --> 00:02:29.439 better record. 32 00:02:36.349 --> 00:02:40.270 I think everyone has a bit of a fascination with 33 00:02:40.310 --> 00:02:46.810 the dark side. Is there anything you can say about 34 00:02:46.849 --> 00:02:48.659 trying to tell people why you did what you did? 35 00:02:50.009 --> 00:02:52.840 It was something that I got caught up in with 36 00:02:52.879 --> 00:02:54.360 the ease of having it on an app. 37 00:03:12.919 --> 00:03:15.520 When the state of Connecticut wants to know what you've 38 00:03:15.560 --> 00:03:18.719 been up to on DraftKings, it doesn't ask you. It 39 00:03:19.439 --> 00:03:24.129 goes directly to DraftKings. Investigators served search warrants on the 40 00:03:24.169 --> 00:03:29.150 gaming platforms, and the platforms handed over all of Carl's records. 41 00:03:29.889 --> 00:03:33.379 What Came Back covers one year, almost to the day, 42 00:03:34.139 --> 00:03:37.500 January 1st, 2025 through January. 43 00:03:37.400 --> 00:03:38.139 5th, 2026. 44 00:03:38.139 --> 00:03:43.400 The records stop on January 5th. The meeting in Carl 45 00:03:43.460 --> 00:03:48.069 Jacobson's office, the one where three assistant chiefs sat him down, 46 00:03:48.449 --> 00:03:52.729 that was also January 5th. Here's what the year looked 47 00:03:52.789 --> 00:04:04.800 like for Carl. $ 4, 464, 884. 26. That's the wagered number. And on 48 00:04:04.879 --> 00:04:09.719 its own, it's a lie of size. Wagered is not lost. 49 00:04:10.280 --> 00:04:14.180 Wagered is churn. The same dollars go through the door, 50 00:04:14.599 --> 00:04:18.699 come back out, and then go in again. So here's 51 00:04:18.759 --> 00:04:20.189 the column that matters. 52 00:04:21.089 --> 00:04:21.470 Net. 53 00:04:22.189 --> 00:04:32.149 It's not $ 4 million, but it's not a small number either. $ 214, 365. 54 00:04:32.449 --> 00:04:40.519 And 74 cents. The machine doesn't round. Carl's salary as 55 00:04:40.620 --> 00:04:45.839 police chief was around $ 180, 000 a year. Put those side 56 00:04:45.879 --> 00:04:49.459 by side, he lost more than the job paid. Every 57 00:04:49.560 --> 00:04:53.709 shift of the last year as chief, every lineup, press conference, 58 00:04:54.370 --> 00:04:59.129 every hour of overtime, the app took. There's another number. 59 00:04:59.860 --> 00:05:03.800 Perhaps one that tells an even more insidious story than 60 00:05:03.839 --> 00:05:07.379 the six and seven digit numbers. 61 00:05:07.379 --> 00:05:07.560 1,366. 62 00:05:07.560 --> 00:05:14.370 That's how many times Carl's personal checking account pushed money 63 00:05:14.509 --> 00:05:17.110 into one of those two apps in that one year. 64 00:05:17.730 --> 00:05:20.949 If you do the division, that comes out to three, 65 00:05:21.310 --> 00:05:25.660 sometimes four transfers a day, every day for a year. 66 00:05:26.610 --> 00:05:29.129 There's only one kind of person who sits down to 67 00:05:29.209 --> 00:05:31.779 move money three or four times a day for a 68 00:05:31.899 --> 00:05:36.120 habit they can't afford. I have experience with the type 69 00:05:36.160 --> 00:05:40.920 of financial documents we've been discussing in regards to Carl's history. 70 00:05:41.459 --> 00:05:45.040 In April, I downloaded my own bank activity from the 71 00:05:45.040 --> 00:05:49.730 10 days it exported as a spreadsheet. In every line 72 00:05:49.759 --> 00:05:53.550 where my checking account or my card touched a sportsbook 73 00:05:53.709 --> 00:05:57.930 is sitting there. Written the way the machine writes. Transfer. 74 00:05:58.310 --> 00:05:58.790 MGM. 75 00:05:59.199 --> 00:06:01.529 Asterix. New Jersey. Card. 76 00:06:01.529 --> 00:06:02.009 7356. 77 00:06:02.009 --> 00:06:05.589 Negative $ 660. 49. No emotion. Clinical. A reference number on the 78 00:06:05.850 --> 00:06:08.189 next line. 28 characters long. 40 lines in 10 days. 79 00:06:08.189 --> 00:06:23.000 9 different companies. Carl Jacobson averaged 3 to 4. But 80 00:06:23.240 --> 00:06:26.600 I hit 10 transfers in a single day quite easily. 81 00:06:26.620 --> 00:06:30.540 I was outpacing Carl straight out the gate. There's a 82 00:06:30.620 --> 00:06:34.509 thing that gamblers do. And I did it too. We 83 00:06:34.529 --> 00:06:37.790 talk about the wins. The scratcher that hit. The lotto 84 00:06:37.829 --> 00:06:41.850 number that came in. The long shot parlay. My Yukon 85 00:06:41.889 --> 00:06:45.790 buzzer beater. I told you that one with my whole chest. 86 00:06:46.509 --> 00:06:49.089 And part of me wants to tell it again. The 87 00:06:49.129 --> 00:06:54.769 story of the wins. Sometimes you'll hear of people's losses, briefly, 88 00:06:55.230 --> 00:06:57.410 but they don't like to talk about those as much. 89 00:06:58.209 --> 00:07:03.040 Sometimes they'll acknowledge them, sometimes they won't. The number no 90 00:07:03.240 --> 00:07:07.220 active gambler likes to talk about, though, is their net. 91 00:07:08.060 --> 00:07:11.740 The number for their career, or even just the last year. 92 00:07:12.300 --> 00:07:17.009 Every bet stacked against every payout. That number never comes 93 00:07:17.110 --> 00:07:20.149 up at the bar, and there's a reason why. Now, 94 00:07:20.230 --> 00:07:23.009 the net isn't hidden from you if you use a 95 00:07:23.029 --> 00:07:27.120 sports betting app. It's there. There's a screen tucked away 96 00:07:27.240 --> 00:07:30.980 behind a few menus that shows you exactly where you stand. 97 00:07:31.600 --> 00:07:34.600 It's not the most convenient to find, but it's not 98 00:07:34.620 --> 00:07:37.870 that hard either. It's just down a hallway that you 99 00:07:37.899 --> 00:07:41.610 have to decide that you want to walk down. And 100 00:07:41.689 --> 00:07:45.410 after a stretch of losing, that hallway starts to look 101 00:07:46.029 --> 00:07:51.060 very long. The net is the number you avoid. When 102 00:07:51.079 --> 00:07:56.899 you look at Carl's page, one, 4.25 million. Looks like 103 00:07:56.959 --> 00:08:00.779 a guy who mostly wins. And I'm quite sure Carl 104 00:08:00.839 --> 00:08:04.540 Jacobson had a few of his own Yukon buzzer beater 105 00:08:04.600 --> 00:08:09.139 stories to tell. The most complete record of Carl Jacobson's 106 00:08:09.319 --> 00:08:12.879 last year as chief of police does not exist at 107 00:08:13.000 --> 00:08:17.000 a headquarters on Union Avenue. It's not in a city file. 108 00:08:17.620 --> 00:08:21.620 It sits on servers owned by two betting companies, accurate 109 00:08:21.660 --> 00:08:25.899 to the second, accurate to the cent. When we run 110 00:08:25.920 --> 00:08:29.500 the math, we have an immediate and obvious problem. Money 111 00:08:29.519 --> 00:08:32.960 was leaving Carl's checking account faster than the job could 112 00:08:33.000 --> 00:08:36.600 put it there. The arithmetic has a hole, and that 113 00:08:36.659 --> 00:08:40.379 money had to come from somewhere. Since July of 2019, 114 00:08:40.379 --> 00:08:45.899 before he was ever chief, Carl Jacobson handled the money 115 00:08:45.919 --> 00:08:51.519 New Haven uses to pay CI's confidential informants. It ran 116 00:08:51.559 --> 00:08:56.879 through the Narcotic Enforcement Program, about $ 5, 000 a month, and 117 00:08:56.960 --> 00:09:00.360 per the sworn statement in that warrant, it ran through 118 00:09:00.500 --> 00:09:05.220 exactly one man. He received it, he dispensed it, he 119 00:09:05.279 --> 00:09:07.879 kept the log. When I got to this part of 120 00:09:07.919 --> 00:09:11.259 the story, I got curious. I had heard of a 121 00:09:11.490 --> 00:09:15.370 confidential informant, and I knew they got paid, but how 122 00:09:15.409 --> 00:09:18.929 the hell does that actually play out in real life? Well, 123 00:09:19.110 --> 00:09:22.370 let's say, for example, a CI agrees to wear a 124 00:09:22.450 --> 00:09:26.429 wire during a narcotics bust. The police come in, make 125 00:09:26.490 --> 00:09:30.340 their arrests. It's not really glamorous, but it's not a 126 00:09:30.379 --> 00:09:35.039 metaphor either. The government quietly paying its citizens to tell 127 00:09:35.139 --> 00:09:37.620 on each other. It's a real part of how these 128 00:09:37.679 --> 00:09:41.980 cases get made. So the fund custodian writes a check, 129 00:09:42.649 --> 00:09:46.610 Somebody cashes it, the actual cash goes into an envelope, 130 00:09:47.210 --> 00:09:49.990 and the officer hands it to the informant, who signs 131 00:09:50.029 --> 00:09:53.389 a receipt for the exact amount. By the book, a 132 00:09:53.470 --> 00:09:57.860 second officer is supposed to witness the handoff. Cash in, 133 00:09:58.250 --> 00:10:02.879 signature back. New Haven system had one man holding all 134 00:10:02.919 --> 00:10:06.159 of it he wrote the request he cashed the check 135 00:10:06.649 --> 00:10:10.230 he carried the cash and he kept the only ledger 136 00:10:10.710 --> 00:10:16.259 the second officer the second signature did not exist So 137 00:10:16.360 --> 00:10:22.580 we get to December 23rd of 2025, two days before Christmas. 138 00:10:23.320 --> 00:10:26.799 A sergeant in the intelligence unit picks up the phone. 139 00:10:27.730 --> 00:10:32.450 What he said right after this quick break. If you 140 00:10:32.470 --> 00:10:35.750 want to skip the ads and support the podcast, you 141 00:10:35.789 --> 00:10:39.830 can do so at patreon.com slash tapes from the dark side. 142 00:10:46.840 --> 00:10:51.000 The sergeant's name is Francisco Sanchez. He works in the 143 00:10:51.059 --> 00:10:55.320 intelligence unit, and the call he makes, two days before Christmas, 144 00:10:55.860 --> 00:10:59.850 is to an assistant chief, David Zanelli. He tells Zanelli 145 00:10:59.879 --> 00:11:03.950 something's wrong with the chief. Not the gambling. Nobody at 146 00:11:03.990 --> 00:11:07.850 the department knows about the gambling yet. On December 23rd, 147 00:11:08.389 --> 00:11:11.769 not a single person in New Haven had any idea 148 00:11:11.830 --> 00:11:14.990 their chief had been quietly moving hundreds of thousands of 149 00:11:15.070 --> 00:11:18.200 dollars out of his own account into two apps for 150 00:11:18.259 --> 00:11:22.340 most of the year. What Sanchez had was smaller, but 151 00:11:22.360 --> 00:11:28.259 it was significant. The informants didn't get paid. November and 152 00:11:28.299 --> 00:11:32.269 then December. Two months, the money that's supposed to reach 153 00:11:32.309 --> 00:11:36.909 the people taking real-life risks to talk to police just 154 00:11:36.970 --> 00:11:40.009 never showed. And the only man who can say why 155 00:11:40.759 --> 00:11:46.320 is Carl Jacobson. Here's how the story goes. Chief Jacobson 156 00:11:46.580 --> 00:11:52.100 gave his lieutenant $ 2, 000 to pay informants. That lieutenant was 157 00:11:52.340 --> 00:11:57.370 Derek Werner. And then Carl walked into Werner's office and 158 00:11:57.399 --> 00:12:01.429 took half of it back, $ 1, 000 out of the envelope. 159 00:12:01.929 --> 00:12:05.909 And where the money was, he left a note, quote. 160 00:12:06.450 --> 00:12:11.669 Took $ 1, 000, $ 12. 2325, Chief Jacobson. 161 00:12:13.649 --> 00:12:16.450 The chief of police wrote an IOU and a cash 162 00:12:16.490 --> 00:12:20.200 fund for confidential informants and signed it with his rank. 163 00:12:21.220 --> 00:12:24.759 But those informants still needed paying. People had done the 164 00:12:24.799 --> 00:12:28.399 work and they were owed money. So Sergeant Sanchez paid 165 00:12:28.440 --> 00:12:31.350 them out of his own pocket. One man at the 166 00:12:31.379 --> 00:12:35.629 top quietly took and one man below him quietly covered. 167 00:12:36.370 --> 00:12:40.039 In that same stretch of December, The chief asks Werner 168 00:12:40.120 --> 00:12:45.549 for one more thing, a personal loan, $ 500. You already 169 00:12:45.570 --> 00:12:51.409 have the other number, $ 214, 000. And here, two days before Christmas, 170 00:12:51.950 --> 00:12:55.129 the same man is asking a lieutenant who reports to 171 00:12:55.190 --> 00:12:59.419 him to float him $ 500. I know what that feels 172 00:12:59.480 --> 00:13:03.139 like from the inside, but I can't describe it in words. 173 00:13:03.899 --> 00:13:06.139 It's something I hope you will never have to feel 174 00:13:06.200 --> 00:13:10.990 for yourself. The men who suspected something was wrong didn't 175 00:13:11.129 --> 00:13:15.580 walk in and confront Carl unafraid. Per the warrant, they 176 00:13:15.629 --> 00:13:18.340 thought if they flagged the chief, the chief would come 177 00:13:18.379 --> 00:13:21.960 for them, move them off their post, kill their overtime. 178 00:13:22.720 --> 00:13:26.259 A lieutenant afraid of what telling the truth would cost him, 179 00:13:26.799 --> 00:13:29.519 a sergeant covering a debt out of his own paycheck, 180 00:13:30.240 --> 00:13:33.919 and a handwritten IOU. Now let's go back and look 181 00:13:33.960 --> 00:13:38.649 at the date on that note again. December 23, 2025. 182 00:13:38.649 --> 00:13:40.549 Those two checks I read you at the top of 183 00:13:40.600 --> 00:13:44.440 this episode, the ones from the kids' accounts, made out 184 00:13:44.480 --> 00:13:49.299 to Carl Jacobson himself, toy giveaway, toy drive, they're dated 185 00:13:49.740 --> 00:13:54.850 December 23, 2025. One for $ 1, 000, one for $ 3, 000. The 186 00:13:55.210 --> 00:14:01.690 administrative assistant who prepared them is named Tina Tremaglio. She 187 00:14:01.730 --> 00:14:05.120 told investigators it struck her as odd A toy drive 188 00:14:05.230 --> 00:14:08.710 this close to Christmas and the checks written out to 189 00:14:08.750 --> 00:14:13.389 the chief himself? This kind of systematic abuse of power 190 00:14:13.909 --> 00:14:18.250 doesn't happen by accident. It takes a while to take shape. 191 00:14:18.990 --> 00:14:22.309 How did none of the assistant chiefs think it was 192 00:14:22.429 --> 00:14:26.419 odd that Carl Jacobson had sole access to the CI fund? 193 00:14:27.159 --> 00:14:29.960 When they asked Zanelli that, he didn't have an answer. 194 00:14:30.519 --> 00:14:34.539 He said they asked Carl repeatedly for access to the fund. 195 00:14:35.220 --> 00:14:38.259 Carl told them that he couldn't let them have access 196 00:14:38.299 --> 00:14:42.049 to it because he wanted to protect them from liability. 197 00:14:42.870 --> 00:14:45.090 Sounds like the kind of thing a good boss says. 198 00:14:45.690 --> 00:14:48.929 Zanelli was coming up on his first year running investigations 199 00:14:49.289 --> 00:14:52.590 and the job comes with an annual audit. He was 200 00:14:52.710 --> 00:14:57.049 prepping for it. On January 3rd, a supervisor in management 201 00:14:57.110 --> 00:15:02.149 services pulls the records for Zanelli In November, Carl Jacobson 202 00:15:02.169 --> 00:15:06.759 had cashed two checks from the informant fund, $ 5, 000 each. 203 00:15:07.159 --> 00:15:13.299 In December, two more, $ 20, 000 in six days. January 5th, 204 00:15:13.639 --> 00:15:18.860 three assistant chiefs confront Carl Jacobson, a phone quietly recording 205 00:15:18.919 --> 00:15:22.230 on the conference table because they were afraid of how 206 00:15:22.269 --> 00:15:26.450 it was going to go. From the affidavit, chief is 207 00:15:26.549 --> 00:15:35.480 asked approximately how much money is missing, and he responds, $ 10, 000. 208 00:15:31.700 --> 00:15:36.000 Quote, I have you guys in a bad situation and 209 00:15:36.019 --> 00:15:39.179 I just ask that you allow me to replace the 210 00:15:39.220 --> 00:15:42.940 money and I'll retire and we fix the books and 211 00:15:42.980 --> 00:15:44.139 pass it over to one of you. 212 00:15:46.299 --> 00:15:50.259 Assistant Chief Etienne responds that Jacobson is asking them to 213 00:15:50.350 --> 00:15:55.070 double down on a wrong. Jacobson responds, No, I understand. 214 00:15:55.590 --> 00:15:58.889 And then later says, I'm just asking for an opportunity 215 00:15:58.950 --> 00:16:02.830 to save myself. Because here, I mean, there's a potential 216 00:16:02.870 --> 00:16:06.120 to go to jail, right? Because I misused government funds. 217 00:16:06.789 --> 00:16:09.139 I won't get a pension. I'll go to jail. 218 00:16:10.639 --> 00:16:15.440 Assistant Chief says, I'm not the judge or jury. Jacobson responds, 219 00:16:16.120 --> 00:16:16.460 I know. 220 00:16:17.200 --> 00:16:19.379 I'm just saying it's not that I'm a bad person. 221 00:16:20.100 --> 00:16:23.769 I have a problem. I fixed my alcohol problem. I 222 00:16:23.809 --> 00:16:26.509 turned to gambling. I don't know why it just got 223 00:16:26.570 --> 00:16:27.370 worse recently. 224 00:16:28.169 --> 00:16:32.440 A.C. Zanelli tells Chief, I've never seen you gamble. Chief 225 00:16:32.460 --> 00:16:34.840 Jacobson responds, It's. 226 00:16:34.759 --> 00:16:43.730 On the app. $ 10, 000. 227 00:16:42.610 --> 00:16:46.210 That's the number Carl confessed to. And the officers in 228 00:16:46.309 --> 00:16:49.429 front of him knew it was a lie the moment 229 00:16:49.669 --> 00:16:53.919 it left his lips. Remember two days earlier, a supervisor 230 00:16:54.059 --> 00:16:58.399 in management services had pulled the checks for Zanelli, two 231 00:16:58.440 --> 00:17:04.059 in November, in December, 5,000 apiece. The men sitting across 232 00:17:04.099 --> 00:17:07.579 from Carl knew the number was at least twice what 233 00:17:07.599 --> 00:17:11.539 he confessed to, but 20,000 wasn't the real number either. 234 00:17:12.279 --> 00:17:15.200 The state was about to put a forensic accountant on 235 00:17:15.240 --> 00:17:20.019 the case. We're not done counting. The next week went 236 00:17:20.079 --> 00:17:22.549 by in a flash. By the end of that day 237 00:17:22.640 --> 00:17:27.069 when the confrontation took place, Monday, January 5th, Carl was 238 00:17:27.150 --> 00:17:30.220 no longer chief of police. but he hadn't been fired. 239 00:17:30.640 --> 00:17:36.150 You see, immediately after that meeting, Carl retired. The paperwork 240 00:17:36.210 --> 00:17:42.130 was sent in the same exact day, effective immediately, pension secured, 241 00:17:42.910 --> 00:17:47.750 at least for now. Carl filed for retirement before anyone 242 00:17:47.849 --> 00:17:50.799 had a chance to react. He never went back to 243 00:17:50.839 --> 00:17:54.099 that office. Cinelli reported it up the chain and had 244 00:17:54.140 --> 00:17:58.359 the locks changed. By Friday, Carl's lawyer called the state's 245 00:17:58.440 --> 00:18:01.660 attorney and to let them know his client was invoking 246 00:18:01.700 --> 00:18:06.250 the Fifth and would not be talking to police. So 247 00:18:06.650 --> 00:18:10.369 Carl didn't run. He didn't try to destroy any evidence 248 00:18:10.490 --> 00:18:13.309 as far as the record shows. What he did was 249 00:18:13.390 --> 00:18:18.980 faster and more efficient. He followed procedure. He exploited the 250 00:18:19.039 --> 00:18:21.740 system that he had been a part of for his 251 00:18:21.779 --> 00:18:27.200 whole career. Retirement filed, the Fifth invoked before an interview 252 00:18:27.299 --> 00:18:31.269 could even be scheduled again. Every move by the book. 253 00:18:31.269 --> 00:18:34.890 27 years of knowing exactly how the machine processes a 254 00:18:34.930 --> 00:18:39.210 man in trouble. On January 23rd, state police seized the 255 00:18:39.250 --> 00:18:43.470 bank records and a forensic accountant from the FBI sat 256 00:18:43.529 --> 00:18:48.359 down with two stacks of paper. Carl Jacobson's personal checking 257 00:18:48.400 --> 00:18:52.940 account on one side, the narcotic enforcement program on the other. 258 00:18:53.500 --> 00:18:55.279 And they started to compare. 259 00:18:55.279 --> 00:18:57.269 2025. 260 00:18:57.269 --> 00:19:06.839 14 checks, $ 5, 000 each, $ 70, 000 total cashed. 23,000 of it 261 00:19:06.880 --> 00:19:11.089 shows up in expenditure reports, money that got where it 262 00:19:11.119 --> 00:19:16.069 was supposed to go, documented, accounted for. The other 47,000 isn't. 263 00:19:16.109 --> 00:19:19.250 Then they went back a year to 2024, another 34,000 cashed, 264 00:19:19.349 --> 00:19:28.720 unaccounted for. $ 81, 500 out of the fund that pays people 265 00:19:28.740 --> 00:19:30.539 to talk to the police, plus the $ 4, 000 that was 266 00:19:30.559 --> 00:19:31.200 supposed to go to the kids. 267 00:19:31.200 --> 00:19:31.359 $ 85, 500. 268 00:19:31.240 --> 00:19:31.380 Gone. 269 00:19:31.400 --> 00:19:33.799 Carl admitted to $ 10, 000. Now the interesting thing is $ 14, 000 270 00:19:33.700 --> 00:19:35.150 of it, they could follow the whole way out of 271 00:19:35.160 --> 00:19:43.109 the fund into the checking account. Carl admitted to 10. Now, 272 00:19:43.170 --> 00:19:46.549 the interesting thing is 14,000 of it, they could follow 273 00:19:46.589 --> 00:19:50.109 the whole way out of the fund into the checking account, 274 00:19:50.730 --> 00:19:55.930 out of the checking account into DraftKings and FanDuel, traced precisely. 275 00:19:56.569 --> 00:19:59.950 Two of the informant checks turned up as photocopies when 276 00:19:59.970 --> 00:20:05.210 the state seized Carl's bank records, 5,000 each deposited into 277 00:20:05.250 --> 00:20:09.210 his personal account. Both of them cashed the same day 278 00:20:09.279 --> 00:20:12.890 they were written No gap, not even a night to 279 00:20:12.950 --> 00:20:17.190 sleep on it. There's a line from Werner in the affidavit. 280 00:20:17.690 --> 00:20:22.130 Carl cashed $ 5, 000 a month. He handed Werner usually two, 281 00:20:22.150 --> 00:20:26.380 never more. Werner told investigators he didn't know what happened 282 00:20:26.400 --> 00:20:29.660 to the rest. For six years, nobody knew what happened 283 00:20:29.680 --> 00:20:32.359 to the rest because there was nobody whose job it 284 00:20:32.400 --> 00:20:38.009 was to know except Carl Jacobson. But the kids' fund 285 00:20:38.109 --> 00:20:41.539 hurts more than the informant money. at least for me, 286 00:20:41.559 --> 00:20:45.329 and it seems like it lingered for Carl as well. 287 00:20:47.109 --> 00:20:52.700 The Connecticut State Police Eastern District Major Crime Unit obtained 288 00:20:52.759 --> 00:20:56.950 a signed and sworn statement. From the executive director of 289 00:20:56.970 --> 00:21:01.779 the New Haven Police Activity League program, we glossed over it. 290 00:21:02.150 --> 00:21:05.170 So I just want to quickly describe what the PAL 291 00:21:05.329 --> 00:21:09.769 actually is. It's a youth program that directly connects law 292 00:21:09.789 --> 00:21:13.549 enforcement officers with children and teens, which you might call 293 00:21:13.569 --> 00:21:17.410 troubled youth programs. A free event they actually hold in 294 00:21:17.470 --> 00:21:21.369 New Haven. It's called Homework and Hangout, 5 to 7 p.m. 295 00:21:21.450 --> 00:21:24.569 on Tuesdays and Thursdays. You can drop your kid off. 296 00:21:24.829 --> 00:21:28.170 They'll be supervised. They can read books, play board games, 297 00:21:28.230 --> 00:21:31.230 or just do their homework. It's a real program with 298 00:21:31.309 --> 00:21:35.210 real tangible benefits for the community. On January 29th, 2026, 299 00:21:35.190 --> 00:21:37.470 at 1248 p.m., the executive director of the PAL announced 300 00:21:42.119 --> 00:21:45.559 received a call from an unfamiliar phone number. He returned 301 00:21:45.599 --> 00:21:48.940 that call, and when the person answered, they said, Hey, 302 00:21:48.960 --> 00:21:51.490 it's Carl. From the affidavit. 303 00:21:52.349 --> 00:21:54.930 Jacobson stated that he was sorry for letting the police 304 00:21:54.950 --> 00:21:58.549 department down, letting him down, and letting the PAL down. 305 00:21:59.430 --> 00:22:02.549 Jacobson also said that he had heard that people were 306 00:22:02.609 --> 00:22:05.950 claiming he had taken money from PAL, and he wanted 307 00:22:05.970 --> 00:22:09.809 him to know this was not true. Jacobson explained that 308 00:22:09.890 --> 00:22:14.000 he had cashed two checks to support a woman's toy drive. 309 00:22:14.700 --> 00:22:17.960 But after the events at the police department, the woman 310 00:22:18.089 --> 00:22:22.490 wanted nothing to do with him or his money. Jacobson 311 00:22:22.529 --> 00:22:25.849 told the director that he deposited the funds back into 312 00:22:25.869 --> 00:22:30.490 the PAL account. The information that Jacobson told him is 313 00:22:30.569 --> 00:22:34.829 consistent with the $ 4, 000 cash deposit into the New Haven 314 00:22:34.890 --> 00:22:40.309 Police Activity League banking account on January 16th, 2026. 315 00:22:41.559 --> 00:22:44.960 Could have been a simple slip of the tongue. I've 316 00:22:45.009 --> 00:22:48.329 never heard of a woman's toy drive. We've all heard 317 00:22:48.430 --> 00:22:52.109 of a children's toy drive. But I think we all 318 00:22:52.170 --> 00:22:55.569 know the most likely reason that Carl got his words 319 00:22:55.650 --> 00:23:04.099 mixed up. Because there was no toy drive. The sportsbooks cooperated. 320 00:23:04.559 --> 00:23:09.140 When Connecticut State Police came with warrants, DraftKings and FanDuel 321 00:23:09.349 --> 00:23:12.599 didn't flinch. They opened the file and handed over a 322 00:23:12.839 --> 00:23:18.140 year of Carl Jacobson's betting activity. Every wager, every deposit, 323 00:23:18.660 --> 00:23:22.960 every dollar to the cent. They knew precisely who Carl was. 324 00:23:22.980 --> 00:23:27.480 He was one of their best customers. Back in episode one, 325 00:23:27.519 --> 00:23:30.519 I said the warrant showed Carl had a customer relations 326 00:23:30.559 --> 00:23:35.210 person assigned to him. That may have been incorrect. At 327 00:23:35.250 --> 00:23:39.079 least the warrant doesn't say that. Where I actually got 328 00:23:39.119 --> 00:23:42.559 that from is a man named Jonathan Cohen, who wrote 329 00:23:42.599 --> 00:23:45.859 a book about the American sports betting industry and who 330 00:23:45.900 --> 00:23:49.160 sat down with a New Haven reporter days after Carl 331 00:23:49.180 --> 00:23:53.079 Jacobson's arrest and read the same 10 pages that we've 332 00:23:53.119 --> 00:23:56.559 been reading through. He described how these companies work. They 333 00:23:56.619 --> 00:23:59.140 find the big fish. They put a line on them. 334 00:23:59.559 --> 00:24:02.539 And the reporter noted in the piece that Cohen was 335 00:24:02.720 --> 00:24:06.240 not talking about Carl specifically and He was saying that 336 00:24:06.299 --> 00:24:10.890 Carl's story fits a pattern. So here's what we actually 337 00:24:11.230 --> 00:24:14.529 know and can prove. I can tell you what this 338 00:24:14.650 --> 00:24:18.390 industry does to men who bet the way Carl Jacobson bets. 339 00:24:19.009 --> 00:24:24.099 That is documented. And it's in job listings, earning reports, 340 00:24:24.519 --> 00:24:28.740 and regulatory filings. I cannot confirm that this was done 341 00:24:29.039 --> 00:24:33.519 specifically to Carl. At least not yet. We've talked about 342 00:24:33.539 --> 00:24:38.000 the gambling ads. They sell you a stadium where everybody's 343 00:24:38.019 --> 00:24:41.869 got 20 bucks on the game. Everybody's yelling at the screen. 344 00:24:42.369 --> 00:24:46.750 Everybody's having a night. That's the picture. Millions of people 345 00:24:47.230 --> 00:24:50.410 having a little fun and some of them winning big. 346 00:24:51.190 --> 00:24:56.259 That is not the business. Everyone in the stadium is losing. 347 00:24:56.960 --> 00:25:00.200 You know this from episode two. The price is baked 348 00:25:00.279 --> 00:25:03.339 into every line on the board and the math doesn't 349 00:25:03.420 --> 00:25:06.920 take a night off. Sure, you might win a bet 350 00:25:07.019 --> 00:25:09.440 or two in the short term. You might have a 351 00:25:09.440 --> 00:25:13.980 10-day winning streak. But over the long haul, you will 352 00:25:14.099 --> 00:25:18.190 never come out ahead. The longer you bet, the more 353 00:25:18.250 --> 00:25:23.710 you wager, the more it is guaranteed you will lose money. 354 00:25:24.329 --> 00:25:27.769 This is not like a game of battleship where each 355 00:25:27.869 --> 00:25:31.180 bet gets you closer to a hit. Nobody in the 356 00:25:31.240 --> 00:25:35.970 stadium is beating the machine in the The only question 357 00:25:36.410 --> 00:25:40.170 is how fast you lose and how much. And if 358 00:25:40.230 --> 00:25:43.009 you are one of those ones who is cursed with 359 00:25:43.049 --> 00:25:45.559 a big win early and you happen to have a 360 00:25:45.619 --> 00:25:50.519 genetic predisposition to betting addiction, then you might very well 361 00:25:50.859 --> 00:25:54.160 have hit the jackpot, but in a way you might 362 00:25:54.240 --> 00:25:59.339 not understand yet. The sportsbook PointsBet, in its own filing, 363 00:25:59.839 --> 00:26:05.220 showed that VIP customers were half of 1% of its users. 0.5% 364 00:26:06.349 --> 00:26:10.609 brought in more than 70% of revenue. Fill your stadium 365 00:26:10.690 --> 00:26:14.579 with 20,000 people, and the business is 100%. But let 366 00:26:14.619 --> 00:26:19.299 me say again very clearly, the other 19,900 are not 367 00:26:19.339 --> 00:26:25.339 winning anything. They're losing small, slowly, on schedule, by design. 368 00:26:26.000 --> 00:26:29.299 Losing at a rate that feels like entertainment. They are 369 00:26:29.380 --> 00:26:33.039 the scenery, and the scenery is what keeps the 100% 370 00:26:33.039 --> 00:26:38.059 from feeling like what they really are. Marks. So there's 371 00:26:38.099 --> 00:26:42.500 a job, a real job, posted publicly. You can probably 372 00:26:42.539 --> 00:26:46.480 find listings for it tonight if you go online. VIP 373 00:26:46.519 --> 00:26:51.440 account manager at FanDuel. Salary, $ 60, 000 to $ 70, 000 a year. 374 00:26:52.009 --> 00:26:57.789 Job description, manage the portfolios of high-value clients, build relationships, 375 00:26:58.269 --> 00:27:02.660 encourage loyalty, keep a documented profile on them. host them 376 00:27:02.819 --> 00:27:06.359 at events. And down in the qualifications, it says you 377 00:27:06.400 --> 00:27:12.279 should be able to, quote, identify customer trigger points. Run 378 00:27:12.319 --> 00:27:17.130 that through any other addiction, a liquor company, hiring customer 379 00:27:17.170 --> 00:27:21.970 relations people who can manage a portfolio of alcoholics. Sounds 380 00:27:22.009 --> 00:27:25.230 a little bit like a bartender, but it's much more 381 00:27:25.309 --> 00:27:30.230 insidious than that. Because a bartender doesn't text you when 382 00:27:30.279 --> 00:27:35.619 you haven't shown up for a drink. In 2023, a 383 00:27:35.759 --> 00:27:40.940 man named Amit Patel pled guilty to stealing $ 22 million 384 00:27:41.279 --> 00:27:45.029 from the Jacksonville Jaguars NFL football team. He was their 385 00:27:45.109 --> 00:27:48.990 manager of financial planning, 31 years old. And the way 386 00:27:49.029 --> 00:27:52.269 he did it is going to sound familiar. The Jags 387 00:27:52.309 --> 00:27:55.109 had given him control of the team's virtual credit card. 388 00:27:55.750 --> 00:28:07.009 One man, four years, and nobody over his shoulder. $ 22, 221, 000. $ 454. 40, 389 00:28:03.009 --> 00:28:10.490 $ 20 million of that went to FanDuel. Patel is serving 390 00:28:10.589 --> 00:28:14.759 six and a half years in federal prison, and in 2024, 391 00:28:14.759 --> 00:28:20.039 he sued FanDuel for $ 250 million. The lawsuit is where 392 00:28:20.079 --> 00:28:25.799 the following details come from. They're not facts, they're Patel's allegations. 393 00:28:26.279 --> 00:28:30.069 They have not been proven, and FanDuel has predictably declined 394 00:28:30.109 --> 00:28:35.450 to comment. Patel says FanDuel made him a VIP, says 395 00:28:35.509 --> 00:28:39.750 they gave him $ 1. 1 million in credits. He says they 396 00:28:39.789 --> 00:28:43.410 flew him to the Super Bowl, the Masters twice, the 397 00:28:43.450 --> 00:28:48.380 college football playoff championship, and Formula One in Miami. And 398 00:28:48.440 --> 00:28:52.059 he says he had a host, an actual person with 399 00:28:52.099 --> 00:28:58.119 a name, Brett Krause. Patel alleges that Krause contacted him 400 00:28:58.640 --> 00:29:02.319 as many as 100 times a day, starting early in 401 00:29:02.359 --> 00:29:06.230