Sept. 4, 2026

S12, Chapter 4: The Machine

Show Notes
Transcript

A check for $1,000 and on the memo line... Toy Give Away.Another one for $3,000... Toy Drive. Both made out to the chief of police. Two days before Christmas.

...

In a final effort to rid us from what I consider to be frankly evil gamlbing ads, I have decided to remove all ads from season 12.

If you'd like to support the show you can do so on Patreon or PayPal.

https://www.patreon.com/tapesfromthedarkside/

https://www.tapesfromthedarkside.com/paypal

I'll keep you updated as I continue to lobby Spreaker / Vox Media for a common sense option to disable gamlbing ads without paying their exorbitant (borderline extortionate) monthly fee.

Patreon
https://www.patreon.com/tapesfromthedarkside

Merch
https://merchfromthedarkside.com/

Leave us a Review (...it really helps!)
https://www.tapesfromthedarkside.com/rate/

Paypal / Venmo Donations
https://www.tapesfromthedarkside.com/paypal/

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

S12, Chapter 4: The Machine

Listen On

Featured Episodes

Recent Episodes

Support On