On 11/13, I was hot. I was up $4,000 since 11/2 and my gambling account had over $5,000 in it. When I opened my DraftKings account, I wanted people to see how smart I was. Winning does that—it makes you want an audience.
On the 16th, I lost a $1,200 bet on the Chiefs against the Broncos, and the downturn started. Over the next 42 days (including that Chiefs game), I made 163 bets, went 14–149, and lost $4,820.
Last night, I finally hit a bet again. 100% Crown Club boost helped a bit.
When I woke up this morning, I checked the app to see how the game ended as I was asleep at half time. High-scoring. Good start. I scanned for Swift first. Then I saw Williams and Burden both had big games. Finally, I flipped to the San Fran side, fully expecting to see CMC with four touchdowns—and instead realized I’d somehow hit a long shot.
For the first time in 42 days, I woke up happy.
So what does this win actually mean to me, and what does it say about gambling psychology?
Let’s rewind to how the money gets there in the first place. I never believe I can beat the book. All I want is to bet comfortably, enjoy the experience, and not get my doors blown in. A 42-day downturn destroys any sense of “fun.” By the end of it, I expected to lose. I stopped enjoying the gambling thread because giving out a losing bet is a worse feeling than losing the bet on your own. Plus more betting and losing leads to a re-deposit which we know if the worst feeling in life.
That feeling—while not some existential crisis—still sucks. I don’t want to feel like a loser.
I’ve written before that it’s not about the money—it’s about not losing. I was down $6,000 on the 2025 season. I’ve had one winning season in the last seven years betting on sports. I’ve mostly quit casino gambling, limited app table games to $1 so I never play them, and I haven’t made a PGA bet since August. I don’t like thinking of myself as having a gambling addiction, but losing $4,000 in a little over a month is, by any honest definition, degenerate behavior.
“But it’s money you won.” That’s the slippery slope.
During that stretch, I was putting well over a grand in action every Sunday. By the end, I was barely getting past $250.
Last night’s winning bet was easily my largest payout—mainly because of the 100% Crown Club boost. That’s pure luck. These are the kinds of games where 80 total points get scored and a bunch of SGP legs magically hit. That’s also part of the problem: most of my bets are long shots. Why lose $500 on a single -110 bet in one night when I can spread $500 over a few weeks and try to get lucky?
The idea of gambling is that it’s supposed to be fun. Losing isn’t fun. In theory, if the money you’re gambling doesn’t affect your net worth, it shouldn’t affect your mood. In reality, it absolutely does. What’s amazing—and dangerous—is how quickly a single big win can flip that feeling completely around. Until the cycle starts again.
Is it worth it? I think so. If you don’t chase a high in life, why go through it at all? As JC would say, it’s a spice of life.
Dangerous words to a bank account.
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