Tales of a New Degenerate Gambler

I never believed I would be the type of person who would be selling myself into truly believing my Super Bowl bet was going to hit, because 

“They want it more”. 

Yet, here Dillon and I were telling ourselves an hour before the game that the Bucs walked with more swagger from the locker room. Naturally that means they are going to win and Tom Brady “wants it more”.

It’s sports bettor science.

Chapter 1: Origin Story

We’ll come back to Super Bowl talk, but gonna track back here about 4 weeks ago. When online sports betting became legal in Tennessee it instantly took off. While all my friends are conversing daily in our group texts about what bets they are making that night. I had to power through and only offer opinions and not make bets. 

I made a promise to myself that I would pay off a certain student loan before I would begin. Well, that happened the Friday of the NFL Divisional round. 

So, I went over to watch the Saturday games and to hang with cousins & my new little cousin (aka future wingman). Within the first 20 minutes I explained to my cousins, Jon and Ashlee, I started a DraftKings account. That is all the spark they needed, and next thing you know, it’s a family affair. We have all become Gambling Degenerates. 

We bet all throughout the games and had a blast doing it. We all won a decent little amount that first weekend. We were hooked. 

I have learned lessons the fun way and the hard way in this young journey of mine. I’ve started a new account and now partnered with Action 24/7 (promo code CTS 100). It’s been 4 weeks, and dadgum it if I’ve not already had late week night fist pumps watching Goran Dragic miss a free throw so the Pistons cover by 6. I have bet on games I would not normally watch. Mainly, I’ve followed and unfollowed my own rules multiple times.

  1. Life is too short to take the under. (This is dumb, I know, and hurts me a lot. But it sounds cool)
  2. Don’t bet on your own team. (The Vols break your heart)

Super Bowl

With this Super Bowl, it was a damned if you do, damned if you don’t situation. Honestly, all week I felt dumb if I bet against Brady, but also felt just as dumb if I bet against Patty Mahomes and the Chiefs. So buyers remorse was at full display for many of us newbie degenerates out there. 

It was so easy to be sucked into all the prop bets. I was astonished at how creating these scenarios in your mind was this easy:

  • Of course there will be a Fat Guy Touchdown. Tom and Patty love their O-linemen!
  • Over 2.5 players attempting a pass? DUH! It’s the Super Bowl. A trick play is inevitable!
  • Tails. Never. Fails.

All those wound up being wrong. 

We had a chance at the Fat Man TD, but a good defensive play ruined that one. No trick pass play was even attempted. And the domination of Tails in the coin flip was ruined. 

We had a small gathering of friends for the Super Bowl, but when that coin hit heads, you would have thought we had a rave and that the heads choosers just won $10K. In reality, we only had 6 people and the most someone got was like $30. 

But hey, Rule #32: Enjoy the little things. 

Now, I’m not trying to beef up the story here, but I had a free $50 bet and I wanted to put that on the 1st TD player. I honestly hovered over Gronk for like 20 minutes, but I was a pansy and went safe with Evans. The disappointment felt when Gronk caught the 1st TD, was a punch in the manhood. 

As is betting the Over/Under for the Super Bowl. It was a very similar feeling to betting Mahomes vs. Brady. You would feel dumb to bet the under, due to the potential of both offenses. On the other hand, taking the over is tough because you give 2 weeks to prepare and both defenses have times of being dominant especially Tampa Bay. 

Action 24/7: This is the site I was safe and probably smart on. I took a solid $50 on Tampa Money line and 15 on a Gronk TD. I did believe Gronk would get one, just had a few chances in the playoffs and it seems like it would be a nice story. Tom loves his boy, and he was getting Gronk a TD. 

DraftKings: I actually had a $25 parlay with a Tampa Moneyline win – Brooks Koepka win(which he did that Sunday) – and the over.

That would’ve been a nice win. But that dadgum Rule Number 1 got me…

Never Bet on Your Team

This is a tough rule to follow. It’s tough to follow, because you feel as if you know that team’s tendencies and how they play certain teams. But, you are wrong, very very wrong! 

Tennessee Vols fan here. If you’ve followed along, this year is a roller coaster. Personally, I feel confident in the talent of Tennessee, but have zero faith in the chemistry. This year in college basketball is very strange with the lack of an offseason. Teams that have multiple young talented underclassmen, have had a pretty hard time gelling. 

Where this led to in my week, I didn’t listen to Ron Slay and took a slightly altered spread for Tennessee to cover in a boosted parlay. Ron said Georgia would play them tough until the end, and by god they did. Tennessee was up 20 in the 2nd half and in the final few minutes let Georgia cut it to as little as 6. 

I lost on the last piece of a 5 gamer at about 10:00 pm. That one hurt, because I believed in my team. Once again, you never believe you are going to become the guy who gets mad at his own team winning. Here we are again upset, because they don’t win by enough….  

Always follow Rule #2. It’s for you sanity, folks. 

UFC, PGA, & NASCAR

Now here are some sports where I know a little bit, but in reality I shouldn’t be betting on frequently. But the online sports gambler’s life never stops and we need to dip our toes into new areas to see if we like it. Also, we are all suckers for those fancy new prop bets and big time odds with +2250 or better. 

Starting with the UFC. I did this one for all the Thicc Boys out there and trusted in Brendan Schaub. Schaub had a special on DraftKings that boosted odds for an Usman, Kelvin, & Rodolfo to win parlay.

That’s all I had. Just faith in one of my favorite podcasters in his UFC picks. This is a prime example of hindsight is 20/20. My man Schaub got 2 out of 3. Rodolfo had to go and ruin everything. When I look back on this bet right here, I think “You know very little about fighting… Why did you take this bet?” 

Now the PGA is different. I only went with 1 bet: Spieth to win. 

Jordan played well at the Waste Management the week before, and I really believed he was on a redemption tour and should be set to win with a relatively weak field at Pebble Beach.  

Jordan has a 2 stroke lead going into Sunday. I had the glass half full gambler’s feeling, where in your mind you think “I had a pretty bad Saturday, I’m due for a good Sunday”. Again, I know these are stupid thoughts. I’m learning….

Boy, did Jordan tank again on Sunday…. Just couldn’t find a great game he needed. 

That not so good luck Sunday continued with NASCAR. 

After the early wreck and delay, I knew the late finish probably wasn’t for me. Again, I know very little about NASCAR. I know names and who is decent. Knowing who is doing well at the moment and what car each person drives, not that knowledgeable. 

Again, betting on this was from some random articles and knowing my Grandma likes Chase Elliot. So went real slim on this one. 3 bets.

  • $5 on Chase Elliot to win
  • $5 on Denny Hamlin to Win
  • $5 on Denny Hamlin to finish top 3. 

Another Monday morning, with no good weekend wins. It was a humbling week for this degenerate. 

Thanks for reading. This is going to be a weekly bettor’s diary of sorts. We will have some fun with it. 

Happy gambling, friends!


If any of my Tennessee friends need a match of up to $100 and would like to help the pod. Head over to Action 24/7 and use code CTS100 and we’ll get you a match for your deposit of up to $100. 

If you are looking for a new bettors podcast too. Follow our guys on The Competition Problem. Ben and Mike are killing it lately!

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