Back when I was in college, a friend of mine won $2,500 on ESPN’s Streak for the Cash. That single event had the precise impact you’d think it would on a bunch of college kids:

“Messy won $2,500 playing for free, imagine how much we could win if we actually gamble!”

Of course we thought we knew more than Las Vegas. How could we not be smarter than the sports books? We were peak, goddamn Millennials and we LOVED to think we knew it all. Turns out we were extremely wrong.

Now, after a decade of growing up, marriage, and getting real jobs, we’ve mostly cooled on our aggressive gambling ways. Thankfully, Ted still let’s me write here at The Tailgate Society, and I’m going to start using this avenue to relieve the gambling itch that keeps circling around.

The best part of gambling is how much you start to care about games you would otherwise never pay attention to, root for teams and players that you would otherwise hate, and it’s a much more intense feeling than just simply being a fan. Everything in life is better with a little money on the line.

We all know how this works, right? I’m a curse. I will inevitably win a bunch of games, convince myself I should get back into gambling, and then go on an incredible losing streak when I start using real money. So, whatever happens, I accept no responsibility for money you win or lose betting these plays, and I strongly discourage any use of these plays in your real life. Live vicariously through this blog, then you can’t really lose.

The Bankroll: $5,000

The Arbitrary Rules: 10 picks ATS or O/U (Against the Spread or Over/Under), 5 picks SU (straight up), 1 teaser, 1 3-way parlay, 1 5-way parlay, 1 random ass futures bet

“Geez Tom, that’s a lot of picks.” Yeah, now you see why I had to quit.

The Source: Vegas Insiders (games 11/18/16 to 11/20/16)

The Picks:

• Against the Spread
  1. CFB: Washington State (+4,5) at Colorado ($110 to win $100)
  2. CFB: Ohio State at Michigan State (+22) ($110 to win $100)
  3. CFB: Texas at Kansas – Under 63 ($110 to win $100)
  4. CFB: Oklahoma State (+4.5) at TCU ($110 to win $100)
  5. NBA: Clippers (-7.5) at Kings ($110 to win $100)
  6. NBA: Nets at Thunder – Over 219 ($110 to win $100)
  7. NFL: Dolphins (-1.5) at Rams ($110 to win $100)
  8. NFL: Eagles (+6.5) at Seahawks ($110 to win $100)
  9. CBB: Clemson vs. Xavier (-3) ($110 to win $100)
  10. CBB: Siena at Kansas (-22) ($110 to win $100)
• Straight Up
  1. NHL: Red Wings at Capitals (-200) ($200 to win $100)
  2. NFL: Titans (+130) at Colts ($100 to win $130)
  3. NBA: Raptors at Nuggets (+140) ($100 to win $140)
  4. CFB: San Diego State at Wyoming (+330) ($100 to win $330)
  5. CFB: Oklahoma State (+170) at TCU ($100 to win $170)
• 6-point, 3-team Teaser
  1. NFL: Bears at Giants (-1.5), Bills (+9) at Bengals, Steelers (-2) at Browns ($100 to win $170)
     • Teaser rules: All 3 teams must cover spreads 6 points in their favor. For example, Giants were originally 7.5 point favorites and we’ve “teased” the line 6 points in our favor to 1.5 point favorites.
• 3-way Parlay
  1. NFL: Dolphins (-1.5) at Rams, Buccaneers (+7.5) at Chiefs, Jaguars (+6.5) at Lions ($100 to win $600)
• 5-way Parlay
  1. NFL: Titans (+130) at Colts, Bears at Giants (-330), Cardinals (+115) at Vikings, Jaguars at Lions (-270), Dolphins (-125) at Rams ($100 to win $1,500)
• Futures
  1. CFB: Ohio State to win National Championship (5/2) ($100 to win $250)

The Damage: 19 bets, $2,100 on the table, $4,390 in potential winnings

Reminder: Don’t actually play these bets. I’m a degenerate and I’m sure this column will be bankrupt in a few short weeks.