Entering a sportsbook can be tricky if you don’t have a betting plan. It was my first time entering a physical casino with a sportsbook included, and I thought I was the king. I entered with $100 as a bankroll and have read about people that go in and start feeling themselves until they get chewed up and spit out. I had followed and written about sports on a consistent basis for about two years at that point and figured I had acquired enough knowledge to leave with some money.

However, I left with $0 because I got greedy.

When you’re winning bets and cashing the tickets, it’s a feeling that is difficult to duplicate. I grew up a New York Yankees fan and growing up in the early 2000s as a sports fan, and I learned one thing: the Minnesota Twins cannot beat us. So I go up to the counter and place a $50 wager for the Yankees to cover the -1.5 run line against the Twins. It’s September 10, 2018, and the Yankees are in Minnesota, so I knew it would be a late-night watching the game, and it would be nail-biting.

The game enters the top of the seventh inning, and the Yankees are winning 1-0 against Kyle Gibson, so my ticket would be good as today’s trash if they cannot find a way to manufacture another run. The Yankees end up scoring six runs in the inning and winning the game 7-2! I sprint to the window and cash out my wager, getting -110 odds and walking out with an addition $45.45 from when I started. I was on Cloud 9 at that point.

Then I decided to try to continue, and for a while, I did. The west coast MLB games were still on, and instead of waiting three hours to determine my bet, I decided to go after over/unders for runs scored in each inning. Watching baseball is a daily occurrence, so I had a plan. Pinpoint games with bad lineups for the home team or a big-named starter to be on the road.

When the commercial break hits in between the middle of the inning, place a $10 bet on the under run total for that inning to hit. It was a foot-proof plan, and it paid off in dividends. Over the next few days, I managed to make $750 doing that with a few bumps and bruises along the way.

I was on fire, and the only way I was stopping was when they run out of money to pay me. My friends (who had been my sounding board) were tired, so they went back to the hotel, but I wasn’t done, and I was not tired. I had turned $100 to $750 in the blink of an eye.

Then it happened.

The television I see is the Arizona Diamondbacks vs Colorado Rockies. I know that Coors Field makes the ball fly, but I ran anyway and decided I was going to make a splash and put all $750 on the Arizona Diamondbacks to win here. I should’ve left with my friends.

Sports betting - Wikipedia

Entering a sportsbook can be tricky if you don’t have a betting plan.

Right-hander rookie Yoshihisa Hirano comes out of the bullpen in the bottom of the ninth for the save opportunity. He’s a 34-year old rookie who played in Japan for years before finding a way into the D-Backs bullpen. Arizona has a 4-3 lead, and all Hirano has to do is close the door and get three outs for the win. It’s the 9-1-2 batters in the lineup.

Gerardo Parra comes off the bench for the pitcher’s spot and singles the first pitch he sees, and now the tying run is on base. If he scores, then we go to extras, and that begins to drop my stomach. Top of the order with a runner on first and nobody out.

Center fielder Charlie Blackmon comes to the plate and has a sacrifice bunt to advance the runner to second base with only one out. Then, second baseman DJ LeMahieu comes to the box. He was 2-for-4 with a run scored in the game and has 14 home runs up to that point. He fouls the first pitch off and takes a splitter for a ball to even the count at 1-1. Then Hirano fires a 93 MPH four-seam fastball, and LeMahieu gets all of it.

I knew from the jump that right fielder Steven Souza Jr was going to be unable to catch the ball. The Rockies won 5-4, and instead of walking away with money, I lost it all on a single swing of a game I shouldn’t have placed a wager on. I get back to the hotel looking like I just dumped, and my friends realize what happened. I explain every painful detail to them, and it feels like a nightmare.

That’s where I learned for the first time in my life. Failing to prepare is preparing to fail. I didn’t think about the Rockies scoring; I thought about the ticket cashing once again. Every bettor has a story like this and probably lost a lot more money than I did.

However, the pain is the same. Winning feels great but losing hurts, and I became every guy that thinks he knows more than the bookies. If you are a bettor and don’t have a plan, you’re essentially asking to lose, and that’s my story.