(Quick note: I did an AMA on Reddit recently. You can find that here. All of my plays since 9/22 are documented here, which is when the $300 run started. For convenience sake, I combine bets of multiple odds on a various game into one bet. For example, I bet a lot on the Patriots to win and the odds would change, but my confidence in the pick didn't waver. I figured it would be tedious to document every time I bet on one game. If you want proof of certain bets, I can provide a picture.)
Hunter S. Thompson once said, “There are many harsh lessons to be learned from the gambling experience, but the harshest one of all is the difference between having fun and being smart.”
It was late on September 21st going into the early hours of September 22nd. I deposited $300 of the last $600 I had into my sports betting account. I sat there and thought two things to myself.
One thought was: “Why can’t I stop myself? I just lost. Why am I doing this again?”
“My strategy works. I know it. I just got unlucky.”
So it goes with gambling.
But after betting on over 200 games in the last month, I’ve won over $100,000.
I can’t remember exactly when I started gambling. In the past, it had always been about fun. You put down $20 and pray for a win. If it’s a close game, the nerves build up and you start shaking and talking to whatever god you believe in. In the moment, you’re sincerely saying that you’ll start praying again or you’ll do whatever the god pleases if your side wins.
When you lose, your day is ruined. When you win, it’s orgasmic.
But for me, it wasn’t until July of this year that it turned into something else entirely.
My strategy was simple: I bet as much as I had in my online bankroll on things that had a high likelihood of happening. Rarely playing spreads, I mainly played money lines (or teams to win straight up).
I was mostly betting on live action. Whenever a team or side was already up by a significant margin, I’d bet a lot to win very little. Other times, I’d play before the game started. It all depended on when the right value would present itself.
For example, the Patriots were playing at home against the Jaguars in week 3 of the 2015 NFL season. The money line was -1050 ($1050 to win $100) and I still thought this a great deal. I bet $9592.52 to win $913.57 knowing the value would never come close to -1050. It would take the Jaguars being up by two touchdowns. At that point, the Patriots would get something close to even odds of $100 to win $100, and I would bet on them to win anyway.
I know what you’re thinking: “Wow, you are crazy. That’s a lot of money.”
My counterargument: “In what world do you think the Jaguars could have possibly won that game?”
I call this a life savings bet. I’d put everything I own on the Patriots winning because there was just no way a team led by Tom Brady would lose at home to Jacksonville. Going into this matchup, New England was 91-15 all time in Brady’s home starts. Even if Tom Brady got hurt and Jimmy Garoppolo came in, I still would have picked the Patriots.
The idea behind this strategy was not to hit a grand slam, but to win a little and let that amount continue to build over time.
I liken it to the offensive style of the 2014 and 2015 Kansas City Royals, who hit singles left and right and win games that way. I find it very fitting that I used some of the money I won to buy tickets to Game 5 of the World Series, the game in which they beat the Mets to become champions. Though their playing style isn’t flashy or easy to root for, it’s methodical and it works.
I won and lost games that had a significant impact on my bankroll, but the triumphs and rock bottoms helped my maturity as a gambler. Since many of my bets are to win small amounts, these aren’t as exciting as the ones where I won thousands of dollars in one sitting.
• • •
I want to point out that, even with success, I still admit that I had/have a gambling addiction. I say had because at least now I can stop and assess when I do and don’t want to play.
During the run, I was going nonstop for three weeks. I woke up and bet on my way to work. I got home and started betting again, continuing until midnight or later. I would do this every day. I bet a few times at work and vowed never to do it again because it clearly impacted how I was performing, even if that bet happened during lunch.
Everyone who knew about this thought I had a problem and showed concern for me.
What I did was incredibly lucky. I could have lost it all and therein dug myself into a massive financial hole. I could have kept lying to people around me and kept being dishonest about how much I’d win or lose. I could have seriously jeopardized my finances for the upcoming months and years of my life.
If you are playing for fun with money you can afford to lose, that’s fine. If you are playing because you want to work towards a financial goal, stop immediately. For yourself and everyone around you.
It’s easier for me to say that now, but trust me, it’s not worth it. I want you to understand that I’m not sharing a get-rich-quick strategy; I’m simply sharing my story.
• • •
With that being said, let’s start with the five worst losses, shall we?
5) When I learned to manage my bankroll - Real Madrid vs. Málaga - lost $5,560
Relative to the other losses, this may seem small, but I will never forget this one. This bet came early on in my run and I’d just eclipsed $13,000 in winnings. I was brimming with confidence. After doing some research, I had a ton of faith in Real Madrid to beat Málaga at their home stadium, Santiago Bernabeu. The past record and matchups all pointed to Real Madrid getting 3 points. In that game, Málaga got a red card and was down to 10 men. Real Madrid dominated the possession 69.3% to Málaga’s 30.7%, and Cristiano Ronaldo was very aggressive with 14 shots.
Yet, only two were on target. That sums up the kind of day it was. Real Madrid ended up drawing Málaga 0-0.
I really thought about putting my entire bankroll on this game. I put $5,560 on Real Madrid to win straight up, and then the rest on them to win or draw. Since it was a draw, I got a push and my money back. This is the exact moment I realized my strategy wasn’t foolproof and that I could lose at any given time. I started playing a little bit more cautiously.
4) When I lost because I didn’t do my research - Northwestern +8/+9.5 at Michigan - lost $11,226
For those who don’t understand spreads, Northwestern +8 means Northwestern has to lose by less than 7 or win for me to win my bet. If they lose by exactly 8, I get my money back. If they lose by 9 or more, then I lose my bet. On the other hand, Michigan -8 means that Michigan has to win by 9 or more for me to win that bet.
Michigan’s defense was stout. In their opening game, they gave up 24 points on the road at Utah. In their next five games, they gave up 14 points total.
Michigan took the opening kickoff back to the house, and the game was pretty much over after that. Northwestern lost all their energy and the Big House was electric. Northwestern failed to get anything going on offense and the Wolverines proceeded to run train on the supposedly great Wildcat defense. It was never close. Michigan won 38-0.
I still don’t know how I convinced myself into thinking Northwestern was a lock. Jim Harbaugh is one of my favorite coaches. I don’t know how I went against him either.
3) When unpredictable things happen because it’s still sports - Georgia at Tennessee - lost $16,500
I picked Georgia to beat Tennessee straight up. I thought the Georgia -3 line was an overreaction to the beatdown the Bulldogs suffered against Alabama the previous week. I felt extremely confident, especially with having Heisman-hopeful running back Nick Chubb on my side.
Alas, on the first play from scrimmage, Nick Chubb suffered a season-ending injury.
Georgia still kept it close and had the lead at halftime, but Tennessee had all the momentum and went on to win 38-31.
2) When I let my emotions get the best of me - Cibulkova vs. Suarez Navarro - lost $26,003.49
Dominika Cibulkova is one of my favorite women’s tennis players. Although she has fallen out of the top ten since getting injured, Cibulkova is still really fun to watch. She is a very aggressive offensive player. Even when Domi is down, it always feels like she’s in control of the match and the result is dependent on whether or not she limits her unforced errors. That she is very attractive is a bonus.
Cibulkova hadn’t lost to Suarez Navarro in their three matches, so I was fairly confident.
Domi was up 3-0 in the first set and went on to lose the first set 6-4. Even though she lost the first set, my personal bias led me to think she’d come back and win the match. I bet again on her to win the second set.
She lost that set 7-5 and the match 2-0.
It’s really easy to get caught up into picking someone to win because you think they’re a great athlete; however, you can’t let that affect how you play or how much you bet on one game. You never know when they’ll have a bad day or match up poorly against someone. For example...
1) When I learned to minimize impulsion - Federer vs. Ramos-Vinolas - lost $39,800
Before this game, I lost nearly $8,000 on the Chargers because Steelers head coach Mike Tomlin decided to go for it from the one-yard line with five seconds left on the clock when they were down 3. Le’Veon Bell ran from the wildcat and punched it into the end zone to give Pittsburgh the win.
Right after the loss, I looked at potential tennis matches in the morning. Roger Federer versus Albert Ramos-Vinolas was it. I set my alarm for early in the morning.
My alarm goes off at 6 a.m. and I saw Federer was in first set tiebreak. I bet $3,125 and stood to gain $500 if he won the first set.
I woke up to watch the tiebreak and saw Federer lose.
“He may have lost the first one, but there’s absolutely no way he loses the second set.”
I immediately bet $3,570 to potentially gain $500 on Federer winning the second set. I decided that I could go back to sleep, wake up at 7:30 a.m., get ready for work and catch the third set.
Federer wins the second set with ease.
“OK, Roger may not be playing his best game but he’s got the momentum and he’s much better than Ramos-Vinolas. I mean, Ramos-Vinolas has never won a set against a top-10 player in ATP play.”
I pounded the third set line. I make bet after bet on Federer to win the set. I was ready to make a life savings bet. When I get down to a little under $47,000, I stop myself.
“You’ve made it too far. Remember what you told yourself when you got to $45,000: this is what you’re taking out no matter what. That’s doubling your salary for the year. That pays off every cent of loans you have. That money will set you free.”
I adhered to the thoughts of the angel on my shoulder and didn’t play anything else. $39,800 was enough.
The third set was hold after hold after hold until Ramos-Vinolas is up 4-3. Federer goes down 40-15, then 40-30, and then the unspeakable happened: ATP #70 broke arguably the greatest tennis player ever. 5-3. Roger’s opponent was not ATP #1 Novak Djokovic, but on that day he might as well have been.
I considered taking a taxi from 181st to Union Square just to watch the rest of the game on my phone.
“I can’t. It would cost too much and take much longer than the train. I’d be late to work.”
I get in the subway.
The next 30 minutes had me doing a lot of thinking.
Please, Roger, I need this.
If he loses, maybe this is a good time to stop.
But he won’t. What if he broke back, tied it up and then took it to tiebreak? Just accept your fate. You watched as he was outmatched in the third set.
There’s still hope.
Well, what are you going to do if he loses?
My mind went blank.
I got off at Union Square and my massive fear was realized: Federer had lost 6-3 in the third set to Ramos-Vinolas in one of the biggest upsets I’ve ever seen.
There are so many times during the run where I should have stopped and walked away. After this loss, I said I would take a break for a month. I didn’t bet for a few days, but then gave in to temptation. The way my strategy goes, there’s a huge favorite every day and it’s really easy to fall back.
I kept trudging along and experienced some of the greatest gambling wins of my life.
5) When I took advantage of a line - Royals/Mets game 3 over 6.5 - Wagered $5,500, won $5,000
Sports betting is all about playing lines that you think are way off and trying to profit from them. I had a few thoughts behind this one in particular.
First, if you watched the 2015 MLB postseason at all, the over on run totals was successful at a pretty frequent rate.
Second, a total of 6.5 is really low. This means both teams have to score a combined six runs or less for the under to hit, or seven runs or more for the over to hit. An average MLB game gets a run total set at seven or eight. The only games that should be getting a line of 6.5 are ones with pitchers like Clayton Kershaw, Zack Greinke, Jake Arrieta, and other Cy Young Award candidates. These pitchers hold their opponents to low run totals and at that point you are betting on whether their own team can score the rest of the runs (i.e. if Jake Arrieta shuts out the Dodgers, can the Cubs score seven runs? If yes, play the over. If no, play the under.). Most Padres home games get a total under seven as well because their ballpark is built in such a way that helps pitchers.
Noah Syndergaard and Yordano Ventura are good, but they’re not Cy Young candidates and they were not pitching in San Diego that night.
Syndergaard was pitching at home against Ventura, which is where Noah gets his best stats. Ventura’s ERA wasn’t exactly the best. Also, since Noah Syndergaard is a fastball pitcher, the Royals were going to feast. According to Grantland’s (RIP) Ben Lindbergh, the Royals had a .292 weighted on base average against power/fastball pitchers in 2015. On top of these things, you never know when the Royals are going to string together a series of hits and blow the game open.
I was at a Gary Clark Jr. concert that night and remember the over bet winning by the end of the third inning. I immediately bought a round of drinks for my friends. It was 4-3 Mets and New York went on to win their only game of the World Series, 9-3.
4) When I was on the right side of the wrong call - Seahawks vs. Lions - Wagered $25,609.26, won $5121.80
If you’re an NFL fan, you’ve seen this highlight enough times to where I don’t need to talk about it. If not, you can watch it here.
My heart was furiously pounding on the Lions’ last drive. When quarterback Matthew Stafford threw the ball to star wideout Calvin Johnson in the red zone, my heart completely sank and I thought I was about to lose close to $26,000.
Until Seattle strong safety Kam Chancellor punched the ball out of Calvin Johnson’s hands at the Seahawks’ one-yard line.
My immediate reaction?
The ensuing debacle over the touchback that resulted was hilarious. No one knew what the right call was should have been until after the game. I didn’t care that the Seahawks got away with yet another officiating mishap on Monday Night Football. All I cared about was that I had just dodged a huge bullet and won more than $5,000. I must have watched that night’s episode of SportsCenter three or four times.
Another time I was on the right side of a poor judgment by a referee happened when Memphis played Cincinnati on a Thursday night NCAA football game. Words don’t do that call justice. You can watch it on YouTube here.
3) When betting on the favorite worked out in my favor - Broncos at Browns - Wagered $28764.92, won $16920.54
I consider this one of the luckiest wins I’ll ever have in my life.
The Browns were home underdogs and took the Broncos to overtime. Peyton Manning was abysmal all game except for one deep touchdown pass to Emmanuel Sanders.
You know who was worse than Peyton Manning?
Josh McCown, the Browns’ quarterback.
After Manning threw an interception to Cleveland linebacker Barkevious Mingo in Broncos territory on the first drive of overtime, the Browns only had to run the ball three times, kick a field goal, and the game would be over.
On first down, they ran the ball and lost yards. The Browns still had hope with the ball at the Broncos 42-yard line.
On second down, McCown was sacked by the best defense in the league for a loss of eight yards. The Browns possessed the ball at midfield, and it was 3rd and 21 to go.
On third down, McCown got sacked AGAIN for a loss of two!
The Broncos got the ball back and Manning led Denver on a 13-play, 72-yard drive to set up a field goal attempt by Brandon McManus. He nailed it and Denver left Cleveland with a win, 26-23.
I really think I only won this because Denver’s defense is so good and Peyton can still channel his amazing regular-season self when it matters.
2) When I rode the hot streaks - Various bets on Jake Arrieta, Patriots, and Packers - Wagered a lot, won a lot
I bet on Jake Arrieta every time he took the mound after his no-hitter on the road against the Dodgers on August 30th. Until he faced the Mets in the postseason, that is — I didn’t want the bet to take away from my experience attending the game in person. I would mainly make first five-inning bets (equivalent to first half in basketball and football) because I wasn’t as confident in the Chicago bullpen to pitch anywhere near as masterfully as Arrieta did. I would also risk another bet on the Cubs F5 -0.5 (to lead by more than a run by the end of five innings) because I knew he wouldn’t give up a run and that it was just on the Cubs offense to put up something on the board.
I’ve also bet on the Packers and Patriots almost every game they’ve played this season. Every time they play at home, I play them. The stats are so heavily in favor of Aaron Rodgers and Tom Brady at home that it’s essentially free money being given away. Rodgers is 46-10 at home all time and, as previously mentioned earlier in the piece, Brady is 91-15 at home in his career.
I ride these trends until they don’t happen anymore, like when the Packers inexplicably lost at home against the Lions in week 10. At that point I’ll lose a lot, but until then, I feel fine seeing it to the end.
“If it’s been lucrative for me so far, why stop?”
1) The best win of my life bar none - Spurs 1Q ML at Wizards- Wagered $12,120, won $8,000
I was pretty hesitant to play this since Washington is my favorite NBA team. I know they always play really well in the first quarter, slump in the second and third, and then finish out strong in the fourth.
I trusted the Spurs’ dominant 1Q trend anyway.
The game got off to a really rough start. The Wizards took a 7-0 lead 1:26 into the game on a Bradley Beal three-pointer. Spurs Coach Gregg Popovich immediately saw things getting out of control early and called a timeout.
A couple of plays later, Tony Parker drew a foul and made two free throws. 7-2 Wizards.
Then began the worst sequence of basketball I’ve ever seen the Spurs play. Danny Green missed a three, Kawhi Leonard missed a three, Tim Duncan fouled Otto Porter Jr., Tony Parker missed a shot, Danny Green missed another three, and Kawhi Leonard missed another shot.
During this time, the Wizards kept scoring. The score was 19-2 Wizards with 7:09 left in the 1st quarter.
All of those feelings came out. That feeling of losing a lot of money. Of convincing yourself that it’s alright to keep playing. Of secretly sinking into an incurable depression for the night and the next morning. At least until you win another bet.
I continued to hope.
“There’s seven minutes left in the quarter. There’s typically three possessions per minute. That means there’s a total of 21 possessions left. The Spurs get 11, the Wizards get 10. This can still happen.”
With 11 possessions, if all went well, the Spurs could score around 22 more points if they turned it around. This would also require the Wizards to miss every shot they took.
The next seven minutes are something I’ll never forget.
Leonard made a shot, Kris Humphries of the Wizards missed a three, Duncan grabbed a rebound, Parker made a jumper, Humphries missed another three, Duncan got another rebound, LaMarcus Aldridge dunked the ball, and Tony Parker committed a foul.
“19-8. 5:27 left in the quarter. About 16-17 possessions left in the quarter. Nine for Washington, eight for San Antonio.”
At this point, the bench units started to come in. I had more faith in the Spurs bench unit than in the Wizards unit. Kawhi, Aldridge, Boris Diaw, Manu Ginobili and Patty Mills are going up against Beal, Ramon Sessions, Nene, Gary Neal, and Drew Gooden.
“Here we go.”
A minute goes by and no points are scored. Every missed shot from here on out stung a little more than it did at the beginning of the quarter. Until…
Leonard fadeaway shot, Beal missed three, Aldridge pass to Kawhi for three, Wizards timeout.
“19-13 with 3:51 left in the quarter. Six possessions for the Wizards, six for the Spurs. This. Can. Happen.”
With 2:35 left in the first quarter, Beal hit a three and put the Wizards up 22-15. Things looked bleak.
Danny Green missed a shot, Aldridge got the rebound and put it back in. 22-17 with 2:23 to go.
“There’s still an outside chance.”
The next minute, there were a total of three turnovers by both teams. Spurs had the ball. 22-17 with 1:24 to go.
Ginobili finger roll layup, Sessions missed shot, Kyle Anderson step back jumper, Nene missed shot, and Ginobili rebound.
“My heart is not moving. I can’t hear it. I don’t feel it. I can barely feel anything. There’s no noise and everything around me is quiet. This is it. 22-21. Spurs have the last possession. I need a bucket. Please, Spurs.”
Ginobili brought the ball past halfcourt and drained the clock. As he started to make a move, Beal fouled him because the Wizards had a foul to give. Six seconds on the clock.
If there were ever a time where my life slowed down and a moment felt like eternity, this was it.
Ginobili went to the inbounder and Kyle Anderson decided not to pass to him. Diaw came up from the free throw line and received the inbounds pass. He looked to pass back to a potentially driving Ginobili, decided against it and instead passed it back to Anderson. Diaw set a pick, Anderson went around it and was right around the free throw line when he ran into Drew Gooden. Anderson threw up a pump fake, Gooden bit and jumped to block the shot, Anderson put his body into him and drew the shooting foul.
“OH MY GOD OH MY GOD OH MY GOD OH MY GOD OH MY GOD OH MY GOD OH MY GOD OH MY GOOOOOOOOOOOOOOOOOOODDDDDDDD.”
Kyle Anderson was at the free throw line for San Antonio down 22-21 with one second left in the first quarter.
“Just make the first one. Just make the first one. Just make the first one. Just make the first one.”
I was frozen.
Kyle Anderson made the first one.
“Okay, at least I get my money back, but it would be so much nicer if he could make this shot.”
And he did.
Wizards turned the ball over to end the quarter. Spurs completed the comeback all the way from being down 19-2. They went on a 21-3 run to end the quarter. 23-22.
It was the best bet I’ve ever won. Per ESPN Stats & Info, the Spurs became the first team in the last 20 seasons to trail by at least 17 in the first quarter and have the lead entering the second quarter.
What made the win even sweeter was that the Wizards eventually went on to win the game 102-99 on a Bradley Beal three.
• • •
A lot of people ask me why I’m still working a full-time job after this run.
I always tell them the same answer: insurance and retirement.
Really though, it’s due to the stability, the sense that I’m growing my network, and the feeling that I’m helping a community. You don’t get that with gambling. It’s very reclusive. It’s also because being a teacher doesn’t require much luck at all.
I’d like to think that there is a lot of skill required to bet on sports. It’s not just that I picked winners with high money lines. I have watched so many games over my lifetime that I have acquired a lot of knowledge about different sports across the globe.
However, I don’t think what I did required much skill. There are people like Haralabos Voulgaris who, on top of their incredible knowledge of the game, have made systems for just one sport like basketball. Voulgaris’s in-season work ethic is incredible and what he does is truly a skill.
For me, I’m still going off hunches and gut instincts with what seem like high-probability plays.
I’m guessing I failed 15-20 times before I crossed the $10,000 line, and I definitely could have failed many times after that as well. In fact, I’ve lost between $20,000-40,000 on a few occasions. It happens. At the end of the day, sports are random. There’s no real system that can consistently win sports bets. Even the best bettors with their computerized systems are happy if they hit 60 percent or higher.
So did I get lucky?