Stories behind the biggest bets

Akillies · Nov 7, 2014

[h=3]Nov 6, 2014, 7:45 PM ET[/h][h=1]Stories behind the biggest bets[/h]<figure class="article-figure"><source>

Holly Stein /Allsport</figure> A compilation of lighthearted, big-bet tales from the gamblers who placed them and the bookmakers who accepted them:

The race back to the sports book began shortly after Buster Douglas took his shirt off.
It was October 1990. Eight months prior, Douglas had stunned Mike Tyson as a 42-1 underdog, and he was now preparing for his first title defense against Evander Holyfield. A ballroom at the Mirage casino in Las Vegas was packed for the weigh-in. Mirage sports book director Jimmy Vaccaro was in attendance and immediately knew he had a problem.
"Holyfield gets on the scale and is svelte, weighs in at like 210 [pounds]," Vaccaro said. "Buster gets on the scale and is like 246. They made him do it again, to make sure it was right, because it was the first time anybody had seen him without his sweat top on. When he took that off, he was the Pillsbury Doughboy."
Vaccaro hung out for a few minutes to listen to the reaction, then hustled back through the back halls of the casino to get back to the book. He knew he was in a race.
"I knew that guys were going to run over to the sports book to bet Holyfield," Vaccaro said. "I was thinking that I'd adjust the price 30 cents, because he was so fat. But before I could get there, we had taken a half-a-million bet on Holyfield. They beat me fair and square."
Holyfield knocked out Douglas in the third round, capping one of the more entertaining bets of Vaccaro's 30-year Vegas career. But it's not close to the biggest he's ever taken.
In 1995, Vaccaro accepted a $2.4 million money line bet from billionaire investor Carl Icahn on Super Bowl XXIX between the heavily favored San Francisco 49ers and San Diego Chargers. Icahn laid 1-8 odds that the 49ers would win straight up and won $300,000 when San Francisco rolled to a 49-26 victory.

Akillies · Nov 7, 2014

Six-figure miscommunication
The biggest bet of Alan "Boston" Dvorkis' gambling career was a complete accident -- a $150,000 accident.
It was a Saturday night in January 1999, the prime of Boston's college basketball betting career. The Arizona Cardinals had just upset the Dallas Cowboys in an NFC wild-card game and were installed as 14.5-point underdogs to the Minnesota Vikings. Boston picked up the phone, called a fellow who moved his action for him and asked to get $15,000 on the Vikings.
Minutes later, the mover called back and told Boston he had $150,000 on Minnesota minus-14.5. There had been some miscommunication.
"I got what?" Boston replied.
Unable to get out of the only six-figure wager of his life, Boston tried to lay some of it off, but had little luck and ultimately said "f--- it" and gambled. "It was the biggest bet I ever made and probably the biggest bet I ever will make," said Boston, a longtime professional sports bettor and poker player, whose normal bet size at the time was $15,000. "I don't even watch the NFL."
Minnesota went on to win and cover the spread on a Leroy Hoard touchdown with five minutes to play in a 41-21 victory. Boston celebrated by "Doing my college basketball work."

Akillies · Nov 7, 2014

$50,000 coin flip
The bettor just wanted to get it over with.
It was Super Bowl Sunday 2010 at the Las Vegas Hilton SuperBook. Just two hours before the Indianapolis Colts and New Orleans Saints kicked off, an older gentleman from California strolled up the window and asked for a $50,000 bet on the coin flip. Normally, the SuperBook accepts a limit of $2,000 on prop bets like the coin flip. "I didn't think he had any analytics that were favoring one side or the other," said SuperBook chief Jay Kornegay with a chuckle. "I remember him saying that he just wanted to get it over with. So we just said, 'Yeah, go ahead.'"
The bettor took heads and won. Kornegay turned to his colleagues and said, "There we go. We haven't even kicked off yet, and we're down $50,000."

Akillies · Nov 7, 2014

'I had lost the biggest bet of my life'
It was March 20, 1987. Professional bettor Alan Denkenson was having dinner at the Sporting Club in New York City.
It would be a sweaty meal.
Denkenson had been hot and was riding a win streak into the biggest bet of his life, a $25,000 wager on the Toronto Maple Leafs plus-1/2 goal versus the Quebec Nordiques.
The $25,000 bet was spread around to different sports books, some offshore, some in Vegas. He normally bet around $15,000 per game, but was pushing his hot streak.
At the time, NHL ties were common. There was only a five-minute overtime with no shootout. Betting teams plus-1/2 goal had been a successful strategy.
"It was different back then," Denkenson said. "The lines were bad and I was riding this streak. I just really liked that game. I have no idea why. It's going on 30 years ago. It wasn't much better than any of the other bets, except that it was as the end of a pretty good winning streak."
Between bites, he kept an eye on the ticker that was scrolling scores along the wall of the restaurant. With around a minute left, the Maple Leafs led 4-3.
"I looked up again and saw the three change to a four, which put the game into overtime," Denkenson recalled. "I had to sweat out overtime, staring at the ticker. I saw a four change to a five and I had lost the biggest bet of my life."
He took it well.
"It was settled the way we settled back then," Denkenson said. "I got my weekly figure. There were lots of other bets and met up with my agent. There was always an agent or runner for each bookmaker or you'd do a transfer from book to book. It was never a hassle back then. It was wide open. It was a different lifestyle."

Soriano12 · Nov 7, 2014

http://www.toptenz.net/top-10-craziest-bets.php

Akillies · Nov 7, 2014

A dirty look from Ali's wife
The rumor was bogus: Larry Holmes wasn't going to throw his 1980 title fight versus Muhammad Ali at Caesars Palace. Per usual, Vegas high-roller Lem Banker was in the know.
The son of a New Jersey candy store bookmaker, Banker arrived in Las Vegas in the mid-1950s. By the time Holmes and Ali were preparing to square off, Banker was one of the biggest sports bettors in town. He had a network of runners and bookmakers. People from all over the country fed him information from East Coast newspapers. His information on the Holmes-Ali fight, however, was from a local source.
Banker's daughter was working for a boutique inside Caesars Palace and would often glance in at the boxers' workouts for her dad. While watching Holmes, Banker's daughter overheard the champ mention that a rumor of him throwing the fight wasn't true and, as the undefeated heavyweight champion, he wasn't going to let that happen. Banker got the news and began spreading out $250,000 in bets on Holmes at Vegas sports books and private bookmakers.
"I remember the comedian Gabe Kaplan was behind me in line at Caesars," Banker, now 87, said. "I told him that Holmes may be the best bet in the last 10 years."
Banker had a ring-side seat for the fight. Miss America Phyllis George and John Y. Brown, governor of Kentucky, were among the celebrities seated near Banker.
"I remember John Y. Brown asked me who I liked. I said 'Holmes,'" Banker recalled. "I looked over and got this dirty look from a beautiful black woman. It was Veronica, Ali's wife. I smiled and said, 'No, I love Ali.'" Holmes beat Ali on a referee technical decision in the 10th round. Banker, 87, says he still bets on sports.

Akillies · Nov 7, 2014

A $286,000 sweat
Seventeen years later, Michael Konik still remembers the feeling. It was sickening.
It was Super Bowl Sunday 1998 at Caesars Palace in Las Vegas. Konik, a freelance writer from California, had just bet $286,000 on Super Bowl XXXII between the Green Bay Packers and the underdog Denver Broncos. Konik bet $220,000 on the Broncos plus-12 and $66,000 on under 49.5 points at Caesars Palace. It was the biggest bet of his two-year career working for the most powerful man in sports betting, "Big Daddy" Rick Matthews.
The game couldn't have gotten off to a worse start for the nervous Konik. Brett Favre led the Packers to an easy touchdown on their opening drive.
"They moved down the field like Denver had a high school defense," Konik, author of the sports betting great "The Smart Money," said during a recent phone conversation. "It was a sickening feeling."
But John Elway and the Broncos answered on their first possession and never trailed the rest of the game en route to a 31-24 upset. It was too many points for Konik's under bet, but the big bet on Denver plus-12 was an easy winner.
Konik watched the game from his Caesars Palace room and returned to the sports book to pick up his winnings later that night. The bettors had won, but the bookmakers had kept their sense of humor. "Nobody likes to hear a bookie whine, Mike," a Caesars Palace book manager told him. "Nobody cares, including the bookie's mother. Because sometimes she bet the other side." He'd need to settle up with Big Daddy Matthews later, but that's a tale you can read more about in "The Smart Mon

Enfuego · Nov 7, 2014

How much was Shrink's fatal Duke/Butler game bet?

Akillies · Nov 7, 2014

Shot girl takes her shot
Sometimes an $800 bet means so much more.
It was June 1994. Beth Raymer was a shot girl at a Florida bar. After a week hustling up $800, it was time to gamble.
Raymer headed to the Palm Beach Kennel Club, where a greyhound named Pat C. Rendezvous was going for a record 33rd consecutive win on a damp June day. The lead-out dog handlers were decked out in tuxedos. The theme from "Rocky" blared from over the loudspeakers.
Raymer bet $800 on the heavily favored Pat C. Rendezvous to win.
"Losing that much money would've been murderous for me at that point in my life," Raymer, the author of "Lay the Favorite: A Memoir of Gambling," recalled. "But I didn't think for a second I would lose."
Raymer was right. Pat C. Rendezvous broke from box No. 3, took command early and pulled away from the field. "She just ran so fast, open on that super slick track," Raymer, who is working on her second book, added. "After that day, I had more confidence as a bettor."

Akillies · Nov 7, 2014

Biggest bet I ever took ...
"The biggest single bet I took was on hockey, believe it or not. We used to have a huge player at the Rio. There was nothing going on that night, except a couple of hockey games. He wagered $250,000 on the [Carolina] Hurricanes. He used to love to wager on big favorites, and the Hurricanes were minus-250 that night. They ended up losing the game in a shootout." -- David Pemberton, director of specialty games at Caesars Entertainment.
"The company [MGM] took a $7.6 million bet prior to me on the Rams' money line, when the Patriots beat them [in Super Bowl XXXVI]. The biggest bet I ever took was a loser. I took $2 million on the Colts in the Super Bowl against the Bears. It was my first year here. There was a powwow for sure, but we were more than happy to take it. It definitely gets your attention, but in the scope of things, we weren't going to be hung out on the game. Now, if I would have taken that on an average Sunday, we're going to have a heck of a decision. But with the Super Bowl, you can shade that pretty easy." -- MGM vice president of race and sports Jay Rood.
"I took a million-dollar bet on the Super Bowl once. It was on the Eagles against the Patriots. He bet $1.05 million to win a million. Winner. He was a really nice guy and a great customer, but I sure didn't want to lose that bet." -- Chris Andrews, veteran Vegas bookmaker, who has worked at multiple Nevada sports books during his 30-plus-year career.

MotorMouth · Nov 7, 2014

Akillies said:
Shot girl takes her shot
Sometimes an $800 bet means so much more.
It was June 1994. Beth Raymer was a shot girl at a Florida bar. After a week hustling up $800, it was time to gamble.
Raymer headed to the Palm Beach Kennel Club, where a greyhound named Pat C. Rendezvous was going for a record 33rd consecutive win on a damp June day. The lead-out dog handlers were decked out in tuxedos. The theme from "Rocky" blared from over the loudspeakers.
Raymer bet $800 on the heavily favored Pat C. Rendezvous to win.
"Losing that much money would've been murderous for me at that point in my life," Raymer, the author of "Lay the Favorite: A Memoir of Gambling," recalled. "But I didn't think for a second I would lose."
Raymer was right. Pat C. Rendezvous broke from box No. 3, took command early and pulled away from the field. "She just ran so fast, open on that super slick track," Raymer, who is working on her second book, added. "After that day, I had more confidence as a bettor."

Here are the payouts from that race.

It was a pretty cool event if anyone wants to watch it, the handlers were even wearing tuxedos

Akillies · Nov 7, 2014

Enfuego said:
How much was Shrink's fatal Duke/Butler game bet?

only he knows

Buckpasser · Nov 7, 2014

Bets $800 to win $40 on a dog race then writes a book about gambling. Sounds right to me.

Sportsguy_USA · Nov 7, 2014

Having worked directly with a few at B-dog in the day...
- Guy doubles down 21 or 24 time. Takes home over half a mill. online
- Women, wins a couple hundred thousand on online roulette. Beautiful luck right? Funny thing this was her second big win. She won big a few months back...then dissappeared from online. Comes back months later plays again,....whamo jackpot. B-dog did everything they could to scrutinize the win (as they would with any big winners) to find any indication of cheating...different IP's, odd digital behavior, backdoor holes, etc. Couldn't find a thing.

Got a few more from russian and eastern european DOS attacks and blackmail, to affiliate tricks and (21 year old living at home making +$30K a month), and more. Exciting days those were....

MotorMouth · Nov 8, 2014

Would love to hear about the affiliate biz, how they were paid , how they scammed,tricked the system etc..

Sportsguy_USA · Nov 10, 2014

Can you elaborate motor mouth? The 21 year old, not scams we caught, but good timing and positioning. Though there were a few tricks used by the affiliates...though elaborate first.

MotorMouth · Nov 10, 2014

Sportsguy_USA said:
Can you elaborate motor mouth? The 21 year old, not scams we caught, but good timing and positioning. Though there were a few tricks used by the affiliates...though elaborate first.

I was asking how much were affiliates paid, by signups, by percentage of losses, etc.
And how did they trick the books.

Hotpizza · Nov 11, 2014

Akillies said:
Shot girl takes her shot
Sometimes an $800 bet means so much more.
It was June 1994. Beth Raymer was a shot girl at a Florida bar. After a week hustling up $800, it was time to gamble.
Raymer headed to the Palm Beach Kennel Club, where a greyhound named Pat C. Rendezvous was going for a record 33rd consecutive win on a damp June day. The lead-out dog handlers were decked out in tuxedos. The theme from "Rocky" blared from over the loudspeakers.
Raymer bet $800 on the heavily favored Pat C. Rendezvous to win.
"Losing that much money would've been murderous for me at that point in my life," Raymer, the author of "Lay the Favorite: A Memoir of Gambling," recalled. "But I didn't think for a second I would lose."
Raymer was right. Pat C. Rendezvous broke from box No. 3, took command early and pulled away from the field. "She just ran so fast, open on that super slick track," Raymer, who is working on her second book, added. "After that day, I had more confidence as a bettor."

Chuckled when I read this, wondered how in the heck is this even a good gambling story. Dog wins pays $2.10 and she makes a whopping $40. Then someone posts the video and the prices, I laughed even harder.

I think the story would've been better if she lost. Go back to pouring shots.

MotorMouth · Nov 11, 2014

Hotpizza said:
Chuckled when I read this, wondered how in the heck is this even a good gambling story. Dog wins pays $2.10 and she makes a whopping $40. Then someone posts the video and the prices, I laughed even harder.

I think the story would've been better if she lost. Go back to pouring shots.

The "story" is what came after that win, that win changed her life,
the fact that the dog paid pennies on the dollar is irrelevant.

Read up on her, she has lived a very interesting life.