Pro Bettor James Holzhauer’s Key to Success

“Holzhauer has dominated “Jeopardy!” like no one else since the current version of the television game show had its premiere in 1984. He won again on the episode that aired Wednesday, pushing his total earnings above $1.1 million, second on the all-time list behind the legendary Ken Jennings.”

The NY Times interviewed Holzbauer in the spring of 2019, asking him several questions of how he was so successful on the popular show.

The big key to his success was going aggressive from the opening bell.  He would go right for the $1,000 questions, skipping the lower tier amounts.

As stated in the NY piece, you could make an analogy to sports betting or poker tournaments. There are big advantages to having a lot of chips early on in a poker tournament. Consequently, the bettor can make plays that other people can’t.

Would you describe the traditional way of playing “Jeopardy!” as overly risk-averse?

“I would definitely say it’s too risk-averse,” explained Holzbauer.  “The funny thing is, my strategy actually minimizes the risk of me losing a game. There’s times in a football game where a team goes for a big TD pass. If you don’t take a risk like that, you’re not going to win. Really, the big risk is never trying anything that looks like a big gamble.”

You can read the full Times interview of Holzhauer here.


The Hammer Crushes Them in Keeneland’s Grade One Gamble

Keeneland Grade One Gamble logoBy Rich Nilsen

Tommy “The Hammer” Massis scored his second major handicapping tournament victory last weekend when he took down the prestigious Grade One Gamble tournament at Keeneland Racecourse.  Topping 123 players with a huge $28,074 bankroll, Massis won an NHC berth, a $10,000 grand prize, and an entry into the lucrative Breeders’ Cup Betting Challenge, which was the main prize he was shooting for.

Massis defeated an all-star cast that included runner-up Paul Weizer, third place finisher Patrick Gianforte, fifth place finisher Dan Hartman, pro player Mike Maloney, among others.  We sat down with this professional horseplayer from Toronto, Canada to discuss his big win and his approach to handicapping.


AGOS: Tommy, how did you first get into horse racing and how long have you been playing the sport?

TM: Oh man, first time I went to the track was when Secretariat ran at Woodbine. I was like 10 years old, and I didn’t realize the significance until like 10 years later.   I was dragged there and I wanted to go home.  I remember my uncle saying, “Just one more race.”  He gave me two dollars to bet on a horse named Kennedy Road, the local star, who was named after a street in Canada.

About five to six years later I started going regularly with my uncle, my cousin, and the guys in the neighborhood, and I’ve been at it ever since.


AGOS: Tell us how you prepared for the high stakes tournament from a handicapping standpoint, and what some of your strategies were going into the day.

TM:  My strategy is that if I can find something to go all in on, that is my preferred strategy, but I don’t have a set one.  I don’t want to do what everyone else does, such as in the Breeder’s Cup Challenge where many players will just bet to “show” and then go all in on the last race.  I try to do the opposite of that.  In this case I found 3 horses that were playable for me on this day.  The greatest thing was that they [Keeneland] changed the rules so that if you didn’t play a race, you were no longer disqualified.  Instead you would be deducted 250 points from your bankroll.  So I was minus 500 because I didn’t play the first two races but I still had my original $2,000 to wager with.  I took advantage of that because I hate to bet show.  For example, if I miss the first race to show on a 1-5 shot, I’m done. I’m on tilt.

So my wager in the contest was $600 or so on the third race.  And that was it.  The contest was over [after my pick won].

The funny thing is that the winner of the last race would have been my “all in” horse.  He was the third horse [of the three] that I liked all day.

My whole goal for playing in this tournament was to get the BCBC spot.   I have no interest in the NHC.  I despise that tournament.


AGOS: Longshot Wilhelmina in race 3 was the key to your success on Sunday.  What got you on this 36-1 shot, and what wagers did you hit with her?

TM: I had $400 to win.  I only played one exacta, a $40 exacta box 6-7 and a $40 press 7-6.  I hit a $2 trifecta, and I got my worst result in the three hole. Most of my trifecta combinations were 6-ALL-7 and 7-ALL-6.  I would have won 3 times as much if they were split.

racehorse Wilhelmina

I would come up with that horse every time, no doubt about it.  I trip handicap and I saw a lot of speed in the race.  So, I looked closely at the off-the-pace horses.  I kept going back to her as the only real closer, and she looked horrible.  However, she could finish a race and come off the pace.  Then, I do what I do.  I looked at the replays.  Her last race was the first replay that I watched.  She got killed out of gate, made a move around the turn and then got killed again at the top of the stretch.  She finished strongly down the middle of the track for third and galloped out really well.  That was it for me.  I didn’t need to see any more.

Especially at Keeneland, I take a close look at the big morning line horses, e.g. 50-1, since most people will just quickly dismiss them.

I also love betting trainers and jockeys I have never heard of.


AGOS: You won the Woodbine Handicapping Challenge last summer which has a completely different format as a traditional $2 w/p structure.  Do you approach that kind of contest differently?

TM: Yes, 100% different.  The $2 w/p format doesn’t fit into the way I play every day at all.   It was a beautiful day and it’s my home track with a great setup, so I decided to play.  I am actually horrible at those contests.  I would have put the line on me at 1000-1 to win that tournament beforehand.

“Racing with Bruno” actually helped me win the Woodbine contest.   Half of my winners were from Woodbine, which I found myself, and the other three were from Bruno’s Saratoga sheet.  With his selections I read him just like anyone else, but as a clocker he is just unbelievably deadly.  That is, if you know how to read him as I do.

I read every track handicapper of every track that I play.  I read every word that they write because they may tell you one tidbit of information that maybe you didn’t know.  They could tell you something about the horse, any little bit of information, such as trouble, being on the wrong part of the track, etc.  The information is free (comes with the cost of the Form) so why not read it.

I really only have the capacity to play one track at a time with all of the work that I do.


AGOS: What information do you rely on in your daily handicapping, and what are the main points of emphasizing when dissecting a race?

TM:  First thing I do is watch replays a day or two after they’ve actually run.  Head-on’s are the most important to me, especially because most players don’t watch them or can’t get them.

I will go back and watch more replays to “fill in the blanks.”  I rarely bet Win.  I am more of a Pick-3 and Pick-4 player.

For me it is watching those replays, making notes, keeping track of biases.

I wasted a lot of time and money on the Sheets.  It’s really tricky, actually, to use them, and if you are just betting the lowest number [on the Sheets], you got no future.   The horses are way overbet.   It was just too much money, too much work, and not enough reward for me.

In a nutshell, I am a replay guy.  I also try to get around the takeout as much as possible.  I look at the Pick-3 and Pick-4, for example, as dividing the takeout by 3 or 4.

I focus on Woodbine.  I don’t spread in my wagers.  I average only 6-8 combinations.  Because why play it otherwise?  You might as well play a Pick-3.  Even with a Pick-3 I don’t like to go more than four combinations.  I try to explain it to guys.  If you are 1x2x5xALL in a Pick-4, for example, why not just put all that money into the 1×2 daily double?  That’s the way I look at it.  If I have to spread that much, then why play.  Even when I play a Pick-5, I rarely have the ticket that has like 80 combinations on it.  I am always trying to have it multiple times.

I am horrible at trifectas, superfectas, and Super Hi-5s.  I know my strengths and my weaknesses.  Not being too stubborn is very important. When I am ‘capping 5 furlong turf races, those races always look like an “ALL” to me, whereas with 6f on the dirt or ploy, that is my specialty.  My strengths are maiden $20,000 claimers, not Grade 1 stakes races.


AGOS: Tommy, what would you like to see changed in our sport going forward?

TM: One major thing. I want racetracks, which they will never do, to realize that this is not about horse racing or entertainment.  This is about gambling and to hire gambling people. It all revolves around the gambling dollar, and I would like see gambling people hired to cater to the players.

They [the track employees] are all clueless about the gambling.  You have to cater to the gamblers if you want to grow the sport.

Interview with Mario Pino, winner of the 2013 George Woolf Memorial Jockey Award


“Since 1950, Santa Anita Park has presented the annual George Woolf Memorial Jockey Award to honor the memory of one of the greatest Thoroughbred riders of all time.  It is prized a one of the most prestigious awards in sports.  The Woolf Award honors riders whose careers and personal character earn esteem for the individual and the sport of Thoroughbred horse racing.  The trophy is a replica of the full-size statue of George Woolf which was created through donations by the racing public after his death.

The statue of George Woolf and a life-size sculpture of Seabiscuit, the great Thoroughbred who was ridden to victory by Woolf in the Pimlico Special and Hollywood Gold Cup, have places of honor in and close proximity to the Santa Anita walking ring.  There the likenesses are admired daily by thousands of racing fans.” — Jockey Guild


Jockey Mario PinoWe had the pleasure of sitting down with veteran jockey Mario Pino who will be awarded the 2013 George Woolf Award this Sunday in California. The annual award “honors riders whose careers and personal character earn esteem for the individual and the sport of Thoroughbred racing.”

Pino just recently passed Earlie Fires as the 10th winningest jockey of all time. A regular winner on the Mid-Atlantic circuit, Pino has rode 6,486 winners over the course of his 34 years for an impressive 16-percent strike rate.


AGOS:  When did you decide you wanted to become a jockey, and how old were you when you got your bug?

MP: I didn’t really want to be a jockey. My uncle suggested this to me, and I didn’t want to be a jockey at all. I wanted to play other sports, like most kids.

I was 12 or 13 when I first went to the racetrack. I had been around horses before but never been around racehorses. I went to the track with a friend of mine who was boarding his horses at our farm. My Dad made a living by boarding horses at our farm. None of them were racehorses. This gentleman had a racehorse and he took me to the track for the first time.

I saw the speed of these horses and it really hit me. I said, “Wow! I could really like this.” So it was around age 13 when I first thought about becoming a jockey.

I went to work at the racetrack around the age of 15. I worked in the morning there and then went to school in the afternoon. I did that for a while. Officially, I was 16 when I rode my first race.

I worked at the track about a year and a half before I rode that first race. You have to work under a trainer and learn the ropes before you are allowed to ride a racehorse.

I had been aboard show horses prior to that, so that gave me a “little” bit of an edge, but I had to work on learning how to ride and to prove myself each time.


AGOS: What were some of the most important lessons you learned as a rider in the early years?

MP: It took me a good 15 mounts before I won my first race. Every race was a learning experience when I rode. As it went along, I really started to get a feel for it. So here I am over 33 years later and I am still doing it.

I can really say that I wanted to learn more than just the fundamentals.

The guy that I came up under said that “there are jockeys and there are horsemen.”  He wanted to me to learn every aspect of the game, from the bottom up. It gives you an edge. I groomed horses and pretty much did it all on the backside. By being a good horsemen first, I could learn to get into a horse’s head. I learned a lot from him.

It pays off because when you are telling the connections after the race how the race was run and how the horse felt, you can really tell them.


AGOS: Tell us about the best horse you ever rode?

MP: No question that was Hard Spun, who ran second in the Kentucky Derby. I rode a lot of good horses that never reached that level, but Hard Spun was the best. He was in the spotlight. It was unfortunate that he had a tough group of horses to run against like Street Sense, who was phenomenal and loved Churchill Downs. He even ran second in the Breeders’ Cup Classic later that year behind a super horse in Curlin. It just shows you how good a horse Hard Spun was.

I felt he could win every horse every time I rode him. He just wanted to cruise along at a high speed. We tried to rate him one time, and it didn’t work out well. So I typically just let the reigns go on him, and he would be fine. That was his style.

He was a thrill to ride.


AGOS: How important is the trainer/jockey relationship, and can you tell  us about any ones in particular?

MP: I rode for a lot of people that I had a good association with over the years, and there are really too many to mention. You get a rapport with the trainer and know what he wants. You work with their horses in the morning and try to make them better. You try to find what their niche is.

For example, I worked with Larry Jones’ horses all the time, so I got to know his horses really well. You get like a bond with the trainer, and it becomes a team effort. It helps to be on the team, because you know what to expect. He or she gains confidence in you, and you have confidence in them. Your heads are working together. That’s how you win or lose, sometimes.


AGOS: What does it mean to you to be voted by your peers and win the prestigious George Woolf Award?

MP: To be voted by the people you ride with over the years, and to be picked by people who do your same job, how can you ask for more than that? When the people that live and breathe the game and are doing the same thing that you are doing, and they vote you in, that is what the George Woolf award is all about. It’s special.

I tried to represent myself well both on and off the track. This is just over the top for me. I had been nominated three times before and had not won. I was never expecting to win it. This is just great.

There are only 60 guys who have ever won the award, and the list is the cream of the crop of the riders.


AGOS: What’s the best day you ever had as a rider?

MP: I won seven races out of nine, with two seconds, at Colonial Downs on July 7, 2002. I had won six races before, but I had never won seven in one day. I got to the last race, having won six races, and I thought to myself “Can I win seven?” He wasn’t the favorite but he got the job done for me.

To win seven in one day at the same track is just tremendous. I was in “a zone” and everything just went so well that day.

I was aboard some nice horses that day and I knew I had a chance to win several races, but I never dreamed I would win seven.


AGOS: Have you suffered any serious injuries?

MP: I broke my back once, my wrist, and also had some collarbone injuries. I even had a fractured skull. I always seemed to bounce back quickly. As soon as I could move, I got myself moving again. I didn’t hold back on anything. A few times I came back sooner than I should have, but that was my mentality. You got to be really hurt to just lay there when you’re down. You got to get up and get moving.


AGOS: What do you have planned this year?

MP: I am going to Presque Isle Downs which opens May 12. I have been going up there the last four years. I have done well every year up there. I really like the Tapeta track.

You have to ride a little differently [on the Tapeta] than on the dirt. It’s almost like how you have to ride on the turf course. You can make up a lot of ground quickly on the turf, and in some ways, it is like that on the Tapeta.


AGOS: From a handicapping perspective, why do you think some riders are best suited to sprints versus routes, or main track races versus turf races?

MP: You have to use your brain more on the turf. You can’t be moving early. It is more of a thinking man’s game. You don’t see a lot of bug boys winning on the grass, for example. You have to save your horse more. You have to save ground. It’s important to know how much horse you have. Being patient is a big plus. When you’re a young rider, you are not as patient. The young riders want to get there; they want to move quicker than they should. There is no doubt that some riders really excel on the grass. If you are paying attention, you’ll notice who they are.

As for sprints, you have to adjust faster. Everything moves faster and you have to respond quicker.

Typically things move slower in the routes and you have to understand that as a jockey.


AGOS: Take us back to your early days as a rider. Specifically August of 1979 and you were on a Del Carrol horse that ran into a monster one afternoon. That horse was ridden by another George Woolf recipient. Tell us about that race.

MP: I remember that like it was yesterday.  It was the first time Bill Shoemaker had the mount on Spectacular Bid. It was an allowance race at Delaware. It was kind of like a show. I was in the lead and looking back, wondering where Spectacular Bid was. Well, he was coming in the 7th path and Bill looked over at me. He said with a laugh “How are you doing jock?” He let it out a notch and Bid drew off to win by about 20 lengths.

I was a young kid at the time. Shoemaker came back after the race and asked, “Who was that kid? He looked over at me like twice.” It was just kind of funny, and you remember these types of things year later.

Shoemaker was an icon to me back then. To be in the same race with him and with “the Bid,” one of the greatest horses of all time, was something special.



1950-Gordon Glisson
1951-Bill Shoemaker
1952 John Longden
1953-Eddie Arcaro
1954-Ralph Neves
1955-Ray York
1956-John Adams
1957-Ted Atkinson
1958-Merlin Volzke
1959-Bill Boland
1960-Bill Harmatz
1961-Peter Moreno
1962-Steve Brooks
1963-Ismael Valenzuela
1964-Manuel Ycaza
1965-Walter Blum
1966-Alex Maese
1967-Donald Pierce
1968-Braulio Baeza
1969-John Sellers
1970-Laffitt Pincay, Jr.
1971-Jerry Lamber
1972-Angel Cordero, Jr.
1973-John L. Rotz
1974-Alvaro Pineda
1975-Fernando Toro
1976-Sandy Hawley
1977-Frank Olivares
1978-Darrel McHargue
1979-Ron Turcotte
1980-Chris McCarron
1981-Eddie Delahoussaye
1982-Patrick Valenzuela
1983-Marco Castaneda
1984-Steve Cauthen
1985-Pat Day
1986-Jorge Velasquez
1987-Don MacBeth
1988-Don Brumfield
1989-Larry Snyder
1990-John Lively
1991-Earlie Fires
1992-Jerry Bailey
1993-Kent Desormeaux
1994-Phil Grove
1995-Edward Maple
1996-Gary Stevens
1997-Alex Solis
1998-Craig Perret
1999-Jose Santos
2000-Mike Smith
2001-Dean Kutz
2002-Russell Baze
2003-Edgar Prado
2004-Robby Albarado
2005-Ray Sibille
2006-Mark Guidry
2007-Jon Court
2008-Richard Migliore
2009-John Velazquez
2010-Calvin Borel
2011-Garrett Gomez
2012-Ramon Dominguez