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.

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About Editor

Rich Nilsen is a 19-time qualifier to the National Horseplayers Championship (NHC), an event he has cashed in four times. He was the first player to finish in the top 10 of the NHC twice. A former executive with and a member of the NHC Players’ Committee, Rich is a graduate of the University of Louisville Equine Business Program and is founder of, a site devoted to horse racing education and promotion.


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