Pick the Winner


Damon Runyon

February 11 1933



What I am doing in Miami associating with such a character as Hot Horse Herbie is really quite a long story, and it goes back to one cold night when I am sitting in Mindy’s restaurant on Broadway thinking what a cruel world it is, to be sure, when in comes Hot Horse Herbie and his ever-loving fiancée, Miss Cutie Singleton.

This Hot Horse Herbie is a tall, skinny guy with a most depressing kisser, and he is called Hot Horse Herbie because he can always tell you about a horse that is so hot it is practically on fire, a hot horse being a horse that is all readied up to win a race, although sometimes Herbie’s hot horses turn out to be so cold they freeze everybody within fifty miles of them.

He is following the races almost since infancy, to hear him tell it. In fact, old Captain Duhaine, who has charge of the Pinkertons around the race tracks, says he remembers Hot Horse Herbie as a little child, and that even then Herbie is a hustler, but of course Captain Duhaine does not care for Hot Horse Herbie, because he claims Herbie is nothing but a tout, and a tout is something that is most repulsive to Captain Duhaine and all other Pinkertons.

A tout is a guy who goes around a race track giving out tips on the races, if he can find anybody who will listen to his tips, especially suckers, and a tout is nearly always broke. If he is not broke, he is by no means a tout, but a handicapper, and is respected by one and all, including the Pinkertons, for knowing so much about the races.

Well, personally, I have nothing much against Hot Horse Herbie, no matter what Captain Duhaine says he is, and I certainly have nothing against Herbie’s ever-loving fiancée, Miss Cutie Singleton. In fact, I am rather in favor of Miss Cutie Singleton, because in all the years I know her, I wish to say I never catch Miss Cutie Singleton out of line, which is more than I can say of many other dolls I know.

She is a little, good-natured blonde doll, and by no means a crow, if you care for blondes, and some people say that Miss Cutie Singleton is pretty smart, although I never can see how this can be, as I figure a smart doll will never have any truck with a guy like Hot Horse Herbie, for Herbie is by no means a provider.

But for going on ten years, Miss Cutie Singleton and Hot Horse Herbie are engaged, and it is well known to one and all that they are to be married as soon as Herbie makes a scratch. In fact, they are almost married in New Orleans in 1928, when Hot Horse Herbie beats a good thing for eleven C’s, but the tough part of it is the good thing is in the first race, and naturally Herbie bets the eleven C’s right back on another good thing in the next race, and this good thing blows, so Herbie winds up with nothing but the morning line and is unable to marry Miss Cutie Singleton at this time.


Then again in 1929 at Churchill Downs, Hot Horse Herbie has a nice bet on Naishapur to win the Kentucky Derby, and he is so sure Naishapur cannot miss that the morning of the race he sends Miss Cutie Singleton out to pick a wedding ring. But Naishapur finishes second, so naturally Hot Horse Herbie is unable to buy the ring, and of course Miss Cutie Singleton does not wish to be married without a wedding ring.

They have another close call in 1931 at Baltimore when Hot Horse Herbie figures Twenty Grand a stand-out in the Preakness, and in fact is so sure of his figures that he has Miss Cutie Singleton go down to the city hall to find out what a marriage licence costs. But of course Twenty Grand does not win the Preakness, so the information Miss Cutie Singleton obtains is of no use to them and anyway Hot Horse Herbie says he can beat the price on marriage licences in New York.

However, there is no doubt but what Hot Horse Herbie and Miss Cutie Singleton are greatly in love, although I hear rumors that for a couple of years past Miss Cutie Singleton is getting somewhat impatient about Hot Horse Herbie not making a scratch as soon as he claims he is going to when he first meets up with her in Hot Springs in 1923.

In fact, Miss Cutie Singleton says if she knows Hot Horse Herbie is going to be so long delayed in making his scratch she will never consider becoming engaged to him, but will keep her job as a manicurist at the Arlington Hotel, where she is not doing bad, at that.

It seems that the past couple of years Miss Cutie Singleton is taking to looking longingly at the little houses in the towns they pass through going from one race track to another, and especially at little white houses with green shutters and yards and vines all around and about, and saying it must be nice to be able to live in such places instead of in a suitcase.


But of course Hot Horse Herbie does not put in with her on these ideas, because Herbie knows very well if he is placed in a little white house for more than fifteen minutes the chances are he will lose his mind, even if the house has green shutters.

Personally, I consider Miss Cutie Singleton somewhat ungrateful for thinking of such matters after all the scenery Hot Horse Herbie lets her see in the past ten years. In fact, Herbie lets her see practically all the scenery there is in this country, and some in Canada, and all she has to do in return for all this courtesy is to occasionally get out a little crystal ball and deck of cards and let on she is a fortune teller when things are going especially tough for Herbie.

Of course Miss Cutie Singleton cannot really tell fortunes, or she will be telling Hot Horse Herbie’s fortune, and maybe her own, too, but I hear she is better than a raw hand at making people believe she is telling their fortunes, especially old maids who think they are in love, or widows who are looking to snare another husband and other such characters.

Well, anyway, when Hot Horse Herbie and his ever-loving fiancée come into Mindy’s, he gives me a large hello, and so does Miss Curie Singleton, so I hello them right back, and Hot Horse Herbie speaks to me as follows:

“Well,” Herbie says, “we have some wonderful news for you. We are going to Miami,” he says, “and soon we will be among the waving palms, and revelling in the warm waters of the Gulf Stream.”

Now of course this is a lie, because while Hot Horse Herbie is in Miami many times, he never revels in the warm waters of the Gulf Stream, because he never has time for such a thing, what with hustling around the race tracks in the daytime, and around the dog tracks and the gambling joints at night, and in fact I will lay plenty of six to five Hot Horse Herbie cannot even point in the direction of the Gulf Stream when he is in Miami, and I will give him three points, at that.

But naturally what he says gets me to thinking how pleasant it is in Miami in the winter, especially when it is snowing up north, and a guy does not have a flogger to keep himself warm, and I am commencing to feel very envious of Hot Horse Herbie and his ever-loving fiancée when he says like this:

“But,” Herbie says, “our wonderful news for you is not about us going. It is about you going,” he says. “We already have our railroad tickets,” he says, “as Miss Cutie Singleton, my ever-loving fiancée here, saves up three C’s for her hope chest the past summer, but when it comes to deciding between a hope chest and Miami, naturally she chooses Miami, because,” Herbie says, “she claims she does not have enough hope left to fill a chest. Miss Cutie Singleton is always kidding,” he says.


“Well, now,” Herbie goes on, “I just run into Mr. Edward Donlin, the undertaker, and it seems that he is sending a citizen of Miami back home tomorrow night, and of course you know,” he says, “that Mr. Donlin must purchase two railroad tickets for this journey, and as the citizen has no one else to accompany him, I got to thinking of you. He is a very old and respected citizen of Miami,” Herbie says, “although of course,” he says, “he is no longer with us, except maybe in spirit.”

Of course such an idea is most obnoxious to me, and I am very indignant that Hot Horse Herbie can even think I will travel in this manner, but he gets to telling me that the old and respected citizen of Miami that Mr. Donlin is sending back home is a great old guy in his day, and that for all anybody knows he will appreciate having company on the trip, and about this time Big Nig, the crap shooter, comes into Mindy’s leaving the door open behind him so that a blast of cold air hits me, and makes me think more than somewhat of the waving palms and the warm waters of the Gulf Stream.

So the next thing I know, there I am in Miami with Hot Horse Herbie, and it is the winter of 1931, and everybody now knows that this is the winter when the suffering among the horse players in Miami is practically horrible. In fact, it is worse than it is in the winter of 1930. In fact, the suffering is so intense that many citizens are wondering if it will do any good to appeal to Congress for relief for the horse players, but The Dander says he hears Congress needs a little relief itself.

Hot Horse Herbie and his ever-loving fiancée, Miss Cutie Singleton, and me have rooms in a little hotel on Flagler Street, and while it is nothing but a fleabag, and we are doing the landlord a favor by living there, it is surprising how much fuss he makes any time anybody happens to be a little short of the rent. In fact, the landlord hollers and yells so much any time anybody is a little short of the rent that he becomes a very great nuisance to me, and I have half a notion to move, only I cannot think of any place to move to. Furthermore, the landlord will not let me move unless I pay him all I owe him, and I am not in a position to take care of this matter at the moment.


Of course I am not very dirty when I first come in as far as having any potatoes is concerned, and I start off at once having a little bad luck. It goes this way a while, and then it gets worse, and sometimes I wonder if I will not be better off if I buy myself a rope and end it all on a palm tree in the park on Biscayne Boulevard. But the only trouble with the idea is I do not have the price of a rope, and anyway I hear most of the palm trees in the park are already spoken for by guys who have the same notion.

And bad off as I am, I am not half as bad off as Hot Horse Herbie, because he has his ever-loving fiancée, Miss Cutie Singleton, to think of, especially as Miss Cutie Singleton is putting up quite a beef about not having any recreation, and saying if she only has the brains God gives geese she will break off their engagement at once and find some guy who can show her a little speed, and she seems to have no sympathy whatever for Hot Horse Herbie when he tells her how many tough snoots he gets beat at the track.

But Herbie is very patient with her, and tells her it will not be long now, because the law of averages is such that his luck is bound to change, and he suggests to Miss Cutie Singleton that she get the addresses of a few preachers in case they wish to locate one in a hurry. Furthermore, Hot Horse Herbie suggests to Miss Cutie Singleton that she get out the old crystal ball and her deck of cards, and hang out her sign as a fortune teller while they are waiting for the law of averages to start working for him, although personally I doubt if she will be able to get any business telling fortunes in Miami at this time because everybody in Miami seems to know what their fortune is already.

Now I wish to say that after we arrive in Miami I have very little truck with Hot Horse Herbie, because I do not approve of some of his business methods, and furthermore I do not wish Captain Duhaine and his Pinkertons at my hip all the time, as I never permit myself to get out of line in any respect, or anyway not much. But of course I see Hot Horse Herbie at the track every day, and one day I see him talking to the most innocent-looking guy I ever see in all my life.

He is a tall, spindling guy with a soft brown Vandyke beard, and soft brown hair, and no hat, and he is maybe forty-odd, and wears rumpled white flannel pants, and a rumpled sports coat, and big horn cheaters, and he is smoking a pipe that you can smell a block away. He is such a guy as looks as if he does not know what time it is, and furthermore he does not look as if he has a quarter, but I can see by the way Hot Horse Herbie is warming his ear that Herbie figures him to have a few potatoes.


Furthermore, I never know Hot Horse Herbie to make many bad guesses in this respect, so I am not surprised when I see the guy pull out a long flat leather from the inside pocket of his coat and weed Herbie a bank-note. Then I see Herbie start for the mutuels windows, but I am quite astonished when I see that he makes for a two-dollar window. So I follow Hot Horse Herbie to see what this is all about, because it is certainly not like Herbie to dig up a guy with a bank roll and then only promote him for a deuce.

When I get hold of Herbie and ask him what this means, he laughs, and says to me like this:

“Well,” he says, “I am just taking a chance with the guy. He may be a prospect, at that,” Herbie says. “You never can tell about people. This is the first bet he ever makes in his life, and furthermore,” Herbie says, “he does not wish to bet. He says he knows one horse can beat another, and what of it? But,” Herbie says, “I give him a good story, so he finally goes for the deuce. I think he is a college professor somewhere,” Herbie says, “and he is only wandering around the track out of curiosity. He does not know a soul here. Well,” Herbie says, “I put him on a real hot horse, and if he wins maybe he can be developed into something. You know,” Herbie says, “they can never rule you off for trying.”


Well, it seems that the horse Herbie gives the guy wins all right and at a fair price, and Herbie lets it go at that for the time being, because he gets hold of a real good guy, and cannot be bothering with guys who only bet deuces. But every day the professor is at the track and I often see him wandering through the crowds, puffing at his old stinkaroo and looking somewhat bewildered.

I get somewhat interested in the guy myself, because he seems so much out of place, but I wish to say I never think of promoting him in any respect, because this is by no means my dodge, and finally one day I get to talking to him and he seems just as innocent as he looks. He is a professor at Princeton, which is a college in New Jersey, and his name is Woodhead, and he has been very sick, and is in Florida to get well, and he thinks the track mob is the greatest show he ever sees, and is sorry he does not study this business a little earlier in life.

Well, personally, I think he is a very nice guy, and he seems to have quite some knowledge of this and that and one thing and another, although he is so ignorant about racing that it is hard to believe he is a college guy.

Even if I am a hustler, I will just as soon try to hustle Santa Claus as Professor Woodhead, but by and by Hot Horse Herbie finds things getting very desperate indeed, so he picks up the professor again and starts working on him, and one day he gets him to go for another deuce, and then for a fin, and both times the horses Herbie gives him are winners, which Herbie says just goes to show you the luck he is playing in, because when he has a guy who is willing to make a bet for him, he cannot pick one to finish fifth.


You see, the idea is when Hot Horse Herbie gives a guy a horse he expects the guy to bet for him, too, or maybe give him a piece of what he wins, but of course Herbie does not mention this to Professor Woodhead as yet, because the professor does not bet enough to bother with, and anyway Herbie is building him up by degrees, although if you ask me, it is going to be slow work, and finally Herbie himself admits as much, and says to me like this:

“It looks as if I will have to blast,” Herbie says. “The professor is a nice guy, but,” he says, “he does not loosen so easy. Furthermore,” Herbie says, “he is very dumb about horses. In fact,” he says, “I never see a guy so hard to educate, and if I do not like him personally, I will have no part of him whatever. And besides liking him personally,” Herbie says, “I get a gander into that leather he carries the other day, and what do I see,” he says, “but some large, coarse notes in there back to back.”

Well, of course this is very interesting news, even to me, because large, coarse notes are so scarce in Miami at this time that if a guy runs into one he takes it to a bank to see if it is counterfeit before he changes it, and even then he will scarcely believe it.

I get to thinking that if a guy such as Professor Woodhead can be going around with large, coarse notes in his possession, I make a serious mistake in not becoming a college professor myself, and naturally after this I treat Professor Woodhead with great respect.

Now what happens one evening, but Hot Horse Herbie and his ever-loving fiancée, Miss Cutie Singleton, and me are in a little grease joint on Second Street putting on the old hot tripe a la Creole, which is a very pleasant dish, and by no means expensive, when who wanders in but Professor Woodhead.

Naturally Herbie calls him over to our table and introduces Professor Woodhead to Miss Cutie Singleton, and Professor Woodhead sits there with us looking at Miss Cutie Singleton with great interest, although Miss Cutie Singleton is at this time feeling somewhat peevish because it is the fourth evening hand running she has to eat tripe a la Creole, and Miss Cutie Singleton does not care for tripe under any circumstances.


She does not pay any attention whatever to Professor Woodhead, but finally Hot Horse Herbie happens to mention that the professor is from Princeton, and then Miss Cutie Singleton looks at the professor, and says to him like this:

“Where is this Princeton?” she says. “Is it a little town?”

“Well,” Professor Woodhead says, “Princeton is in New Jersey, and it is by no means a large town, but,” he says, “it is thriving.”

“Are there any little white houses in this town?” Miss Cutie Singleton asks. “Are there any little white houses with green shutters and vines all around and about?”

“Why,” Professor Woodhead says, looking at her with more interest than somewhat, “you are speaking of my own house,” he says. “I live in a little white house with green shutters and vines all around and about, and,” he says, “it is a nice place to live in, at that, although it is sometimes a little lonesome, as I live there all by myself, unless,” he says, “you wish to count old Mrs. Bixby, who keeps house for me. I am a bachelor,” he says.

Well, Miss Cutie Singleton does not have much to say after this, although it is only fair to Miss Cutie Singleton to state that for a doll, and especially a blonde doll, she is never so very gabby, at that, but she watches Professor Woodhead rather closely, as Miss Cutie Singleton never before comes in contact with anybody who lives in a little white house with green shutters.

Finally we get through with the hot tripe ala Creole and walk around to the fleabag where Hot Horse Herbie and Miss Cutie Singleton and me are residing, and Professor Woodhead walks around with us. In fact, Professor Woodhead walks with Miss Cutie Singleton, while Hot Horse Herbie walks with me, and Hot Horse Herbie is telling me that he has the very best thing of his entire life in the final race at Hialeah the next day, and he is expressing great regret that he does not have any potatoes to bet on this thing, and does not know where he can get any potatoes.


It seems that he is speaking of a horse by the name of Breezing Along, which is owned by a guy by the name of Moose Tassell, who is a citizen of Chicago, and who tells Hot Horse Herbie that the only way Breezing Along can lose the race is to have somebody shoot him at the quarter pole, and of course nobody is shooting horses at the quarter pole at Hialeah, though many citizens often feel like shooting horses at the half.

Well, by this time we get to our fleabag, and we all stand there talking when Professor Woodhead speaks as follows: “Miss Cutie Singleton informs me,” he says, “that she dabbles somewhat in fortune telling. Well,” Professor Woodhead says, “this is most interesting to me, because I am by no means skeptical of fortune telling. In fact,” he says, “I make something of a study of the matter, and there is no doubt in my mind that certain human beings do have the faculty of foretelling future events with remarkable accuracy.”

Now I wish to say one thing for Hot Horse Herbie, and this is that he is a quick-thinking guy when you put him up against a situation that calls for quick thinking, for right away he speaks up and says like this:

“Why, Professor,” he says, “I am certainly glad to hear you make this statement, because,” he says, “I am a believer in fortune telling myself. As a matter of fact, I am just figuring on having Miss Cutie Singleton look into her crystal ball and see if she can make out anything on a race that is coming up tomorrow, and which has me greatly puzzled, what with being undecided between a couple of horses.”

Well, of course, up to this time Miss Cutie Singleton does not have any idea she is to look into any crystal ball for a horse, and furthermore, it is the first time in his life Hot Horse Herbie ever asks her to look into the crystal ball for anything whatever, except to make a few bobs for them to eat on, because Herbie by no means believes in matters of this nature.

But naturally Miss Cutie Singleton is not going to display any astonishment, and when she says she will be very glad to oblige, Professor Woodhead speaks up and says he will be glad to see this crystal gazing come off, which makes it perfect for Hot Horse Herbie.

So we all go upstairs to Miss Cutie Singleton’s room, and the next thing anybody knows there she is with her crystal ball, gazing into it with both eyes.

Now Professor Woodhead is taking a deep interest in the proceedings, but of course Professor Woodhead does not hear what Hot Horse Herbie tells Miss Cutie Singleton in private, and as far as this is concerned neither do I, but Herbie tells me afterwards that he tells her to be sure and see a breeze blowing in the crystal ball. So by and by, after gazing into the ball a long time, Miss Cutie Singleton speaks in a low voice as follows:

“I seem to see trees bending to the ground under the force of a great wind,” Miss Cutie Singleton says. “I see houses blown about by the wind,” she says. “Yes,” Miss Cutie Singleton says, “I see pedestrians struggling along and shivering in the face of this wind, and I see waves driven high on a beach and boats tossed about like paper cups. In fact,” Miss Singleton says, “I seem to see quite a blow.”


Well, then, it seems that Miss Curie Singleton can see no more, but Hot Horse Herbie is greatly excited by what she sees already, and he says like this:

“It means this horse Breezing Along,” he says. “There can be no doubt about it. Professor,” he says, “here is the chance of your lifetime. The horse will be not less than six to one,” he says. “This is the spot to bet a gob, and,” he says, “the place to bet it is downtown with a bookmaker at the opening price, because there will be a ton of money for the horse in the machines. Give me five C’s,” Hot Horse Herbie says, “and I will bet four for you, and one for me.”

Well, Professor Woodhead seems greatly impressed by what Miss Cutie Singleton sees in the crystal ball, but of course taking a guy from a finnif to five C’s is carrying him along too fast, especially when Herbie explains that five C’s is five hundred dollars, and naturally the professor does not care to bet any such money as this. In fact, the professor does not seem anxious to bet more than a sawbuck, tops, but Herbie finally moves him up to bet a yard, and of this yard twenty-five bobs is running for Hot Horse Herbie, as Herbie explains to the professor that a remittance he is expecting from his New York bankers fails him.

The next day Herbie takes the hundred bucks and bets it with Gloomy Gus downtown, for Herbie really has great confidence in the horse.


We are out to the track early in the afternoon and the first guy we run into is Professor Woodhead, who is very much excited. We speak to him, and then we do not see him again all day.

Well, I am not going to bother telling you the details of the race, but this horse Breezing Along is nowhere. In fact, he is so far back that I do not recollect seeing him finish, because by the time the third horse in the field crosses the line, Hot Horse Herbie and me are on our way back to town, as Herbie does not feel that he can face Professor Woodhead at such a time as this. In fact, Herbie does not feel that he can face anybody, so we go to a certain spot over on Miami Beach and remain there drinking beer until a late hour, when Herbie happens to think of his ever-loving fiancée, Miss Cutie Singleton, and how she must be suffering from lack of food, so we return to our fleabag so Herbie can take Miss Cutie Singleton to dinner.

But he does not find Miss Cutie Singleton. All he finds from her is a note, and in this note Miss Cutie Singleton says like this: “Dear Herbie,” she says, “I do not believe in long engagements any more, so Professor Woodhead and I are going to Palm Beach to be married tonight, and are leaving for Princeton, New Jersey, at once, where I am going to live in a little white house with green shutters and vines all around and about. Good-bye, Herbie,” the note says. “Do not eat any bad fish. Respectfully, Mrs. Professor Woodhead.”

Well, naturally this is most surprising to Hot Horse Herbie, but I never hear him mention Miss Cutie Singleton or Professor Woodhead again until a couple of weeks later when he shows me a letter from the professor.

It is quite a long letter, and it seems that Professor Woodhead wishes to apologize, and naturally Herbie has a right to think that the professor is going to apologize for marrying his ever-loving fiancée, Miss Cutie Singleton, as Herbie feels he has an apology coming on this account.

But what the professor seems to be apologizing about is not being able to find Hot Horse Herbie just before the Breezing Along race to explain a certain matter that is on his mind.

“It does not seem to me,” the professor says, as near as I can remember the letter, “that the name of your selection is wholly adequate as a description of the present Mrs. Professor Woodhead’s wonderful vision in the crystal ball, so,” he says, “I examine the program further, and finally discover what I believe to be the name of the horse meant by the vision, and I wager two hundred dollars on this horse, which turns out to be the winner at ten to one, as you may recall. It is in my mind,” the professor says, “to send you some share of the proceeds, inasmuch as we are partners in the original arrangement, but the present Mrs. Woodhead disagrees with my view, so all I can send you is an apology, and best wishes.”


Well, Hot Horse Herbie cannot possibly remember the name of the winner of any race as far back as this, and neither can I, but we go over to the Herald office and look at the files, and what is the name of the winner of the Breezing Along race but Mistral, and when I look in the dictionary to see what this word means, what does it mean but a violent, cold and dry northerly wind.

And of course I never mention to Hot Horse Herbie or anybody else that I am betting on another horse in this race myself, and the name of the horse I am betting on is Leg Show, for how do I know for certain that Miss Cutie Singleton is not really seeing in the crystal ball just such a blow as she describes?