The following is a guest post by John Douglas, who enjoys intelligent discussions around writing and focuses on portfolio enhancement through options.

Part 2 in a 4 part series where through a strange time warp-or perhaps just a dream- the narrator is transported back to the early part of the twentieth century. He is charged with re-discovering the lessons of two of the country’s greatest legends, and revealing these lessons to a new set of traders and odds-makers. Click here for Part 1.

Chapter 2:  Titanic Thompson: A Legend Among Legends

I’m in Chicago? I suppose so-that’s what the signs say and it appears that I’m in what they used to call a “speakeasy.” You know, you can read about these things, and look at those old black-and-whites, but actually being here is really an exhilarating sensation. There’s a certain rawness and sense of optimism that seems to pervade every action. I guess you would say that it’s all so unfiltered-maybe a little scary.

I just met a guy from Arkansas. Jesse told me I would like him, since we both played a little golf. By way of introduction, let’s hear from Lowell Douglas:

“The greatest gambler and hustler in American history was born…in Rogers, Arkansas on November 30, 1982; the gambling legend was named Alvin Clarence Thomas. Through the next 82 years, Mr. Thomas was destined to touch the lives and pocketbooks of almost every high-stakes golfer, card player, dice thrower, checker player, pool hustler, horseshoe pitcher, bowler, pistol marksmen, skeet shooter, and general gambler that ever tried the shortcut to the American dream of quick dollars and high life-styles. Titanic, as he was known shortly after his twentieth birthday, was a brilliant strategist with unbelievable skill in setting up a wager or a game to his mathematical advantage.”

Another writer, Richard Campbell, speculated as to how Titanic Thompson would have described himself:

“Thanks to the grace of God, I was, in no special order, a gifted golfer and a pretty good pool player. The horseshoe throwing champion of the whole world, including Europe. The trap shooting champion of the state of Arizona. Regimental sharpshooting champion during World War l. An expert on figuring the mathematical probability on anything, and on occasion-in fact, on a lot of occasions, I was a high-stakes gambler. I was born with natural good looks, world-class physical skills and a real good brain… and while it is true that in my life I did kill five men, it is the God’s truth that they all tried to either rob me, or kill me or someone close to me, like the pretty girl on that St. Francis riverboat when I was only about twenty…

You see, back in the heyday, the roaring 20’s, everyone was hustling everyone else. Every state, city, and street corner was filled with guys-from big city bankers, politicians and stockbrokers, to the shoeshine boy on the corner-hustling anyone within earshot, just trying to make a buck while the getting was good. Sure, it was a different time. But the ingredients were the same as today.

Greed, madness and appetites became insatiable. Even with all this going on around me, I think I kept my head pretty damn good. Back then, we had bigger-than-life athletes to hear and read about. Jack Dempsey. Red Grange. Babe Ruth. And, I related to them and associated with people like them because I always considered myself to be-first and foremost-a truly gifted athlete and a fierce competitor. Pure and simple. Now, when it came to playing golf, I won hundreds of thousands of dollars by beating some pretty tough competitors. You probably never heard of them, or even me for that matter…. Now, you need to understand one important thing. When I say ‘tough competitors’, I am talking about cold-blooded, cold-eyed, stare-you-down, walk-all-over-you and take every cent-you-got, type of competitors… The truth is, I made my reputation on the fact that I would bet any amount of money on my ability to do it, figure it out, or know when it was going to happen. And “it”, was sometimes anything you could imagine, but most of the time you couldn’t…but I could.”

I had no idea how long the guys seated at the table had been playing poker. I did, however, have a real good idea of the hands on favorite to walk away with massive amounts of cash. That is, if he were allowed to walk away. Despite the dimly lit lights and haze of cigar smoke, I had no problems recognizing one of the more boisterous players. He was the most notorious gangster in Chicago’s history. His name was Al Capone.

“Titanic, you’re about the best gambler I’ve ever seen. I know you were cheatin’. But I can’t prove it. I’m the best at what I do, and I’ll give you the benefit of the doubt that you’re the best at what you do. Given that-I got no business gambling with you, except I enjoy your company. Besides, I enjoy watching those poor fools that think they got a chance with you when they don’t. There is absolutely no gamble to it as the longer the game lasts, the deader they become. They got no chance!”

Titanic looked at me and winked. “I got one more trick up my sleeve,” he told me as we walked out into a Chicago evening. Al Capone had stopped to buy some oranges from a street vendor. As they walked down the sidewalk, Titanic suddenly stopped and addressed big Al. “I’ve been thinking about what you said back there Al. I don’t think I could sleep tonight if I didn’t give you a chance to get your money back. How about me bettin’ you that I can roll this orange from right here into that gutter across the street in one try?”

“Ti, you never stop the hustle, do you? I’m not going to bet with you with your game, not now or in the future. Now, I’ve heard stories about how good an arm you’ve got. Heard that you could have been a major leaguer at one time. Is that so?”

“Well Al, I got no idea whether I would have made it to the majors or not, but I did have a pretty good arm a while ago-still do as a matter of fact.”

“Okay Ti, what do you want to bet that you can throw that there orange on top of that six-story building across the street-from here?”

I watched with amused fascination as Al Capone and Titanic Thompson settled on the terms of the bet. What Al didn’t know was that Titanic had managed to switch out an orange with a large lemon. The aerodynamics of the lemon made the task somewhat easier. Titanic quickly hurled the lemon, in the dim light, over the six-story building. Al Capone pulled out another wad of cash and paid off the bet.

Chapter 3:  Master of the Game

It seemed that I could drift in and out of the lives of Thompson and Livermore. All I had to do was think about one or the other, and that’s all it took. In fact, fate actually brought them together a couple of times.

I don’t recall how long I had been standing, but it didn’t seem to matter. Time seemed both slow and fast and had no meaning. I knew there was a twenty-first century, and I felt like I had one foot in each century. Maybe I did. Maybe we all do. But at the moment, Titanic Thompson moved awkwardly around a massive-looking billiard table. Maybe it wasn’t his night as his younger opponent had already taken him for over $10,000.

“I’ve never seen Titanic play so bad,” I remarked to Jesse, “the kid he’s playing seems invincible.”

Titanic must have over-heard me. He shot me a quick, piercing look, with just the slightest trace of a grin. Or was it a grin? It was too fleeting to tell, and as usual, the smoke and lack of ventilation always clouded one’s vision.

“Rack!” The young pool shark had run the table yet again, and yelled out for the young boy that scampered from table to table, to rack the balls again. “Same game, Ti?”

“I don’t know. I guess I’m kinda tired tonight. Last night’s poker game took it out of me, I guess. Tell ya what though, I’m down about fifteen grand to you, why don’t we just play best two out of three games for the fifteen thousand, but I’ll bet you another thirty thousand that I’ll win all three games.

The young hustler could hardly contain his excitement. After all, hadn’t he won easily? But the kid didn’t have all the cash to put up. That didn’t pose a problem, though, as a couple of guys sitting at the bar gave a ‘thumbs up.’

Matches of this nature always seem to create a lot of on-lookers. Many other players began to saunter over, and numerous side bets sprang up, as if on cue.  It took a good half-hour to write down all the bets. Titanic had turned his stake over to the owner of the establishment, and walked outside. He remained outside, breathing in the late-night air, until the rack boy came out to bring him in.

Titanic Thompson was a good 6’3” and in superb physical condition. I never saw him take a drink or smoke tobacco. When he walked back in, I noticed more of a spring in his step. He seemed intent but relaxed.

The “kid” as they called him, had the break. It appeared to me that the break was a bit too hard. Sure enough, he had sent the cue ball sailing off the table. It would have been a good enough break-if the kid hadn’t scratched.

Titanic glided effortlessly around the large table. The shots that he missed before now seemed to dive and scamper into the pockets. The cue stick moved gently, but decisively. It became a magician’s wand, wielded by a wizard. Titanic Thompson ran the table without changing his facial expression, or breaking his rhythm. Half way thru the second game, Ti seemed to miss an easy shot, but left his opponent with nothing. The young gambler nonetheless tried a difficult bank shot, which came close, but missed. The game was over. Titanic broke for the last game of the evening. Again he ran the table, and carefully placed the cue stick on the table. “Kid,” he said, “you’re one hell of a player. I was just plain lucky to finally turn it my way.”

I looked at Jesse Livermore. “I don’t believe what I just saw. In fact, it wouldn’t do any good to tell anybody what just happened. Nobody could possibly understand what happened tonight unless they were right here. “

Jesse grinned and was quiet for a moment. Finally he spoke. “A man can spend years at one thing and not acquire a habitual attitude towards it quite unlike that of the average beginner. The difference distinguishes the professional from the amateur. It is the way a man looks at things that makes or loses money for him in the speculative markets. The public has the dilettante’s point of view toward his own effort. The ego obtrudes itself unduly and the thinking therefore is not deep or exhaustive. The professional concerns himself with doing the right thing rather than with making money, knowing that the profit takes care of itself if the other things are attended to. A trader gets to play the game as the professional billiard player does- that is, he looks far ahead instead of considering the particular shot before him. It gets to be an instinct to play for position.”

“But,” I said, shaking my head in amazement, “it’s not just that Titanic was shooting shapes and coldly calculating the next series of shots. It goes well beyond that point. He understood the mind of the ‘kid’ and played out every conceivable angle. In short, Titanic thought through several dimensions and permutations, even as he appeared distracted.”

I still couldn’t believe what I saw. As time went on, and the years went by, the people that witnessed the affair always said the same thing-“you just had to be there.”

T0 be continued…