Arnold Rothstein, Dark Genius of the Mob

Rothstein had promised Carolyn that after he made a lot of money he would retire from being a gambler. Rothstein was comfortable discussing his philosophy of gambling with his wife, but never the actual mechanics, and certainly not the people he interacted with. At Saratoga he pawned all of the expensive jewelry he had given Carolyn to obtain cash. This was more lucrative than borrowing the money at a higher interest rate. By the end of the honeymoon, which coincidentally coincided with the end of race season at Saratoga, Rothstein had won $12,000 and got Carolyn's jewelry out of hock.

Returning to New York, Rothstein decided to open his own gambling house. He rented two brownstones on West 46th Street and he and Carolyn took up residence in one, while the other was outfitted with roulette wheels, faro and poker tables. Rothstein then went to "Big Tim" Sullivan to discuss "protection." Sullivan, an Irishman who believed in marriage and large families, was delighted that his protégé had wed. His wedding gift to Rothstein was protection, but with a string attached; Rothstein had to take on William Shea, a deposed building inspector, as his partner.

Shea, a self-proclaimed anti-Semite, distrusted Rothstein from the beginning of their relationship and felt that his partner was always cheating him. Rothstein, who Leo Katcher claims "made a lot of acquaintances, but few friends," did not mix well with others and was constantly in the habit of referring to people as "chumps." When a group of Rothstein's detractors got together to take advantage of his pool playing vanity, a Broadway legend was created.

The group brought Jack Conway, a Philadelphia sportsman and accomplished jockey, who happened to be an expert pool player, to town. One night at Jack's, a popular Manhattan hangout, Rothstein walked in and was invited to sit down with the group as they discussed baseball and prizefights. During this talk it came out that Conway was "probably" the best amateur pool player in the country. Rothstein, unaware of Conway's background or that he was being set up, sensed a challenge and jumped at it.

The two men agreed to play to 100 points for $500 at John McGraw's Billiard Parlor. The game began on a Thursday night at 8:00 p.m. By the time it ended, at 4:00 a.m. Saturday morning, some 36 hours later, Rothstein was rumored to have won over $10,000. The match received so much publicity that it was reported on in two of the New York City newspapers. In one account Rothstein was referred to as "a well-known sportsman."

To increase the winnings at his gambling house, Rothstein was in constant search for what the gamblers called "marks." A mark was a wealthy individual who enjoyed gambling and believed he could "beat the house." One of the first "marks" that Rothstein was able to land was Charles Gates, whose father had become wealthy from the invention of barbed wire. Gates came in and dropped $40,000 at the roulette wheel and faro games.

Gates wrote a check for the amount and accompanied William Shea to the bank the following morning to cash it. By evening Shea had not returned with the money. Soon Shea sent word that he was keeping the entire $40,000 because he felt he had been cheated by Rothstein in the past. After consulting with Sullivan, Rothstein told "Big Tim" that he was going to let Shea keep the money, of which one third he was entitled to anyway, but that he had to sign a contract releasing him from the partnership. When Rothstein caught up with him, Shea was drunk and readily signed the papers thinking he had pulled a fast one on his "sheenie" partner. After Shea sobered up and realized the blunder he had made he went crawling to Sullivan for help.

"Nothing doing," Sullivan told him.

Rothstein realized that using attractive women could be a great help in bringing in the marks. One of the women Rothstein utilized was Peggy Hopkins, a beautiful ex-show girl. One night Hopkins brought in Stanley Joyce, a man she would later wed, and Percival H. Hill, of the American Tobacco Company. While Joyce dropped $17,000, the unlucky Hill ended his night of gambling by signing over an IOU to Rothstein good for $250,000. Rothstein suffered through a restless night wondering if he would have any trouble collecting the money. Carolyn urged that if he did collect, that he keep his promise to her and retire from gambling. When morning arrived, Rothstein took a cab to the offices of the American Tobacco Company and collected a certified check for a quarter of a million dollars. Carolyn, however, did not collect on the promise made to her.