On his income tax forms, Ruby did not itemize personal deductions and claimed only his own exemption. For 1962, Ruby reported salary income of $650 from the corporation controlling the Carousel, and $900 for 1961.350

Ruby and officers of the Internal Revenue Service frequently discussed methods of satisfying his large excise and income tax liability.351 In 1960, the Government filed tax liens for more than $20,000.352 In November 1962, the Government rejected Ruby's offer to pay $8,000 to compromise the assessed taxes of more than $20,000 because he had not filed returns for other Federal taxes and had not paid these taxes as they became due. These other taxes, for the period September 1959 through June 1962, amounted to an additional $20,000.353 In June 1963, Ruby submitted an offer of $3,000 to compromise all past assessments; the offer was not acted upon prior to November 24, 1963.354

Other Business Ventures

In addition to nightclub management and ownership, Ruby participated in numerous other commercial ventures. He was able to do so primarily because work at the clubs consumed few of his daytime hours. Many of Ruby's ventures related to show business, others were somewhat speculative promotions; almost all ended unsuccessfully.

While operating the Silver Spur Club, Ruby sold costume jewelry at discount rates,355 and, in about 1951, he sold sewing machine attachments at the Texas State Fair.356 Approximately a year later, he managed a talented young Negro boy, "Little Daddy" Nelson. The boy appeared at the Silver Spur, the Vegas Club, and the Bob Wills Ranch House. In about 1953 or 1954, Ruby took "Little Daddy" and his parents to Chicago to obtain a television appearance for him. However, shortly after their arrival, Ruby was confronted by a second woman claiming to be "Little Daddy's" mother. Upon advice of counsel, Ruby decided to .abandon the venture.357

In 1954, Ruby became interested in the sale of pizza crusts to Dallas restaurants.358 He is also reported to have sold an arthritic preparation 359 and to have manufactured and sold "Miniron," a liquid vitamin formula.360 In about 1958 or 1959, Ruby attempted to build and sell log cabins at a Texas lake resort.361 In early 1959, he investigated the possibility of selling jeeps to Cuba.362 He is also reported to have furnished entertainment for a Dallas hotel,363 to have promoted records for musicians 364 and to have sold English stainless steel razor blades.365

In October 1963 Ruby assisted the producers of a carnival show, "How Hollywood Makes Movies," appearing at the Texas State Fair.366 At about this time Ruby also sought to open a new club in Dallas. He conferred with numerous persons and placed advertisements in Dallas newspapers in an attempt to obtain financial backing.367 Assuming that he would be occupied by the new club, Ruby offered his oldest brother, Hyman, a managerial post at the Carousel. However, Hyman, who had recently lost his sales territory, declined the offer because he felt he was too old for the nightclub business.368