He was known for his significant role in media industry deals, including enabling the Time Warner merger in 1989 and selling television stations to News Corporation in 2000.
After this unsuccessful bid, he invested in a television program packaging company partially owned by his father-in-law, Isaac D. Levy, a co-founder of CBS.
[3] In 1961, Siegel created a small conglomerate called Baldwin-Montrose through a three-way merger involving the Old Crown Brewing Corporation based in Fort Wayne, Indiana, Montrose Chemical Co., and Baldwin Rubber Co.
In 1962, he purchased General Artists Corporation, a talent agency representing entertainers including Pat Boone, Perry Como, and Jackie Gleason.
[3] In the mid-1980s, Siegel played a crucial role at Warner Communications as a "white knight," helping the company resist a takeover attempt by Rupert Murdoch's News Corporation.
This arrangement created barriers for Murdoch, who was then an Australian citizen, due to federal laws limiting foreign investment in U.S. broadcast licenses.
[3] In 2000, Siegel completed his final major deal, selling Chris-Craft's 10 television stations to Murdoch's News Corporation for $5.3 billion.
The humorist Art Buchwald notably remarked that Siegel deserved an Academy Award for earning the most money in Hollywood without ever making a movie.