Well, I turned up all kinds of interesting information about Sidney Kessler. I'll do my best to summarize it here without posting full details on every point.
He was born June 20, 1897 to Polish immigrant parents in New York. I don't find him in early census years, but I do have his have his 1917 WWI draft registration. His mother's name is Yetta. His employer is L.K. Liggett, the drug store, at an address on Broadway in Manhattan.
In 1930, he is in the census at 645 Ocean Ave. in Brooklyn with his wife Frances and daughters Charlotte, age 8, and Louise, 5. His occupation is pharmacist. (Hmm. This is our supposed bootlegger?)
The next records are all from Ancestry's passenger lists database—ship and air manifests documenting more than 30 arrivals in New York from San Juan, Puerto Rico between the years 1936 and 1954. Usually he is traveling alone and carries one or two bags. On several trips he is accompanied by his wife, and on two by Peter Siskind.
The dates of the trips cluster like this: 10 trips between 1936 and 1940; 7 trips between 1944 and 1948; a flurry of 14 trips between February 1950 and April 1952 and then a final trip in September 1954. The trips are by steamship until 1944, after which they are air flights on Pan Am or Eastern Airlines.
Each record includes the passenger's local address. For the early trips, Sidney's home address is the same Ocean Avenue apartment from 1930. In the mid-'40s, he began using 101 Central Park West as his local address. This turns out also to have been the home address of his daughter Charlotte and her husband Henry Kimelman, of whom more later. For the last handful of trips, Sidney is using different hotels for his New York address.
While rich in new detail, this information generally fits what we already knew. Kessler was traveling regularly to Puerto Rico in the second half of the 1930s, presumably establishing distillery operations, arranging product shipment, dealing with officialdom and more. The frequency of his visits falls off during the war years and until the time of the sale of the company in 1946.
I don't know when Kessler first begins spending time during his trips not in Puerto Rico but in nearby St. Thomas, Virgin Islands. San Juan was the gateway city to the eastern Caribbean, so even later when he was shuttling to St. Thomas, he continued to travel through San Juan on the way to New York. I imagine he had come to know the Virgin Islands during his earlier trips and was intrigued with its potential for tourism and development.
After the sale of the liquor business, he decided to go all out for his dream and put together plans to build a grand resort hotel, one of the island's first, near the capital city Charlotte Amalie on St. Thomas. The investors in the project are Kessler, his two sons-in-law Henry Kimelman and Eliot Fishman, and a fourth man Benjamin Bayles. Plans are laid during the trips in 1947 and '48.
Construction begins in 1949 and Kessler is on scene to oversee things throughout 1950, when the hotel opens in mid December. Baseball star Jackie Robinson is on hand for the opening. Then Sidney continues to travel to New York throughout the next year as he moves his family and wraps up business on the mainland. After 1951, he lives in St. Thomas full time.
Before I leave the subject of passenger lists, I want to note there are no visits to the islands prior to the time of his association with American Spirits. He had not done any business involving Puerto Rican rum before 1935, at least none that required travel to Puerto Rico. My point is that so far we see no evidence of his involvement in the liquor business, either legally or not, before then. It doesn't mean he wasn't a bootlegger, not a mild mannered pharmacist, but we don't see it yet.
There is lots of other interesting stuff, however. Most of it has nothing to do with Walter Ruby, but now that we're getting to know Kessler, we might as well flesh him out.
• On January 5, 1930, Joseph Weber, a 31-year-old broker living at at 75 Lenox Road, Brooklyn, poisoned himself after brooding over losses said to have amounted to approximately $100,000 in the stock market. Before he became unconscious, he telephoned to his friend, Sidney Kessler, 645 Ocean Avenue, informing him that he was "very ill" and attempted to administer an antidote to himself. When Kessler arrived, he found his friend in a coma and Weber died at Kings County Hospital.
• In 1943, there was controversy in Congress over Roosevelt Administration policy in Puerto Rico, where there had been some unrest. The Bell subcommittee of the Committee on Insular Affairs conducted hearings on political, economic and social conditions in the U.S. owned commonwealth.
The following exchange from the hearing is between Cong. Fred Crawford (R-Mich) and a witness named Lee D. Miller:
Mr. MILLER: So then I went to see Mr. Bash and Mr. Bash said he was going to see if there was some way he could stop Carioca Rum.
Mr. CRAWFORD. Who is Carioca Rum?
Mr. MILLER. Carioca Rum is a domestic corporation which is wholly owned by the...
Mr. CRAWFORD. Can you give us the names of any individuals connected with them?
Mr. MILLER. The name of Sidney Kessler, the individual who originated the whole deal. You ought to get Moe Goldman up here. He will tell you.
Mr. CRAWFORD. ...I have spoken to Mr. Moe Goldman, who admits that he was the agent, also admitting that he has not the financial background to swing this deal himself. This was said in front of a witness. The shipment of 10000 empty barrels were filled with this residue grain mixture by the "J. Younge Grain Co.," at Peoria, Ill., and the whole scheme was undoubtedly concocted by one Sidney Kessler of Rum...
Intriguing to be sure. To learn more we'd need to get a full copy of the multi-volume committee hearings.
• The Virgin Isle Hotel was a considerable success as Kessler's vision of a Virgin Islands tourism boom came true. On April 18, 1957, just one month after his winning streak on the game show Twenty One had come to an end, Charles Van Doren married Geraldine Ann Bernstein at the Virgin Isle Hotel, and the couple honeymooned there for a week. The bride, a former secretary Van Doren had hired to respond to his fan mail, was a niece of hotel owner Sidney Kessler.
• A Sidney Kessler was involved in a scandal involving an ambassadorial appointment in the Kennedy administration. However, I just now realized that this was a different Sidney Kessler.
* However, we do get into politics next through Kessler son-in-law Henry Kimelman. Kimelman gained wealth via multiple business interests in the Virgin Islands, where he served as the first commissioner of commerce. He became involved in politics in the '60s, served as chief of staff in Stewart Udall's Interior Department, and became a close confidante to Sen. George McGovern of South Dakota.
McGovern was visiting with Kimelman on St. Thomas in December 1969 when news broke of Sen. Edward Kennedy's accident in Chappaquiddick, and it was Kimelman who convinced McGovern that this gave the senator an opening to run for president. Kimelman became the campaign finance chairman and chief fundraiser.
Kimelman's name was on President Richard Nixon's enemies list.
On February 29, 1972, Sidney Kessler was listed among significant contributors to the McGovern campaign. Kessler contributed $1000. Kimelman kicked in $24,000 and a colleague in his West Indies Corporation added $10,000. McGovern lost.
Henry Kimelman served in the Carter admistration as ambassador to Haiti during the regime of dictator Baby Doc Duvalier.
• Sidney Kessler died in St. Thomas at the age of 94 on July 7, 1991. Henry Kimelman passed away in 2009, leaving wife Charlotte Kimelman, three children and seven grandchildren.