This is one of those stories in radio that seems a bit too strange. But on the face of it, numerous other public figures, and even politicians have owned media outlets. So maybe it's not that improbable that once, in the history of the CIA, a known spook happened to also buy WINS-AM in New York City in 1953.
Let's start before he was in the CIA. Lt. Col. John Elroy McCaw was from from Aberdeen, WA. He founded the first radio station in Centralia, WA; KELA-AM, in 1937 and owned the Lewis and Clark Hotel where it was originally housed. Years later McCaw also bought station KYA (with John D. Keating) in San Francisco, KPOA in Hawaii [SOURCE] and WINS in New York. It appears that most of his large acquisitions involved Keating and/or Charles Skouras. His company in that acquisition was Gotham Broadcasting Corporation. In the book Big Deal: Mergers and Acquisitions in the Digital Age author Bruce Wasserstein praises McCaw's work but not his paperwork, calling him a "freewheeling entrepreneur." One of his wife's obituaries refers to his "his handshake deals." But he was very successful despite that undercurrent of chaos. I'll quote Wasserstein:
"He converted New York station WINS to the country's first rock station in the middle 1950s, and within 9 years flipped the station for twenty times more than he had paid. At his height, Elroy McCaw owned interests in dozens of radio, television and cable television companies."His wife Marion was no slouch either. After the end of WWII she started her own radio station KAPA-AM in Raymond, WA. None of this mentions that he had another job. It's not the kind of job you put on your resume, and not the kind of job where you can always tell people what you did at work today. Information is scant. But we know that the Office of Strategic Services (OSS) was formed at least officially in 1942 by President Roosevelt. Lacking cooperation from existing U.S. agencies, early agents were trained by the British. President Truman dissolved the department in 1945, but it's functions were divided between the War Department and the State Department. By the end of the year the term "Central Intelligence Agency" was appearing on documents to describe the collection of intelligence groups, and by 1947 it was official. He has no entry in Wikipedia except in the biographies of his now wealthy heirs. But one of his wife's obituaries get's into the details. [SOURCE].
Throughout the war, she [Marion] commuted from Washington D.C. when necessary while Elroy served at Army Air Forces Headquarters in the Pentagon as Executive Officer and Special Assistant to General McClelland, head of USAAF communications. He was also McClelland’s liaison to OSS.His exact involvement as you expect, is unknown. I've never filed a FOIA request and I don't intend to. But I have to admit I'm curious. Many businessmen served in the military during wartime— notably Robert S. McNamara who left Harvard to serve in WWI, then left Ford to serve as Secretary of Defense under Kennedy. Very few figures would be so high profile. An issue of the The O.S.S. Society seems to bear a note from son Bruce McCaw looking for more information from retired OSS members about his fathers life. (The operations referred to involve radio controlled ships.)
"My father, Lt. Col. John Elroy McCaw, worked on OSS Special Projects known as operations Aphrodite, Simmons, and Javaman. He worked with OSSers John Shaheen and Jim Rand and is particularly interested in Javaman, which called for blowing up the tunnel connecting Kyushu and Honshu prior to the invasion of Japan.”Another obituary of notes that the family moved to Seattle in 1953. Several sources note that he died in 1969 suddenly, after a brief illness. The cause is never listed but it's clear that his finances were in disarray due to his informal business practices. When his estate was cleaned up, all that remained was a single cable company with fewer than 30,00 subscribers. His sons built that up and bought heavily into cell networks, then sold out to AT&T. Today most of them are listed by Forbes. More here.