His career spanned more than seven decades; the events he covered included the sinking of the Andrea Doria in 1956, the assassinations of JFK and Martin Luther King Jr., the Beatles' first trip to the United States, and the attacks on the World Trade Center on 9/11.

[7][1] His father, a dentist, became a professional magician later in life; he got his start in magic by performing tricks to entertain children when he would go to schools to teach them about proper dental care.

[5] Pressman worked for various New York City newspapers after his return from Europe before becoming a reporter in 1954 for what then was NBC's radio station WNBC, and moved over to television in 1956.

But to generations of mayors, governors and ordinary New Yorkers, he was Gabe: the short, rumpled, pushy guy from Channel 4 who seemed always on the scene, elbowing his way to the front and jabbing his microphone in the face of a witness or a big shot.

He was sent by the network to report on many historic events, including the 1956 sinking of the Andrea Doria, Elvis Presley's Army stint which went through Brooklyn, one-on-one interviews with Marilyn Monroe, Harry S. Truman and Fidel Castro, the 1964 arrival of the Beatles at Kennedy Airport, the assassination of Malcolm X, chasing after newly inaugurated New York mayor John Lindsay in the streets during the 1966 transit strike, the 1968 Democratic National Convention in Chicago, where he reported on the clashes between demonstrators and police, and the aftermath of the assassinations of John F. Kennedy, Robert F. Kennedy and Martin Luther King Jr.[2][10] Pressman was a reporter for NBC News at the Woodstock festival in upstate New York in 1969.

[2][10] Pressman has been credited with helping create the New York City institution known as the "perp walk," which was born in the 1970s when he clashed with famed District Attorney Robert Morgenthau over access to filming notable suspects after they had been arrested.

Cullum in Billy Crystal's HBO film 61*, reporting unfavorably on the baseball exploits of Roger Maris (played by Barry Pepper).

[19] Up until the time of his death in June 2017, Pressman still worked part-time at WNBC, mostly as a blog writer about New York City news on the station's website, and he was active on Twitter.

[7] A few months before his death, he covered the 255th annual Saint Patrick's Day Parade in New York, which reportedly was the last time Pressman was on-air.