Simon was born in Newark, New Jersey and raised in Irvington, New Jersey. As a teenager, Simon competed at amateur wrestling in YMCAs. Before becoming a professional wrestler, he worked as a truck driver in the Garment District in New York City, New York.
Simon made his professional debut in the mid-1950s as "Larry Simon", wrestling on the independent circuit in the Eastern United States. In 1957, he joined the Dallas, Texas-based promotion Big Time Wrestling under the ring name "Crusher Duggan", winning the NWA Texas Heavyweight Championship later that year.
In September 1961, Simon joined in the Minneapolis, Minnesota-based American Wrestling Association. He adopted the persona of "Otto Von Krupp", a German wrestler who wore jackboots and a swastika on his back. Simon formed a tag team with Bob Geigel, with the duo winning the AWA World Tag Team Championship in November 1961, holding it until Malenko left the promotion in January 1962.
On July 19, 1961, Simon unsuccessfully challenged Buddy Rogers for the NWA World Heavyweight Championship in Jacksonville, Florida.
In 1962, playing upon Cold War tensions, Simon adopted the persona of "Boris Malenko", an agent of the Soviet Union. He was occasionally billed as "The Great Malenko"; a pun, with "Malenko" being Russian for "little", or as "Dr. Malenko" or "Professor Malenko". He built his career in South Florida, where his gimmick made him a hated heel among the Cuban population. Over the next decade, he held the NWA Florida Heavyweight Championship twice, the NWA Florida Tag Team Championship twice, the NWA Southern Heavyweight Championship (Florida version) once, the NWA Southern Tag Team Championship (Florida version) once, and the NWA Brass Knuckles Championship (Florida version) eight times. His main rivals included Eddie Graham, Wahoo McDaniel, Johnny Valentine, Joe Scarpa, and José Lothario. In an angle in 1966, after Malenko bloodied Sammy Steamboat by biting his ear, Eddie Graham stormed the ring and punched Malenko's dentures out of his mouth, then crushed them.
In 1970, Malenko returned to Big Time Wrestling, where he held the NWA American Heavyweight Championship and the NWA Texas Tag Team Championship. He had a heated feud with Wahoo McDaniel, with McDaniel defeating him in a hair versus hair match in July 1970. A bout between the two in the Astrodome set a longstanding attendance record. In December 1970, McDaniel defeated Malenko in a loser leaves town match, marking his departure from the promotion. During his time with Big Time Wrestling he was managed by Lord Charles Montegue.
On May 9, 1972, Malenko and Bob Roop defeated Bearcat Wright and Bobby Shane to win the NWA Florida Tag Team Championship, and six days later, Malenko defeated Wright in singles competition to win his eighth and final Florida Brass Knuckles title in Orlando. On June 24, 1972, Malenko and Johnny Weaver defeated Mike Webster and The Professional for his second run with the Florida Tag Team titles.
Malenko toured Japan with All Japan Pro Wrestling in 1973 and New Japan Pro Wrestling in 1974. During his time with NJPW, Malenko wrestled a number of high-profile bouts with Antonio Inoki.
In the late 1970s, Malenko wrestled for the Knoxville, Tennessee-based promotion Southeastern Championship Wrestling, winning both the NWA Southeastern Heavyweight Championship (Northern Division) and the NWA Southeastern Television Championship in 1978. He became the manager of Jerry Blackwell after it was claimed he had acquired the mortgage to Blackwell's family farm, forcing him to fight on his behalf. The angle ended after Ron Garvin paid off the mortgage, freeing Blackwell to attack Malenko.
Malenko retired in 1979 and opened a training school in Florida with his sons Dean and Joe.
Simon had two sons, Dean and Joe, both of whom became professional wrestlers.
Simon was Jewish.
Simon died in September 1994 from leukemia.Finishing moves
Russian Sickle (Lariat)
Russian Sleeper Hold (Sleeper hold)
Biting the opponent
"The Great Malenko"
"The Mad Russian"
American Wrestling Association
AWA World Tag Team Championship (1 time) - with Bob Geigel
Championship Wrestling from Florida
NWA Brass Knuckles Championship (Florida version) (8 times)
NWA Florida Heavyweight Championship (1 time)
NWA Florida Tag Team Championship (2 times) - with Bob Roop (1 time) and Johnny Walker (1 time)
NWA Southern Heavyweight Championship (Florida version) (1 time)
NWA Southern Tag Team Championship (Florida version) (1 time) - with Johnny Valentine
National Wrestling Alliance
NWA Hall of Fame (Class of 2016)
NWA Big Time Wrestling
NWA American Heavyweight Championship (1 time)
NWA Texas Heavyweight Championship (1 time)
NWA Texas Tag Team Championship (1 time) - with Killer Karl Kox
Southeastern Championship Wrestling
NWA Southeastern Heavyweight Championship (Northern Division) (1 time)
NWA Southeastern Television Championship (1 time)