Simon made his professional debut in 1955 as "Larry Simon", wrestling 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 Simon left the promotion in January 1962. In 1962, playing upon
Cold War tensions, Simon adopted the persona of "Boris Malenko", an agent of the
Soviet Union. 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. 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 1980 and opened a training school in Florida with his sons
Dean and
Joe. He died of leukemia in Tampa Florida at age 61 in late 1994. ==Wrestlers trained==