Drucker was born in New York City, New York. He was hired as a referee by the National Basketball Association in 1953. By the early 60's he was regularly officiating two to four games in the NBA Finals each season. In 1969, when the two-year-old American Basketball Association was raiding the NBA for talent, he took the risk, along with three other NBA "lead" referees — Joe Gushue, Earl Strom and John Vanak — and jumped to the financially uncertain ABA. Their contracts were the first multi-year officiating contracts in pro basketball history. Such was Drucker's stature and reputation, that his total salary, as a referee and Supervisor of Officials, along with a $25,000 signing bonus, was more than double the average NBA player's salary. It made him, at that time, the highest paid referee in the history of basketball. Within a year, all other pro basketball officials benefited, as their salaries more than doubled. As a result, officiating professional basketball evolved from a part-time 'second job', to a full-time career, with greatly improved working conditions, benefits and pension plans. It was the first time in history that a league had promoted the quality of its officials which improved the ABA's credibility, and as a by-product enhanced the public's interest in, and respect for referees.
In the ABA, Drucker officiated and also served as the league's Supervisor of Officials. With the ABA-NBA merger in 1976, Drucker was one of only a handful of ABA referees hired by the NBA to return. When he retired after the 1976-77 NBA season to become the NBA's Supervisor of Officials, his 24 consecutive seasons of officiating was the longest string in pro basketball history. It remains the record for longest tenure for a pro referee among those whose entire career was during the era of only two referees per game. During that span he officiated 6 All-Star Games (3 NBA, 3 ABA), a higher total than any other official in pro basketball history other than Mendy Rudolph and Earl Strom both of whom officiated seven. When he retired, his total of 38 NBA and ABA championship round games officiated was the second highest in pro basketball history.
In his 24-year officiating career (17 in the NBA and 7 in the ABA), Drucker was well known for his even-handed officiating for visiting teams in an era when many officials were criticized as "homers" - favoring the home team. In a 1969 interview with Newsday's Stan Isaacs, he said, "I think there is a part of me deep down that enjoys calling a foul against the home team and then standing out there alone, almost defying the cries of the hometown mob."
As a result, assigning Drucker to "big games" was commonplace, and he officiated the deciding game of league championships eight times—four times in the NBA, in 1963, 1965, 1966 and 1968, and four times in the ABA, in 1971, 1972, 1974 and 1976. Of the nearly 400 referees who have officiated in the NBA and ABA, only two others Mendy Rudolph and Joe Crawford have officiated in more deciding games. With a reputation for making "gutty calls" and not "protecting" superstars he holds the distinction of being the only referee ever to eject Wilt Chamberlain from an NBA game, calling three technical fouls on Chamberlain on January 3, 1962. In the late 1950s and early 1960s he was involved in what the press called a heated "feud" with legendary Boston Celtic coach Red Auerbach. His second ejection of Auerbach in a one-month period led to the coach's 3-game suspension by NBA president Maurice Podoloff on November 13, 1961.
Drucker's career gave him a courtside view of key moments of the NBA's first 35 seasons. He was the last active NBA referee to have officiated in 1953-54—the last season before the NBA introduced the 24-second clock. That same season, he was selected to officiate the only regular-season game in NBA history that experimented with rims 12 feet, rather than 10 feet, off the ground. He officiated the games when Bob Pettit scored his 15,000th career point and Wilt Chamberlain scored his 25,000th. He officiated the last game in the history of the ABA—the deciding game 6 of the 1976 ABA Championship Series, the deciding game of the 1963 NBA Finals, Bob Cousy's final game as a Boston Celtic, and the deciding game of the 1966 Finals, Red Auerbach's last game.
Drucker is also the link to referees whose careers span the entire history of the NBA. He partnered on the court with Sid Borgia and Hall of Fame Referee Pat Kennedy whose NBA careers started in the NBA's first season, 1946–47, and as the NBA's Supervisor of Officials, Drucker hired Joe Crawford, who was still officiating during the 2015-16 season.