Longtime New York Yankees owner George Steinbrenner died this month of a heart attack. He was one of Major League Baseball’s icons from a managerial standpoint. His death shocked the sports world as players and celebrities came to mourn the passing of “The Boss,” arguably the most influential owner in baseball history.

Steinbrenner ruled the Yankees for more than 37 years, mostly with an iron fist. He was both loved and hated as owner, but no one can deny his success and how he built the franchise into one of the most successful in history. His Machiavellian rule forced players to conform to his rules or else they would be traded or let go. One of his more famous decrees was that a Yankee player’s hair could not be longer than the collar of the uniform. First baseman Don Mattingly was ordered to cut back his mullet-like hair back in the ‘80’s. When Mattingly refused to cut it, he was benched. This paved the way for a new hands-on approach to sport ownership.

The Yankee boss did whatever it took to win and knew how to get a return on an investment. In 1973, he bought the team for $10,000,000. Today, the franchise is estimated to be worth more than $1.5 billion. He was notorious for the hiring and firing of his management. He hired and fired 17 managers during his first 17 years as the Yankees owner. Manager Billy Martin alone was hired and fired on five separate occasions. He wasn’t a big fan of free agency when it was introduced but it did bring him Catfish Hunter and Reggie Jackson, which led to World Championships in 1977 and 1978. He was known for some wild dealings, many of which baseball fans thought were unfair since the Yankees are the wealthiest franchise. Those deals went sour in the ‘80’s, the first decade for the franchise without a championship ring since 1910.

In the ‘90’s, he built a dynasty with shortstop Derek Jeter and manager Joe Torre. The Yankees won World Championships in 1996, 1998, 1999, 2000 and 2009. His 37 years at the helm were the longest in club history. Along the way, he earned seven World Series titles and 11 pennants. His persona even had a recurring role on the hit sitcom Seinfeld and was voiced by Larry David.