It may be one of sports' ultimate ironies that Steinbrenner was initially against free agency, considering how well he put it to use. He once famously said, "I am dead set against free agency. It can ruin baseball."
He would soon change his mind. In 1974, he signed Catfish Hunter to a $2.85 million salary for four years, a lucrative contract at the time. He signed "Mr. October" Reggie Jackson to a contract after 1976, which spurred the Yankees to back-to-back championships. There were many, many others - some successful, others not so much. He signed Dave Winfield to a record contract of 10 years, $23 million in 1980.
Other signings in the 1980s didn't work out so well. Free agent busts like pitcher Ed Whitson and outfielder Steve Kemp were a big reason that the Yankees didn't win a championship in the 1980s.
However, his open checkbook was a big reason he was named the most powerful man in sports by The Sporting News.