December 15, 1980 – Continuing his trend of signing the biggest free agent stars on the market, George Steinbrenner and the Yankees make Dave Winfield the richest player in baseball when they signed him to a deal that ended up being worth $23 million over 10 years.
Initially happy with the deal, Steinbrenner grew furious with Winfield when he realized that the deal had a clause that caused it to increase over the life of the deal from $16 million to what turned out to be $23 million. That eventually led to Steinbrenner being “banned for life” from running the Yankees after he hired Howie Spira, a known gambler with mob connections to dig up dirt on Winfield.
When Steinbrenner had to step away from baseball he hired Gene “Stick” Michael to run the team as the GM. Under Michael the Yankees focused themselves on developing young players and he made important free agent signings of Wade Boggs and Jimmy Key. Developing prospects also meant being smart with them as he was when he traded the 28-year-old Roberto Kelly for the 30-year-old Paul O’Neill.
So in a way, it was this day 29 years ago that started the dominoes falling that eventually lead to the Yankees dynasty of the 1990’s.