Dave Winfield becomes the highest-paid player in the history of sports, when he agrees to a ten-year free-agent deal with the Yankees worth a record $16 million.

Dave Winfield becomes the highest-paid player in the history of sports, when he agrees to a ten-year free-agent deal with the Yankees worth a record $16 million.

Dave Winfield (.276, 20, 87) becomes the highest-paid player in the history of sports, when he agrees to a ten-year free-agent deal with the Yankees worth a record $16 million. After announcing the former Padres outfielder’s deal, team owner George Steinbrenner tells 34 year-old Reggie Jackson (.300, 41, 111) who had been asked his opinion about the acquisition by The Boss and had heartily endorsed the signing, he will not be offered an extended contract when he becomes a free agent at the end of the season because of his age.

Outfielder Ron LeFlore, who hit .257 with 97 stolen bases for the Montreal Expos last season, signs as a free agent with the Chicago White Sox.
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Outfielder Ron LeFlore, who hit .257 with 97 stolen bases for the Montreal Expos last season, signs as a free agent with the Chicago White Sox.

Outfielder Ron LeFlore, who hit .257 with 97 stolen bases for the Montreal Expos last season, signs as a free agent with the Chicago White Sox.

Astros Sign Nolan Ryan: MLB’s Highest-Paid Player in History

Astros Sign Nolan Ryan: MLB’s Highest-Paid Player in History

1979 – The Houston Astros sign free agent pitcher Nolan Ryan. The former California Angels ace and future Hall of Fame member signs a four-year deal worth $4.5 million, making him the highest-paid player in major league history. Ryan also becomes the first player to earn a $1 million annual salary.

After sixteen years with the Cincinnati Reds, Pete Rose signs a four-year, $3.2 million deal with the Phillies

After sixteen years with the Cincinnati Reds, Pete Rose signs a four-year, $3.2 million deal with the Phillies

1978 – After sixteen years with the Cincinnati Reds, Pete Rose signs a four-year, $3.2 million deal with the Phillies. Other teams which pursued “Charlie Hustle” include the Mets, Braves, Pirates and the Royals. The deal temporarily makes Rose the highest-paid athlete in team sports.

In the third annual free agent re-entry draft Pete Rose, Tommy John and Darrell Evans are the biggest names among the eligible players.

In the third annual free agent re-entry draft Pete Rose, Tommy John and Darrell Evans are the biggest names among the eligible players.

1978 – In the third annual free agent re-entry draft held at the the New York Plaza Hotel, Pete Rose, Tommy John and Darrell Evans are the biggest names among the eligible players.

New York Yankees ink free agent outfielder Reggie Jackson
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New York Yankees ink free agent outfielder Reggie Jackson

On November 29, 1976, in perhaps the most celebrated free agent signing ever, the New York Yankees ink outfielder Reggie Jackson. The slugger signs a five-year deal worth $3.5 million. Jackson had listened to offers from the Expos and Orioles, Jackson had played for the Orioles in 1976 after he was traded to them by…

California signs free agent Don Baylor to a six-year, $1.6 million deal

California signs free agent Don Baylor to a six-year, $1.6 million deal. The Austin, Texas native, who played with the A’s last season after being dealt by the Orioles in the Reggie Jackson trade, will become the first Angel to win the MVP Award (1979) until Vladimir Guerrero cops the honor in 2004.