A Look At George Steinbrenner's Big-spending Yankees Moves
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Home Editorials

George Steinbrenner’s big moves that changed American baseball forever

Michael Bennington by Michael Bennington
February 9, 2026
in Editorials, George Steinbrenner, Trades, Yankee Legends
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George Steinbrenner was the first MLB team owner to splash big on players. It set in motion a trend that fans see today as well as made baseball a lucrative and high-paying sport drawing attention off the field. The Yankees under him made the first of many big moves when he signed former Oakland A’s star Catfish Hunter for five years at a then-astronomical price of $3.35 million.

Big spending by the owner helped the Yankees restore their glory. They poached Ed Figueroa and Dock Ellis, who were starting pitchers for the Angels and the Pirates respectively. The lineup also got a boost with Mickey “the Great Gozzlehead” Rivers and Willie Randolph.

George Steinbrenner went all-in by signing former A’s slugger Reggie “Mr. October” Jackson to a five-year, $2.9 million contract, ushering in the turbulent, albeit profitable, Bronx Zoo era. Former Red ace Don Gullett was contracted for six years at $2 million but was forced to spend most of his two years in the Bronx battling arm problems.

Closer Sparky Lyle famously went from Cy Young to Sayonara when the Yankees signed free agent Goose Gossage (6 years, $2.75). George Steinbrenner acquired Andy Messersmith, a star player, from Atlanta for $100,000. He was the ancestor of Carl “American Idle” Pavano, who only played in six games for New because of an injury. Rawly Eastwick, who was a middle reliever, gets a five-year deal worth $1.1 million.

The Yankees, who had won the World Series twice in a row, strengthened their starting pitching by signing medical genius Tommy John for four years and $1.4 million and former Red Sox star Luis Tiant for two years and $875,000. Tiant later said, “It’s great to be with a wiener!” while promoting Yankees Franks.

George Steinbrenner wanted to get back to the World Series for the first time in three years, so the Yankees signed former Padres slugger and All-Star outfielder Dave Winfield to a huge 10-year deal worth $23 million. This big splash showed how much the Yankees were desperate to win. Steinbrenner later called Winfield “Mr. May” because of how badly he played in the postseason, especially in the World Series.

After Boss George Steinbrenner decided to make the Bronx Bombers into the fast Bronx Burners, the Yankees traded with Cincinnati for outfielder Ken Griffey and signed fast former Reds outfielder Dave Collins to a three-year, $2.25 million contract. Griffey and Collins spent most of the season looking for a permanent spot.

The Yankees signed heavyweight slugger Don Baylor for four years for $3.7 million and former Tigers right-fielder Steve Kemp for five years at $5.45 million. They did this to beef up a weak lineup and this paid well.

Phil Niekro, an old knuckleball pitcher, was kicked out of the Braves, where he had lived for a long time, with no warning. George Steinbrenner welcomed him for a two-year, $1.4 million deal. Toby Harrah, a former All-Star defensive end who had three sacks, was traded from Cleveland even though he was past his prime.

Pitcher Ed Whitson, who went on to become manager Billy Martin’s future sparring partner and boo-bird target, signed a $4.25 million contract for five years. The big fish was Rickey Henderson, a master base thief, who was awarded a five-year contract worth $8.6 million.

The Phillies and Pirates traded for starting pitchers Charles Hudson and Rick Rhoden. Doug Drabek, who would become a star pitcher, was sent to Pittsburgh as part of the Rhoden deal.

Another big name George Steinbrenner signed was former Giants hitter Jack Clark, who signed a deal for two years and $3 million. The Yankees also obtained John Candelaria ($700,000 for one year) and Rich Dotson, both of whom are older pitchers who are getting worse (trade with the White Sox).

Steve Sax, a former second-sacker for the Dodgers, was signed for three years and $4 million to replace longtime star, Willie Randolph. This was the biggest deal then. The Yankees also try to strengthen their starting staff by signing Andy Hawkins for three years, $3.6 million and Dave Lapoint to a contract of three years, $2.5 million. Mel Hall, a batter for Moody, comes to the team from Cleveland in a trade during spring training.

The strange starting pitcher Pascual Perez was signed for three years at $5.7 million, and the Mets traded former wunderkind Tim Leary.

When George Steinbrenner couldn’t sign Barry Bonds, the Yankees settled for Danny Tartabull and gave him a deal worth $25.5 million over five years. Mike Gallego, an infielder who was a free agent, got a three-year deal worth $5.1 million.

The Yankees raised the Red Sox’s agony by signing Wade Boggs, the Red Sox’s all-time batting champion, for three years at $11 million. Starting pitcher Jimmy Key had a four-year deal worth $17 million, and the Angels traded for outfielder Paul O’Neill and pitcher Jim Abbott.

John Wetteland, a closer, arrived from Montreal in exchange for Fernando Seguignol, an outfielder. Meanwhile, veteran shortstop Tony Fernandez signed a $3 million deal for two years.

The Mariners traded first baseman Tino Martinez and middle reliever Jeff Nelson to the Yankees. Kenny Rogers, a pitcher, agreed to a contract of four years and $19.5 million.

Temperamental Hideki Irabu, a Japanese pitcher nicknamed George Steinbrenner’s “fat pussy toad,” had a $12.8 million deal for four years. David Wells, a pitcher who was very popular with heavyweight fans, signed a three-year deal worth $13.5 million.

Chuck Knoblauch, an All-Star second baseman, was traded by the Yankees from Minnesota for pitching prospect, Eric Milton, Danny Mota, Brian Buchanan, and Cristian Guzman, all of whom had played in the minor leagues, and $3 million. A four-year deal worth $6.6 million helped George Steinbrenner fetch Cuban defector pitcher Orlando “El Duque” Hernandez.

George Steinbrenner also got five-time Cy Young winner Roger Clemens from the Toronto Blue Jays. This kept up the Yankees’ tradition of getting big names who used to play for the Red Sox. Mike Mussina, a longtime star for the Baltimore Orioles, signed a six-year deal worth $88.5 million to join the starting team.

David Wells, a big pitcher, returned to the Bronx for the second time, signing a three-year deal worth $13.5 million thanks to George Steinbrenner. However, the bigger prize was Jason Giambi, a power hitter who was lured from Oakland with a seven-year deal worth $120 million. Rondell White, an outfielder, joined the team for two years and $10 million, and Robin Ventura, a third baseman, joined for one year and $5 million.

Larry Lucchino, president of the Boston Red Sox, named George Steinbrenner’s Yankees “the Evil Empire.” This was after they signed the highly sought-after Cuban pitcher Jose Contreras for four years and $32 million, and went on to add Japanese superstar hitter Hideki “Godzilla” Matsui for three years and $21 million.

A-Rod and the $179 million left on his record $252 million, the 10-year deal was traded for Alfonso Soriano and a player to be named. Texas agreed to pay the Yankees $67 million of that amount, which was the most cash in a trade in the history of the major leagues then. Jeff Weaver, two prospects, and $3 million were traded for Kevin Brown and his $15 million contract from L.A. Gary Sheffield, a baseball player, had signed a three-year deal worth $36 million.

George Steinbrenner acquired Montreal’s pitcher Javier Vazquez and gave Starter Jon Lieber $4 million for two years, reliever Tom Gordon $7.25 million for two years, and outfielder Kenny Lofton $6 million for one year.

Carl Pavano, a pitcher, got a four-year, $40 million deal but he spent most of the next three years on the disabled list. This was George Steinbrenner’s most fallacious move. Jaret Wright agreed to a three-year contract worth $21 million while Tony Womack signed a two-year deal worth $4 million.

George Steinbrenner went for Johnny Damon, the hero of the World Series, with a four-year, $52 million deal. This makes Boston very angry. The Yankees next awarded Kyle Farnsworth a $17 million, three-year deal because they wanted him to help Mariano Rivera close games.

Kei Igawa, a pitcher who had never pitched before, got a five-year deal worth $20 million making it the high point of George Steinbrenner’s big splashing. Andy Pettitte then had a $16 million deal for one year and a $16 million option for 2008.

Did the big spending of the owner really help the Yankees? Leave your comment below.

(Source: Sports Illustrated)

Tags: George SteinbrennerYankees trade
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