Is winning the offseason worth it? Depends on the year


George Steinbrenner and the New York Yankees once made a habit of winning the offseason. Not coincidentally, they won a lot of titles, too.

It hasn’t happened since 2009, when splashy signings CC Sabathia and Mark Teixeira helped New York “buy” its 27th World Series championship.

“The Boss” died a year later. Since then, the sport the Yankees once dominated with large expenditures has instead become all about efficiency. While the Bronx Bombers will still run one of baseball’s highest payrolls in 2022, it has been odd to watch New York stand by while this year’s top free agents have gone to the Minnesota Twins (Carlos Correa), Texas Rangers (Corey Seager and Marcus Semien ) and of course, the crosstown Mets (Max Scherzer).

In fact, second-year Mets owner Steve Cohen seems intent on filling the void Steinbrenner left behind as the Big Apple’s biggest spender, willing to pursue a championship at any price.

But what is winning the offseason even worth? To get an idea, here’s a look at clubs who have “won” the offseason since it last worked for the Yankees:



Offseason Winners: Seattle Mariners

World Series Winners: San Francisco Giants

Relieved to have Adrian Beltre’s $64 million, five-year deal off the books — yes, really — Seattle sent a trio of prospects to Philadelphia for 2008 AL Cy Young Award winner Cliff Lee, signed Chone Figgins for $36 million and acquired Milton Bradley from the Cubs. They also locked up ace Félix Hernández on a $78 million, five-year deal. Those Mariners won 61 games — a clean swing and a miss.


Offseason Winners: Boston Red Sox

World Series Winners: St. Louis Cardinals

Boston acquired All-Star slugger Adría González from San Diego for three minor leaguers, including Anthony Rizzo, then signed speedy outfielder Carl Crawford for $142 million. They won 90 games, but the fit wasn’t right, and the Red Sox dumped both players to the Dodgers in August 2012.

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Offseason Winners: Los Angeles Angels

World Series Winners: San Francisco Giants

Several teams made big splashes: Prince Fielder signed with Detroit for $214 million, the Marlins dropped $191 million on free agents Jose Reyes, Mark Buehrle and Heath Bell, and of course, the Angels lured Albert Pujols away from St. Louis for $240 million over 10 years — and added CJ Wilson for $77.5 million. The Angels won 89 games and finished third in the AL West. The Giants, whose top winter add was Melky Cabrera, won the World Series for the second time in four years.


Offseason Winners: Toronto Blue Jays

World Series Winners: Boston Red Sox

Toronto dug deep into its farm system, unloading Noah Syndergaard and several other future big leaguers for Mets ace RA Dickey and Marlins veterans Mark Buehrle, Josh Johnson and Jose Reyes. They also essentially traded manager John Farrell to the Red Sox, who went on to claim the World Series. The Jays, meanwhile, won 74 games.


Offseason Winners: New York Yankees

World Series Winners: San Francisco Giants

Another stab at a signature Steinbrenner offseason. With Derek Jeter entering his final season before retirement, the Yankees signed Masahiro Tanaka from Japan for $155 million, pried Jacoby Ellsbury away from the rival Red Sox for $153 million, convinced Georgia-born Brian McCann to leave Atlanta for $85 million, and also brought in Carlos Beltran. Robinson Cano left for Seattle, but hopes were still high in the Bronx. New York won 84 games and missed the playoffs.


Offseason Winners: Chicago Cubs

World Series Winners: Kansas City Royals

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Washington signed Max Scherzer for $210 million and also acquired minor leaguers Trea Turner and Joe Ross, but the budding Cubbies stole the offseason. President of baseball operations Theo Epstein poached longtime Rays manager Joe Maddon, signed Jon Lester for $155 million and traded for Houston center fielder Dexter Fowler. Chicago won 97 games, but the moves didn’t pay off in a title until a year later.


Offseason Winners: Chicago Cubs

World Series Winners: Chicago Cubs

The Cubs signed Jason Heyward to the winter’s second-biggest deal at $184 million — trailing only David Price’s $217 contract with Boston — and added Ben Zobrist ($56 million) and John Lackey ($32 million). They also traded out talented-but-frustrating shortstop Starlin Castro. It worked, although the homegrown stars were still the biggest contributors. Chicago ended its 108-year title drought on the backs of Anthony Rizzo, Kris Bryant and Javier Báez.


Offseason Winners: Boston Red Sox

World Series Winners: Houston Astros

The Red Sox get a narrow nod here after acquiring ace Chris Sale from the White Sox and reliever Tyler Thornburg from Milwaukee, just ahead of the Mets re-signing Yoenis Cespedes, the Cardinals adding free agents Dexter Fowler and Brett Cecil, and the Dodgers retaining free agents Kenley Jansen, Justin Turner and Rich Hill. Houston also made a decent splash, acquiring McCann from the Yankees and signing Josh Reddick ($52 million) and Beltran ($16 million).


Offseason Winners: New York Yankees

World Series Winners: Boston Red Sox

The Yankees replaced manager Joe Girardi with Aaron Boone, then acquired NL MVP Giancarlo Stanton from the fire-selling Marlins. Stanton had 38 homers and 100 RBIs in his first year, yet Boston won the AL East. The Red Sox were pushed over the top by free agent acquisition JD Martinez ($110 million), along with previous headline acquisitions Price and Sale.

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Offseason Winners: Philadelphia Phillies

World Series Winners: Washington Nationals

San Diego stunned the sport by signing Manny Machado to a $300 million, 10-year deal, but the Phillies still won the winter by adding Bryce Harper, JT Realmuto and Andrew McCutchen. Harper signed a record $330 million, 13-year contract, Realmuto came in a trade from Miami and McCutchen was added for $50 million. Philadelphia won 81 games, then watched its NL East rival — and Harper’s former team — win it all in October.


Offseason Winners: Los Angeles Dodgers

World Series Winners: Los Angeles Dodgers

The Yankees seemed to have made the biggest splash by signing Gerrit Cole to a $324 million deal in December, but then the Dodgers poached 2018 AL MVP Mookie Betts from the Red Sox. It worked perfectly for LA, which hoisted the World Series trophy inside baseball’s COVID-19 bubble that failed.


Offseason Winners: San Diego Padres

World Series Winners: Atlanta Braves

With a lineup headed by Machado and Fernando Tatis Jr., the Padres bolstered their pitching staff by trading for Yu Darvish, Mike Clevinger and Joe Musgrove. They also locked in Tatis with a $340 million, 14-year deal, the longest in baseball history. The Mets and Cohen, in his first year as owner, also made a splash by acquiring Francisco Lindor, Carlos Carrasco and James McCann, but the Braves won the title thanks to a series of trade deadline additions by general manager Alex Anthopoulos.


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George Holan

George Holan is chief editor at Plainsmen Post and has articles published in many notable publications in the last decade.

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