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A Historical Look at Yankee Offseason Activity

By Mike Whiteman

November 8, 2021


The offseason has begun, and coming off what has been an unsatisfactory season, Yankee fans are clamoring for big changes, some calling for a complete overhaul.

To get a historical perspective on the franchise’s rebuilding activity, I decided to look at some meaningful Yankee offseasons in the free-agent era. A note – there are some significant Yankee roster moves missing in this post, such as the Dave Winfield free agent signing, and the Roger Clemens and Alex Rodriguez deals. My focus was on winters that represented a significant change in direction or roster composition. Embed from Getty Images


Season: The Yankees returned to prominence after a twelve-year postseason drought, winning the American League pennant. Unfortunately, the team suffered an embarrassing World Series sweep at the hands of the Big Red Machine, the Cincinnati Reds.

Offseason: Free agency was still in its infancy, and smarting from his loss, George Steinbrenner went all-in. He grabbed the Reds’ postseason ace Don Gullett. He then made perhaps his most famous and successful Free-Agent acquisition, Reggie Jackson. The team also traded for the Orioles long-time centerfielder Paul Blair and All-Star shortstop Bucky Dent.

Results: World Series Champions in 1977 and 1978.


Season: Just a disaster. Tragedy (Thurman Munson’s death), injury (Goose Gossage), poor performance, in-season managerial change. After winning the past three AL flags and 1977-78 World Series’, the Yankees finish in fourth place with 89 wins.

Offseason: They traded the silent pillar Chris Chambliss to Toronto for Rick Cerone to fill Munson’s huge shoes, along with starting pitcher Tom Underwood. The brain trust also dealt with Seattle for 25-year-old All-Star centerfielder Ruppert Jones. As usual, Steinbrenner also hit the free agent market, and brought in longtime Astro and lifetime .300 hitter Bob Watson along with swingman Rudy May.

Results: Yankees regain AL East title in 1980, but lose to Kansas City in playoffs.


Season: The Yankees won the AL pennant in the strike shortened season and took a two game to none lead over the Dodgers in the World Series. Then the team lost four straight games and the World Series, prompting the infamous apology to the fans from George Steinbrenner.

Offseason: This was the height of the Steinbrenner lunacy. He felt the team needed more speed and defense, and the ill-fated “Bronx Burners” came about, with Ken Griffey Sr. and Dave Collins added in the offseason and starting pitcher Doyle Alexander joining at the end of Spring Training.

Results: The 1982 season was utter chaos. Collins and Alexander were disasters; Griffey was at least serviceable. The team went through three managers, fell below .500 and to fifth place.


Season: A mediocre 76-86 season.

Offseason: In retrospect, one of the most consequential Yankee offseasons of modern times. Jimmy Key and Wade Boggs came to the team via free agency. Icon Paul O’Neill and pitcher Jim Abbot were imported via trade.

Results: Buck Showalter’s 1993 team was tied for first place in the AL East as late as September 5th. They ran out of steam and finish in second place behind Toronto, but the turning of the corner out of the gloomy 1989-1992 era was complete.

1994 Season: Ended due to work stoppage with the Yankees leading the AL East

Offseason: Beef it up even more – the team picks up former Cy Young Award winner Jack McDowell and elite closer John Wetteland in trades and signs free agent shortstop Tony Fernandez.

Results: On paper the 1995 Yankees looked unbeatable, but they scuffled through the season and were under .500 as late as September 3rd. A furious 20-5 rally pulled the team into the AL Wild Card spot, but they lost to Seattle in the first round of the playoffs.


Season: The Yankees return to the postseason but are dispatched by the Seattle Mariners.

Offseason: In what felt like an overhaul, Kenny Rogers, Dwight Gooden, and Mariano Duncan were signed as free agents. The team dealt for Tino Martinez, Jeff Nelson Joe Girardi, and Tim Raines

Results: 1996 World Series Champions. Beginning of a dynasty.


Season: The Yankees suffered a historic collapse at the hands of the Boston Red Sox, falling in the ALCS after forging a three game to none lead.

Offseason: The weak link was diagnosed as the starting rotation, and the team went all-in to fix it. The Yanks opened their checkbooks for starters Carl Pavano and Jaret Wright, both pitchers with suspect histories but solid 2004 showings. They dealt for future Hall of Famer Randy Johnson to lead the staff. Embed from Getty Images

Results: The trio combined for 26 wins and a 4.41 ERA in 2005. The Yanks won the AL East on the strength of a potent offense and were kicked from the playoffs by the Angels.


Season: The first without postseason since 1993.

Offseason: The checkbooks were wide open, as CC Sabathia, Mark Teixeira and AJ Burnett signed lucrative free agent contracts. Brian Cashman scored under-the-radar trade for outfielder/first baseman Nick Swisher.

Result: 2009 World Series Champions


Season: Injuries, age, and poor performance dropped the Yankees to third place and out of the postseason.

Offseason: The Yankees signed free agents Brian McCann, Jacoby Ellsbury and Carlos Beltran. They imported Masahiro Tanaka from Japan. There’s was of 2009 in the air.

Results: Injuries, age, poor performance once again in 2014. Yanks once again missed the playoffs.

As you can see, some worked out better than others. I do think there are lessons to be learned:

1. Health matters. If a player has a history of injuries, chances are likely that putting on the Pinstripes won’t suddenly change this. Gullett, Wright, Pavano, and Ellsbury all had medical red flags that unfortunately proved to be true.

2. Temperament matters. Not everyone is a good match for the bright lights of New York. McDowell and Johnson particularly had high profile meltdowns; Johnson’s encounter with a cameraman came even before he threw a pitch in Pinstripes. Guys like Alexander, Collins and Pavano were wrong from the start, and thankfully for their careers left New York and again became productive players elsewhere. On the other hand, folks like Jackson, Sabathia, Girardi, Martinez and O’Neill all embraced being a Yankee, and became pillars of successful teams.

3. Take smart risks. Roberto Kelly for Paul O’Neill wasn’t celebrated by Yankee fans in 1992. Dealing Chris Chambliss wasn’t all that popular either. The young players sent for Martinez and Nelson in 1996 was seen at the time as a significant price.

4. Don’t forget complimentary pieces: Swisher and Duncan weren’t picked up to be prime pieces, but both were pushed into more prominent roles by injury and circumstance. Blair’s signing paled in comparison to Jackson’s celebrated addition, but he was an important bench piece for the 1977 World Series winner.

5. Be bold. The Reggie Jackson and CC Sabathia recruitments and signing are well known and historic in nature. The team put on the full court press, leading with the two most valuable Yankee assets – money and tradition. That’s a tough force to resist.

This offseason looks a bit more uncertain than others. Will Hal Steinbrenner constrain Cashman’s spending? What effect will the to be negotiated collective bargaining agreement have on the game’s economics and particularly the wealthier teams, whom MLB has sought to reign in?

What we do know is that the Yankees have as demanding a fan base in the sport, and the Yankee business model isn’t losing, so I suspect there will be plenty of fireworks this offseason.

That being said, winning the offseason doesn’t always translate to wins on the field.


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