Love them or hate them, the New York Yankees are undoubtedly the most historic and accomplished sports franchise in the United States of America. Their 27 World Series championships are far-and-away the most in baseball. The next closest North American franchise with that many titles? The Montreal Canadiens with 24.

The Yankees have been so dominant for a century because they’ve always known when to make the big moves. Sure, they hand out hundreds of millions consistently to land the big stars, but they’ve also made some trades and signings that appeared minor at the time. Only then did the world learn who these superstars were some time later.

But nobody is perfect, and the Yankees have also made a series of controversial trades and free agent signings. Nonetheless, they’ve been dominant in just about every single decade since they got Babe Ruth. Here’s a look at the 8 best and 7 worst moves in Yankees history.

15. Best: Signing Gary Sheffield

Evan Habeeb-USA TODAY Sports

The New York Yankees have always been heavy spenders, but landing Gary Sheffield to a $39 million contract over three years in 2003. Sheffield was coming off of a 39 home-run season with the Atlanta Braves and was one of baseball’s best pure hitters during his career.

Sheffield’s first season with the Yankees was a massive success — he clubbed 36 home runs, 121 RBI with a .290 batting average with a 3.9 WAR. The Yankees reached the ALCS before their infamous collapse against the Boston Red Sox, after having a 3-0 series lead. Sheffield hit 34 home runs and 123 RBI the following season with a 3.8 WAR, once again helping the Pinstripes win the AL East.

Sheffield was slowed down by injuries in 2006 and was later dealt to the Detroit Tigers, but he contributed significantly at a rather low price during his three years with the Yankees.

14. Worst: Signing Brian McCann

Adam Hunger-USA TODAY Sports

The Yankees appeared to be geniuses for signing the perennial superstar catcher in 2013. Brian McCann was a seven-time All-Star with the Atlanta Braves and among the league’s elite at the position. Brian Cashman signed McCann to a five-year deal worth $85 million, but the Yankees learned to regret it quickly.

In his first season with New York, McCann batted .232 — the second worst average of his career. McCann also posted a 1.8 WAR after posting a wins-above-replacment of 2.0 or better in six different seasons. His .286 OBP was also one of the worst of his career.

2015 was slightly better, as he did club 26 home runs and raised his OBP to .320, but McCann did bat just .232 and struck out 97 times. After another disappointing year in 2016, the Yankees traded him to the Houston Astros. Safe to say the Yankees regret this deal.

13. Best: Trading For Roger Clemens

Joe Camporeale-USA TODAY Sports

Though his career could be stained for his allegations of PED usage, there’s no denying that Roger Clemens made a huge impact in the Bronx. The Toronto Blue Jays traded Clemens to the Yankees in 1999 in a blockbuster deal that sent David Wells the other way. Clemens won 14 games with New York and helped them win the 1999 World Series, adding to the legendary dynasty of the ’90s.

Clemens impressed again in 2000, going 13-8 with a 3.70 ERA and 188 strikeouts. The Yankees would win their third-straight World Series championship. Clemens went 20-3 in 2001 with a 3.51 ERA, capturing his sixth Cy Young Award. The Yankees would win the AL Pennant, but lost to the Arizona Diamondbacks in the World Series.

Clemens then went 30-15 over his next two seasons with New York before joining the Houston Astros. But his ultra-dominance made the Yankees a dynasty, and they didn’t have to give up much to acquire him.

12. Worst: Re-Signing C.C. Sabathia

Adam Hunger-USA TODAY Sports

The Yankees signed C.C. Sabathia to an albatross $161 million contract over seven years in the winter of 2008. Sabathia would emerge as a cornerstone of the Yankees 2009 World Series Championship team — going 19-8 with a 3.37 ERA. Sabathia had the chance to opt out of his contract after the 2011 season to max out on a big deal.

He chose to stay with the Yankees but was given an extra year on his contract worth $25 million plus $25 million more in a vesting option. Sabathia has not been the perennial All-Star pitcher since 2012, and New York has been stuck with a past-his-prime veteran. This doesn’t sit well for the Steinbrenner brothers, who have tried to rebuild the team from within while avoiding the high-spending ways of their later father, George.

Perhaps they should have avoided giving him that mega deal.

11. Best: Trading For Paul O’Neill

Andy Marlin-USA TODAY Sports

Paul O’Neill didn’t seem like a player that would have such a great career in New York to the point of appearing as himself in an episode of Seinfeld. The Cincinnati Reds happily gave him away to the New York Yankees in 1992 in exchange for Roberto Kelly. O’Neill would spend nine seasons in Pinstripes, playing in four All-Star Games and being a cornerstone piece of the Yankees’ four World Series championships — in 1996, 1998, 1999 and 2000.

O’Neill hit 281 home runs, batted .288 and finished with 1,269 hits. He was a cornerstone piece of the Yankees dynasty and played superb defence in right field. He batted .300 or better every year from 1993 to 1998. They got all of that just from having to trade away Kelly. A bargain, indeed.

10. Worst: Signing Carl Pavano

via sportsonearth.com

The Yankees always love spending big money, and Carl Pavano was thrilled to take $39.95 million over four years from the Steinbrenners in 2004. Pavano was coming off of an All-Star season with the Florida Marlins and was a key part of their 2003 World Series Championship team that upset the Yankees.

Pavano’s first year in New York was a disaster, as he went 4-6 with a woeful 4.77 ERA while allowing 17 home runs in just 100 innings pitched. Pavano missed all of 2006 after suffering broken ribs in a car accident.

2007 was also a disappointment for Pavano. His season was cut short after undergoing Tommy John surgery; this came after fellow Yankee pitcher Mike Mussina called him out by saying Pavano had to prove he wanted to stay in New York. He posted a terrible 5.77 ERA in 2008, and the Yankees finally got rid of him when he joined the Cleveland Indians the following season.

9. Best: Trading For Roger Maris

via yarkbarker.com

The city of New York should find a way to honour the Kansas City Athletics, because that franchise happily shipped their star veterans to the Bronx. Take the case of Roger Maris, for example. The Athletics traded him to New York, along with two other players, for Norm Siebern, Hank Bauer, Don Larsen and Marv Throneberry.

Siebern enjoyed a nice tenure in Kansas City, but Maris became an icon in New York. In seven seasons with the Yankees, Maris reached three All-Star Games, won two American League MVPs, the 1960 gold glove and helped the team win the World Series in 1961 and 1962. Maris also posted an incredible 7.3 WAR in 1960 and followed it up with a 6.7 WAR the following season.

Trading away the legendary Don Larsen seemed like a huge risk, but it paid major dividends for the Yankees, who would later retire Maris’ number nine.

8. Worst: Trading Mike Lowell

Steve Mitchell-USA TODAY Sports

The Yankees were never high on the future All-Star, drafting him in the 20th round way back in the 1995 MLB Draft. Four years later, Mike Lowell was traded to the Florida Marlins in exchange for Mark Johnson and Ed Yarnall, who failed to produce in the majors. The Lowell trade would hurt the Yankees in two different ways. First off, we’ll take a look at his stats.

Lowell batted .279 in his career with 223 home runs. He was a four-time All-Star and won the 2005 Gold Glove Award. He was one of baseball’s best third basemen in the 2000s, but New York basically gave him away.

Second, Lowell was a huge part of the Marlins’ 2003 World Series-winning team, who defeated none other than the Yankees. Secondly, Lowell was a part of the rival Boston Red Sox 2007 World Series team — another reminder that New York paid the price for giving up on his talents so early.

7. Best: Trading For Alex Rodriguez

Adam Hunger-USA TODAY Sports

Talk to a ton of New York Yankees fans, and a handful of them are sure to tell you they didn’t like him, respect him and wish they never traded for him. Alex Rodriguez made himself one of the most despised players ever with his greed, arrogance, PED usage and inability to come through in the postseason. That being said, A-Rod was the cornerstone of the Yankees from 2004 to 2012, whether fans want to know it or not.

In the Bronx, Rodriguez won the 2005 and 2007 American League MVPs, won three Silver Slugger Award, reached seven All-Star Games and led the AL in home runs twice. He sits sixth all-time in home runs for Yankees with 351. A-Rod was also a huge part of the Yankees’ 2009 World Series-winning team.

No matter how controversial he was and how much you may hate A-Rod, he was a mega star for the Yankees. No way they win that 27th championship without him.

6. Worst: Signing A.J. Burnett

Kim Klement-USA TODAY Sports

A.J. Burnett enjoyed an up-and-down three seasons with the Toronto Blue Jays from 2005 to 2007. He opted out of his contract and signed a lucrative five-year deal worth $82.5 million with the Yankees in 2008. Though New York would win a World Series the following year, Burnett A) didn’t have much to contribute and B) Made the team regret that deal many years later.

His first season there wasn’t so awful, as Burnett went 13-9 with a 4.04 ERA. In his second season with the Yankees, Burnett went 10-15 with a woeful 5.26 ERA — far and away the worst of his career. Burnett struggled once again in 2011, going 11-11 with a terrible 5.15 ERA. Burnett was then traded to the Pittsburgh Pirates, ending a disastrous three season tenure with the Yankees.

5. Best: Signing Reggie Jackson

Andy Marlin-USA TODAY Sports

Though the general consensus among sports fans today is that athletes are ridiculously overpaid. Really, David Price makes five figures per pitch thrown?! But you can say Reggie Jackson was vastly underpaid when the Yankees signed him in 1976 to a five-year contract worth $2.96 million. That $2.96 million in 1976 is worth around $12.5 million today. The Yankees would live to wish they probably paid the man more.

Jackson was a five-time All-Star with the Yankees. He won two World Series championships with New York (in 1977 and 1978). Jackson is best remembered for hitting three home runs in Game 6 of the 1977 World Series, clinching the Commissioner’s Trophy for the Pinstripes. Jackson was so clutch in the playoffs that he earned the iconic nickname of ‘Mr. October.”

The Yankees got all of that for $2.96 million, in case we didn’t mention that.

4. Worst: Trading Tommy Holmes

via en.wikipedia.org

The Yankees already had a loaded outfield that consisted of the great Joe DiMaggio and a pair of other stars in Tommy Henrich and Charlie Keller. Despite so much promise in Tommy Holmes, the Yankees chose not to make room for him and traded him to the Boston Braves before the 1942 season.

Holmes managed to bat .302 in an 11-year career with 88 home runs and 581 RBI. Holmes was an All-Star in 1945 and 1948 and led the National League in homers once. The Yankees didn’t live to regret the Holmes trade too much, since they had dynasties in the ’40s and ’50s. But you can always wonder how many more championships they would have won if they kept Holmes, or even got more for him in the deal.

3. Best: Signing Mariano Rivera

Rich Shultz-Pool Photo via USA TODAY Sports

652 career saves, 13 All-Star appearances, five World Series championships, one-time World Series MVP, a number 42 retired and one of the most unhittable pitches of all time — Mariano Rivera’s cutter.

The Yankees got the all-time leader in saves plus the best reliever in MLB history at a major bargain of a price. Despite not showing so much promise early on, New York signed him in 1990 to a cheap contract that included a bonus that is worth just north of $4,800 in today’s dollars. Rivera became a huge part of the Yankees success for 19 years and was reliable almost every big game (save for Game 7 of the 2001 World Series and the 2004 ALCS). Nobody at the time thought the signing of Rivera was a big deal, but the best reliever in baseball history made every other team regret not taking a chance on him when he was young.

2. Worst: Trading Fred McGriff

Jonathan Dyer-USA TODAY Sports

The Blue Jays gave away Roger Clemons in 1999 to the Yankees, but it was a nice thank-you gift since the Yankees had sent Fred McGriff north of the border for relatively nothing 18 years earlier. McGriff wasn’t part of the Toronto Blue Jays’ 1992 and 1993 championship teams, but he was sent in a package deal that brought over legends Joe Carter and Roberto Alomar. So technically, McGriff did help the Jays win two titleS!

But the man was a superstar himself. McGriff racked up a career .284 batting average, 2,490 hits, 493 home runs and 1,550 hits. He was a five-time All-Star, three-time Silver Slugger Award winner and won the 1995 World Series with the Braves. The Yankees gave up on McGriff way too early and it’s the worst move in franchise history.

1. Best: Trading For Babe Ruth

via thesportpost.com

Considering Babe Ruth is the greatest baseball player of all-time, this was an easy choice for number one. Boston Red Sox owner Harry Frazee was in a financial hole and sold The Great Bambino to the rival New York Yankees in 1919 for $100,000. That dough bought the Red Sox 86 years without a World Series championship. It helped the Yankees become the most iconic and successful franchise in American sports.

Ruth’s 714 home runs are the third-most all-time, and most of his career 2,873 hits, 2,213 RBI and large portion of his .342 batting average came with New York. Ruth helped New York win four World Series championships and put them on the path of all-around greatness. The Yankees kept finding ways to bring in more legends like Lou Gehrig, Mickey Mantle, Yogi Berra and Joe DiMaggio after Ruth left. The best hitter of all-time turned baseball, the Yankees and America forever.

All of that for $100,000.

  • Ad Free Browsing
  • Over 10,000 Videos!
  • All in 1 Access
  • Join For Free!
GO PREMIUM WITH THESPORTSTER
Go Premium!

Videos