As a New Yorker, I’m getting used to see the Yankees fighting for first place. As a New Yorker, I’m naturally stubborn so I keep thinking back to some of the Yankees’ biggest mistakes this century.

Is it right for me to think about decisions made a decade ago that have no effect on me? Probably not, but that’s the territory of being a baseball fan – we think about what went wrong and what we’d have done instead, even though we’d probably have made the team much worse.

So for fun, let’s do that today by reviewing 15 of the Yankees’ biggest mistakes since the calendar turned over to the 21st Century (and reasons why they’ve only won two World Series rings in that time).

There’s a couple of things to keep in mind for this list, the first being that character issues and the contract given to Aroldis Chapman – or even acquiring him in the first place – is not on this list. Some people may view it as a mistake, fine, but I personally don’t. Also, any current contracts that the Yankees are responsible for (i.e. Jacoby Ellsbury) aren’t on here either, though parts of the current Yankees team will be addressed.

In addition, individual games are not a part of this list; that includes the 2004 American League Championship Series, which wasn’t so much a mistake by the Yankees as it was the Red Sox showing heart and hustle. Simply put, these are almost entirely all personnel moves.

Ready to critique Brian Cashman’s moves knowing that we wouldn’t have done much better? Let’s do it.

15. Letting Xavier Nady walk

via bronxbaseballdaily.com

We start off this list with what may seem like a questionable choice, but let’s think about this for a second. After being acquired at the 2008 trade deadline from the Pittsburgh Pirates, Nady slashed .268/.320/.328 with 12 home runs, 40 runs batted in, 11 doubles, and compiled a 1.1 WAR; not the greatest numbers in the world, but Nady brought a level of clutch hitting to the table that had been lacking for the season’s first four months.

Coming into 2009 as the starting right fielder, Nady hit .286 with four doubles in the team’s first seven games before hurting his elbow – and, later, undergoing Tommy John surgery. With Nick Swisher firmly entrenched as the team’s starting right fielder and Hideki Matsui leaving, the Yankees could have easily brought the 31-year old Nady back on an incentive-laden contract to serve as the designated hitter. Instead, they signed Nick Johnson as his replacement, which, as we’ll explain later, failed badly. Nady wasn’t great for the rest of his career, but he was a high-character guy who’d succeeded once before in New York. What gives, Cash?

14. Jose Contreras

Linda Cataffo/New York Daily News

When the Yankees-Red Sox rivalry was a bit more competitive and didn’t simply rely on aging veterans in September games that meant nothing for entertainment, the two actually had some high-profile competitive matches in free agency. Look no further than the Yankees-Red Sox race for Cuban star Jose Contreras, who the Bronx Bombers were hoping would be the second coming of Orlando ‘El Duque’ Hernandez.

El Duque, Conteras was not, though he might have been El Disappointment. Though Conteras was 7-2 with a 3.30 ERA and a 72-30 K-BB ratio in 2003, everything fell apart for the then-32 year-old in 2004 with the Cuban right-hander going 8-5 with a 5.64 before the Yankees shipped him off to the White Sox. Really, the mistake here is Cashman allowing the Red Sox to get the best of him and rushing into a contract, though it did earn the Yankees their Evil Empire nickname.

13. Jorge Posada’s final season

Barton Silverman/The New York Times

When you contribute a lot to an organization and you mean a lot to someone – and they mean a lot to you – you never want to be disrespected. So when the Yankees stripped All-Star and ‘Core Four’ member Jorge Posada of his catching duties following the 2010 season (both as a result of injuries and because Jesus Montero was on the prowl), he had reason to be upset.

Yankees manager Joe Girardi dropping Posada, a mainstay in the middle of the lineup for over a decade, to the nine spot was too much for the All-Star, who withdrew himself from the lineup. Feeling remorseful, Posada would apologize, but the Yankees really messed up by treating a member of the family like he was nothing so quickly. At least they made up a few years down the line when his number #20 was retired in 2015.

12. Making Dave Eiland a scapegoat

Robert Sabo/New York Daily News

Like with Nady, I’m sure that this is a weird one that you probably weren’t expecting, but the Yankees’ treatment of Dave Eiland continues to bother me seven years later. Long story short, Eiland was Ron Guidry’s replacement at pitching coach for Joe Girardi’s first coaching staff in 2008 and won a World Series with the team in 2009, but left the team for close to a month in 2010 and was let go when the team fell to the Texas Rangers in the 2010 ALCS. Yet, the team wouldn’t really comment about why they let Eiland go. Why? Murray Chass, once with the New York Times, had an idea.

“Given the way George Steinbrenner dispatched hitting and pitching coaches if the Yankees didn’t win everything, Dave Eiland’s dismissal as their pitching coach seemed like just another in a decades-long line of such dismissals… The dismissal, as it turns out, stemmed from the 25-day leave of absence Eiland was granted in June. Neither the coach nor the Yankees said why Eiland took the leave other than to say it was to take care of a personal matter.”

Chass hasn’t exactly been correct with all of his theories in the past, but that makes sense. Still, why make Eiland the scapegoat of all people? It comes off as such a confusing decision..

11. Nick Johnson’s return

via pinstripealley.com

We’ve talked at length about Nick Johnson’s Yankees career enough times, especially the second stint, but can we go back to why this deal made no sense? As I mentioned earlier, even with Xavier Nady coming off Tommy John surgery, he’d have been close to ready for Opening Day 2010, so why not bring him back on an incentive-laden contract? Vladimir Guerrero was an option and could hold down the fort for two years, right?

Instead, the Yankees guaranteed $5.5 million to a player that had missed nearly two of the past three seasons and was coming off what could have easily been a fluke season for the Washington Nationals and Florida Marlins. If there’s any positive to this signing – and trust me, this is a positive – it’s that Cashman didn’t simply move Jorge Posada to designated hitter and promote Jesus Montero to the majors at the age of 21.

10. Javier Vazquez…twice

Ron Antonelli/New York Daily News

Fool me once, shame on you. Fool me twice, shame on Brian Cashman for thinking that Javier Vazquez was the answer as the replacement for Joba Chamberlain in the rotation after the 2009 season. There’s no denying that Vazquez, who had gone 15-10 with a 2.87 ERA and a 238-44 K-BB ratio in 219.1 innings for the Atlanta Braves, was coming off a great season, but did he forget what happened in Vazquez’s first stint with the Yankees?

Remember when Vazquez, acquired from the Montreal Expos for Nick Johnson and other prospects, couldn’t handle New York and went 4-5 with a 6.92 ERA after the All-Star Break in 2004? Remember Game 7 of the 2004 ALCS? So why would things work out this time? It shouldn’t surprise you that Vazquez lost his rotation role by May, went 10-10 with a 5.32 ERA, and allowed 32 home runs. Come on, Cash…

9. Over-reliance on prove-it deals

via wikimedia.org

Trust me when I say that I’m all for prove-it deals, which are usually either one-year contracts or multi-year contracts full of incentives (i.e. a pitcher coming off Tommy John will have a team option for the second year; a player off a bad season will have a team option – or an option that kicks in for a certain milestone); I’m actually a huge fan of the idea and the Yankees have had some success in that department – Bartolo Colon revived his career with one and who knows where the Yankees would have been in 2012 if Eric Chavez hadn’t shown enough flashes during his prove-it deal the prior year – but like any good idea, one can’t keep relying on it over and over again.

There have been prove-it deals that have made sense on paper – the Yankees needed a third baseman after Alex Rodriguez went under the knife following the 2012 season and Eduardo Nunez was now the shortstop, so Kevin Youkillis sounded appealing – but Cashman has been too dependent on these contracts in recent memory. Why was Travis Hafner signed after the 2012 season to a one-year deal when they could have acquired a designated hitter through trade? Did Brian Roberts have to be the second baseman after Robinson Cano left for Seattle? Thankfully, Cashman seems to be straying less away from these types of contracts, returning to his roots of buying high in trades.

8. The Tyler Clippard Trade

Adam Hunger-USA TODAY Sports

We can talk all we want about bad trades, but the Yankees trading Tyler Clippard after the 2007 season – not the most recent one where they re-acquired Clipaprd last summer – has to be on here. After going 3-1 with a 6.33 ERA in six starts for the Yankees during the 2007 season, Cashman offloaded the 22-year-old ‘Yankee Clippard’ to the Washington Nationals for Jonathan Albaladejo. You saying ‘who???’ says it all.

I get that Cashman wanted another bullpen arm and may have thought that there was too much depth in the rotation for Clippard to break through, but let me read off some names. Eric Gagne. Troy Percival. Keith Foulke. David Riske. I’ll even raise you Octavio Dotel. Those guys were all available in free agency and could provide something out of the bullpen (on paper, at least) but the Yankees traded a valuable arm for Jonathan Albaladejo. Why?

7. The Kyle Farnsworth Experiment

via theplayerstribune.com

Then again, maybe Cashman was so desperate to add another bullpen arm because of what Kyle Farnsworth did – or didn’t do – from the bullpen in his three years as a member of the Yankees. All things considered, I think Farnsworth is a good guy and I think he was treated pretty badly a few years ago with the Mets, but he was awful in pinstripes. Why would the Yankees offer a mediocre reliever $17 million over three years?

Well, mediocre Farnsworth was, pitching to a 4.33 ERA in 181 games with the Yankees and allowing 72 walks in 170.1 innings before being dealt to the Detroit Tigers at the 2008 trade deadline, And before you ask if the reliever market in 2005 was that bad where Farnsworth got that contract, it pretty much was if you weren’t a closer. What, Billy Wagner was going to pass up on closing so he could be the setup man for Mariano Rivera in the primes of their careers?

6. Not rebuilding earlier

Brad Penner-USA TODAY Sports

On this one, I’m conflicted – and I’m not the only person who feels that way. There’s a belief out there that after the Yankees’ 2012 American League Championship Series loss to the Detroit Tigers, the team should have broken the foundation and began rebuilding; trading Curtis Granderson, letting key free agents walk, testing the waters to see if anyone would take a chance on Alex Rodriguez, etc… The Yankees did let key free agents like Russell Martin, Nick Swisher, and Raul Ibanez walk, but they replaced them with players on prove-it deals.

This leads to an interesting conversation: what if the Yankees simply looked at 2013 (and a couple more seasons) as a rebuild while prospects like Michael Pineda, Aaron Judge (a first-round pick in 2013), Mason Williams, and others developed? One of the common arguments is that if the Yankees hadn’t continued attempting to contend, they wouldn’t have the young stars they have now, but that’s a different conversation for another day. Who knows? Maybe rebuilding earlier would have kept Robinson Cano in pinstripes…

5. Kei Igawa’s contract

via wikimedia.org

I get it. Cashman needed another starter after the 2006 season and it would help to add a left-hander – oh no, I’m not even going to try defending the Kei Igawa deal, which was $20 million over five years…but with a $26 million posting fee. The stats should speak for themselves. 2-4 in sixteen games (thirteen starts) over two years? Bad. Having a 6.66 ERA in those sixteen games with a 53-17 K-BB ratio over 71.2 innings? Even worse. Realizing that Igawa’s career ERA was only below six for just under two innings?

The worst part about all of this is that, in a way, I almost feel bad for Igawa. It’s hard to feel bad for someone who made that much money, sure, but he genuinely seemed like a good kid who couldn’t adjust to a city that never sleeps. At least he’s not Carl Pavano…

4. The Phil Hughes situation

via nj.com

We talk so much about the ‘Joba Rules’ and how conflicted the Yankees were keeping him in the bullpen as opposed to the rotation, but what about Phil Hughes? After struggling as a starter in his first two and a half seasons, the Yankees moved the former first-round pick to the bullpen midway through the 2009 season and saw instant success as Hughes pitched to a 1.40 ERA and a 65-13 K-BB ratio in 51.1 innings out of the pen from June 8 until October 4.

So if I can ask, why wouldn’t the Yankees want to consider that for the 2010 season and beyond? Three starters were essentially guaranteed in C.C. Sabathia, A.J. Burnett, and Andy Pettite – as well as the incoming arrival of Javier Vazquez – so why not keep Hughes in the pen and pursue another starting option? That’s not to say Hughes has been bad as a starter, as he’s gone 75-67 with a 4.46 ERA since returning to the rotation in 2010, but I’d have liked to see him remain a full-time reliever.

3. Not trading for Tim Hudson

Kelley L Cox-USA TODAY Sports

Fine, saying that Hudson would have been the key to winning a World Series sooner may be a bit much, but this was a possibility the Yankees actually considered. After the collapse-that-shall-not-be-spoken-of in 2004, the Yankees needed pitching. Kevin Brown was a liability, Javier Vasquez could at least fetch something on the market, and was Orlando Hernandez really worth bringing back? Instead of Carl Pavano – who, in fairness, was the top prize on the market – or Wright, why not turn to Tim Hudson?

In fact, if not for the Braves suddenly swooping in with a ‘holy grail’ package of Charles Thomas, Dan Meyer and Juan Cruz, reason stands to think the Yankees would have made the deal for Hudson given Oakland’s asking price: a starter who could contribute soon and an outfielder with a bat. All the Yankees probably would have had to offer up was Chien-Ming Wang, Shelley Duncan, and pitching prospect Matt DeSalvo and they’d have had Hudson.

2. The Joba Rules

via nj.com

I know that I’ve talked about this a lot on my own in the past, but here’s what really continues to bother me with the Joba Chamberlain situation. With him being competent in the rotation in 2009 – from June to August, Chamberlain was 6-3 with a 4.58 ERA and a 69-40 K-BB ratio in 88.1 innings, which isn’t by any means good, but it’s not bad for a 24 year old – and struggling in the bullpen in 2010, why not allow him another starting chance either that year or in 2011? Was it really that dangerous?

Nothing is going to diminish Chamberlain’s electric bullpen days from 2007-08, especially in the final two months of his rookie season, but how things ended sucks. This wasn’t so much a mistake as it was a massive mess from all parties.

1. Carl Pavano

AP Photo/Nick Wass

For as much as I’d argue that the idea of not rebuilding earlier should be the winner here…can anything really beat the American Idle? When you get paid nearly 40 million to go 9-8 with a flat 5.00 ERA in 26 starts across four years, I think you pretty much win the title automatically; I’m still asking myself why the Yankees would give Pavano a four-year deal when he only had two winning seasons prior to 2005 — and, yes, his 2004 18-8, 3.00 ERA campaign was impressive — but the guy was not at all worth the money he was paid.

Why, Brian Cashman, did you give this guy a four-year deal? What about his past three or four seasons screamed that he was worth this contract? There is nothing that the Yankees can do in the near-future that will remove this from the top spot.

What do you think the Yankees’ biggest mistakes are this century? Make sure to let us know in the comment section below!

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