The New York Yankees are not accustomed to missing the playoffs, let alone missing them in consecutive seasons. The last time that happened was in 1993.

The Yankees are in danger of missing the postseason for the second straight year, and it is entirely likely heads will roll again.

The first candidate on the chopping block: Brian Cashman, the team’s general manager since 1998. Cashman has four World Series trophies on his resume, and his contract has not been extended beyond this season.

Not helping that speculation: Principal owner Hal Steinbrenner had the opportunity to back his GM at the owners meetings earlier this month but instead played the wait-and-see card.

“We’ll be talking about that soon enough,” Steinbrenner told reporters. “You know me. We’ve got enough things to worry about during the season.”

In other words, he won’t discuss Cashman’s situation until he knows the team’s final standing. The Yanks currently sit 7.5 games out of first place in the American League East and 3.5 out of the second wild-card spot with two teams ahead of them.

Cashman has always gotten the clamps put to him as the Yankees GM but sometimes unfairly simply because his organization allows him to spend the most money. Expectations are always a World Series title in the Bronx, but with other front offices utilizing resources as wisely as ever, Cashman’s seemingly endless reserve of cash just don’t buy what it did in the past.

The rich teams have found less and less success by trying to outspend others, and predicting success based on alphabetical order works just as well as predicting based on dollars dished out, according to Brian MacPherson of the Providence Journal

Cashman and the Yankees are the poster boys for that lately. After an offseason of going back on their word about trimming payroll, the Yankees spent big on free agents to the tune of $471 million.

Jacoby Ellsbury, Masahiro Tanaka, Carlos Beltran, Brian McCann, Hiroki Kuroda, Brian Roberts, Kelly Johnson, Brendan Ryan and Matt Thornton are what that money bought, and aside from Ellsbury and Tanaka, who has been on the disabled list since July 8, there hasn’t been a good return on the investments. Johnson, Roberts and Thornton aren’t even on the team anymore, and the seven-year Ellsbury contract could end up looking terrible if a decline cements itself within the next couple years.

Noticeably absent from that list of players signed last offseason is Robinson Cano, the second baseman who spent his entire career in Yankee pinstripes before heading to Seattle to become an MVP candidate and possibly help that franchise into the postseason this year. Cashman didn’t seem overly interested in pursuing Cano most of last winter, saying time and again that the team was “more engaged with others.” Cano eventually signed with the Mariners for 10 years and $240 million. If that was Cano’s asking price all along, Cashman was wise to not hand it to him on the wrong side of 30 years old.

Still, it doesn’t reflect well on Cashman that Cano is having success while his acquisitions are gone, ineffective or injured. That’s not the lasting impression you want to leave come October without a contract for the next season.

So Cashman got to work in July. The primary goal was to save the Yankees’ floundering season, and secondly, his job security.

On July 6, with the Yankees 4.5 games out of the division lead and 4.5 out of the second wild-card berth, Cashman made his first shrewd trade. He picked up Brandon McCarthy from the Arizona Diamondbacks in what looked like a desperation move considering McCarthy was 3-10 with a 5.01 ERA at the time. But since getting to New York, McCarthy has gone 5-3 with a 2.47 ERA and 56 strikeouts against nine walks.

Two weeks later, Cashman completed a two-year pursuit of San Diego Padres third baseman Chase Headley. Since that trade, Headley has given the Yankees Gold Glove-caliber defense and a .341 on-base percentage.

“I have more work to do,” Cashman told Wallace Matthews of the day of the Headley trade. “I’m going to still continue to try to improve on what we have.” 

He lived up to that statement. In the final minutes of the non-waiver deadline, Cashman acquired Martin Prado from the Diamondbacks. 

Prado has hit seven doubles and four home runs for the club and is hitting .375/.388/.688 with a 1.075 OPS and three of those homers over his last 12 games. He has also played four different positions and is credited with giving the clubhouse a newfound life

This trio of trades has helped the Yankees slightly in the standings, but they are still on the outside looking in at the playoff picture. Cashman did what he could, but the Yankees still have so many other flaws to overcome, some of them Cashman’s doing in previous years. It is unlikely they can upend two more teams to find a berth.

Ultimately, the marquee, high-priced players are the last ones to pay the price when things like this happen. And since manager Joe Girardi signed a contract extension last winter, and since Cashman does not have a deal in place for the next one, failing to RSVP for the playoffs for a second consecutive year could mean the end of his era with the Yankees.

Anthony Witrado covers Major League Baseball for Bleacher Report. He spent the previous 3 seasons as the national baseball columnist at Sporting News, and four years before that as the Brewers beat writer for The Milwaukee Journal Sentinel. Follow Anthony on Twitter @awitrado and talk baseball here. 

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