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Future Hall of Fame shortstop Derek Jeter is one of the greatest New York Yankees of all time and a seemingly bulletproof figure in the Bronx, but that didn’t stop Yankees general manager Brian Cashman from being brutally honest with the Captain in 2010.

According to Ryan Hatch of NJ.com, a profile piece on Cashman by Sports Illustrated‘s S.L. Price revealed that the GM was very frank with No. 2 during 2010 contract negotiations, as he told him he would rather have then-Colorado Rockies shortstop Troy Tulowitzki when prodded by Jeter.

Cashman also proclaimed: “We’re not paying extra money for popularity. We’re paying for performance.” The two sides ultimately reached terms on a three-year deal.

While Jeter went on to play four more seasons for the Bronx Bombers, including three All-Star campaigns, Cashman wasn’t exactly off-base in terms of anointing Tulowitzki. The current Toronto Blue Jays star was just 26 years old at the time of the conversation, and he went on to have a career year in 2011 to the tune of a .302 batting average, 30 home runs and 105 RBI.

Tulowitzki is still one of the best shortstops in the game to this day, while Jeter retired at the conclusion of the 2014 season.

Cashman’s bluntness is somewhat understandable in hindsight since he was trying to get the upper hand in negotiations, but his brutal honesty very well could have rubbed Jeter the wrong way, and it may do the same to Jeter-worshiping fans who are catching wind of the story five years later.

Despite the fact that Cashman and Jeter had an up-and-down relationship at times, per Price (h/t Hatch), the GM called the Captain “the greatest player I will have ever had.”

Jeter is a five-time World Series champion, a former World Series MVP and a 14-time All-Star, which cements his status as one of the best to ever put on a pair of cleats.

Cashman’s comments regarding Tulowitzki speak to the fact that baseball can be a cutthroat business, but it doesn’t detract from what Jeter accomplished during his 20-year career and how much he has always meant to the Yankees organization.

Follow @MikeChiari on Twitter. 

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The MLB clubs that consistently make October runs don’t just have stars on the diamond and master button-pressers in the dugout, they also have savvy general managers calling the shots in the front office.

From Brian Cashman in the Bronx to Billy Beane and Brian Sabean on opposite sides of the Bay, there are all sorts of top-flight execs around the league.

As the 2015 season approaches, now is the perfect time to sift through the array of candidates and build a list of the best of the best. In the process of constructing the top 10, a variety of factors were taken into consideration. Here are the four most important:

1. The number of World Series titles—after all, that’s what it’s all about
2. The number of playoff appearances
3. The GMs’ track record on the trade block, the free-agent front and in the draft
4. The Payroll Limitation Factor

That final bullet point requires a bit of explaining. Baseball is not an even playing field—not even close. Last year, the Los Angeles Dodgers opened up the season with a $229 million payroll, while the Miami Marlins fell at the opposite side of the spectrum with just under $46 million in commitments.

The idea of the “Payroll Limitation Factor” is to take that drastic disparity into consideration in the ranking process. Each GM gets a score from zero to five, with zero representing no limitations and five representing the most. As a result, the GMs are graded on the basis of what they’ve accomplished with the means available.

Cashman, Beane and Sabean all end up near the top of the list, but none of them claims the distinction of the No. 1 spot.

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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 ESPNNewYork.com 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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When the New York Yankees drafted Derek Jeter in 1992, the 18-year-old shortstop entered an organization with a cloudy future. Over two decades later—through no fault of his own—he’ll exit New York with the Yankees staring down an uncomfortably similar fate.

During Jeter’s reign in the Bronx, the Yankees dominated the sport. Led by a resurgent farm system, the core of a dynasty was erected in the mid-’90s.

Despite experiencing October failure throughout most of the 2000s, no franchise has been more successful since the day Derek Jeter became the shortstop in New York.

Despite the cloudy future that hovered over the Yankees when Jeter was drafted, the outlook changed quickly and swiftly thanks to factors such as Gene Michael reviving the farm system, Buck Showalter nurturing young, ascending talents like Bernie Williams, Mariano Rivera and Andy Pettitte, Joe Torre arriving as manager and George Steinbrenner‘s hefty wallet.

As with any franchise, times change.

Jeter is still around, but the faces and symbols of his most successful years are long gone.

From Steinbrenner‘s death to Torre’s awkward parting to age and attrition breaking apart a dynastic core, the Yankees changed considerably as Jeter transitioned from superstar to solid contributor.

Now, as Jeter embarks on his farewell tour in 2014, the future of the organization is as murky as it was the day the all-time-great shortstop arrived. 

In fact, due to a win-now edict, poor farm system and imperfect leadership options, projecting how the Yankees will look over the next five years—both aesthetically and in the win column—is a fool’s errand. 

If the post-Jeter future in the Bronx were up to some Yankees fans, a rebuilding effort would commence in 2015 and beyond.

Due to the immense pressure to win a World Series every single season, the Yankees won’t allow themselves to traverse down that type of path. That was proven this winter when the team blew past their self-imposed $189 million salary cap in order to procure talent to reach the postseason.

On the surface, signing Jacoby Ellsbury, Brian McCann and Masahiro Tanaka to lucrative, long-term deals is a great way to improve a team that limped to an 85-win finish last summer.

Yet, without some help from the farm system, the Yankees will be unable to field a consistent winner over the next five years.

Unfortunately for a franchise that built a dynasty based on homegrown talent, impact players are not on the horizon for 2014 or the foreseeable future. During a three-part series on the Yankees farm system, Andrew Marchand and Wallace Matthews of ESPN New York took a look at the issues surrounding New York’s inability to produce stars. 

When asked about the state of the system, Brian Cashman was blunt in his assessment.

“It’s not as good as we need it to be in terms of results,” Brian Cashman said. “There are a number of reasons behind that. At the end of the day, we’ve had some misses, without a doubt. We’ve had some guys who didn’t make their projections, who failed to cross the finish line. So basically it’s fair to criticize where we’re currently sitting.”

Unless you believe in Michael Pineda’s shoulder, Manny Banuelos‘ elbow or J.R. Murphy’s catching ability, the Yankees are going to have to spend in free agency to replace Jeter and the rest of their aging roster over the next few years.

While money is rarely an object for this franchise, the long-term payroll sheet is far from clean. In 2015, the Yankees already owe over $148 million to nine players—including a mind-boggling $22 million to Alex Rodriguez, per Cot’s Baseball Contracts. 

Eventually, money will come off the books and new stars will arrive, welcomed to New York with glitz and glamour.

The team will only have $86.1 million on the books when the 2016 season concludes. As Chris Cwik of Sports on Earth points out in this free-agent primer, that winter’s class of available stars could include both Giancarlo Stanton and Stephen Strasburg.

Regardless of the cost, the Yankees will find talent. A fertile farm system could sustain success for much less money, but the team doesn’t have that luxury right now.

Beyond procuring talent in the years after Jeter’s retirement, a major leadership void could emanate in the Bronx.

Jeter’s captaincy has been a constant for the Yankees for years, but the veterans surrounding him—from Jorge Posada to Mariano Rivera to Andy Pettitte—all shared a similar trait: They came through the system. 

Prior to this winter, Robinson Cano was the logical choice to be the next leader of the Yankees. Not only was the star second baseman great; he was a Yankee from the day he arrived in America. Upon signing a $240 million contract to play in Seattle, Cano’s opportunity to become Jeter’s heir apparent in the clubhouse disappeared. 

Now, for the first time in a long time, the next Yankees leader will likely be a mercenary. Yes, a former free-agent signing must ascend to the throne of clubhouse enforcer. This winter, Brian McCann arrived in New York with a reputation as a fiery leader from his days in Atlanta.  

Owner Hal Steinbrenner didn’t mince words about McCann’s best traits, per Daniel Barbarisi of The Wall Street Journal.

“He’s a very smart guy, and he knows that this is Derek Jeter’s clubhouse,” said Steinbrenner. “And he’s said that. But I think naturally he’s a leader, and that comes out. It’s just a matter of time.”

Steinbrenner may be right about McCann, but another catcher actually represents the best in-house option for the transition away from Derek Jeter’s captaincy.  

According to Joel Sherman of the New York Post, manager Joe Girardi, a former catcher and teammate of Derek Jeter, is the bridge that will link this era of Yankee baseball to the next successful run. 

“Thus, even in Jeter’s farewell tour, Girardi becomes more important than ever. For in 2014 and beyond, he will be the link to this recent glorious past, the one most responsible for maintaining the Yankee Way. He must keep the standards and win totals high,” Sherman writes.

Sherman, while undoubtedly correct, stumbles upon some of the future issues within this organization.

Girardi, a legitimately excellent manager, is the bridge to that gap and deserves to be given power within the club. Yet, the team needs an on-field leader to emerge in order to sustain long-term success.

In a perfect world, that leader will be cultivated through the farm system, nurtured by Girardi and allowed to flourish on the field and in the clubhouse.

That formula—great organization, excellent manager, history of stars—was perfected by the St. Louis Cardinals. As Albert Pujols’ reign ended, Yadier Molina’s began. Both learned under the tutelage of Tony La Russa.  

The Yankees aren’t the Cardinals. If they were, Jeter’s departure would just be a grand farewell on the path to bigger and better things.

In this case, it’s not. When Derek Jeter retires, an organizational shock could overtake the Bronx. Not only will the Yankees need to replace a shortstop; they’ll need to carve a new identity and rethink a long-term plan for success.

Brian Cashman and Joe Girardi, much like Gene Michael and Buck Showalter in the early ’90s, are smart enough to navigate through this transition. Now comes the hard part: actually doing it. 

Will the Yankees struggle without Derek Jeter? 

Comment, follow me on Twitter or “like” my Facebook page to talk about all things baseball. 

Statistics courtesy of Baseball-Reference and FanGraphs, unless otherwise noted. All contract figures courtesy of Cot’s Baseball Contracts.

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It’s not official yet, but the careers of Mariano Rivera and Andy Pettitte, much like the former Yankee Stadium, will come to a close on a note as anticlimatic as can be. For only the second time in the wild-card era, the New York Yankees will not make the postseason.

Every team goes through its highs and lows, some longer than others, and the Yankees have dominated baseball since the 1994 strike: 17 playoff appearances in 19 seasons, 13 American League East division titles, seven American League pennants and five World Series championships.

But as inevitable as a decline was, the Yankees can only blame themselves for missing the playoffs this year; the front office made horrible moves in the offseason and the team blew a huge chance to get back in the playoff picture. Yes, the Yanks were cursed with injuries this year, but if they made the right moves and built on the momentum they had a few weeks ago they’d be looking at a playoff berth.

Going into the offseason already knowing Derek Jeter and Alex Rodriguez would be out for a long period of time, GM Brian Cashman and the Yankees staff had upgrades to the left side of the infield at the very top of their wish list. As Russell Martin was a free agent and the Yankees’ top catching prospects were not ready at the time, they also needed help behind the dish.

Cashman had to act on a predetermined budget from the Steinbrenner brothers, as they wanted to cut payroll to $189 million for the 2014 season. With their options limited, they decided to go with Eduardo Nunez (career .683 OPS in 783 plate appearances) and paid Kevin Youkilis $12 million as well as spending $2 million for Travis Hafner. Both players had an extensive injury history.

In the outfield, they decided to bring back a 39-year-old Ichiro, giving him $13 million for two years. They let Martin walk and sign with Pittsburgh for a reasonable two-year deal worth $17 million. Instead of responding by signing another free agent catcher like Mike Napoli, A.J. Pierzynski or David Ross, they decided to go into the season having Francisco Cervelli and journeyman Chris Stewart share the duties.

When spring training hit, more disaster occurred.

CF Curtis Granderson and 1B Mark Teixeira suffered freak injuries and were put on the disabled list for the first few months of the year. Desperate, the Yankees signed Lyle Overbay to play first and traded for washed-up OF Vernon Wells, having to pay the latter $14 million until the end of 2014, a move I absolutely ripped to shreds the moment it happened.

Thanks to a plague of injuries and horrible moves by Cashman, the Yankees began the season with only Robinson Cano and Brett Gardner as returning starters and potential black holes at catcher, 1B, SS, 3B, LF, and RF, and DH, probably their worst lineup in 20 years. But the team played very well through the first two months of the year, starting 30-18 thanks to stellar pitching and timely hitting.

That didn’t last long, as Wells and Overbay predictably turned into pumpkins and Youkilis and Hafner got hurt and missed pretty much all of the second half. Surprisingly, even CC Sabathia struggled this season. At the deadline, the Yankees brought back Alfonso Soriano, and he was arguably the biggest reason why the Yankees didn’t fall out of the chase.

After hitting rock bottom in Chicago, the Yankees were only one game over .500 and seven games out of a playoff spot. Still, they proved resilient, as they went off on a 22-12 run, capped by a 3-1 series victory over the Orioles at Camden Yards to climb within a single game of the wild-card spot. However, they were unable to build on that momentum, losing three out of four at home against the Red Sox in the most excruciating way possible two weeks ago, getting swept at Fenway last week, and losing two out of three to the woeful Blue Jays this week, all but killing their chances of baseball in October.

Despite all the injuries, underachieving by Sabathia and others and awful signings like Wells and Hafner, the Yankees still had a chance this season, especially this month. They blew it, not because they weren’t good enough, but because they underachieved and were poorly prepared to begin with.

The blame not only goes on the players, but also the front office for making poor moves in the winter.

Instead of sticking to the budget and making smart moves like bringing back Russell Martin, getting AJ Pierzynski on a reasonable deal or bringing in a Nate Schierholtz, they went with putting out Chris Stewart as the everyday catcher, acquired aged names like Vernon Wells and Ichiro and even overpaid an injury-prone Kevin Youkilis.

That’s why they’re missing the playoffs, not the injuries.  And even when they had a chance to get in position for the wild card, they lost key games.

As for the future, don’t get me started.

The Yankees’ farm system is dryer than the Sahara. Despite Cashman‘s commitment to it since 2005, the Yankees have failed to develop legitimate players that are contributing to this squad or likely will in the future. Any players who look promising, like Joba Chamberlain or Dellin Betances, become busts.

It’s a sad situation. Because of this, the Yankees could end up being mediocre-to-bad for several years, at least until they either get sold to an owner who wants to spend money to win or the next “Core Four” show up and a competent general manager puts the right pieces around them.

The Yankees problems are rooted in the front office, and these problems will affect the team’s play this year and beyond.

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Brian Cashman has been the general manager of the New York Yankees for nearly 16 seasons, but several people around the game suggest that he could be getting “a little tired” of the organization, reports Nick Cafardo of the The Boston Globe.

Cafardo believes that, should an attractive GM position open up elsewhere, Cashman could be persuaded to leave New York. He cites the Los Angeles Angels of Anaheim as a possibility, if owner Arte Moreno decides to can current GM Jerry Dipoto.

The Seattle Mariners asked to speak with Cashman about their GM opening prior to the 2008 season, but the Yankees used their contractual right to block the interview. It’s unclear as to whether or not they would do so now.

Moving to a different team to fill the same position would be a strange move for Cashman. He’s under contract with the Yankees for 2014, and he wouldn’t have a larger role in his first season with a new team. If he were moving for a promotion of some sort, then it would make sense. Because he’s not, envisioning such a situation is difficult.

This doesn’t mean that such a move wouldn’t be a good move for Cashman, though. The Yankees are entering a delicate stage in their franchise’s history. The goal is to get under $189 million because of the luxury-tax threshold for 2014, and the Bombers are desperately in need of a roster overhaul.

Alex Rodriguez, 211-game suspension or no 211-game suspension, still has a contract large enough to ruin a team for multiple seasons. Mark Teixeira still has a ton of money on his contract, as does CC Sabathia. Robinson Cano is also in line for a massive new deal.

The pitching staff is old (and mostly ineffective), and the offense is stagnant. Mariano Rivera is also set to retire come the end of the season, so entering a rebuilding phase now may be the most logical step for the franchise.

Seeing as this would put Cashman in a difficult position with some of the team’s biggest stars, a lateral move may not be a terrible idea.

Jon Heyman of CBSSports.com says that both parties do not want to “sever an overwhelmingly positive longstanding relationship,” so it’s not easy to choose whom to believe. Cashman has disagreed with the Steinbrenners in the past, but he’s mostly built winners in his time with the Yankees.

This is a situation to monitor moving forward, though there’s really no indication that Cashman has plans to leave.

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About six or seven years ago, the Yankees had one of the most improved minor league systems in baseball, thanks to a new commitment to growing young talent by general manager Brian Cashman. He wanted to try to keep the team competitive by growing arms and bats in place of the usual expensive acquisitions it would have otherwise made.

The cream of this crop was a 20-year-old right-hander from Southern California who was also a first-round pick in the 2004 draft. At the same time, another 20-year-old out of Lincoln, Neb. was taking the minor leagues by storm and made it to the big leagues only a year after being drafted. Their names are Phil Hughes and Joba Chamberlain, and they were the face of what was supposed to be a new era of Yankee baseball, one that would focus on improving and sustaining the franchise through a surplus of young talent for years to come. Chamberlain and Hughes were set to be the centerpiece for this new golden era.

Chamberlain, armed with a high-90s fastball and a devastating slider, became an instant rock star in his debut in 2007, showing mortality only in the infamous bug game in Cleveland in the American League Division Series. He would make his move to the rotation in 2008 and dominated until injuring himself in August.

Hughes struggled in his first three years in the big leagues as a starter but found a home in the bullpen assuming Joba‘s old role as Mariano Rivera’s eighth-inning setup man for the 2009 World Series champions. At the same time, Chamberlain struggled and labored through the ’09 campaign thanks to an innings limit that routinely forced him to exit games early down the stretch and almost cost the Yanks Game 4 of the World Series.

In the 2010 season, Hughes beat out Chamberlain for a rotation spot and took the AL by storm, winning 18 games and earning an All-Star appearance in Anaheim. Chamberlain struggled in a role he once dominated and lost the setup job to David Robertson, the likely successor to Rivera next season. Hughes struggled down the stretch and was lit up twice in the American League Championship Series to Texas.

For the next three years, both pitchers continued to struggle. Chamberlain was forced to undergo Tommy John surgery in 2011 and has never been the electric reliever he once was. In fact, even worse.

Hughes struggled with a “dead arm” in 2011, won 16 games in an up-and-down 2012 and has struggled big time with a 4.99 ERA this year. Both are free agents this winter, but it is unlikely either will make a good payday and the Yankees probably will not bring either back.

Alas, the two pieces that were expected to help complete the puzzle of a new age of Yankee baseball—its own version of John Smoltz and Tom Glavine—never panned out after all the signs of talent and the nasty stuff they once had faded.

Why did this happen? It’s not like they weren’t good enough. They were. Injuries had a lot to do with it, as Hughes pulled his left hamstring in his rookie year while pitching a no-hitter in Texas and suffered a dead arm in 2011, the same year Chamberlain had Tommy John surgery.

But you know what? This one is on the Yankees front office.

Ever since Chamberlain came up, you’ve probably heard the phrase “Joba Rules” repeated several times, referring to how the team would use him. In 2008, the Yanks kept him in the bullpen until there was a need for starting pitching, and even then they still tried to keep him under wraps by limiting his innings.

In 2009, it really hit the fans when the team decided to regulate his workload. Through the end of July, he was 7-2 with a 3.58 ERA and was finally starting to pitch more effectively. But then manager Joe Girardi and GM Brian Cashman began to put an innings and pitch limit on him. In his last nine starts, he never threw over 100 pitches and only pitched into the sixth inning. His ERA ballooned to 4.75 that season and that was the end of Joba Chamberlain as a starting pitcher.

The Yankees never learned their lesson with Joba, as Hughes’ effectiveness as a pitcher waned when they tried to coddle him. And many of the Yankees’ recent former top pitching prospects like Manny Banuelos and Dellin Betances have gotten hurt or have pitched so ineffectively as starters that they have been relegated to relief duty.

Heck, look at the Nationals and how well their team has done since the 2012 playoffs after shutting down Stephen Strasburg. It’s understandable that teams do not want to force their young arms too hard as fledgelings, but their conservative handling of pitchers can often hurt them anyway.

If the Yankees are going to get back to being World Series contenders, they need to be less conservative with any future young arm that climbs his way through the minors. Otherwise, they’ll just be another huge waste of talent like Joba Chamberlain and Phil Hughes.

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It appears that Brian Cashman‘s opinion only means so much when it comes to how the New York Yankees handle their roster. 

According to Joel Sherman of the New York Post, the Yankees general manager was against the club trading for Alfonso Soriano, but ownership overruled him to send prospect Corey Black to the Chicago Cubs for the 37-year-old outfielder.

As Sherman points out, this isn’t the first time that the Yankees have done something that goes against Cashman’s personal ideas.

The general manager was against the club re-signing Alex Rodriguez when the star third baseman opted out of his contract in 2007, attempted to convince ownership to re-sign catcher Russell Martin last season and was against re-signing Ichiro Suzuki.

Rodriguez will make $29 million this season and at least $20 million for every season until 2017, according to Spotrac. Martin has gone on to play an integral role for the Pittsburgh Pirates and their successful season to this point, while Ichiro is hitting .270 with six home runs and 26 RBI to this point of the season.

The Yankees will owe Soriano $7 million over the next two seasons, as the Chicago Cubs agreed to pay much of the $24 million left on his contract, per Buster Olney of ESPN.

Soriano is 0-for-8 at the plate in his two games since returning to the Yankees and is hitting .249 with 17 home runs and 52 RBI on the season.

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With less than 10 days until the trade deadline, the New York Yankees continue to hover above .500, but are seven games back in the AL East and 3.5 games behind the Orioles for the second wild card spot.

This is the time that Brian Cashman usually pulls a rabbit out of his hat by acquiring a player who helps take the Yankees on another playoff ride.

That’s why I titled this article “What to Expect When You’re Expecting.”

Sure, the piece mimics the title from a mediocre, year-old movie, starring a beautiful cast consisting of Cameron Diaz, Jennifer Lopez and Brooklyn Decker. But this rom-com truly depicts the puzzling question that most Yankee fans are dealing with.

The Yankees have to make a blockbuster trade, right?

Back in 2006, the Yankees made a splash by bringing in Bobby Abreu in a seven-player deal. Cashman traded for Xavier Nady and Ivan Rodriguez in 2008. In 2010, New York brought in Lance Berkman and Kerry Wood to bolster the lineup and bullpen. Last season, with a week remaining before the deadline, Cashman traded for Ichiro Suzuki to aid an ailing outfield.

History shows that when the Yankees have needed late-season help, Cashman has managed to give his team the necessary boost.

But this season, the Yankees need more than a boost.

Derek Jeter and Alex Rodriguez have both suffered setbacks in their rehab; Mark Teixeira and Kevin Youkilis are both out for the season. Curtis Granderson should be back soon, but it is doubtful he will contribute quickly to the lineup after breaking his hand yet again.

If the Yankees want to grab a postseason spot, they will need to bring in more bats. There are plenty of players out there that could revive the lineup: Alex Rios, Michael Young and Jonathan Lucroy are names that come to mind as guys who could be dealt.

But here’s the million-dollar question: What’s the cost?

Now I’m going to say something that most Yankee fans don’t want to hear. This team is old and ailing and the stars are only getting older. Sure, the pitching staff and Robinson Cano may be keeping New York in contention for a playoff spot, but I’m not putting any money on a deep playoff run.

I’m not pronouncing New York as a seller, but more like a cautious buyer. What do I mean by that? Bringing in a Rios or Young might not be worth what New York would send back. Buy at a bargain; sell if the offer is too sweet to pass up.

It’s a tough thing to swallow, especially for someone who was born into the Jeter, Rivera, Pettitte and Posada era, but the Yankees need to start moving out with the old and in with the youth. 

Maybe it means trading Robinson Cano for some blue-chip prospects or swapping a starter like Phil Hughes for a young hitter. The Yankees also have a plethora of bullpen arms that could be shopped around. The good news is there are plenty of options out there.

Does Cashman believe a player or two now is worth a couple prospects for the future? Or will selling now lead to a brighter future?  It all depends on how Cashman sees his team right now.

What should we expect when we’re expecting?

Yankee fans expect championships, not just playoff appearances. Maybe playing it safe this year could help bring our lofty expectations to a more rapid reality. I’m not suggesting the Yankees won’t do anything—I’m just warning you that they might not do much.

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This might not be the best time to take issue with Brian Cashman, the general manager of the New York Yankees. After a slow start, the Yankees are in third in the American League East, only 1.5 games behind the Tampa Bay Rays entering their three-game series.

The Yankees and the Baltimore Orioles are also leading the wild card race, although even the lowly Minnesota Twins are only 8.5 games behind with two-thirds of the season to play.

Nonetheless, the Yankees appear to be hitting their stride. They are third in the A.L. in hitting with a .266 average. They lead the league, make that the majors, with 80 home runs.

But, as Shakespeare might say, therein lies the rub.

The Yankees live and die by the long ball.

Cashman has allowed the Yankees to get old and slow. It’s not his fault that Brett Gardner has missed most of the season depriving the Yankees of the league’s leading base stealer in 2011.

Now that Curtis Granderson has morphed into a full-time home run hitter, his speed on the bases has been neutralized. And a running game doesn’t necessarily rely solely on speed: Savvy baserunners like Granderson, Derek Jeter and Robinson Cano can swipe bases based on their experience and ability to read pitchers.

Playing hit-and-run puts pressure on pitchers to throw more fastballs. It puts infielders in motion, creating holes for hitters to shoot for.

It takes the defense out of its comfort level.

You might be inclined to blame manager Joe Girardi for the Yankee’s reluctance to play small ball more often. He can only play the cards he has been dealt, however, and Cashman has given him a one-dimensional team that will overpower most opponents but might be lacking come the postseason.

And let’s face it, the Yankees don’t measure their success by whether they make the playoffs. Call it arrogance, but the Yankees expect to be in the World Series every season.

Wait, let me clarify that.

They expect to win the World Series every year. Girardi, remember, switched his uniform number to 28 after the Yankees won their 27th World Series in 2009.

That’s why this series against the Rays is important even though it is only June. The Rays might have the best rotation in the league and lead the A.L. with a 3.41 ERA. The Yankees are eighth with a 4.07 ERA.

And although the Rays are near the bottom with a .236 team batting average, they have scored just 19 fewer runs than the Yankees.

They are, in fact, reminiscent of Joe Torre’s Yankee teams, relying on a mix of youth and experience, blending solid pitching with situational hitting and some long ball thrown in for good measure.

The Rays are seventh in the league with 59 homers.

This is the formula it usually takes to win in October. The Texas Rangers were probably the best team in 2010 but the San Francisco Giants shut down the Rangers potent offense.

The Rangers lineup was more imposing than the St. Louis Cardinals, even with Albert Pujols, but the Cardinals pitched better and hit when it mattered the most.

That is apparent again this season. After a 22-11 start, the Rangers have lost 10 of 12 and five of six, mostly because their pitching has faltered.

If the Yankees want to be the last team standing around Halloween, then Cashman needs to swing a deal for a good contact hitter and maybe another starting pitcher.

He has to hope that Gardner will breathe new life and energy into the Yankees with fresh legs when he returns. The Yankees don’t have a Will Middlebrooks like the Boston Red Sox do, infusing some youth and pop into the lineup.

And Gardner is no Jacoby Ellsbury—the injured Red Sox center fielder who gives them speed and power at the top of the order.

The Yankees are restocking their farm system in the amateur draft. That won’t pay any dividends, however, this season.

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