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In reality, Brian Cashman is on the path to becoming one of less than 30 executives in The National Baseball Hall of Fame and Museum. In New York, his job is critiqued and questioned on a yearly basis.



Since taking over for Bob Watson as Yankees general manager in 1998, the franchise has produced one of the greatest runs of success in baseball history. During Cashman's reign, the Yankees have made 14 trips to the postseason, nine appearances in the American League Championship Series, six World Series visits and captured four World Series titles.

The Cashman Years Year W-L Record AL East Finish Playoffs 1998 114-48 1st Won WS (4-0) 1999 98-64 1st Won WS (4-0) 2000 87-74 1st Won WS (4-1) 2001 95-65 1st Lost WS (4-3) 2002 103-58 1st Lost ALDS (3-1) 2003 101-61 1st Lost WS (4-2) 2004 101-61 1st Lost ALCS (4-3) 2005 95-67 1st Lost ALDS (3-2) 2006 97-65 1st Lost ALDS (3-1) 2007 94-68 2nd Lost ALDS (3-1) 2008 89-73 3rd -- 2009 103-59 1st Won WS (4-2) 2010 95-67 2nd Lost ALCS (4-2) 2011 97-65 1st Lost ALDS (3-2) 2012 95-67 1st Lost ALCS (4-0) 2013 85-77 3rd -- Baseball-Reference

Yet in New York, memories fade and the present is accentuated. In other words, Brian Cashman is facing pressure to turn around a team that just missed the postseason for just the second time in two decades. If he can't construct a roster built for October baseball and turn around a barren farm system, his legacy, despite all the success, will be questioned. Even harsher, his almost life-long affiliation with the New York Yankees franchise won't last forever.

Of course, when evaluating the job Cashman has done and will seek to do, money plays a major role in determining his effectiveness in New York's front office. Blessed with nearly unlimited resources from the Steinbrenner family, Cashman has never had to work under strict payroll restrictions like small-market teams such as Oakland and Tampa Bay.



Until now.



Well, to be fair, the Yankees' self-mandate to fall below the $189 million luxury tax threshold, in order to reap the benefits and spend more in 2015 and beyond, isn't exactly as challenging as winning with a payroll under $60 million. It is, however, a challenge, especially when factoring in existing long-term deals that were given out well in advance of the new payroll edict.



Cashman's extreme success always could be tied back to his enormous financial advantage, but his future successes, or failures, will take more creativity and ingenuity. For New York to finally embrace the excellence of their general manager, he will have to prove himself by winning big during a complete franchise makeover.



Along with financial clout, Cashman, although part of the front office decision-making before being promoted to general manager, was afforded the rarest of gifts upon taking over in 1998: A roster comprised of young, homegrown, dominant stars. In Derek Jeter, Andy Pettitte, Mariano Rivera and Jorge Posada, a dynasty core was in place. Now, with the exception of a 39-year-old Jeter, the "Core Four" are gone to retirement.

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Transforming the Yankees back into yearly title contenders without the luxury of those veterans or unlimited financial muscle will take a combination of creativity, luck and Cashman's recent draft picks proving experts wrong.

Although moving on from a 43-year-old closer and 41-year-old starting pitcher doesn't seem like a roster conundrum, there is a leadership void surrounding the New York clubhouse for the first time in 20 years. If Jeter's injury issues cost him more time in 2014, the team will be without all of the core members of Cashman's earlier teams. Finding the next leader, both on and off the field, is imperative when assembling the team this winter.



This is where Cashman's biggest order of business, Robinson Cano's free agency, comes into play.



If the Yankees shell out upwards of $200 million to secure Cano's ability for the next seven-plus years, he'll be looked at as the next great Yankee, leader of the franchise and spokesperson for the clubhouse. Historically, Cano hasn't profiled as a personality that loves that kind of attention, but Cashman's commitment, or lack thereof, to Cano will put the spotlight on him moving forward.



Assuming Cano is re-signed, Cashman's job becomes about filling in the rest of the roster, one he deemed to have many issues during a season-ending press conference, with enough quality to make it back to October. As Steve Politi of The Star-Ledger chronicled, Cashman's six-word quote summed up his feelings on the team.



"We’ve got a lot of problems."

Free agency is ripe with players that fit New York's needs. Shin-Soo Choo could add a dimension of on-base prowess to the top of the order. Brian McCann could add left-handed pop to the lineup. Josh Johnson could bring strikeout ability to the rotation. Japanese star Masahiro Tanaka could fill the quality-innings void left by Pettitte's departure. Brian Wilson could bring proven closer insurance in the absence of Mariano Rivera.

What do all those potential additions have in common? Price tags. From over $100 million to less than $10 million, they will all cost serious money to bring aboard. Even with the retirements of Rivera and Pettitte, and the possible free-agent departures of Phil Hughes, Joba Chamberlain, Curtis Granderson and Hiroki Kuroda, there's not enough money under the $189 million threshold to fit every possible answer into New York's 2014 roster.

2014 Yankees Payroll Obligations (Non-Arb. Eligible Players) Player Total Contract 2014 Salary Alex Rodriguez 10 yr/$275M (08-17) $26,000,000 Mark Teixeira 8 yr/$180 (09-16) $23,125,000 Vernon Wells 7 yr/$126M (08-14) $2,400,000 CC Sabathia 5 yr/$122M (12-16) $23,000,000 Alfonso Soriano 8 yr/$136M (07-14) $5,000,000 Derek Jeter 1 yr/$12M (14) $12,000,000 Ichiro Suzuki 2 yr/$13M (13-14) $6,500,000 Cot's Baseball Contracts

Of course, if Cashman's farm system, something he demanded more say in during a 2005 contract negotiation, was ready to provide Joe Girardi's roster with contributors at a league-minimum rate, the supply and demand aspect of this winter would be easier to calculate. Outside of Michael Pineda, a trade acquisition from Seattle in 2012, expecting any of New York's young players to fill major roles in 2014 is far-fetched.

As you can see, there's a dilemma for Cashman and Co. By sitting out the major free-agent period, the team can easily stay under the $189 million tax for 2014. If Alex Rodriguez's 211-game suspension is upheld in arbitration, the task won't even be difficult. However, if the team wants to catch the Red Sox and compete in 2014, reinforcements are needed.

Fans are wiser than ever before, but also more impatient. If Cashman devises a plan that leads to another season without October baseball, even if it sets up New York to be major players in future free agent classes that could include Clayton Kershaw, David Price and Jason Heyward, fans will grumble at two straight years without postseason baseball in the Bronx.

To save his legacy, and maybe even his job, Cashman must walk the tightrope between contention and the sneakiest rebuilding process in baseball. If he can somehow put together a team capable of playing October baseball, restock a farm system that is close to barren and keep the payroll flexible for the next half-decade, Yankees fans will have no choice but to embrace an executive who successfully bridged the gap between one great era to another.



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