New York’s roster looks like a pair of blackened lungs stained from decades of smoking Paul Malls outside of Mustang Sally’s. Wasted draft picks and monumental failures on both the international and major-league free agent markets have left the Yankees with arguably the most poorly-constructed roster in baseball history given their unlimited resources and endless stream of revenue. This year’s payroll is a shade above $202 million, second only to the Los Angeles Dodgers ($235M). That’s roughly $8M per player. Entering Saturday, the Yankees trailed first-place Baltimore by six games in the American League East, just two games above. 500 with a horrific minus-31 run differential, the worst in the league among teams with a winning record. In fact, the only other team entering Saturday with both a negative run differential and a winning record is the St. Louis Cardinals, but at minus-1, they’re one good weekend away from being out of the red and back into the green. The fact the Yankees are in a pennant race with such an awful run differential indicates they’ve been lucky, not good, a byproduct of a mediocre division with no real clear-cut favorite. They hung around long enough through late June and mid-July to coax Cashman into pursuing minor upgrades at the trade deadline, even at the expense of a rare prospect that might actually pan out at the major-league level. Shortly after acquiring former Red Sox shortstop Stephen Drew and his .176 average in exchange for Kelly Johnson, with the assumption that Drew would replace free-agent failure Brian Roberts at second base, the Yankees shipped 23-year-old infield prospect Peter O’Brien to Arizona in exchange for Martin Prado, a 30-year-old veteran infielder whose OPS+ has plummeted by more than 20 points since his career year in Atlanta in 2012. In a nutshell, the Yankees sought to correct their incredibly nearsighted plan to replace Robinson Cano and supplement the inevitable decline of 40-year-old Ichiro Suzuki with two players who don’t play either of those positions. Prado and Drew made just their second career starts in right field and at second base, respectively, Saturday in Boston. This should come as no surprise considering Cashman felt it made more sense to stick his $85 million catcher, Brian McCann, at first base for a week instead of giving prospect Kyle Roller (23 home runs this year in the minor leagues, including 11 at AAA Scranton) a two-week cup of coffee in lieu of one of the 13 pitchers they’re carrying on the roster, as if playing first base requires nothing more than a glove and a pulse. You’d think an organization that routinely celebrates the historic career of Hall of Fame first baseman Lou Gehrig would have a little more respect for the position. If Cashman were the GM in 1939 he probably would’ve told Joe McCarthy to stick Bill Dickey at first base when Gehrig retired. O’Brien may never be more than a fringe major-leaguer/trade chip for use in future deals, but prior to being dealt to Arizona, he had clubbed 33 home runs this year in the minor leagues, including 23 in just 72 games at AA Trenton. Prado, already in his decline, is owed $22 million over the next two years, not including what New York has to pay him for the remainder of 2014. The Yankees are stuck with him, just like they’re stuck with Alex Rodriguez ($61 million owed over the final three seasons of his contract), C.C. Sabathia ($73 million owed through 2017), Teixeira ($45 million over the next two years) and others, a list that doesn’t even include the $486 million worth of free agents added during the offseason. The team stuck in an endless “win now!” loop never has an eye on its future because its interpretation of the future is always the next homestand or road trip. Prado for two more years and $25 million on a roster cluttered with bloated contracts and declining veterans makes zero sense for a franchise that needs to get younger. The Yankees never allow themselves to push the reset button in fear of alienating a fan base already drifting away from the ballpark at an alarming rate. You can’t blame Cashman for injuries to Masahiro Tanaka, Ivan Nova, Michael Pineda and Sabathia, four fifths of his Opening Day rotation, but the lousy draft picks, questionable player development and lack of major-league ready talent at the minor-league level is his cross to bear. Over the past decade, only 11 of the 500+ players drafted by the Yankees have contributed for New York at the major-league level. Two of them, Ian Kennedy and Joba Chamberlain, failed to progress beyond a certain level (arguably the fault of the Yankees themselves) and are now pitching elsewhere. Mark Melancon, now one of the top setup men/closers in the National League, was inconceivably traded to Houston four years ago for a declining Lance Berkman. Three gems have emerged from an otherwise odious pile of rubbish – closer David Robertson, All-Star setup man Dellin Betances and speedy outfielder Brett Gardner. The other five – pitchers Chase Whitley, Preston Claiborne, Adam Warren, Shane Green and David Phelps – barely qualify above the league’s standard for replacement-level players. Some bad luck has certainly been a factor, such as 2008 first-round pick Gerrit Cole enrolling at UCLA instead of signing with the Yankees and then three years later winding up with Pittsburgh, where he’s now one of the league’s top young starters, but most of this has to do with poor decision-making. This is why the Yankees can’t get younger. Instead of replacing retired players or departed free agents with homegrown talent, they just sign whatever premier free agent is available that year on the open market. As is often the case in free agency, they overpay and wind up stuck with contracts no one wants within two or three years. There’s no end to this cycle. The Yankees could’ve taken a step in the right direction by trying to unload some of these bloated contracts at the trade deadline. Pay someone – anyone – to take Teixeira for the next two years. Dump McCann and foot the bill for $60 of the $85 million he’s owed for the next five years. They chose to be buyers instead, clinging to a false hope of October success in a league where they’re severely overshadowed and outmatched by the dominance of Detroit, Oakland and Los Angeles. And they’re doing it with a mismatched, patchwork roster resembling that of a men’s slow-pitch softball league, not a major-league franchise with a once proud tradition of excellence and intelligence.
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