New York Yankees



New York Yankees, The New York Yankees have now missed out on the postseason two seasons in a row for the first time since 1992-93 (1994 was the strike shortened season with no playoffs). If George Steinbrenner were still with us, he’d probably hit the winter meetings with a billion dollars on hand, and ready to rock-n-roll.

However, the Yankees and GM Brian Cashman went out last season and spent a boatload of money on Jacoby Ellsbury, Brian McCann and Masahiro Tanaka — yet still missed out on the playoffs — while watching the mainly homegrown Kansas City Royals reach the World Series. This development might suggest locking up ridiculously high priced free agents to lengthy deals is no longer the guaranteed formula for success as it used to be for New York.

Expecting Cashman to have the green light from ownership to spend some money is still a fair assumption — because after all they’re still the Yankees — but they have a ton of needs and one must wonder how much they’re willing to allocate into a particular position, as spreading it around some might behoove them. Derek Jeter‘s gone, and the organization must know that it is now in uncharted waters: for the first time in 20 years the Yankees have no true face of the franchise. It appears they also have no sure plan to make it back to the postseason in 2015 — as there is a changing of the guard in the American League.

New York needs to make a big splash as it does nearly every offseason — and I truly believe they will — but with C.C. Sabathia‘s struggles in 2014, could the Yankees be willing to add another pitcher to an unthinkable amount of money? And if they’re, could it be Jon Lester?

Yes — and yes.

The Yankees have shown over the years that they aren’t afraid to bring former Boston Red Sox legends to the Bronx. Roger Clemens, Johnny Damon and Ellsbury all made the adjustment nicely and clearly offered no bias towards the Bronx Bombers when New York was offering them a king’s ransom to jump aboard.

Lester was traded by Boston to the Oakland Athletics at the trade deadline and it’s safe to say that Billy Beane doesn’t have the cash to keep him in Oakland. Whispers suggested after Lester was traded that he’d be willing to return to the Red Sox in 2015 when they can make an effort to contend again. However, in all honesty, almost every player says that after spending a large portion of their career with a particular organization. They all say it, but it rarely happens.

I’ve always thought that the Yankees starting staff should be a minimum of 3/5 left-handed to counter left-handed batters’ ability to take advantage of Yankee Stadium’s short porch in right field. Although it might not be as stark as it once was, left-handed pitchers are still the greatest equalizer in attempts to curb left-handed power.

Lester had the best statistical season of his career in 2014, with a combined record of 16-11, a 2.46 ERA, 1.10 WHIP and 9.0 K/9. And he did a good portion of that with a lousy team in Boston getting little to no run support. He’s still clearly one of the best pitchers in MLB, but he’s going to want to be paid as one of the best pitchers in MLB as well.

It would surprise me if he will settle for anything less than a six-year $120 million contract. But, in reality, at 30-years-old this will be the only huge payday (relative to baseball paydays) of his career and while six years might be fine, he could want $25 million per which would be $150 million.

The Yankees should give it a whirl. They’ve put themselves in a really dire quandary in recent years by not adequately stacking their farm system and really have no legitimate answers from within to rely on.

Michael Pineda can’t stay on the field, neither can Ivan Nova. Even when he does he thinks he is way better than he is and is kind of annoying, and Sabathia is seemingly a shell of his former. Tanaka needs help, and adding Lester would undeniably give the Yankees the best right-left duo of any rotation in the majors.