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This winter is the Yankees’ best chance in years to finally address their pitching woes

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The Yankees can right the wrongs of the last half-decade this offseason.

MLB: New York Yankees-Workouts Kim Klement-USA TODAY Sports

We say it every offseason: the Yankees need to improve their pitching. Nonetheless, it seems season after season that the New York outfit comes up one or two arms short of making the World Series. How much longer can they go on like this? When will they finally banish their perennial bogeyman of not enough quality pitching?

They tried to address it last winter with the largest splash of all. Yankees pitching has been a porous mess for as long as the current championship window has been open. So they reeled in the biggest fish on the market, Brian Cashman’s white whale: Gerrit Cole. Doing so amounted to slapping a Cole-sized bandage over a dam full of holes. It plugged up most of the cracks, but invariably, some leaks still remain.

Now with three starting pitchers hitting the free agent market in Masahiro Tanaka, James Paxton, and J.A. Happ, the dam threatens to burst once more. No amount of slapdash repairs and temporary fixes will keep it intact. The Yankees need to commit once and for all to going all in on a pitching upgrade mission.

Don’t get me wrong; signing Cole was real sea change relative to the previous strategy of filling out the rotation. While in years past, the Yankees balked at signing the best available starting pitcher, last winter, they did what needed to be done. However, you can’t win by simply drawing an ace without a good hand. The Yankees must push all their chips to the center of the table, something they have so far been unwilling to do.

Instead, the recent history of Yankees decisions regarding pitching acquisitions is littered with hesitation and poor decisions.

The Yankees mismanaged Sonny Gray, forcing him to throw a pitch mix that he was uncomfortable using. They deployed Lance Lynn in a highly inefficient manner. Then, they let both pitchers go for practically nothing. It’s especially damning that Gray and Lynn flourished in their first post-Yankee years, both earning Cy Young votes. What the Yankees wouldn’t give to have either stud in the rotation now.

The Bombers have also failed to capitalize on recent strong free agency classes. Yes, they signed Cole, but as previously noted, one pitcher is not the cure-all to their ails. They never made any sincere attempt at signing Patrick Corbin, who went on to play a major role in the Nationals’ World Series title last year. Instead, they signed an aging J.A. Happ to an expensive deal only $6 million less per year than it would have cost to secure Corbin.

And just this last winter, it was clear that there would still be holes in the rotation even after inking Cole to his record-setting deal. Surely the likes of Hyun-Jin Ryu, Zack Wheeler, or Dallas Keuchel could have contributed down the stretch. Ditto for relievers. They signed Zack Britton and Adam Ottavino in 2019 and said, “good enough.” Boy, could the Yankees have used a Blake Treinen or Darren O’Day this year to bolster the ‘pen.

The biggest blunder in my mind has been the immobilization at the trade deadline. There are too many pitchers to count on both hands — starters and relievers alike — who the Yankees passed on. Justin Verlander, Gerrit Cole, and Zack Greinke spring to mind first, and clearly all three were integral in the Astros’ latest World Series appearance.

The 2020 deadline was particularly painful, given the thin state of the bullpen. With Ottavino falling out of the circle of trust, decent relievers like Mychal Givens, Miguel Castro, Archie Bradley, or Trevor Rosenthal would have been welcome reinforcements, especially considering the basement prices for which they were acquired. But over and over again, the Yankees have been hesitant to sell a single chicken, out of fear that it hatches a golden egg.

The Yankees must be active players this offseason. The past inactivity has necessitated this push. There is a plethora of good free agent options who could be signed for below-market prices, and the Yankees may not get a better shot in the next couple years to affordably fill multiple areas of need. Any of Tanaka, Kevin Gausman, Charlie Morton, Corey Kluber, or Jake Odorizzi would surely improve the rotation as it currently stands. The Yankees also need to be in the market for at least one (if not two) of Rosenthal, Liam Hendriks, Trevor May, Blake Treinen, Brad Hand, Alex Colome, or Jake McGee to fortify their weakened bullpen. We will have more in-depth analysis for most of these free agent targets coming soon on PSA, so stay tuned for that.

Now is not the time to pinch pennies or to be frozen with indecision. It is not the time to let clear improvements to the rotation and bullpen slip through their fingers. This winter, the Yankees must be buyers in a seller’s market.