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The cautionary tale in Yankees’ pursuit of Gerrit Cole

Other than CC Sabathia in 2008, there was no free agent I’ve ever wanted more than Cliff Lee.

In the winter of 2010, Lee was finally a free agent after torturing the Yankees. He dominated the Yankees in the playoffs with the Phillies in 2009, and then again with the Rangers in 2010. The Phillies had shockingly traded Lee to the Mariners after the 2009 season for no reason whatsoever. After that, the Mariners traded Lee to the Rangers at the 2010 deadline. Lee had thus played for three teams over a 12 month span, and conventional wisdom said the Arkansas native would return to the Rangers or sign with the Yankees.

Back in 2010, top free agents actually signed with teams before Christmas, and every Yankee fan under the sun wanted Lee in their stocking for the 2011 season. The Yankees were coming off a tough ALCS loss to Lee’s Rangers. They were as talented as any team in the league, but pairing Lee with prime CC  would have given them the most devastating one two punch since Randy Johnson and Curt Schilling.

The Yankees were a loaded team in need of an additional front line starter. Sound familiar?

Lee was 32 at the time, but had remained relatively injury free. He had a smooth, low movement delivery that scouts thought would hold up over time. Because of this, Brian Cashman had no hesitation about offering Lee a six year, $140 million contract taking him through his age 38 season.

It wasn’t enough.

Lee ended up spurning the Yankees and the Rangers and signing with the Phillies, the team that had sent him packing in 2009. It turns out Lee had never wanted to leave Philly. He loved the ballpark, the fans, and the blue collar feel of the city. He also apparently wasn’t overly concerned with money. Lee ended up signing for $115 million, $25 million less than what the Yankees were offering.

$115 million sounds like a ton of money to you and me. It is, but it is almost unheard of for a top free agent to turn down that kind of money. Ninety-five percent of free agents take the highest offer, with Lee being one of the rare exceptions. It probably didn’t help that Yankee fans allegedly spit on Lee’s wife and tried to shower her with beer during the 2010 playoffs when he was pitching for the Rangers. The savages that fill the Yankee Stadium upper deck during playoff games are usually an asset. They weren’t this time.

The Cliff Lee story had a bizarre ending. He dominated in 2011, but lost his only playoff start. He was great in 2012 and 2013, but the team never got back to the playoffs. Lee tore up his elbow in 2014 and just like that, he was done at 35. Lee completed just three-and-a-half years of his five year contract before abruptly retiring.

The parallels between Lee and Gerrit Cole are painfully obvious. The Yankees tried to trade for Lee in 2010. They tried to trade for Cole in 2018. Lee eliminated the Yankees before heading to free agency. Cole did the same about a month ago. In 2011, they needed a second ace to pair with Sabathia. Today, they need a second ace to pair with Luis Severino. Back then, they had a great squad, but Lee would have made them the overwhelming favorite. Today, adding Cole would undoubtedly give the Yankees the most lethal roster in the Majors.

By donning a Boras Corp hat 20 minutes after losing the World Series, Cole seemed to indicate money would be the main factor in his decision.

Conventional wisdom says Cole will either choose his hometown Angels or the deep pocketed Yankees.  But conventional wisdom doesn’t always matter in these situations.

Just ask Cliff Lee.