Yankees Can’t Lose Out on Gerrit Cole for a Third Time

The Yankees have to sign the right-handed free agent no matter what it costs

Nine years ago tomorrow, I slipped into a deep and long depression. Not because it was winter and freezing cold or because the Rangers were wasting Henrik Lundqvist’s prime with a bad defense and mediocre roster or because the Giants would soon suffer the Meltdown at MetLife against the Eagles to ruin their season or because I still wasn’t over the ALCS loss to the Rangers. I became depressed because Cliff Lee turned down the Yankees.

At the time, the first month-plus of free agency had been reported as a mere formality and Lee signing with the Yankees was deemed inevitable. They needed him. They desperately needed him, and after failing to successfully trade for him in July of that season and having the ALCS swung against them because of it, they weren’t going to be stopped. Lee was going to be a Yankee and after beating them in Games 1 and 5 of the 2009 World Series and Game 3 of the 2010 ALCS, he was going to help them win games in October rather than help them lose.

I still remember seeing Jon Heyman’s tweet of a “mystery team” suddenly being involved in the Lee sweepstakes. The term “mystery team” has haunted me since that day and even the word “mystery” still bothers me. Eventually, the mystery team would be revealed as the Phillies and Lee was going back to Philadelphia even though the team had screwed him over by sending him to baseball Siberia in Seattle the prior offseason after trading for Roy Halladay. The Phillies’ offer was for five years and $120 million. It was less than the Rangers’ six-year, $138 million offer and much less than the Yankees’ six-year, $148 million offer with a player option for a seventh year at $16 million. I wrote this reactionary blog at the time with tears streaming down my face.

Lee was the one that got away … twice. Brian Cashman’s unwillingness to include Eduardo Nunez in the July 2010 deal for Lee (only to release Nunez in the spring of 2014) allowed Texas to swoop in and get him, and Lee not caring about taking substanially less money and years to pitch for a team which had shipped him away left the Yankees standing empty-handed. Maybe Andy Pettitte doesn’t briefly retire after the 2010 season if the Yankees land Lee, and the team has a rotation of CC Sabathia in his prime, Lee in his prime, Phil Hughes coming off an 18-win, All-Star season, Pettitte and A.J. Burnett. Unfortunately, Lee went to the Phillies, Pettitte did retire and the Yankees turned to Freddy Garcia’s smoke-and-mirrors act and gave Bartolo Colon a chance to ressurect his career. Miraculously, Garcia and Colon were good enough for long enough and Ivan Nova emered as a major-league starter for the Yankees to reach the postseason, but once the Yankees got to October, Colon wasn’t allowed to start, Garcia was ineffective and Nova pitched like you would expect a rookie to pitch in the playoffs. (The Yankees’ inability to hit with runners in scoring position, especially in Game 5 also played a big role in their first-round elimination.)

This offseason, an offseason followed by the exact six-game ALCS loss nine years ago (win Game 1 on the road, lose Game 2 on the road, lose Game 3 at home, lose Game 4 at home, win Game 5 at home, lose Game 6 on the road), the Yankees have a chance to sign another starting pitcher who has already gotten away twice.

Nearly a month ago, I wrote Don’t Expect the Yankees to Sign Gerrit Cole. I wrote it because why would Yankees fans expect the team to sign the most-coveted free-agent pitcher this offseason when he would likely command the most money of any pitcher in history? It’s not 11 years ago when the Yankees offered CC Sabathia a record-breaking contract on the first day of free agency and continued to outbid themselves to persuade him away from his home of California and put him in pinstripes, and it’s not nine years ago when they made the highest offer to Lee. The Yankees don’t operate the way they did a decade ago, and they have 10 years of mixed results to show for it.

The Yankees were unwilling to take on Justin Verlander’s salary at the 2017 waiver deadline, and he single-handedly swung the 2017 ALCS in the Astros’ favor by winning Games 2 and 6. After coming within a game of the 2017 World Series, the 2018 Yankees’ payroll was cut by $50 million. After falling short again in 2018 because of their starting pitching, the Yankees were unwilling to give Patrick Corbin an additional year on his offer and he ended up in Washington. The Yankees have had several chances to drastically upgrade their rotation either through free agency or a trade over the last three seasons and they have come up short each time, unwilling to offer enough money or unwilling to depart with their prospects. Combine all of this with the front office thinking starting pitching isn’t why they lost in the ALCS again, and you will understand why no Yankees fan could think it’s a given they would make a realistic run at Cole this winter.

That has all changed over the last week with the Yankees flying across the country to meet with Cole followed by reports the Yankees won’t be denied by the ace and that the team has either offered or is prepared to offer Cole a seven-year, $240 million contract, breaking both the average annual salary and total contract records for a starting pitcher. I have gone from accepting a rotation of Luis Severino, James Paxton, Masahiro Tanaka, Jordan Montgomery and J.A. Happ to now accepting nothing short of Cole in the rotation. The reports of the Yankees finally remembering they’re the Yankees after years of counting their pennies and nickel-and-diming their way to a 10-year World Series drought appears to be over has made me believe in the Yankees’ financial prowess again. It has made me believe they are done wasting seasons and opportunities in this current championship window.

The Yankees missed out on Lee twice. Once because they were overvalued their prospects and once because he turned down their offer.

The Yankees have already missed out on Cole twice. Once because they drafted him despite knowing he wanted to attend college and once because they didn’t want to part with Miguel Andujar or Clint Frazier. They can’t miss out on him a third time. They can’t.


My book The Next Yankees Era: My Transition from the Core Four to the Baby Bombers is now available as an ebook!