What If With Mad Matt: The Yankees Should Sign Jon Lester


For those of you who may be familiar with my work, I spent a large chuck of the season writing a column called “The Way It Was, And The Way It Should Still Be” where I wrote about baseball’s meaningful past and sitting back and enjoying the moment. You also know I can be out there with my opinions and ideas, hence the name “Mad Matt.”

Throughout the off-season, I’ll take a break from writing about the past and living in the now and look towards the future and focus on the possibilities that could arise in the coming months. Every move has a domino effect attached to it and every move has an impact on the team. Here, I’ll analyze what that effect may be before it happens and determine what effect it would have on the team or a particular player. This is “What If” and I’ll be putting my always off-beat ideas on front street throughout the off season. Enjoy!

More from Yankees News

The Yankees pitching staff was the strength of the 2014 season which is surprising considering four of the five Opening Day starters were on the disabled list at one point or another. Ivan Nova needed Tommy John surgery, C.C. Sabathia went down with a degenerative knee, rookie superstar Masahiro Tanaka went down with a partially torn UCL and Michael Pineda injured his oblique. Still, the rotation was a real

Mandatory Credit: Kim Klement-USA TODAY Sports

strength throughout the season and the team was able to finish the year with good news. Tanaka was able to avoid Tommy John surgery and Michael Pineda returned and continued to be a dominant force on the mound. The absence of four starters caused the Yankees to get a good look at the young rookie Shane Greene who looked like anything but a rookie.

But the saying “You can slap a Yankees jersey on a fan and he’d give you five quality innings” isn’t exactly a good thing. The staff struggled with a lot of issues and their depth dwindled away really. They need a major reinforcement for the rotation come 2015. Lucky for the Yankees the Red Sox were unable to agree to a contract extension with their ace Jon Lester and instead shipped him off to Oakland. Now this helps the Yankees in two ways; if they sign Lester they won’t have to give up a draft pick and it virtually eliminates the chance Lester returns to Boston.

The Red Sox have been firm with their policy of not signing players over 30 years old to long term deals and that caused them to low ball Lester and fail to come to an agreement on an extension. The odds are low that he’ll end up back in Boston and Jon Heyman of CBS Sports recently said the Lester race is likely between the Chicago Cubs (Note the Theo Epstein connection) and the Yankees and the way I see it Lester is a perfect fit for the Yankees.

Predicted Deal: 6-years $120 million dollars

Six years at $120 million would be perfect for Lester and the Yankees. Unlike someone like C.C. Sabathia, whose contract has looked horrible as he’s faltered significantly in recent seasons, Lester is not reliant on his fastball to find success and is instead a more polished pitcher. His fastball speed was never as high as Sabathia’s so he’s learned how to mix his pitches and locate better. Pitchers like this typically age better (Think a Tom Glavine-type pitcher) and find it easier to maintain health and consistency. A deal that keeps Lester under contract for a significant amount of time would ensure the team has an ace going forward. Of course, on the Yankees, he’d be the number two starter.

The Rotation With Lester (Age shown is age on Opening Day):

Masahiro Tanaka RHP (26)

Jon Lester LHP (31)

Michael Pineda RHP (26)

C.C. Sabathia LHP (34)

Shane Greene RHP (26)

Now, the rotation I listed above is subject to change. The Yankees were very impressed with what they saw in Brandon McCarthy and have expressed interest in resigning him. Ivan Nova will return sometime in May or June and the Yankees have discussed the possibility of a six-man rotation. Also, there is uncertainty about whether Hiroki Kuroda will actually retire or if he’ll decide to return for another season. As of now we’re work off of this template.

Mandatory Credit: Anthony Gruppuso-USA TODAY Sports

Tanaka is the Yankees’ undisputed ace. Yes, he partially tore his UCL which usually means Tommy John surgery. But he underwent rehab, as was the doctors’ recommendation, and returned to finish out the season. It’s not unheard of to see a pitcher go a long time without needing Tommy John and Tanaka could do just that. But if he does wind up needing surgery, having Lester as the number two starter would be a quick fix as he’d bump up to the ace without a problem. Tanaka and Lester could go from being opponents in one of the 2014 season’s most exciting pitching duels to forming perhaps the best one-two punch in all of baseball. If Michael Pineda, who would be the number two without Lester and the ace without Tanaka, could finally stay healthy he would be an amazing luxury to have as your number three pitcher. As a I wrote about before C.C. Sabathia is bound to have a better season in 2015 and the former workhorse of the staff would be an awesome fourth starter if he could regain any bit of his former self. As for Shane Greene… well… Let’s touch on that now.

The Odd Man Out: Shane Greene

Shane Greene came up to the Major Leagues as an obscure prospect who had been impressive in the minors but was viewed as a fill in for the ailing players. But Greene performed very well, going 5-4 with a 3.78 ERA and 81 strikeouts in 78.2 innings. He earned a lot of attention around baseball as his 14 big league starts were very good for a rookie… especially a Yankee rookie. But if the Yankees sign Lester he’d be bumped down to the number 5 spot in the rotation and, unless they go to a six-man rotation, he’d be sent down to the minors following Ivan Nova’s return. If the Yankees sign Lester and

perhaps Brandon McCarthy, Greene would start the season in Triple-A in a five-man rotation or eventually end up back in Scranton/Wilkes-Barre when Nova returns if they go with a six-man. That’s not to knock Greene, as he was exceptional in his rookie season. He’s just the bottom man on the totem pole and the numbers game bumps him out.

Beat The Cubs:

Theo Epstein can be best buddies with Lester, all he wants but Lester isn’t going to buy into the whole “be patient we’ll win soon” mantra. Jeff Samardzija didn’t buy into it and demanded to be traded. He ended up in Oakland. The Cubs fought hard to acquire Masahiro Tanaka in the off-season and Tanaka didn’t buy into it. Lester wants to win and the Cubs can say how much they think they’re going to compete in 2015 but in reality they likely won’t. There isn’t much starting pitching on the Cubs either and being the star on a pitching staff of “Eh’s” isn’t something to necessarily be proud of. You win with pitching. One pitcher isn’t going to make Chicago’s staff a strength. Tanaka knew it, Samardzija knew it and Lester knows it too. We saw last year what happens when the Yankees and Cubs go head-to-head for a high priced free agent.

Final Say:

Lester is the perfect fit for the Yankees and they have to be the front runner to get him. Along with Tanaka and Pineda he’d help to form one of the best one-two-three punches in baseball. If Sabathia can return to some form of his old dominance, the Yankees will have two very formidable lefties in the rotation sandwiched in with the righies in Tanaka, Pineda, Greene and even top prospect Luis Severino, who fans can expect to see at some point in 2015. Lester is the right move for the present and the future as he’ll likely age well and won’t cost a draft pick. Yankees, if you’re reading this, I think Lester wants to play with Ellsbury again. Get him fitted for pinstripes.