If the Cubs Miss Out on Jon Lester, They Must Pounce on Max Scherzer

As we all know, the Chicago Cubs are heavily pursuing free agent pitcher Jon Lester. With the connection of Lester and Cubs President Theo Epstein, it seems to be a good fit for Lester. He'd also be the ideal number one starter for Chicago.

As of right now, I'd have to say that the Boston Red Sox are the frontrunners. The Cubs are a rebuilding team and are still maybe two or elite pitchers away from being a contender which may be two years from now.

What makes me think Boston is in the lead for the services of Lester is the acquisitions of Pablo Sandoval and Hanley Ramirez. That shows Lester the Red Sox's willingness to be a winner right now.

It was also reported that initially, the Red Sox offered Jon Lester a contract of 6 years and between the $110-$120 million range. It was reported just the other day that the Cubs offered Lester 6 year deal worth "just north" of $135 million. The question for Lester is, what do you want more? To win right now and take less money, or to take more money and be a part of a team with a much brighter future.

We'll see, but if the Cubs miss out on Lester, they can't just give up on the offseason, they must chase Max Scherzer. Scherzer is just as good, if not better than Lester and Scherzer would probably cost the Cubs more as well. It'd be worth it, though. The Cubs are in desperate need of a legit number one starting pitcher. Here's what the starting five would most likely look like on Opening Day as of right now: Jake Arrieta, Kyle Hendricks, Travis Wood, Edwin Jackson and Tsuyoshi Wada. Not very good.

Adding Scherzer to that would be a great first step and then maybe adding a nice number two or three in guys like; Jake Peavy, Francisco Liriano or Jason Hammel. 

There's a lot of options for the Cubs right now. Personally, I'd be very upset if the Cubs miss out on Lester. He'd be great at the top of the Cubs rotation. Before free agency, I was hoping of acquisitions of Lester, Cole Hamels and Jake Peavy. That doesn't seem like reality now as the Cubs have already said they won't overspend and be heavy spenders this offseason.

Now I can see the Cubs acquiring Scherzer, Peavy and maybe Liriano. Which would give the Cubs a nice top three starters. In reality, don't expect all three. I'd be surprised if two of those names were signed by Chicago but regardless, the Cubs must sign Jon Lester or Max Scherzer. It's crucial for their future.

Realistic Expectations for the Cubs This Offseason

With the hiring of Joe Maddon, the Cubs are expected to be a lot more aggressive in free agency. According to front office, Maddon didn't change their plans. They were to be aggressive regardless. But what is realistic for the Cubs this offseason? 

The Cubs are interested in the big names this winter like; Jon Lester, Max Scherzer, Jake Peavy, James Shields and Russell Martin. There were also reports yesterday stating that the Cubs will call the Philadelphia Phillies to inquire about Cole Hamels. If one thing is apparent, the Cubs need pitching.

Is it realistic they land two of the top free agent pitchers available? I personally don't think so. I predict the Cubs will land either Lester or Scherzer and possibly add James Shields or Jake Peavy at the right cost.  

The first domino to fall will most likely be Martin to the Cubs. ESPN's Buster Olney predicts that Martin is destined for the Windy City. I agree. Position wise, catcher is the weakest position for the Cubbies. Especially in the infield with every position set in stone except for catcher. Expect Martin to be the first domino to fall.

Now, the Cubs biggest need is obviously pitching. I don't see where they could wrong with any of these guys available. Personally, Jon Lester is a favorite of mine. I'd love to see him in Cubbie blue. You can't go wrong with him or Scherzer.

I wouldn't mind seeing Scherzer in a Cubs uniform either. He's made a name for himself as one of the top pitchers in the league over the past few seasons. With all that said, I'd be surprised if Lester or Scherzer don't end up with the Cubs.

The Cubs may want to save some money for next offseason with possibly an opportunity to sign David Price. Price, of course has the connection with Joe Maddon, his former manager in Tampa Bay. That's also where the James Shields to Cubs connection comes in as well. Its a more likely possibility to see Shields on the Cubs then Price.

Personally, I wouldn't mind the Cubs signing Lester or Scherzer then signing Peavy or Shields and then finding a way to also trade for Cole Hamels. That would be a nice three-headed monster. I doubt the Cubs could pull that off, but you never know.

The Cubs future is filled with excitement with pitching as the only area of concern. Their infield will be great with the impending arrival of last year's Minor League player of the year, Kris Bryant. Bryant is loaded with talent. 

The Cubs could have a roster as soon as this upcoming season consisting of; Kris Bryant, Javier Baez, Starlin Castro, Anthony Rizzo, Arismendy Alcantara and Jorge Soler. Lots of pure talent. A very young team that is destined for success.

In the end, these are my predictions for the Cubs offseason:

Jon Lester: 6 years, $135 million

Russell Martin: 4 years, $72 million

Cole Hamels: Via trade with Phillies

& expect a lot of small signing as well. 

All in all, it will be a busy offseason for the Chicago Cubs!