Lester is in Cubs Sights, but What if They Miss?

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Everyone knows that the Chicago Cubs really covet Jon Lester. They have not hid their desire to add a top of the rotation starter to their rotation which already boasts breakout pitcher Jake Arrieta and emerging potential talent like Kyle Hendricks. Before the 2014 season ended, everyone looked right at Lester saying that he was the most likely pitcher the Cubs would pursue, and make an enticing offer to persuade him to join the team on the North Side. This was confirmed when he met with Theo Epstein and Jed Hoyer earlier this week. The only question was would they be able to offer a more enticing opportunity and a richer contract than their top competitor the Boston Red Sox.

Yesterday, news came out about the details of the Red Sox initial offer to Lester, which was for six years and somewhere between $110-120 Million. My initial thoughts were that the Cubs should be able to beat that offer and give him a contract which offered him more money per year. In fact, if their offer was for less than the $120 Million the Red Sox offered, I would be extremely disappointed.

Now, you should know that the six years for $120 Million is only the Red Sox initial offer. You would be foolish to believe that this was their first, last and only offer. Every team is going to offer their hopeful contract offer before breaking out the big guns. The Red Sox throw this offer out to Lester and allow the Cubs and the other teams interested in Lester (Atlanta Braves and St. Louis Cardinals among others) to set the market. Even if the Cubs do beat the contract offer to Lester that the Red Sox offered him, Lester’s agent will go back to the Red Sox giving them a chance to beat the new highest offer. If they do, he goes back to the Cubs (or whoever made the highest offer) and the game of financial chicken begins. Which team will blink first and not be willing to give that extra million or that extra year.

The question is, will the Cubs beat the Red Sox offer, and will their best offer (whatever that may be) be the best offer Lester receives? For that matter, will Lester even accept the best offer or will he pick the team he wants to pitch for money be dammed? No matter how much money the Cubs offer Lester, he may choose to return to Boston where he has comfort and familiarity. I would not blame him for turning down an extra couple of million to return to a place you called home for several years. If that happens, then I cannot place any fault on the Cubs. If you make the highest offer and the player decides to go elsewhere, there is little you can do but wonder what you could have done better to convince your target.

No matter how this shakes out though, even if the Cubs have the highest offer and Lester choose a different team for whatever reason, the Cubs will be called cheap for not offering so much money that only a fool would choose comfort over cold hard cash. In my opinion that would be unfair, but you cannot win a war against those who feel that the Cubs are too cheap to put a real offer on the table that would be impossible to turn down. That is going to be a hard image to turn down until the Cubs actually win one of these bidding wars.

As has been pointed out, the Cubs have offered just enough the last few years to say they tried to make a reasonable offer only to be beat out by a better offer. Some say they have finished second best in too many deals for things to just be a coincidence. Some fans feel as though Epstein, Hoyer and Tom Ricketts are just playing lip service and giving fans just enough hope that they will clary to sign the top talent to drive up excitement and sales. Some fans will not believe they are serious until they actually win one of these bidding wars, no matter the cost.

The Cubs have been deemed the “bridesmade” around baseball because they always finish second as they did with Russell Martin. This is where things get a little funny.

Fans were glad the Cubs passed on signing Martin after seeing the deal the Toronto Blue Jays gave him, but at the same time point to that deal to prove their point that the Cubs do not care enough to win to go above and beyond what they are comfortable with in order to sign their targets in free agency. Seriously, some were glad the Cubs passed but mad that they didn’t spend whatever they had to in order to get a guy they targeted. Same will happen if the Cubs miss out on Lester as well.

However, if the worst happens, and the Cubs are once again outbid for Lester’s services, there are still other top if the rotation options out there for them to explore. Lester is not the only arm on the market, he is just the one that is connected to the Cubs the most. There is still Max Scherzer and James Shields out there.

I know what you are saying though, if they are not willing to pony up the big bucks for Lester, why would they ofer more for these two? After all, Scherzer will be vastly more expensive I am sure, though Shields might be a little less.

Epstein and Hoyer know that the Cubs need to add pitching. They cannot afford to stand still and go into 2015 with what they currently have in the rotation. That will not even be enough to appear as though you are contending for anything more than last place.

Scherzer is likely waiting for Lester to sign, so he knows how much he can ask for and get in a deal. If the Cubs sign Lester to my ideal six year and $150 Million, Scherzer could easily ask for $175 over the same time frame and likely get what he wants. If the Cubs miss on Lester all together, expectations by the fans will turn desperate and expect the team to turn to him to lead their pitching staff the next several years. How likely that would be if they could not afford Lester, I am not so sure. Though the Cubs could surprise us and sign one or both.

Shields on the other hand, while one of the big three available this off season, might get a little less than Lester. His talent and work ethic would be a very fine addition to the Cubs staff, maybe even at a lower price. He might not be as good as Lester, but he will still be a major upgrade over what the Cubs currently have and will be a welcome addition.

Other names that might be available, though not as flashy would be Justin Masterson and Brandon McCarthy. If the Cubs have to settle for these two, you know you will hear fans complain about being cheap as usual even though they would still be welcome additions to the rotation.

With only Arrieta and likely Hendricks locks for the 2015 rotation, anything is possible with who the Cubs sign. Perhaps they sign two or three of these guys, maybe just one. Though, the possibility remains that they will miss on every one of their targets this winter; which will of course start a loud chorus of fans saying “I told you so” and more people calling the Cubs cheap for not spending whatever they have to in order to get the guys they want.

As I have said in the past, there are players you over pay to sign and those you do not. Martin is not one of the players you over pay to sign, but Lester is. Now let me add to that. There is over paying for players, then there is throwing stupid money at players to get someone you feel you need. Even teams with money to burn have a limit they are willing to give to every player they have their eyes set on, and they will not exceed that.

Over pay those you must get, but do not throw stupid money at them just to get them. I hope the Cubs do not need to over pay Lester or anyone else they desire this winter; but if they do, I hope they do not throw stupid money at him in order to sign him.

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4 Replies to “Lester is in Cubs Sights, but What if They Miss?”

  1. If & When the Cubs sign Lester, I would like to see them Front Load the Contract so if they go the extra year it doesn’t hurt at the end of the contract as much.

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