I stayed up as late as I could last night awaiting the news on Jon Lester. Naturally the news broke just a few minutes after I turned things off and went to bed that Lester had agreed to a 6-year $155 million deal with the Chicago Cubs.

I don’t sense that many people will be upset with Jon Lester for this decision. The heat, from both fans and the media will be directed at the Red Sox.

How will they react? Will there be a subtle leak in an attempt to turn PR to their side? (#SmearCampaign)

Their best move will be to acquire talent to try and fill the void in the starting rotation.

Here’s a sampling of articles from this morning:

Red Sox’ lowball offer last spring led to Lester’s depature – Sean McAdam says the Sox didn’t lose Lester last night, they lost him last spring.

When it came to Red Sox’ pursuit of Jon Lester, we should have known better – Rob Bradford says that the “Red Sox offered less than their competition, less than it would have taken to get Lester re-signed, at every step of the way.”

Red Sox have work, explaining to do – Gordon Edes says that the Red Sox have let Lester fans down twice, first with his trade to Oakland and now this.

Red Sox made curious strategy change in Jon Lester pursuit – Peter Abraham says that this will go down as one of the strangest chapters in Red Sox history.

Red Sox wouldn’t overpay for Jon Lester – Michael Silverman says that the Sox wanted to be in the hunt, but weren’t upset at not getting him.

What now? Potential Red Sox targets with Jon Lester off the board – Alex Speier looks at where the Red Sox go from here.

Jon Lester Was Everything a Red Sox Player Was Supposed to Be — So Why Is He a Cub? – Chad Finn laments the loss of the lefty.

The Red Sox don’t like to take heat from the media. They will respond one way or the other. Here’s hoping it is in the form of player acquisition, not some sort of whisper campaign or Boston Globe article from Bob “The hitman” Hohler.

Does John Henry appear on Felger and Mazz today? Does Larry Lucchino make some jabs at his former protege, Theo Epstein?

Or does Ben Cherington just go about his business of building a competitive baseball team? Let’s hope it’s that.


Gronk! The Interview. – Lindsay Czarniak interviewed the Patriots tight end for ESPN The Magazine. It’s a must-read.

Larry Bird’s Greatest Shot Was the One He Didn’t Take – Larry Bird fans are very familiar with the former Celtic’s background, but this Indianapolis Monthly feature by Sean McCabe is worth a read.


25 thoughts on “Red Sox Facing Heat After Losing Lester To Cubs

  1. Something you won’t read from a lot of the media…

    The Red Sox could learn something from the Patriots. The Pats lost Talib on 3/4/14, by 3/14/14 they had acquired Brandon Browner and Darrell Revis.


    1. The exact same people that are killing the Red Sox right now (and killed them in March for the ‘slap in the face’, destroyed the Patriots and praised the Broncos to no end, in March of 2014.


  2. “Tigers completely bungled the Scherzer extension talks in the spring”…. said no one, ever. Why? Because neither of these are bungles.

    If I am Lester’s agent, I NEVER NEVER NEVER NEVER NEVER would advise him to take an offer from the Red Sox — or even negotiate with them — a year before you’re one of the two major pitching free agents on the market. Whatever the Red Sox are offering today in the spring will absolutely be there in the fall, too. Unless they are literally offering you the best contract in baseball history (i.e. Kershaw money), there is no reason to extend, unless you fear an injury will derail you. And given Lester’s reputation for good health and his good conditioning, that probably wasn’t a huge concern.

    Here’s the deal that would have extended Lester in the spring: 7 years, $210M. That’s it. That’s literally the only deal I, as Lester’s agent, would have advised him to take. Yes, the Sox’s offer was a “lowball”, but it was a starter for negotiations. If the sticker price on a car is $40,000, you don’t sit down with the dealer and say, “Okay, I’ll offer $39,500.” You sit down and offer $30k. The dealer responds with “nope, $40k”… and then you get down to business. That’s how negotiations work. The Levinsons clearly DID NOT WANT TO NEGOTIATE this spring — and that’s exactly what I would have done, too! The only thing you’re likely to do by negotiating with the Sox in spring training is leave money on the table.

    It frustrates me that nobody in the media — or fans, for that matter — even tries to understand how contract negotiations actually work. The power is entirely in the hands of the player in situations like Lester’s — so if Result X occurs, it’s entirely because that’s what the player wanted. Lester and his agents wanted to see what the market would pay for his services. They ALWAYS wanted to see what the market would pay for his services. Every single thing they’ve done and said has demonstrated that. It’s easy to just say “cheap carpetbagger owners cheap out on poor Jon Lester” and get some column/radio pop, but it’s unfair. You can’t negotiate with someone who doesn’t want to negotiate.
    The window the Sox really had to negotiate with Lester was TWO springs ago. Then, he was coming off his worst season as a professional. But… would you give big money on a 6 or 7 year deal to 2012 Jon Lester? 9-14, 4.82 Jon Lester? The Jon Lester whose ERA+ had declined every season since 2008? Of course not. The risk that he was on the decline was too great. You let him pitch in 2013 and see what happens. And, of course, what happened was that 2012 turned out to be an outlier. That’s the risk you take. It didn’t pay off in this case, but it’s a reasonable baseball decision, and engaging in Tony Maz 20/20 Hindsight is ridiculous.


    1. Amen. I will never blame Lester for taking what he believes is the best offer. Moreover, the Red Sox initial offer was ridiculous. However, as you point out in any negotiation you have offers & counter-offers and we NEVER heard from Lester or his agents what the “discount” would be.


    2. Kinda fits in with your car analogy:

      @jeffpassan The toughest part for the Red Sox has to be this: Had they offered Lester a deal for $115-120 million last spring, he would have signed it.

      (As usual, national guys have everything.)


      1. Except that’s a false narrative. NO DEAL would have gotten Lester to sign. How do I know that? Because HIS AGENTS REFUSED TO NEGOTIATE. Even if you’re “insulted” by a 4/70 offer… how does that disincentivize someone who loves Boston so much that he’ll take a hometown discount?

        This is not a situation where the Sox offered 4/70, the Levinsons countered with 6/150, and the Sox walked away and tabled discussions. In that case, all of this criticism of the Sox misreading the market and such would be 100% correct. But that’s not what happened. What happened is that the Sox offered 4/70, and Lester walked away. He can say whatever he want, but what he DID was indicate very clearly that he had no intention of signing a deal any earlier than 7 days after the end of the World Series.


        1. But Dave, if you buy that Lester and his family enjoyed their time in Boston and found it comfortable here, isn’t there even the slightest possibility that had the Sox first offer been in that 5-for-110 neighborhood he would have been willing to sign instead of testing the market? We know that if Boras was his agent that would never have been the case, but aren’t other agents like the Levensons, etc. a little more willing to negotiate with their clients’ first choice?

          I don’t think it’s a given that a higher initial offer from the Sox would have kept Lester in Boston, but I wouldn’t complete dismiss the idea out of mind either.


          1. I don’t. And here’s why: because if that offer would have kept him in Boston, he would have asked for it (or ordered his agents to ask for it).

            He did not. By all accounts, he got the 4/70 initial offer, and decided to table conversation until after the season. Due to not wanting “distractions”. Well… Jon Lester has two smart, highly-paid agent brothers working for him. He could have done exactly what he did here — have them go off and do all the legwork and negotiation, then come back to him and say “this is the best the Red Sox will do right now”. He can take it, counter, or decide to postpone. How much of a distraction is that? For Pete’s sake, you could probably get that all done in a week.

            But he didn’t do that. He and the Levinsons broke off conversations until right before the trading deadline.



          2. Dave:

            I mostly agree with you…let me add this. Chicago ended up paying Lester $20 mill more than the reported Sox offer. Did the Sox not know the Cubs were at $155 when they offered $135? There are no secrets. Further why did Chicago offer $155 when it appears $140 would have gotten it done. The simple answer is the Sox offer of $135 was not serious and Chicago was afraid a team (Dodger or perhaps the Yankees) would swoop in at the last minute and overwhelm Lester with cash.

            My perspective has been that Lester was never going to sign with the Sox. He saw all the money given to outside the organization FA’s and how home grown guys had to either fight and leave (Ellsbury) or take a hair cut (Pedroia). He did not want any of that. When Kershaw turned down 6 @$145 we all knew Lester’s value. The Levinson’s certainly knew and advised their client. When the Sox offered 4@$70 they could have countered with 6@$140 but they didn’t. They knew two things…1) Lester did not want to be in Boston because ownership was schizophrenic in its team building approach and 2) That there would be several teams lined up after the season to give Lester $150 mill. Once the Sox traded Lester (the really stupid move in all this if they wanted him back…which they never did) Lester started counting golden eggs.


          3. Another question to ask was who benefits from the leak of 4/70. I think we all know the answer to that question. I agree with LTD that Lester did not want to sign here and frankly once the Red Sox knew that they made the trade (which I believe was a good move).


        2. This is exactly what happened, but it doesn’t matter. The likes of Mike Mutnansky, Toucher, Rich and Adam Jones have been in the driver’s seat of the “Sky is Falling” phony storyline since March.


  3. Round-up of best Tweets that the Globe will use as a muse for its upcoming special on how Jon Lester was not who you thought he was:


    More here:


    Get to work, Globies. Lots of great ideas there.

    On the Gronk interview, the photoshoot was even better. They posted some shots of Gronk with a kitten that I have to think is more mature than he is:



  4. Well, I guess the bright side is that even though they “lost” Lester in December (for the second time), they still managed to get something for him the first time they lost him in July. That piece (Cespedes) likely will be included in a deal for pitching. I’d go after Scherzer, personally, because I think he’s a great pitcher, but if they sign Shields as their #2/#3 guy and are able to acquire a #1 in a deal involving some of their suddenly-expendable prospects (Hamels?), that would be good enough, given the improvements on offense (including the Castillo signing), to get them into contention before the July 31 deadline. Also, Buchholz, in his on-again, off-again career, is due to be “on” again in 2015, right?


  5. So Jon Lester is now the 2nd highest paid pitcher based on annual salary only behind Clayton Kershaw??
    That’s insane.
    Is he even top 5 in the American league?? Or the National league for that matter??
    The media mythology campaign that’s been underway re: Lester’s career has been something to see. Lots of air brushing going on.
    Been a good pitcher, not great but a good pitcher who’s pitched some big games but 170 million if the vesting option kicks in??
    Wild overpayment.
    The Red Sox will be fine.


    1. I do think that Lester’s durability has been very undervalued, at least publicly. He’s made at least 31 starts each year since 2008 (of course you could make the argument this workload could eventually catch up with him). It is interesting that the guys who they’ve brought in, Porcello (avg 30 starts/yr in career) and Miley (95 starts over last 3 years) have been durable, as has Hamels if they land him.
      These guys are younger , poor man’s version of Lester, who is a top 15 starter in the league. But, no, he’s not worth 170M at 31 years old.


      1. Cole Hamels is statisically at least the equal of, if not superior to, Lester. Even if you drop Lester’s 2012 season, Hamels’ average WAR is significantly better than Lester’s over the past 5 seasons — like a whole win better. Yes, it’s the NL, but that’s a significant difference, and calling him a “poor man’s Lester” is selling him WAY short.

        p.s. I think Porcello is terrible — utterly overrated. If he pulls out another 3 WAR season for the Sox, I’ll be overjoyed.


        1. Yes I wasn’t clear but I was referring to the guys they got not Hamel. He would be an upgrade on Lester and is slightly younger and cheaper.
          Even though he’s a flawed player, I thought they would get more for Cespedes.


          1. I think the fact that he contractually couldn’t be offered a qualifying offer at the end of the year diminshed his trade value vs. what you’d think he’d command.


  6. Can someone clue us in as to why the Sox didn’t want Lestah back? The money was ridiculous, we know, but there seemed to be other reasons for not being more aggressive. What say y’all?


    1. In 9 Seasons he won more than 16 games once. His career ERA is 3.58. His reputation has been made because he has won some big playoff and WS games but he has lost a few of those as well. So it came down to this…with numbers that are good but not exceptional was the organization willing to guarantee the guy $25+ mill a season considering that he is 31 and pitchers past 30 generally are on the down side?

      We all like Jon Lester but the Bill Belichick in me says get rid of him a year or two early than be saddled with a bad contract later on.

      At the same time I think Ben C. needs to make a statement…he trusts the farm system and whats coming. Whether it is Owens, Renaudo or one of the other guys the Sox have to believe their system will produce + arms. As such they did not want to tie up the money needed to sign Lester and therefore block development. It might not be your thinking but I do think it was theirs.


    2. The Cubs gave Lester a possibly 7 year contract. I’d be willing to bet that the allure of breaking the Cubs non-WS winning streak was very strong as well. Please define “want” in this context. Should they have offered ten years?

      On a related note, I’m thoroughly enjoying the meltdown that some Sox fans are suffering from. These are some of the same people (not necessarily you, Elvis) that said Duquette deserved 75% of the credit that Theo received from footy pajama wearing Homers such as myself, some of the same people that hate Lucchino more than they want the Red Sox to win and would rather be proven “right” and some of the same people that thought the Sox had no chance to win in 2013 until Koji threw the very last strike.


Comments are closed.