As tomorrow’s MLB trade deadline approaches, most people seem convinced that the Red Sox will trade lefty Jon Lester, rather than sign him to an extension.

It’s hard to believe that it has come to this, but here we are.

Tim Britton of the Providence Journal has a post with all the coverage his paper has done on the Lester situation since January, showing us the winding road this drama has taken.

How did we get here? The path that’s led the Red Sox to the verge of a Jon Lester trade

The always excellent Alex Speier also looks at the Lester situation, and how 2014 has been about coming of age for the pitcher.

Eye of the storm: Amidst chaos, Jon Lester comes of age

In many ways, the focus on where Lester ends up obscures a more significant story. How did Lester arrive at this point? How did he, over the course of 12 years, transform himself many times over into a pitcher who now is at the absolute zenith of his career, who looks like someone at the height of his powers and knows it?

The 2014 season marks a coming of age. It has been a year littered with potentially uncomfortable questions — about his contract talks with the Sox, about the possibility of being traded. Yet Lester has seemed more secure than ever in fielding those inquiries about what is happening around him off the field, and it is precisely because of his newfound comfort in who he is on the mound.

As always, it amazes me how Speier is just at another level with things like this and his analysis.

Lester has been in the consciousness of Red Sox fans since the Winter of 2003-04 when he, as a then a  prospect, was being mentioned as part of a possible trade to Texas for Alex Rodriguez. In that case, it shows that sometimes it’s better not to give up the prospects for a player you think is the missing piece to your team.

Now, he’s on the A-Rod side of things, possibly being traded himself for younger, tantalizing prospects. But Lester is more than just another guy, we’ve seen him grow, we’ve seen him beat cancer, and come back to be the best pitcher on a World Series winning team.

It’s hard to know what is going on behind the scenes at Fenway. Who is calling this? Larry Lucchino? John Henry? Probably not Ben Cherington or John Farrell. I’d love to know what Cherington’s thoughts on this really are. Has Lucchino gone back to how he was when Theo Epstein finally had enough and walked out?

This really is more about the Red Sox and where they are than it is about Lester. Jon Lester is going to be fine, wherever he goes. But what about the Red Sox? If Lester is gone, the Red Sox are still here, and we have to deal with that. Are they in turmoil again?

Will the Globe smear Lester if the team trades him? While it doesn’t always happen, (it just seems that way) you have to believe they’d have a hard time coming up with material on him.

Let’s put away the notion that the Red Sox could trade him, get talent back and then sign him back here as a free agent come fall. If they can’t sign him now without any competition, how in the world are they going to sign him when teams like the Dodgers, Angels, Yankees or Mets are out there with open checkbooks?

Of course, they might not trade him at all, and end up signing him before he hits free agency which would render all the hand-wringing and anger completely moot.

I don’t know that I would bet on that outcome though.


39 thoughts on “It’s Wall to Wall Jon Lester as Trade Deadline Approaches

  1. I don’t understand the schizophrenia of the attitude towards the Red Sox I’m seeing from the local baseball press. Well, I do…. they’re reflecting the viewpoint of the fans, and basically writing what the fans want to hear. But I don’t know why some of the more reasonable voices haven’t chimed in on this issue.

    I like Lester; I like his competitiveness and his work ethic and the way he has, since he was a rookie, fought each batter hard and didn’t get rattled by baserunners. (Contra a certain other youngish pitcher whose name rhymes with Play Tuchholz.) All things being equal, I’d take the risk and pay market value for him, even if you’re looking at late-contract deadweight, because I like the risk/reward calculus on that. So in a sense, I disagree with the stance the Red Sox appear to be taking on this.

    But given that they do have some sort of stance — and it appears to be “we’re not paying him more than $X”, with $X being a number that Lester does not appear willing to sign for without testing free agency first — none of what has transpired so far should be shocking or controversial. OF COURSE you look to trade him, because “prospect + market overpay for Lester” is greater than “market overpay for Lester”, whether or not you actually want to retain him. The Red Sox now know EXACTLY what it will take to retain Lester: an offer equal to the best offer received from someone else. He’s made that clear both by his comments about being willing to resign with the team AND by his agents’ apparent unwillingness to engage in serious negotiations with the team. (And the line that he was “insulted” by the $70M offer is BS, plain and simple. Negotiations are negotiations. If you’re insulted by that offer, you counter with 10/$300m, and then get down to the real business now that all that’s out of the way. Not negotiating after $70m means you don’t want to negotiate, end of story.) Given that, there’s no reason to avoid trading him if you can.

    Some other factors I haven’t seen mentioned by anyone writing about the situation:

    — Let’s not forget that Lester’s a cancer survivor. That means that it’s almost certainly impossible to insure his contract, whatever it may be. That is a nontrivial element to consider when comparing signing Lester to a, say $200M deal vs. signing a Max Scherzer to the same deal.

    — How exactly is it a “no brainer” for an organization that’s stocked with young pitching to spend a significant amount of cash on an older pitcher when there are glaring offensive needs and no young players in the pipeline to fill them?

    — If you want to see the result of signing beloved players to huge contracts based on past performance without a coherent plan as to why you’re doing it…. just look 400 miles or so to the south to City of Brotherly Love. Just be careful that you don’t accidentally wind up with Ryan Howard’s contract on your books if you do. (Side note: Can someone tell me how, exactly, Ruben Amaro has kept his job?)


    1. I can’t think of a single member of the Boston media, including guys like Fatty and the Forehead that love to think of themselves as real investigative reporters, that hasn’t acted as if they’re trying out to be Lester’s next agent, since opening day of this season.


      1. Nobody really is anymore. Didn’t Pete Abe already say that Lester to BAL is done, last night?

        Even the team’s own personal PRs firm don’t get breaks like the national guys (Rosenthal, Passan, etc.).

        If you are that good on the sources, you’re not working in a local market.


  2. From the content of your crackerjack analysis, it’s clear that baseball is a distant fourth for you. No need to explicitly clarify it.

    – Assclown

    p.s. Josh Beckett


  3. “Every story, every discussion, every issue is about contracts, money, griping players and off-field nonsense. Every. Single. One.” Yes, that’s why in the past month we’ve had: The Decision 2, Carmello-Watch, countless stories on the NBA salary cap, countless stories on the NFL salary cap, will Kevin Love be traded b/c of his contract, Marshawn Lynch’s hold-out, Jimmy Graham’s (TE) contract, Johnny Manziel’s off-field nonsense, Chicago Blackhawk stars’ contracts, Bruins cutting guys because of contracts and Ray Rice. Just to name a few.


  4. Baseball at the upper end is an economic oddity to me. The idea that you would generically guarantee a 30+ person $150 mill to perform an athletic event seems crazy to me because you have to realize that getting $150 mill of value out of that player probably will not happen. Heck in all of sports right now the only players I think might return that type of investment by selling seats, increasing advertising and merchandizing coupled with helping the team become appreciably better are Lebron James and Peyton Manning.

    So if I am Sox ownership I have to be looking at the Lester contract and be thinking…there is no way we get value out of signing this guy. He has been on our team the last three years and we are going to finish last in the division two of them (yes I know they won the WS in the third one but it is not like Lester put the team on his back and carried them there). Having said that, there are only a few people on the planet who can throw the ball like Lester does today. If we do not sign him what do we do? It is a conundrum. But worse, it shows either a lack of faith in the arms coming through the system or unrealistic demands from the entertainment side of the business that can’t allow another down year in 2015.

    In the end I think Lester gets traded. I don’t think the Sox can invest in a pitcher when they supposedly have pitching depth in minors when what they really need is outfield power. I also don’t think the Sox ever really considered coming off 4/$70m. I think they value Lester at $15.5 mill a season and their projects say a 30 year old pitcher has 4 good seasons in him. Unfortunately there are 7 teams out there with money to burn who are chasing the elusive commodity that is left handed pitching.


    1. I’d add that I don’t think they’d avoid trading him for more pitching, either. I really do think that they’re stockpiling assets for a run at Stanton in the offseason, on the thought that they could assemble a package so good that it would offset the Marlins’ desire to hang on to him.


    2. Just because the market is willing to pay someone doesn’t
      mean he’s worth it.

      Barry Zito age 29 – 7 years $126M from Giants

      Mike Hampton age 28 – 8 years $121M from Rockies

      Kevin Brown age 34 – 7 years $105M from Dodgers
      Lester is a pitcher who has never won 20 games, and only won more than 15 twice, never won a CY Young and people want to pay him $30M a year?
      I don’t get it. I like him a lot and hope that after he’s traded he ends up back with the Sox, but not for crazy money.


      1. Gary Tanguay has DEMANDED many times of the last couple of weeks (filling on 98.5) that winning one World Series in 2009, proves that giving Texeira and Sabathia many guaranteed seasons was the correct move.


      2. Wins for a pitcher are meaningless. Where does Lester rank in ERA, strike outs, walks, home runs and innings pitched? That’s what matters.


    3. Baseball at the upper end is an economic oddity to me.

      Same. It’s the game but I have to wonder if this is not a shift in something bigger. MLBPA seems to want to make sure Lester hits the market, as well.

      After seeing the recent sales, between the Dodgers and Clippers, I have to think that’s one end of it. Second, I think that FSG sees the same ratings decline that MLB seems to ignore. To me, I think the “economic oddity’ is going to come up when TV contracts all come up with FOX, ESPN and Turner in 2020-2021. Baseball will still do well in baseball markets but it seems to be turning into a regional sport, much like hockey is. They already have a great soccer club that’s a global brand. You want to sell now, or soon, before any of this starts to really show up on radars.

      Are we sure that, two months from now, we won’t see another Charlie Gasporino article about FSG wanting to sell the Sox? You want to sell with maximum flexibility, not being locked into a bad roster.


      1. BSM, I could write a book on what baseball has done wrong from a marketing and PR slant to alienate an entire generation of fans. Having said that Summer = TV abyss/wasteland. Baseball for all its problems and over saturation still delivers better local and national summer TV numbers than almost any other type of programming. If the Dodgers local package is worth $4 bill over 17 years how much is the national package worth to ESPN? It still is a sport that broadcasts 162 games for each market and there is no counter programming. Football starts in September. Hockey and Basketball are for all intents and purposes over in May/early June. So unless MLS grows to a phenomenon in the next 5 years the MLB TV deal will still be worth Billions.

        I also would have thought $125 game day tickets at Fenway would have killed fan interest. I was wrong on that as well…at least so far. Anecdotally, my 10 year old nephew gets taken to about 15 games a year between my brother-in-law, his grandfather (my father) and me. He loves going to Fenway (and McCoy). He plays basketball and swims, but does not watch Baseball on TV. I wonder what type of fan he will be when he grows up?


        1. PR slant to alienate an entire generation of fans.

          MLB has issued a response by reminding you and I that they made over 7B in revenue last year.

          still delivers better local and national summer TV numbers

          What does it compete against? When it does have competition… I get that each sport kinda enjoys their own exclusive window, but that has to be troubling.

          So unless MLS grows to a phenomenon in the next 5 years the MLB TV deal will still be worth Billions.

          But, if your sport has already lost part of a generation, going on a complete one, how is that going to play out in the future? Once you lose one generation, or more, how do you get them back? They’ve most likely moved on. I think its underplayed heavily and they should get some folks from advertising to remind them as to why you target younger demos (customers for life).

          I wonder what type of fan he will be when he grows up?

          MLB seems to either ignore the question or not want to answer it. There is so much that needs fixing. The draft, being able to trade picks, the length of games, and we could go on and on. I’d also argue that MLB, in effort to create more parity, is killing their product. MLB, like the NBA, was built upon superteams in big markets. If you declaw the bigger market teams (LA, NY, BOS, etc) from being able to be big players, you increase mediocrity. Casual fans don’t like mediocrity, or will not stand it for long.

          My prediction, what I made above, is that if the national numbers continue to drop, these big national TV contracts won’t be there. We’re in the midst of a “sports TV boom” right now but what happens, in 2020, when the average cable bill (so no VoIP or Internet) is $250 due to sports? There will still be good local markets (this one) but that’s something like 1/3rd of what most teams bring in via TV.

          I know you could go on forever with this but MLB is doing absolutely nothing to address anything. They seem to be content just reminding everyone how much revenue they made. From the looks of the post-Selig era, they’re doing their best to maintain the status quo, as well.


  5. Take the comparison of Lester at in-season negotiated salary with a FA market salary. Assume for the sake of argument the difference is a year of salary and a bump of $3M/year amounting to something like $45M total. Also consider that salary on the books for 2015 is under $80M if what I read is true. Would that $45M difference be worth the cost of a pick up of 1-3 significant prospects in trading Lester now (the prospects having no signing bonus and being 1-3 yrs closer to the majors compared with the amateur draft) and then signing Lester in the off-season? This would seem rational when viewed in comparison to what they did with Dice-K, and his numbers are in 2007 dollars.

    I can’t know if this type of analysis is even happening in the organization, but I think it would be kind of rational.


  6. If you are to read one column today, Jason Gay (WSJ) nails it on the current state of sports media today:

    If you’re going to create a 12-month, 365-day cycle, you’re going to have to generate material. News actually sleeps. Luis Suárez cannot bite an opponent every day. You’ll have to manufacture topics. And some of them will be marginal. In a click-driven environment, it’s not sufficient to run for three-yard gains. It’s helpful that questions are loud and pushy and maybe even a little bananas.


    1. yep, no doubt about it. Less is more in my view. I watched, read and listened more to sports media when there was LESS of it. Since it’s gone 24/7 they act outrageous i.e. CLOWNS just to get people to pay attention to them……Sad thing is, it works.


  7. “If Lester is gone, the Red Sox are still here, and we have to deal with that. Are they in turmoil again?”

    I can’t believe I’m typing this out, but JUST LIKE FELGER said today (and blew Tony away in the process), this ownership with two different GMs has rebuilt (leading to rings) on the fly three times. Not allowing them some slight benefit of the doubt is well, it’s ludicrous. I can’t listen to another second of the Mutt’s of the world whining and crying and carrying on like babies.


  8. “The coverage of this story is so off the deep end, like everything else in this city. The fact that some assclowns are actually trying to rationalize the Sox front office’s point of view is ridiculous.”

    What utter and complete nonsense.

    At least 99% of the Boston sports media has attacked the Red Sox on this front, continuously, since Opening Day.

    You’re simply not paying attention.


  9. 4m ago @JeffPassan Source: Jon Lester has been traded.

    Jon Heyman is saying it’s Oakland.

    @alexspeier: Trying to confirm, but hearing Lester and Gomes might be moving for Cespedes

    National guys scoop the locals yet again. Have to wonder, if you work for NESN or the Globe, on why you’re not getting fed this so you can break it?


    1. I think Cespedes is actually pretty good return–a bona-fide slugger coming into his prime–particularlyl since Boston still has the chance (though I can’t speak to Lester’s fondness for Lucchino) to re-sign him later this fall. A cleanup hitter for a rental of an ace? Boston could’ve done worse.

      So I wonder if even Shaughnessy could type up a gloom-n-doom “Curse of Lester” column. (Hmm, how would that go? “Curse of the John?”….no….”Curse of the Les?”….nah, not that either….damn, it’s hard to find a phrase as pretty as “Curse of the Bambino”….but anyway.) Frankly, I don’t think he can. Cespedes is a legitimate asset. Combine that with Lackey’s trade, and we’re almost back to the Sox of the 80’s, and the mirror-image of what Boston’s been all year–oodles of hitting, and no pitching in sight. (Yes, I realize we have the youngsters, but at this point they’re still a little…up-and-down.)


  10. Would have been a bit hypocritical given the players involved.

    I see more and more T&R tweets @ the other morning show. Sounds like what Ordway said about their summer rating might be true.


  11. I was clear you were making a point about baseball. It just wasn’t a good one. If you don’t think the media doesn’t obsess over contracts, salary caps and other non-game related issues in other sports (all year long), you’re just not paying attention.


  12. Merloni always sounds childish. After being boring for years he’s really turned up the INDIGNATION and OUTRAGE lately. Sorry, Louie. Taking crap lessons from Tanguay et. al isn’t going to save your career, it’s just one less person for sensible people to care about.


    1. Does anyone recall that there was a bidding war between 98.5 and ‘EEI for him? How ridiculous is that in hindsight? I mean, I didn’t understand it at the time. I loathed him as a player. What I’d heard and seen of him when he first started in the Boston sports media made me think he wasn’t long for the industry. His voice is grating and his antics are derivative and tired. He just seems sleazy in general. Seriously, is anyone out there saying that they like this guy or his show? I’d say he’ll be gone when his contract is up, but he’s the type that will take a huge pay cut to stick around.


      1. He owes everything to Ordway. Ordway also knew enough to keep his contributions limited to hide the fact that he was not all that great at this. To use a baseball metaphor, he’s a bullpen scrub who was great in a limited role, but who stinks as a starter.


      2. Does anyone recall that there was a bidding war between 98.5 and ‘EEI for him

        Has to be up there in the “Puzzling Decisions” category during Double Jeopardy. I’d still rank that one below Tanguay having a radio show.

        The show has fans, no doubt. I’ve expressed my opinion on not being a fan before, but all that matters is ratings. They made some gains 3.5->4.4 (G+Z went from 8.9->6.2) between Winter and Spring, but lets see how those sustain over the next two books, with the Fall rating being the teller if the Fauria move worked.


  13. What follows is the VERY ENTICING line that Tim Benz just used to close out one segment, head to a commercial break, and preview the next, RED HOT segment.

    “Twitter was not kind to Ben Cherington yesterday. In particular with one thing that he said. We’ll have that coming up next.”

    So now Twitter is a singular entity?

    I digress and rest my case, Tim Benz has quickly become one of the biggest douchebags in this media market.

    Free Fauria!!! (bumper stickers coming soon)


  14. My pet peeve today: the “There’s no way Lester is coming back; you’re stupid if you think so” chorus of the mediots, combined with the “if they were willing to pay him the money, they would have done it already” adjunct argument.

    Not only is that dead wrong (there is never ‘no way’ — if the Sox offered Lester $50m a year for 15 years, guess what — he’d be back!), but yesterday’s events make it MORE likely that Lester will be back next year, not less. Here’s why:

    1) The reason the Sox weren’t willing to extend themselves to sign Lester is because it didn’t make sense to them to extend him when the team was as flawed as they were. To use a metaphor: say you’re a professional porch-deck competitor. (Stay with me here…) There’s a super-awesome chair that you can buy for $700. You have a budget of $1000. Does it make sense to buy that chair if you don’t currently have a table and three other chairs to pair it with? No. But what if you DO have that table and the other chairs? Now $700, even though it’s ridiculously pricey, might be something you’re very willing to pay, if the completed table and chair set leaves you in the running for first prize.

    Yesterday’s deals shored up a lot of issues for the 2015 Sox. If the youngsters show promise in the next two months, we could be looking at a serious contender next year. It’s very, very, VERY possible — hell, Cherington basically said this explicitly — that the Sox will open the checkbook for a starter if that’s what they need to win the division, etc. next year. Their first target would be, unquestionably, Lester, as he’s a known and proven quantity.

    2) The mediots LOVE to conflate “the Red Sox will not pay for veterans” with the truth, which is that the Red Sox will no longer enter into long-term deals unless they absolutely have to. Then they spin that into “because Lester will get 6-year contract offers in the offseason, there’s no way the Red Sox will sign him.” Which is spectacularly ignorant of the strategy that the Red Sox won a World Series by pursuing. No, they’re almost certainly not going to give Jon Lester a Justin Verlander contract. But those 6 year deals are probably going to come in at an AAV of $22-26m at most. IF it makes sense for them from a competitive/team building stance, the Red Sox would happily offer him more than that on a shorter contract. They can easily put out a 3-year, $28m per year contract with, say, some sort of option or 4th year extension trigger at the same rate, that would (I believe) leave him tied with Verlander for the second highest annual pitcher salary in MLB (behind Kershaw — and nobody else is getting Kershaw money anytime soon; he’s a special case). That’s putting $112m out there. It’s a highly competitive offer, because Lester will still be young enough at the end of the deal to reasonably expect another 2-3 year deal at fairly substantial money IF he stays healthy. So financially, it becomes a risk calculation: he would stand to make more if he stays healthy, but a longer term would insure him against possibly losing his health/ability at some point in the next 3-4 years. How do I know this is what the Sox are likely to do? Because this is, more or less, what they did with Shane Victorino, among others: overpay in the short run in exchange for a shorter-term contract than others would potentially offer.

    That doesn’t mean they will get Lester back if they do this, of course — if the Yankees are desperate enough, they’ll offer him $28m for 7 years or something, and the Sox won’t go near that kind of money for pretty much anyone these days. But Lester’s conduct during this season has made it very clear that while he wants to get paid, he definitely wants the Sox to be players in his free agency. (That makes sense for a lot of reasons — the more rich teams in the bidding, the better, after all — but in this case it seems likely that he legitimately likes it here and would be inclined to stay if the money was right).

    I really should just stop expecting thoughtful analysis from the Boston media, shouldn’t I.


    1. Yet, if they signed Lester and by year 4 he regresses into a middle of the rotation starter or worse (a very real possibility with a pitcher over 30), the Red Sox would get killed for tying up all that money in a “stiff” (I can already hear YARM’s shrill voice in my head). Same way the Beckett deal got criticized in some corners when it went down, and in hindsight the way the Crawford deal gets ripped now. Doesn’t matter to the Shaughnessy’s of the world. Whatever angle he can take to be contrarian. It wouldn’t bother me so much if the rest of the national media didn’t trot out ole CHB as though he speaks for the fans of Boston or is even in tune with them. In my almost 40 years on this planet, 39 of them in Boston, I have yet to find one person who isn’t a media member either locally or nationally that praises Shaughnessy. Not one person. It’s maddening.


  15. Is there any truth to the rumor that Buckley and Merloni flew to Oakland for Jonny L’s presser and were spotting sitting in the front row weeping hysterically??


    1. Merloni hasn’t been this devastated since Nomar got married.

      At least Buck is honest about his situation.


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