The Chris Sale / Jon Lester Conundrum

Is there any pitching-related matter with the Boston Red Sox that Shank can't hang around the neck of the Jon Lester trade?

OAKLAND, Calif. — The Red Sox locked up Xander Bogaerts and Chris Sale in the last two weeks, committing $265 million of John Henry’s money to a couple of players that would have been free agents at the end of this season. It’s a serious commitment that should warm the heart of Red Sox Nation.

I am a fan of the Bogaerts extension, but not so sure about Sale, who was scheduled to pitch Tuesday night in Oakland.

Sale was hoping to stop the bleeding after the Sox lost four of their first five games, getting outscored, 41-24. Alex Cora’s five-man rotation surrendered 26 earned runs in 21 innings in those five games, yielding 11 home runs. Aggregate ERA: 11.14. It was a big bowl of yuck.

But I’m thinking bigger picture today (first time for everything! - ed), wondering if the contract extension to Sale was a sound baseball decision, or perhaps overcompensation for past sins. Did the Sox let their mistake on Jon Lester rush them into a mistake on Sale?

Seems like now is never too early for Shank to preemptively second guess and pile on, is it?

'Bostoned Out', Revisited

One of Shank's favorite pastimes - second guessing the Red Sox:

Letting go of Jon lester remains one of Sox dumbest moves They have still not recovered

— Dan Shaughnessy (@Dan_Shaughnessy) September 28, 2018

...which included a World Series championship in 2013, but never mind that.

Here's what we wrote about this five and a half years ago:

Without a hint of irony, Shank then drops this one on Lester:

Is he Bostoned out?

“Yeah, sometimes,’’ he said. “Sometimes I want to strangle myself. It can be intimidating, especially when you have seasons like last year. It’s tough. You know [you’re bad] and your teammates are trying to pick you up and everybody else knows [you’re bad] and you’re trying to break even on the whole deal. You try to live with it and move on.

“If you can play in Boston and survive and do good, I think you can play anywhere.’’

So, the columnist arguably the most responsible for contributing to an athlete's feeling of being 'Bostoned out', asks that question of Jon Lester with a straight face? Who said irony is dead?

Curses! Another Blown Lede

No one loves a good curse more than The CHB. So it stands to reason that today's excrement exercise is one big kiss off to 108 years of Cubs failure

In true Shank fashion, he tries to make poetry out of prose -- "They blew a lead of 6-3 with two out and nobody aboard in the eighth inning. Manager Joe Maddon was being measured for a Grady Little cap. [T]he Cubs ... won it when lefty Mike Montgomery retired Michael Martinez on a grounder to Kris Bryant with the tying run aboard at 12:47 a.m. You could hear Harry Caray hollering'Cubs win' and 'Holy cow' in hardball heaven." -- and in the process completely misses the actual drama of the game. No surprise there.

Even less surprising to those of us who have tortured ourselves to bring you this column for going on 10 years, is his attempt to stick it to the Red Sox in the process. Indeed, this was one of the classic World Series, and Shank spends most of it writing about the Red Sox.

Let's start with Theo Epstein, who has now "has punched his ticket to Cooperstown as the man who killed two curses."

Since The CHB doesn't seem to remember what he previously wrote about Theo, I'll remind him: 

• "Epstein is a student of the game, but it's a mistake to say he knows more about baseball than [Larry] Lucchino or anyone else." 
• "It was charged [in 2005] that Sox management conducted a ''smear campaign" against Epstein. How? Where's the campaign?"   
• "Epstein made a ton of bad moves in the later years of his tenure, then went to Chicago for a $19 million contract and watched from afar as the Sox decomposed. ... Mistakes were made. Money was spent badly. The Sox lost their way and tried to throw money at their problems." 

There's Jon Lester, "who was famously lowballed, then traded, by the smarter-than-everybody Sox in 2014, did what he proved he could do in Boston: he came up big in the big moment. Lester was called upon to pitch in relief and stuffed the Indians for three innings." Well, not exactly. Lester allowed two runs in three innings work, and it was his wild pitch that cut the Cubs lead to 2 in the bottom of the fifth, giving Cleveland hope they could come back.

There's John Lackey, who gave up 3 runs in 5 innings in a Cubs loss Game 5.

There's Terry Francona who "[had] a commanding World Series lead, only to see it implode over the final three games."

Imagine what Shank would have said if this had happened while Francona was managing the Red Sox. Oh wait, it did:

The greatest choke in baseball history ended the only way it could have ended, with the Red Sox gagging on the Camden Yards lawn one last time. ... Say goodbye to Terry Francona. In the midnight confessions, Francona spoke of “the mess we got ourselves in,’’ then said, “We needed to take care of business and we didn’t.’’ 

In historic fashion.

Wouldn't losing a 3 games to 1 lead in the World Series, dropping the final two on your home field, be even worse?

Yes it would. I can think of only one thing worse: Shank's column.

The Obligatory Jon Lester Column

Who knew Shank was capable of two columns in a day outside of spring training?

But Lester and the Cubs had other plans. After two quiet nights in Wrigleyville, the Cubs finally strung together a few hits and Lester and the Chicago bullpen did the rest.

It had to be strange for Francona to watch Lester start Game 5.

Their relationship was special when they were together in the Red Sox organization. Francona paid extra attention to Lester the rookie, and when the kid was diagnosed with anaplastic large cell lymphoma, the manager took Lester’s worried parents aside and said, “We will take care of your son.’’

Stupid Tweets, by Dan Shaughnessy - III

We can barely believe a guy who gets paid to watch baseball games for a living actually wrote this tweet:

Actually, 1) We can believe it - after all, it's Shank! 2) Honest introspection and self-criticism are not this guy's strong suits.

Life After Lester

The Red Sox not getting Jon Lester was a "debacle" of epic proportions, says The CHB.

Why?

Why is it so critical to bring back a guy who pitched on two teams that finished in last place in the past three years? As the saying goes, "I can lose just as easily without you..."

Why is it so critical to have him?

Answer: It's not. Lester is a terrific pitcher. He also has never won 20 games, he's had exactly one season with an ERA under 3.13, he's never led the league in anything except for K/9 ratio, which he did in 2010 -- four seasons ago. He's basically parlayed the best 143 inning stretch of his career into a world-beating contract. Bully for him, but that's not reason for the Red Sox to go batty. Has The CHB forgotten the lessons of 2011-12?

There is, in fact, a better pitcher available in Max Scherzer. If money is no object, which it isn't according to Shank, then the player the Sox should break the bank for is Mad Max.

Would I have liked it for the Sox to have brought Lester back? Sure. Is it the end of the world? Hell no.

Back to the hyperventilating of Shank. He complains that John Henry et al weren't available to comment on the "departure of Lester." Excuse me, but Lester departed in July, in a trade for Yoenis Cespedes. Cespedes, in turn, brought Rick Porcello, a player who is five years younger than Lester, and thus entering his prime, and whose overall value (WAR, or wins above replacement) was nearly the same as Lester's last year, and over the past three years has been less than one game less.

Let's remember one more thing. When the Sox failed to re-sign Roger Clemens at the end of the 1996 season, The CHB was highly critical. One year later, the Red Sox landed the reigning NL Cy Young Award winner. And Pedro Martinez was even better than Clemens.

These things have a way of working themselves out. Just don't expect The CHB to admit that.

Right And Wrong

Turns out Shank was right in the end, as Jon Lester signed with the Chicago Cubs about an hour ago. Earlier rumors had this signing going down between Boston and the Cubs, so while the CHB was right in the end, he wasn't exactly on point approaching the finish line.

While I can't speak for my co-blogger here, I'm okay with Shank's prediction, as that's what a columnist should do. I would encourage it, and not for the obviously self-serving reason of being able to bash Shank after the fact. Give an opinion and back it up, that's not too much to ask.

What we can agree on is a lack of consistency in his application of reason, logic, or whatever the hell it is that Shank uses to change opinions from one column to the next. Generally speaking, that's been demonstrated with many of Shank's posts since this site's been up for the near decade of its existence, and with this Lester signing in particular. It should be entertaining to see his reaction, if any, to this signing.

Lack of Knowledge Doesn't Equate Lack of Opinion

Nobody knows where Jon Lester is going to sign.

Yet The CHB seemed so sure just a few months ago that the Red Sox were NOT going to sign him.

And while acknowledges Lester isn't saying anything, that doesn't stop The CHB from expressing -- without a wit of evidence, mind you -- that the Red Sox have "bungled" this and that Lester has been "insulted" by the Sox.

And The CHB is pessimistic, as always, that Lester will choose Boston. Big surprise there.

Forget Me Not

So Jon Lester is the antidote, the savior, the solution. Just spend whatever it takes to get him, and that's the panacea the Red Sox are seeking.

Don't get me wrong: What's not to love about Lester? He's been a big part of two World Series wins, and he's held up under severe scrutiny during and after the "chicken and beer" controversy.

But he'll be 31 when the season starts next April, he has a lot of mileage on him, and he's going to be very, very expensive. All of which are trivialities The CHB mocks, per usual, pointing to John Henry's comments from last spring about what empirically constitutes a good or bad baseball deal, and emphatically arguing "hopefully [that] philosophy is out the window."

How painful it must be for The CHB to continue to be proved wrong. Three World Series titles in 10 years ... doesn't that make Henry and Co. perhaps just a little smarter than your average baseball guy? Not one iota, according to His Shankess. The 2013 World Series win was a "fluke," he says, as if it's possible to win 97 regular season games (tied for the best record in baseball) and then go 11-5 in sweeping three playoff series on luck alone.

Outbidding the world on Lester comes down to "being competitive in the marketplace," argues The CHB, again forgetting those three trophies. (Since he is so clearly suffering from dementia, I've posted a photo below to help jog his memory.)

Should Red Sox management go long and deep on Lester when there's actually a better, younger pitcher available on the free agent market? Readers will never know, since Shank doesn't even acknowledge the existence of Max Scherzer.

And yes, The CHB appears to have forgotten his own questioning of Lester's integrity back in February.

I don't know what's ahead for the Red Sox, but I see a dementia screen in Shank's future.

Dan Shaughnessy Orgasm Watch

OK, maybe you can do without that visual, but look at whom the Boston Red Sox just made some offers:

Free agents Jon Lester and Pablo Sandoval have been offered multiyear deals to play for the Red Sox, according to a major league source.

Lester, who met with Red Sox owners last week in Atlanta, is believed to be looking for a six- or seven-year deal in the range of $23 million-$25 million per year.

According to a major league source, the Red Sox offered him between $110 million and $120 million over six years, which would average $18.3 million-$20 million a year.

Lester also visited with the Cubs, who along with the Red Sox were expected to be the most aggressive in their pursuit, and the lefthander will meet with the Braves Thursday. He also could make trips to Toronto and St. Louis. It’s not clear where the Yankees stand in all of this, but they, too, could enter the Lester market.

Sandoval is seeking six years for up to $20 million per year, and the Red Sox and Giants appear to be the front-runners for the third baseman’s services. Details of the Red Sox’ offer to him were unknown.

Shank had a major hard-on for 'The Panda' a month ago; let's see what he says a) if he's signed by the Sox and b) if he's signed, what Shank will say about Sandoval with his first serious batting slump, despite his insincere "promise never to rip Sandoval for being out of shape or going on the disabled list."

He Apparently Found the Daisy's of KC

The CHB shows off his knee-jerk reactionism in today's column, yet another that pretends to be on the World Series but is really just a series of shots at the Red Sox.

Let's begin!

"Having watched the Giants in October of 2014, does Red Sox general manager Ben Cherington still think a team can win a World Series without an ace?"

This suggests Cherington said something along those lines, which he didn't. What Shank is referring to is the Red Sox' trade of Jon Lester last July. What Shank ignores is that 1) the Red Sox were going nowhere and 2) Lester is a free-agent to be and was set to walk.

What Shank could have noted is that 1) the Royals are one game away from winning the WS without an ace and 2) if the Giants win, it will extend a streak whereby the WS winner was the team with the home runs during the regular season -- a place the Red Sox are much better position for with Yoenis Cespides (the player received in exchange for Lester) than without. But that ruins Shank's argument.

• Who should the Red Sox sign: James Shields or Pablo Sandoval? Probably not Shields, based on the Series performance.

Yes, Shields has shit the bed in the post-season. And yes, Sandoval is hitting up a storm (.360 through Game 6). So naturally we should make $100 million decisions based on a handful of games, right? Guess who is hitting just 10 points less than Panda? The immortal Brandon Crawford. Perhaps we can make it a package deal.

• Did you know that Back Bay watering hole Daisy Buchanan's is closing? 

Where is The CHB going to get his pre- and post-game drink on now? My guess is he's not allowed in Sonsie.

He's Green with Envy

The CHB can't figure out the Red Sox.

I know, I know...that's funny and all given that he never could.

But in the wake of the Jon Lester and John Lackey trades, he's trying to understand what the Sox are planning for 2015.

How's this: To do better than in 2014.

Oh, and what bothers him is the money: "The one conclusion we can draw from all this is that the Sox are intent on not overpaying older players," he writes. "No more long-term deals."

That's a dumb conclusion.

For what John Henry et al have been saying is that there are huge downsides to doing such deals. That does not, however, mean they won't 1) sign players to long-term deals or 2) sign older players. But it does mean that being cautious is the coin (get it?) of the realm.

And given the outcomes of the past couple decades, is that a bad thing? In other words, how would you like to be New York right now, paying A-Rod (age 39) and CC Sabathia (33) a combined $28 million this year* -- for a total of eight games played.

The Red Sox might be a large market team -- but they aren't that large.

So "Kansas City on the Charles," Shank? I think not. When was the last time KC won three World Series in 10 years?


*Assuming they pay A-Rod the $3 million owed outside of his suspension.

Disbelief

I'm having trouble believing this - a balanced, decently written column by Shank without the trademark trolling questions, petty, vindictive swipes, personal insults or axe-grinding agendas.

MINNEAPOLIS — Jon Lester was in a good mood as he sat at his interview station in a grand ballroom of the downtown Hyatt Hotel on Monday afternoon. The Red Sox southpaw was barely bothered while, a few yards to his left, dozens of cameramen and reporters elbowed each other for access to Derek Jeter’s table.

If not for a few Boston scribes asking about his impending free agency, Lester might have gone unnoticed during the mandatory media session for baseball’s All-Stars.

Lester’s contract status is going to be the big story in Boston baseball for the next few months. He is the ultimate commodity: a 30-year-old power pitcher who has won two World Series, never misses a start, has demonstrated he can perform in a tough market, and is having his best overall season (9-7, 2.65 ERA, 29 walks, 134 strikeouts in 129 innings).

The Obligatory Jon Lester Column

Shank turns his attention to the Red Sox pitching ace, who's in the final year of his contract. Shank speculates what could have been, had the Manny Ramirez for Alex Rodriguez trade been successful, for the 900th time:

There are several million “what would have been?’’ thoughts attached to the notion of A-Rod coming to the Red Sox and Ramirez going to the Rangers. It means the 2004 Sox season would have been a whole lot different. We never would have seen Ramirez win World Series MVP, and the Sox would have been the ones strapped with the shameful legacy of A-Rod.

Nomar Garciaparra would have been traded for Magglio Ordonez. There would have been no “Tessie,’’ no “Fever Pitch,’’ and no image of Ramirez diving and cutting off a Johnny Damon relay throw that was bound for the infield.

A-Rod and his purple lips would have set up house on the left side of the Fenway infield and we’d probably never have seen Orlando Cabrera, Edgar Renteria, Julio Lugo, or Stephen Drew. Cameron Diaz and Madonna would have come to Fenway Park. Biogenesis would have made deliveries to the Back Bay.

And Jon Lester would have pitched for the Texas Rangers.

Shank also wonders whether Lester was being truthful when he said he'd take the home team discount if the Red Sox choose to extend his contract:

“I’m not going to go back on what I said,’’ Lester said Monday. “I said what I said from the heart. I mean it. We’ll see where it goes from there. We still got a long way to go.

“It’s going to be a tough process. That’s why I tell those guys, ‘Call me when you got something.’ I don’t want to hear about the day-to-day of it. I’ve got to worry about the field. I can’t worry about that other stuff. It will take care of itself.’’

Any bets on the obligatory John Farrell column for tomorrow?

UPDATE, at 8:39 PM - recent developments indicate better odds for an obligatory David Ortiz column.

At Smith Barney, They Earn It

That's the most recent observation from Captain Obvious:

FORT MYERS, Fla. — The worst-kept secret of Red Sox spring training finally spilled out of the ball bag Wednesday before the Sox played the Miami Marlins at JetBlue Park.

Jon Lester will be the Opening Day starter against the Yankees in New York Monday afternoon.

“That’s a surprise in camp — in Camp No Surprise,’’ said manager John Farrell.

Lester will become the first Red Sox pitcher to start three consecutive openers since Pedro Martinez started seven straight from 1998-2004. The only other lefties to start three straight openers for the Sox are Mel Parnell and Babe Ruth.

No shots at John Henry or Larry Lucchino? What gives? And what's a column on Jon Lester without a mention of birds and Buds?

Getting Lester back on track has been one of the top goals of the spring of 2013. Still only 29 years old, the big southpaw is 85-48 (.639) over seven seasons, but he slumped badly beginning in the infamous September of 2011. In his last four games of ’11, Lester went 0-3 with an ERA of 8.24. He gave up 25 hits and 12 walks in 19⅔ innings. After manager Terry Francona was fired, Lester was fingered as one of the chicken-and-beer brigade and he seemed to carry psychological baggage into the 2012 season.

That'll never get old, will it?

In a rare moment of guilty feelings / candor, Shank then mentions this:

“It’s all about standing tall,’’ Lester said after Wednesday’s outing. “It sounds simple, but for whatever reason I morphed into it from 2011 to 2012. I was pitching like I was 5-10 instead of like I’m 6-4. You can see it. You look at it, side-by-side, even someone who doesn’t know anything about baseball [I think he was looking at me when he said this] can see it. I couldn’t dig out. I don’t know how it worked out in my head, but it wasn’t good. So this spring I overhauled everything and I’m back to being me.’’

Translation - 'shut your piehole about me for a while and let me pitch.'

We'll see if that's 'message received' or not.

Bostoned Out?

Shank sits down with Red Sox pitcher Jon Lester and asks him a few questions.

FORT MYERS, Fla. — Grim. Glum. Red Sox lefthander Jon Lester last year looked like a 50-year-old coal miner who was falling behind on his child-support payments. He was joyless and angry. He was Ralph Nader. He was Bill Belichick. Lester was the personification of abject unhappiness.

What's a Shank column about the Red Sox without a gratuitous mention of Bill Belichick?

He looked like Nomar Garciaparra during his final days at Fenway in 2004. He looked like a guy who was “Bostoned out.’’ Lester went 9-14 with a 4.82 ERA for the last-place Red Sox. He hated pitching for Bobby Valentine, a hideous skipper who left him on the mound to take an 11-run beating against the Blue Jays at Fenway in July. Lester looked like he’d rather be a scuba diver for Roto-Rooter.

“There’s a little bit of a chip there,’’ Lester acknowledged Wednesday afternoon after the Sox’ second official workout for pitchers and catchers. “I want to prove that last year was a fluke and not have it happen again.

“I don’t think it’s a matter of talking about last year. You can just see it in some guys. We’ve never had a season like that. We’ve never got our ass kicked that bad. It’s frustrating and it’s humbling. Nobody wants to be that team.

“It was miserable.’’

Are you happy playing baseball in Boston?

“I love baseball,’’ Lester answered. “I love Boston. People don’t see me other than the fifth day and when I’m out there, but I’m not out there to kid around. I’m not out there to joke around with hitters.

“At the same time, I’m having fun. It may not look like it, but I’m having fun. I love to pitch, I love everything that there is to pitching. I take everything I do very serious. I want my game to go the way it should be. If it doesn’t, I’m going to be [upset].’’

Without a hint of irony, Shank then drops this one on Lester:

Is he Bostoned out?

“Yeah, sometimes,’’ he said. “Sometimes I want to strangle myself. It can be intimidating, especially when you have seasons like last year. It’s tough. You know [you’re bad] and your teammates are trying to pick you up and everybody else knows [you’re bad] and you’re trying to break even on the whole deal. You try to live with it and move on.

“If you can play in Boston and survive and do good, I think you can play anywhere.’’

So, the columnist arguably the most responsible for contributing to an athlete's feeling of being 'Bostoned out', asks that question of Jon Lester with a straight face? Who said irony is dead?

Sunday Follies

Yesterday, The CHB went after Larry Lucchino, writing that Lawyer Larry was guilty of a "ridiculous spin" and that he "simply cannot just tell the truth." Lucchino apparently didn't respond to a Shaughnessy email (The CHB can use a computer! Who knew?), which, coupled with a few extra cold ones, left Dan stewing in the summer heat.

Buzz gone, Shaughnessy awoke to a raging hangover and the realization that in his Schnapps-fueled frenzy, he mistyped Lucchino's email address. Bummer, dude.

So here's The CHB's take on Jon Lester after two good starts in a row: "We can debate the merits of keeping Valentine, Beckett, Lackey, and other misfits of the wreckage of 2012, but there can be no doubt about Jon Lester."

But here's what he wrote on July 18: "[T]here is no excuse for Lester. This is sheer underperformance. And it is killing Boston’s baseball summer."

And on March 4: "This year is a little different. He is not just another established starting pitcher down here with the Red Sox getting his work in. He is a man on a mission to make amends."

Back to July 18: "He looks like a guy who just hates being here. There was sports-talk radio babble about trading Lester at the All-Star break. Now we wonder. Maybe it wasn’t such a bad idea."

But on Aug. 19: "Despite this terrible season, he is something the Sox can build on. Lester is a keeper."

Flip. Flop.

Oh, and how embarrassing for the columnist who has been calling out Adrian Gonzalez to learn that it was not the All-Star first baseman but now-traded Kelly Shoppach who complained to management about Valentine. Oops. Does that make The CHB a liar? By his math, it most certainly does.