John Lackey wanted to leave the Red Sox

Two years ago could you have imagined that John Lackey would be the one dumping the Red Sox, and not vice versa?

Lackey made it clear that if the Red Sox tried to exercise their $500,000 option on him for 2015, there was a strong likelihood that he'd retire. But that option nevertheless increased his trade value. At the very least the option gave leverage to the Sox or any other team negotiating a contract extension. They could offer less than market value to Lackey, whose choices would be to accept a few million to pitch or retire once the $500k option was exercised.

Immediately after Lackey was traded to St. Louis, Ken Rosenthal announced that Lackey informed the Cardinals he would honor the $500,000 option, and not retire. Had Lackey told the Red Sox that he'd be willing to play for $500,000 in 2015, there's no way the Sox would have traded him. In essence, Lackey engineered this trade.

Remember when all of us wanted Lackey to be included with Beckett and Crawford in the Great Purge of 2012? Then last year we became Lackey fans as he helped the team win a World Series. And now he is the one who orchestrated his departure.

The Cards and Lackey might come to terms on a new contract extension anyway. But isn't it odd that this option was a point of contention for Lackey here in Boston, then he gets traded and it's no longer an issue? He did not want to stay here.

Lackey had enough of the Red Sox. The way the non-negotiations went between Jon Lester and the front office probably had a lot to do with that. Once the Sox started shopping Lester, Lackey wanted out. He gave the Red Sox an incentive to trade him, with the threat of future uncertainty if they didn't. He also kept his trade value up with his performance on the field, and by never threatening to retire if a team besides the Red Sox wanted to exercise his $500k option.

If the Red Sox were the Titanic, sinking slowly into the North Atlantic, John Lackey got himself a spot on a lifeboat by threatening to blow up half the ship if he wasn't allowed off.

And here's the kicker. The Sox included that $500,000 option when they signed him as a way to mitigate the risk of his elbow issues. The idea was that he might miss a long time due to injury (which he did), costing the team lots of money (which he did), but that the team would recoup the loss with a year of almost free service.

But it's the Cardinals who look to benefit from that nearly free year that the Red Sox paid for. The Sox bought the the insurance policy and made all the payments, the Cardinals are cashing it in. And that's because Lackey wanted to leave.

Photo Credit: Barry Chin/Boston Globe

If Stephen Drew is worth a utility infielder, why didn't the Red Sox just sign a utility infielder in the first place?

With Stephen Drew's departure in exchange for Kelly Johnson, it's time to look at how the Red Sox managed and mismanaged the short-stop situation in 2014.

The Sox should have anticipated defensive difficulties at short. Signing a defensive backup would have been a perfectly normal and prudent thing to do. That backup could have been used in the late innings of close games, especially games the Sox were leading.

I didn't mind when the Red Sox removed Xander Bogaerts from short-stop. He couldn't field his position, and you can't afford to have poor defense at short, especially when the offense is struggling to score runs. I don't care what the move might have done to Bogaerts' development or self-esteem. The Major League level is not the place to nurture prospects and worry about their confidence. It's the place to win games or lose them. Bogaerts' defense was not helping them win.

However, when Bogaerts' defense compelled the Sox to act, signing Drew was a completely wrong decision, utterly incorrect in every single way. Moving Bogaerts to third was also unwise. But he was hitting well when few other Sox batters were, and the Sox had no third baseman. In other words, because the rest of the team was sucking at the plate, and another young infielder (Middlebrooks) was having difficulties, Bogaerts stayed in Boston. But was moved to third. Drew was signed to play short.

If the Sox felt that Bogaerts' defensive issues were so critical that they were worth $10 million to address, they should have sent Bogaerts to Pawtucket to work on it, not sign an overpaid replacement and shift Bogaerts to an unfamiliar position he'd have to learn on the fly at the Major League level.

The Sox tried to play it both ways, removing Bogaerts' glove from short-stop, but keeping his bat in the Major League lineup. If only they could have sent his glove to Pawtucket and kept his bat in Boston.

It didn't work. Why would anyone think it would?

What the Sox truly needed at that time was flexibility in their infield. Again, a Kelly Johnson type of utility infielder could have been acquired as a defensive replacement for Bogaerts, and perhaps to play in Boston for a few weeks while Bogaerts focused on defense in Pawtucket. The solution was something cheap and flexible, like I like my women.

However, Stephen Drew did not bring flexibility, he brought abject inflexibility. Because he was going to play at short-stop. Period. And he was going to play every day because you don't spend $10 million on backups. Period. Drew even seemed to have a negotiated limit for how long he'd stay in Pawtucket getting ready to play in Boston.

And of course, Drew's bat was nonexistent, and Bogaerts' hitting went down the tubes as he shifted to third. Bogaerts' defense was still bad over there. The fiasco cost millions, defense at short improved but defense at third was degraded, and offensive production decreased.

Now Drew is gone. Again. Notice the increased flexibility in his departure. The Sox can make choices with what they want to do in the infield. Bogaerts will be back at short again. However I don't think this experience has helped his development. It certainly hasn't helped the Red Sox win games in 2014.

Stephen Drew is evidently worth a utility infielder on the trade market, who will make $3 million in 2014, instead of the prorated portion of $14 million that Drew was signed for. So why didn't the Sox sign a utility guy to begin with? Why didn't they pick up a defensive specialist at short? Why didn't they either keep Bogaerts where he was, or send him to Pawtucket to work on his problems without it hurting the team in Boston?

Stephen Drew wore a 7 on his jersey here. I think that should have been modified slightly to be a giant question mark.

Photo Credit: John Tlumacki/Boston Globe

The Red Sox didn't even try to keep Jon Lester here

I'd rather have Yoenis Cespedes now than next to nothing when Jon Lester walks as a free agent. That's not why I'm disappointed/enraged at the Red Sox today. I'm mad because I'd much much much MUCH rather have Jon Lester over Yoenis Cespedes. There's essentially nobody the Sox could have gotten in exchange for Lester that would have left me content. Unfortunately the Sox made no legitimate effort to keep Lester here. The fact that he's gone, and that we'll never know how much of a hometown discount he would have accepted to stay, leaves me shaking my head.

How could the Red Sox do this to themselves?

The Sox traded a guy who had recently become a bona fide Ace, and who had also grown into a leader, for a Homerun Derby winner. That's like trading Kevin Durant for the winner of the slam dunk contest. And this happened because the Sox hardly tried to keep their Ace. That lack of effort is the most irritating aspect of what unfolded at the trade deadline.

The $70 million offer for 4 years offer was an insult, not a starting point. You can't negotiate with insults. Watch Shark Tank and see how the potential investors react when someone makes an absurd demand. Or go to a car dealership and offer to buy a brand new Mercedes for half the sticker price. The dealer won't make a counter offer, they'll just move on, because it's clear you're not serious.

I've heard some people question Lester's camp for not making a counter-offer, but how do you counter a joke? How can you negotiate with someone who thinks that you're worth slightly more money a year than Clay Buchholz was? How can you negotiate with someone who is clearly terrified of long-term commitment, which I'm sure is something Lester wants? Lester has been underpaid by the Sox for years, this is his chance to cash in, and the Sox were too cheap.

Or were they? Were they cheap or did they want to make a token offer they knew would get rejected? They've done similar things before.

These cloak and dagger, deceptive, disingenuous tactics are what we've come to expect from the Red Sox front office. And don't exclude Ben Cherington from these mind games. He's King John's pawn, he's Lord Lucchino's foot soldier. He's happy to be their puppet, or to stay out of baseball decisions when his masters get involved.

The Red Sox have no clue what it will cost to sign Lester in the off-season. They don't even know what his hometown discount rate might have been. That's the proof that their "negotiations" with him were not negotiations. If you don't at least come away with knowing what the other party wants, then you haven't negotiated.

If Lester signs a massive deal somewhere else, let's say $200 million for 7 years, I won't praise the Red Sox for knowing the price would be too high. They don't know anything. They made a crap offer that pissed off their Ace, then failed to immediately make a legit offer, then traded their best player from the 2013 World Series run. They sent a pitcher with 110 career wins, a 3-0 record in the World Series, and 2 rings to Oakland in exchange for a guy with 66 career homeruns and 2 HR Derby trophies.

If this had been the end of a hard fought negotiation, then it would be easier to accept. It's not, though.

5 years and $100 million, perhaps with a vesting option for a 6th year. Maybe 5 years at $110 million. That might have been enough to keep Lester. We simply do not know, though. We'll never know. Which is why this whole situation pisses me off so much.

Photo Credit: Barry Chin/Boston Globe

I'm not a fan of Yoenis Cespedes

The Red Sox traded Jon Lester along with Jonny Gomes to Oakland for an outfielder with decent power who doesn't get on base as often as you'd like.

That's Yoenis Cespedes. Cespedes will also be costing the Sox $10.5 million in 2015, and is scheduled to hit free agency after that.

He's 28, but he's also Cuban, so let's call it 28ish.

He hit 26 homeruns last year and 23 the year before. He's on pace to hit a similar amount this year. He'll probably be more of a power hitter in Fenway's friendly confines. Nevertheless, his career OBP is .318, and that just sucks for someone you want to hit in the middle of the lineup. He doesn't walk much, he does strike out a lot, he doesn't see lots of pitches.

He's an improvement, don't get me wrong. He's a solid player, he's better than anything the Sox have in the outfield today. But he's what you get for your Ace? For the guy who was your playoffs MVP last year? For a guy who won games for you this year even with some of the worst run support in baseball?

The Red Sox didn't sign Lester because they were worried about the future. So the future is this 20-30 HR outfielder who strikes out a lot and struggles to get on base 30% of the time? That's the future the Sox intend to build?

Photo Credit: Getty Images/Ezra Shaw

Red Sox should trade Jonny Gomes for Jonny Gomes

Four times in Major League history has a player been traded for himself, as the "player to be named later" in a deal. The most recent was in 2005 when the Blue Jays sent John McDonald to Detroit for a player to be named later, and McDonald was returned to Toronto as that player.

The Red Sox should do this with Jonny Gomes. Because Jonny Gomes saves franchises. He comes to town teams get better. He is to struggling ballclubs what John Taffer is to struggling bars. I discovered this history of teams improving once Gomes arrives through legitimate research. I'm surprised Gomes doesn't talk about it.

The Red Sox could send Gomes to a team looking for an heroic clubhouse presence, along with "cash considerations" (nudge nudge, wink wink) for a player to be named later. A few days after, that team could send Gomes back to the Sox as the named player. The Red Sox are almost guaranteed to resurrect their season, the other team gets a few bucks (and probably wins every game Gomes sits on the bench for them, deceiving the other team by pretending to get ready to pinch hit), everyone wins.

There's plenty of baseball left, and a few weeks ago we saw this team win a few games in a row and get right back into being almost close to the race. Jonny Gomes is the infusion of energy that this team needs to get over the hump and win 95% of its remaining games, with or without Jon Lester.

Because phonebooth.

Photo Credit Jeff Roberson/AP

The Oakland A's had Moneyball, the Red Sox have Cheapball

The Red Sox don't want to spend to keep Jon Lester. He's over 30, and John Henry recently read a study about teams overpaying for players over 30, and underpaying players under 30. Jon Lester is 31, so the Red Sox don't want to overpay to keep him. That's why the Sox might even ship Lester before Thursday's trade deadline.

The study John Henry is partially basing this significant baseball decision on makes sense. It makes sense that a player over 30, who has proven what they can consistently do at the Major League level, would get more money, even more money than their production merits. Such players come with guarantees, or at least the closest things to guarantees you can get. There's also a short supply of such players, and high demand, which drives the cost up.

For the Sox to keep Lester, they'd have to "overpay" for what Lester gives them. So what? When has that stopped the Sox before? They overpaid to extend David Ortiz, they overpaid to bring Stephen Drew back. So Drew is worth $10 million a year and Lester only worth $17.5 million? That's what the Sox offered Lester before the 2014 season.

The Sox have also been able to benefit from Lester while underpaying him. He makes $13M this season, and made under $12M in 2013. Before that he never got paid more than $8 million a year.

One problem facing Henry and his value study is that the high end SP market is overwhelmingly made up of pitchers 30+ years old, with a few 29 year olds mixed in. Henry's philosophy pegs him into a corner, since there are essentially no proven, high end SP free agents under 30, he'll never be able to sign one OR re-sign one. Meanwhile, the rest of baseball seems happy to sign these guys. So while Henry can pat himself on the back for saving money, other teams will win games thanks to their overpaid players.

Overpay to win, or save to lose?

John Henry's unwillingness to overpay for 30+ year old talent is like someone buying a 6-pack of beer and staying home by themselves on a Friday night because drinks at bars are more expensive. He'll keep more cash in his pocket but the people who went out will have more fun.

There's no salary cap in baseball. The Red Sox are one of the most valuable sports teams in the world. Their cash flow is one of their biggest competitive advantages. The Sox can overpay for a key player and not be crippled by it. Yet they're the ones being cheap? Because of a study?

John Henry doesn't want to exploit that edge. He's figured out that the 29 other teams are wasting money, and he won't do it. He'll get his 6-pack of beer and drink by himself while other teams are having fun at the World Series.

Had Jon Lester's contract expired after the 2012 season, John Henry might have used this study to justify not re-signing him then. Lester would have been 29, and Henry might have wanted to avoid signing a soon-to-be 30 year old to a long term deal. So if Lester had been a free agent before the 2013 season, it's possible that Henry wouldn't have wanted to sign him.

What would that have meant for the 2013 season? There wouldn't have been a parade in Boston.

Parades are expensive. John Henry and the Red Sox have become cheap.

Photo Credit: AP

Do the Red Sox have a chance at making the playoffs?

The offense scored 14 runs off 18 hits. John Lackey threw only 76 pitches in 7 innings. The Sox have outscored their opponents 22-2 in the last 3 games. That's 5 wins in a row and 8 of their last 9. Unfortunately, what happened in Anaheim last night had more of an impact on Red Sox playoff hopes than what happened in Toronto. The Orioles beat the Angels 4-2.

The Red Sox magic number is 72 to win the division, 70 to win the Wild Card. Yet they have 63 games left to play. They need help to make the playoffs. In fact they've dug themselves such a deep hole that they need help from more than one team. Even if the O's lost, even if the second Wild Card holding Mariners lost, there are a multitude of teams in the Red Sox way. It seems preposterous to even discuss the Sox making the playoffs.

We've been so starved for success this season, that any sequence of games that aren't painful to watch feels like winning a championship.

Don't get me wrong, I'm enjoying the wins. Monday night's victory was 2 hours and 45 minutes of great hitting and good pitching. The Sox hit 4 homeruns. They were 7 for 13 with RISP. They knocked in 8 runs with 2 outs. Eight starters got hits, 7 scored, 6 knocked runs in. Xander Bogaerts didn't commit an error, Dustin Pedroia didn't get caught stealing, and AJ Pierzynski didn't strikeout.

I want to see the Sox finish strong and go into 2015 with some momentum. I want to see players establish themselves and perhaps win jobs on the 2015 team. It would indeed be amazing to see this team somehow make the playoffs. However, there's a difference between cheerful optimism and wishful fantasy. The Sox playing postseason baseball in 2014 would be miraculous. So would winning MegaMillions. So would being stranded on a tropical island with Kate Upton and Scarlett Johansson, with only one bikini, and I'm the one who brought all the sunscreen.

There's a chance it might happen, but don't hold your breath.

The Sox have only partial control over their destiny. Their success needs to be coupled with failures by other teams (plural). They have 37 games remaining against AL East opponents. Only 6 against Baltimore. Maybe Baltimore loses 8 in a row, and the Sox clean up against the Jays, Yankees, and Rays. It's possible. It does depend on Baltimore losing, and losing badly. And the other AL East teams also losing.

And how much faith can one have that this Sox team will continue to roll for the rest of the year? I remember the 7-game win streak this team went on at the end of May and into June. That success was the meat in a failure sandwich. A 10-game losing streak came before it, a 5-game losing streak after it. The Sox played .318 baseball (7-15) in that 22-game stretch, despite the winning streak.

This current 8-1 run comes after the Sox had a 1-7 skid, which was part of a 5-13 stretch. In the last 27 games, the Sox are 13-14. Yet the Sox Information Ministers on NESN were talking wishfully about playoff chances, and looking at the trade deadline as a day to buy, not sell.

I'm not saying all this to bring you down, Sox fans. I'm saying this because these wins should be enjoyed individually, not as part of a potential charge back into the pennant race. It makes me look forward to tonight's game. It does not, however, make me look forward to October baseball.

Photo Credit:
Darren Calabrese/Associated Press - The Canadian Press

Red Sox Trade for Jake Peavy

The Red Sox have acquired Jake Peavy in a three team trade. The Sox sent Jose Iglesias to Detroit, and a trio of spellcheck challenging minor leaguers (infielder Cleulius Rondon and pitchers Francelis Montas and Jeffery Wendelken) to the White Sox. The Red Sox also acquired reliever Brayan Villareal.

Peavy is one of those guys who look like great players around the trade deadline. In actuality he's just good. He's 8-4 with a 4.28 ERA. He's never really succeeded in the American League. Apart from last year's 3.37 ERA. I'd completely forgotten that he won the NL Cy Young in 2007. He was once a great pitcher.

He, however, is still a good pitcher, and the Red Sox needed a good pitcher. Clay Buchholz's status remains a mystery. Brandon Workman has pitched well but it's risky to rely on a 24-year old to keep your rotation stable. Peavy fits snugly in the middle of that rotation, behind Lester and Lackey, ahead of Dempster and Doubront.

Losing Jose Iglesias hurts. He was hitting .330, and was getting on base (.376 OBP). He provided depth and options on the left side of the infield. Then again, he was hitting .205 in July, with only 1 extra-base hit all month. Even when he had been hitting well, he hadn't been hitting for power.

You have to make this move. Pitching is so much more valuable than an infielder.

One reason the Red Sox could fail during this playoff push is lack of pitching. They're not going to fail because they lack a light-hitting left-infielder. Peavy solidified their rotation. Getting 11 starts from a pitcher like Jake Peavy is worth Jose Iglesias. Peavy is also under contract for next season.

Peavy doesn't push them over the top, but he fills holes that might have sunk the ship.

Red Sox Make Small Moves on Deadline Day

On Monday I wrote that I didn't want the Sox to be buyers or sellers on Deadline Day. I wanted them to do nothing. That's essentially what they did.

They traded Matt Albers and Scott Podsednik to the Diamondbacks for Craig Breslow. Albers was a righty, Breslow is a lefty. Breslow's pitched in 40 games this year for Arizona and has a respectable 2.70 ERA and 1.18 WHIP. You may remember him from 2006 when he made 13 appearances for the Sox.

The Sox also traded Lars Anderson to Cleveland for Steven Wright. Here's a highlight video:

He's actually a minor league knuckle-ball pitcher. He's 27 years old, and is 9-6 with a 2.49 ERA in AA Akron this year. He hasn't had much success in the minors. But he hasn't been a failure either.

A very dull Deadline Day for the Sox. I'm glad they didn't give up any young talent. They have a chance to make the playoffs this year, but they're not Championship contenders. And if they do win, it will be because of the players they have, not any additional pieces.

What Should the Red Sox Do at the Deadline?

Should the Red Sox be buyers or sellers? The correct answer is "no." The Sox should neither buy or sell, unless presented with extremely juicy deals.

If the Red Sox were a blackjack hand, they'd be a hard 16. The trickiest hand to play. Do you hit and likely bust? Do you stay and likely get beaten by the dealer? No matter what you do, it probably won't work out. Your best hope is the dealer busts.

The Sox are only 4 games out of a Wild Card spot, but they have 4 teams to leapfrog over. They're 10th out of 14 teams in the American League. They're not quite out of it, and not quite into it.

It's conceivable that if Beckett and Lester pitch up to their capabilities, the Red Sox could go on a serious run. They could claim a Wild Card spot, win the play-in, and even win a playoff series.

But there is no move (apart from acquiring Felix Hernandez), that could spark this run. Trade deadline moves typically add missing or complimentary parts to help an already well-run machine function at peak efficiency.

The Sox are more than just a tune-up or a spare part away from playing well. They already have an abundance of bit players. What's kept them from winning has been their best two pitchers playing like their two worst pitchers.

And if the Sox do go on a run, it will be because those pitchers perform at their top level. Not because they acquire some right-handed bat at the deadline, or a lefty set-up guy.

The Sox shouldn't sell because they're not out of it. They have a chance.

They shouldn't buy either. They theoretically possess the talent to. If they do win, it will be because of the players already on the roster.