John Lackey, maybe you heard, is in the second year of a five-year, $82.5 million contract. He's the highest-paid pitcher in Red Sox history by kind of a lot (I think 14 million bucks is kind of a lot, anyway).

And as he gets ready to take the mound on Monday night against Josh Tomlin (11-5, 4.07 ERA while making about 1/24th of Lackey's 2011 salary) it is absolutely fair to call the first 16 months of John Lackey's tenure in Boston an epic failure. A spectacular wipeout. "Cowboys & Aliens" with a lousy WHIP. 

How bad has it been? Well, think about this: In his eight years in Anaheim -- which now almost has a "Vin Baker in Milwaukee" feel to it -- Lackey had an ERA of 3.81. Not worth $82.5 million, but not too shabby, right? 

Well, Lackey just finished July with an ERA of 4.61 and a WHIP of 1.61. That ERA was 89th among all MLB starters for the month, and the WHIP was 122nd (out of 144).

So, John Lackey was in the bottom 10-15 percent of all major league starters in July.

And it was his best month of the season.

Look, I've written this before -- it's always important to remember that there are things going on in Lackey's personal life that are very likely playing a factor in his struggles. And John Lackey didn't walk into Theo's office in December 2009 with a gun and demand $82 million. We get it.

And I think most fans understand that Lackey -- now an even 50 starts into his Sox career with an ERA of 4.96 and WHIP of 1.47 -- will never be the guy Theo tried to sell us on when he was signed. That's not going to happen.

But Lackey has a change for redemption. A chance to start over. A chance to earn his keep, even.

It sounds like Clay Buchholz isn't going to pitch again this season. That leaves a serious hole in the rotation. Sure, Erik Bedard was brought in, but we are talking about a guy who has started a total of 46 games over the last three years and on Friday gave up five runs in 1 1/3 IP in his first start in about a month. This isn't exactly Cliff Lee, redux. 

But it speaks to the confidence -- or lack of it -- regarding both the health of Buchholz and the ability of Lackey to be the No. 3 starter in a postseason series that this move had to be made. The Sox gave up a couple of legitimate prospects (Chih-Hsien Chiang had an OPS of 1.050 at Portland) to bring in a very good but almost always hurt Erik Bedard.

And they didn't make the Bedard deal because Andrew Miller is terrible or because Bad Tim Wakefield is always lurking. The Red Sox know they are in a position that allows them to make the playoffs with substandard fourth and fifth starters the rest of the regular season.

The Bedard trade, of course, wasn't made for August or September. We know that. And Bedard could turn out to be a miss, three starts and hello to the DL. But it was a trade that had to be made, and not just because of Buchholz.

Think about it: If John Lackey was your classic No. 3 starter to date -- think an ERA around 4.00 -- how much different would you feel about the chances of the Sox to win the World Series? I still think they are -- at worst -- second favorite to the Phillies, but that no-doubt No. 3 guy is all that's really missing. The lineup, Lester/Beckett and Bard/Papelbon? Not a weakness to be found.

But if we can assume Buchholz is out for the season and the Red Sox are done making moves when it comes to adding starting pitching (I think both are at least pretty safe assumptions), well, a potential weakness suddenly emerges.

John Lackey is going to be part of the postseason rotation.

No way around it. You are going to see Lackey in October. Could be Game 3 or Game 4, but get ready for Lackey in an immense playoff spot. 

And we arrive at redemption. 

If Lackey pitches well in the playoffs -- nobody is thinking Bob Gibson, but something close to the Lackey that we saw in the postseason over the last decade -- and the Sox win the World Series, nothing else will have mattered. His Red Sox career would no longer be defined by showing up teammates or Terry Francona or a 6.00 ERA or his failure to take postgame responsibility for a loss.

He'd instead become Derek Lowe circa 2004, a disaster for six months and then a hero forever (OK, or at least until Lackey gets bombed in a May start, bitches out Pedroia for botching a grounder and blames the eight runs in 2 2/3 IP on an inconsistent strike zone).

Do I think Lackey is going to pitch well in the postseason? Nope. No real evidence over the last year and a half to make me think he can put together three or four superior starts against the likes of the Yankees and Rangers (we're still at the stage, after all, where Lackey can give up 11 hits and four runs in 5 2/3 IP vs. the Royals and the spin is that it's another step forward).

But thanks to injury and failure of others to step up and make a case (if Miller is just OK, you've got a Game 4 controversy) you've got a clear scenario.

John Lackey in October.

It will either be redemption or confirmation.

For sure.