What the Jon Lester signing means for him, the Cubs and the Red Sox

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SAN DIEGO — This is the sixth Winter Meetings I’ve attended, but it is the first one where I’ve attempted to maintain my health and sanity via (a) relatively healthy eating; (b) a minimum of drinking; and (c) an effort to go to bed and wake up at a reasonable hour.

Well, a lot of good that did me because if I was up drinking last night I would’ve seen the Jon Lester news when it happened. As it was, I was getting into bed.

But that’s not too big a deal, actually, as my highest and best purpose is to talk about what the big news means, not to break it, so let’s now talk about what this biggest of Winter Meetings news means for Lester, the Cubs and Red Sox.

What it Means for the Cubs: Instant Credibility and Instant Pressure

Theo Epstein and Jed Hoyer’s rebuild of the Cubs has been meticulous and measured since they came to Chicago before the 2012 season. The team they inherited sported Alfonso Soriano, Aramis Ramirez, Carlos Pena, Marlon Byrd and Carlos Zambrano. In the manager’s chair: Mike Quade which, well, the less said about him the better. It was a team with big bad contracts and a long future of 90-loss seasons staring it in the face.

Well, since then the team has lost 101, 96 and 89 games, so I guess that future continued superficially, but behind the scenes the dismantling and reconstruction has been remarkable, even if it has been low key. Team Epstein-Hoyer has added a ton of high-upside position players, including Javier Baez, Jorge Soler, Kris Bryant and Addison Russell. They also have rejiggered the pitching staff with some smaller pieces like Jason Hammel and Jake Arrieta, and weathered some missteps along those lines as with Edwin Jackson.

But while all of the moves they’ve made — with the exception of Jackson anyway — made sense and improved the club, but didn’t really ignite the fan base or signal to them that, yes, the era of the rebuild is over and the era of truly competing is here. It’s been a long three years for Cubs fans who just want to see some good baseball and who don’t salivate over prospects.

The Lester move — and to a lesser extent the unexpected hiring of Joe Maddon just prior to that — changes all of that. They are signals to Cubs fans that the time to win is now, their team is credible and not laughable and that they expect to contend. After all, one does not spend $155 million on a pitcher and toss aside the manager they just hired a year ago for a big name like Maddon with the expectation of improving to .500.

But the other side of that credibility coin is pressure. No matter how many moves a team makes, it’s hard to improve by the 20 wins or so one would expect the Cubs will need in order to pull off the worst-to-first trick. And for all of the promise the folks who salivate over prospects have felt around this club, they were the worst team in the NL Central last year. And they still have some issues that need to be addressed. The pitching, primarily, as Lester is still mortal and can’t take the hill every second or third day. Prospects are great, but sometimes they don’t pan out as promised. For as excited as the Cubs and every Cubs fan has a right to be today, each offseason there are teams which make big splashes that cause everyone to crown them the offseason champs. Very, very often, however, those plans don’t survive engagement with the regular baseball season.

Signing Jon Lester is the move the Cubs had to make. It improves them tremendously. Whereas the past few years have given anyone any real expectation of a winning Chicago Cubs team coming soon, now it is totally realistic to expect them to contend in 2015 and beyond. But with any set of expectations comes pressure, and the pressure occasioned by making such a big splash is going to change the way the fans, the media and even Jed Hoyer and Theo Epstein think about and approach the Cubs going forward.

What it Means for Jon Lester: Time to Join The Big Boys Club

There is no question that Jon Lester is a top of the rotation starter. With the exception of 2012, he has been a consistent and durable pitcher. He’s never experienced arm trouble of any note, pitching fewer than 200 innings only once in the past seven seasons and, that season, tossing 191 and two-thirds. He dominated in the 2013 postseason and he was certainly treated like an ace this past season, sought-after by Billy Beane and the A’s in a midseason trade that cost a big slugger in Yoenis Cespedes and asked to pitch the A’s to victory in an elimination game. Of course that victory did not come and the fact that they were even in that game and didn’t win the division was a function of an overall A’s collapse, but that had nothing to do with Lester, who was fantastic for Boston before the trade and continued to be fantastic for Oakland after. Heck, he left that elimination game with a lead.

It’s crazy to expect tons and tons more from Lester — he was already part of two World Series winning teams in Boston — but expect it people will. They’ll look at that contract and realize that it slots right behind Clayton Kershaw, Justin Verlander and Felix Hernandez and, despite the fact that being a “Cy Young Pitcher” is not the only definition of an ace, a lot of people will expect him to be that “Cy Young Pitcher.”

In Boston, there were all manner of people who found themselves on the other end of TV cameras and reporters’ digital recorders after a game more often than Lester did. In Chicago, he will now be The Man. That won’t change the type of pitcher Lester is and, if he pitches the next six seasons exactly like he’s pitched the past six, the Cubs will be happy with what they get. But the job will be harder now and will carry with it more pressure for him to be perceived as the kind of pitcher who carries a team on his back. And, if he doesn’t, he’ll hear a lot about it.

What it Means for the Red Sox: A Lot of Work to Do, Baseball and P.R.-wise

The P.R. fallout is going to be first and it’s going to be big, because this is Boston and nothing is small when it comes to Boston, especially when there is criticism to be leveled. And there will be no small amount of criticism here, with the “How did We Lose Lester” game rivaling the “Who Lost China” stuff from the 1950s. The Boston press will demand scapegoats and if there are no reasonable ones, by golly, they’ll create a couple.

And even if that is all overheated and silly, there is a core of reasonable inquiry to be had about it all. The fact is, the Red Sox misread the market for Lester last offseason when they, reportedly, only offered Lester $70 million and he would have, reportedly, gladly stayed in Boston for $110 million. As it was, they fell short in the bidding again this week, going only as high as $135 million. That’s going to lead to some scorchingly hot takes in the Boston Globe and some serious hooting and hollering on sports radio. Boston has seen this happen in the past, of course, but it’s never fun, one imagines, and Ben Cherington, John Farrel and ownership are going to have to take a lot of time in the coming days and months addressing a lot of criticism.

More important, however, is that they address the starting rotation. It’s hard to imagine that they can put together one that is as good without Lester as they could have with Lester, but that is the task ahead of them. And it won’t likely be accomplished with anything close to a one-to-one answer to the Lester deal. Max Scherzer is the only free agent starter in Lester’s league, and he reportedly wants $200 million. Between that dough and the fact that, it would appear, the Sox have never considered Scherzer to be as desirable as Lester, you have to figure that’s not happening.

James Shields is a possibility. As is, potentially, a trade for Cole Hamels, but that will likely cost an awful lot in terms of prospects to happen. Mookie Betts may be a starting point for Ruben Amaro in talks, while the Sox will likely try to hold on to Betts and package other guys to Philly. Other trade targets include a lot of guys who are rumored to be available, but whose teams will likely drive a hard bargain. Guys like Rick Porcello, Jordan Zimmermann, Johnny Cueto and guys like that. Now matter how that all goes down, if it even goes down, it’s going to take a lot of work.

Losing out on Lester will not be the end of the world for Boston. But it does mean the beginning for a winter that will likely be a general pain in the butt for everyone involved.

So that’s what it all means for Boston, Chicago and Lester. Now, here’s what it means for you and me and everyone who yaks about baseball: we need to relax. One signing does not a pennant win or lose. You’ll see, in the coming days, an awful lot of talk about how “the balance of power” has shifted in the NL Central and the AL East and stuff like that. Don’t believe most of it. It’s in the same vein as the talk that had the 2012 Phillies winning it all and various Marlins and Blue Jays teams winning the offseason in the past couple of years. Which is to say that it’s mostly hot air.

Jon Lester makes the Cubs better. His absence will make the Red Sox worse. But he is, in the beginning and the end, only one man, and able front offices in Boston and Chicago will have a lot more to say about how their teams do than Jon Lester will. Let’s have fun with it all now, but let’s let the baseball season get underway before we declare there to be definitive winners and losers.

Pirates hire Ben Cherington as their new general manager

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The Pittsburgh Pirates have hired Ben Cherington as the team’s new general manager. They do so after the general manager meetings ended, but better late than never.

Cherington served as GM of the Boston Red Sox for four years, winning the World Series in 2013, but resigned during the 2015 season after Dave Dombrowski was named Boston’s new president of baseball operations. Which was a defacto demotionn for Cherington who, until then, had the final say in baseball decisions. Dombrowski, of course, was fired late in the season this year. Cherington went on to work for the Toronto Blue Jays as a vice president, but was seen as biding his time for another GM position. Now he has one.

Cherington takes over in Pittsburgh for executive vice president and general manager Neal Huntington, who was fired after a 12 years at the helm. Also fired was team president Frank Coonelly. Travis Williams replaced Coonelly recently. While the Pirates experienced a few years of contention under Huntington and Coonelly, they have slid out of contention in recent years as the club has traded away promising players for little return, all while cutting payroll. There’s a very big rebuilding job ahead of Cherington.

The first move he’ll have to make: hire a manager, as the team still hasn’t replaced Clint Hurdle since he was dismissed in the final weekend of the regular season.