Ben Cherington

Red Sox general manager Ben Cherington begins second roster overhaul


For the second time in 22 months, Ben Cherington must find a way to turn a last place team into a winner — and fast.

Boston isn’t a patient place. Long, gradual improvements don’t go over well for a fan base which has enjoyed three world championships in the last 10 years and pays some of the highest ticket prices in the game.

Rebuilding? That’s for other teams in other cities.

In Boston, the turnaround has to be on-the-fly, with little time elapsing before an also-ran becomes a title contender again.

After the disastrous 2012 season, when the Sox finished with their worst record since the mid-1960s, Cherington took an aggressive approach to off-season.

He re-invested the massive financial savings that came out of the mega-deal with the Los Angeles Dodgers into solid major league free agents in their prime.

The plan worked like a charm then, as the Red Sox improbably went from last to first by winning the World Series in 2013.

On Thursday, Cherington began his second overhaul in much the same way.

He shipped out Jon Lester, Jonny Gomes, John Lackey, Andrew Miller and Stephen Drew, but instead of accumulating a host of prospects, mostly focused on obtaining proven, established players in return.

Throughout, Cherington was guided by one principle: “To be as good as we can, as quickly as we can.”

In the off-season that followed 2012, the Sox targeted the likes of Mike Napoli, Shane Victorino, David Ross, Ryan Dempster, Gomes and Drew.

He wasn’t interested in stockpiling more potential and waiting to see if the talent evaluations were on-target.

It was the same approach on Thursday. He didn’t look for the best high-ceiling, low-cost prospect from the A’s in dealing Lester and Gomes. Instead, he received a 28-year-old power-hitting outfielder, who himself is under control only through the end of next season.

And when he shipped out Lackey to the Cardinals, owners of one of the best and deepest farm systems, he didn’t hold out for blue-chippers Oscar Tavares or Carlos Martinez or Stephen Piscotty. He opted for Allen Craig, 30, and Joe Kelly, 26, both part of the Cardinals team that faced the Sox in the World Series last October.

Why? Because Cherington was in a hurry.

The Red Sox aren’t the Rays, whose best return for ace David Price was an 18-year-old shortstop at Single A. No, the Red Sox intend to try to win next year.

Potential? The Sox already have plenty of that, especially starting pitching (Anthony Ranaudo, Matt Barnes, Allen Webster, Rubby De La Rosa, Henry Owens, Brandon Workman) and left-side infield help (Garin Cecchini, Deven Marrero).

No, what they wanted was a short-cut. The two biggest trades that Cherington pulled off were old-fashioned baseball trades.

You have pitching? We need hitting.

You need hitting? We have pitching.

And so, deals were born, though they weren’t easy to execute.

“Prospect deals are typically easier to pull off,” said Cherington. “Most of the time, you’re getting calls from contenders and it’s tough to get proven major leaguers from contenders because it doesn’t typically make sense to give up proven major leaguers if you’re contenders.

“But I think the quality of our guys (being shopped) and the fact that they’re playoff tested and recently playoff-tested. As far as the return, time will tell. We’re happy with what we did. We think it fits with what we’re trying to do, which is to focus on major league or near-ready major league talent.

But as painful as it was to get to this point, we really wanted to see if we could take advantage of the unfortunate circumstances and make it into something better.”

There’s more to do, of course. Either by packaging some of their own prospects or by signing free agents, the Red Sox need more established starting depth this winter. It would be foolish to head into next season with the fragile Clay Buchholz and the still improving Kelly as their own experienced starters.

But this much is clear: the club’s offense is vastly improved over the last 24 hours and so is its own inventory of young pitching.

There’s no guarantee that they can execute another quick turnaround. But they determined Thursday that there was only one way to try: to do what worked when they were faced with the same challenge two years earlier.

Kyle Schwarber is on a private plane en route to Cleveland

PHOENIX, AZ - APRIL 07:  Kyle Schwarber #12 of the Chicago Cubs bats against the Arizona Diamondbacks during the MLB game at Chase Field on April 7, 2016 in Phoenix, Arizona.  (Photo by Christian Petersen/Getty Images)
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This is happening, people.

Earlier we heard Joe Maddon being non-committal about Kyle Schwarber joining the Cubs for the World Series. Now it seems pretty clear that the Cubs are committal indeed: Jon Morosi reports that Schwarber is en route to Cleveland from Arizona on a private jet and that he’s expected to DH in Game 1 tomorrow night.

Schwarber hasn’t played in a game that counted since April 7. His potent bat is could be a windfall for a Cubs team that didn’t have a game-changing option at DH in the American League park.

Schwarber lost the whole season due to a knee injury, but he hit .246/.355/.487 with 16 homers and 43 RBI in 69 games as a rookie in 2015. His big coming out party was in the playoffs, however, when he hit three homers in five postseason games while going 7-for-13 with two walks in five games.

Carlos Santana in left field? Sure, OK.

CLEVELAND, OH - OCTOBER 15:  Carlos Santana #41 of the Cleveland Indians celebrates after hitting a home run in the second inning against J.A. Happ #33 of the Toronto Blue Jays during game two of the American League Championship Series at Progressive Field on October 15, 2016 in Cleveland, Ohio.  (Photo by Maddie Meyer/Getty Images)
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Paul Hoynes of the Cleveland Plain Dealer reports that Indians First Baseman/DH Carlos Santana shagged some flyballs in left field during the Indians’ workout today.

Sure, why not? Santana has played one game in the outfield in his major league career and that was over four years ago, but the Indians will have to play in Chicago without the DH, meaning either losing Santana’s bat or that of Mike Napoli.

It would be up to Terry Francona to decide if that happens, but ultimately I don’t think he’ll make it real and, rather, will just forget about it, because Santana’s defense out there would in no way be smooth.

I’m sorry. I’m sick today and I’m on a lot of cold medicine.