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Boston Red Sox starting pitcher Jon Lester heads to the bull pen before a baseball game against the Kansas City Royals in Boston, Sunday, July 20, 2014. (AP Photo/Michael Dwyer)
Boston Red Sox starting pitcher Jon Lester heads to the bull pen before a baseball game against the Kansas City Royals in Boston, Sunday, July 20, 2014. (AP Photo/Michael Dwyer)Michael Dwyer/Associated Press

What Is Red Sox's Best 'Plan B' After Digging Own Grave in Losing Jon Lester?

Jason CataniaDec 10, 2014

When it comes to losing out on former ace Jon Lester, the free-agent left-hander they lowballed then traded away before lowballing again, the Boston Red Sox have no one to blame but themselves. Now, the Sox have their work cut out for them as far as putting together a legitimate rotation in a market for starters that suddenly is both diminishing in terms of options and escalating in terms of dollars.

With Lester having signed a six-year, $155 million contract with the Chicago Cubs late Tuesday evening, per Carrie Muskat of MLB.com, that means three starting pitchers have come off the board through the first two days of the winter meetings.

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Also on Tuesday, the Pittsburgh Pirates re-signed lefty Francisco Liriano to a three-year, $39 million pact, via Rob Biertempfel of the Pittsburgh Tribune-Review, and the day before landing Lester, the Cubs brought back righty Jason Hammel for $20 million over two years, per Jon Heyman of CBS Sports.

And because Lester's massive deal has set the price for an elite arm, there's a good chance that a bunch of other free-agent pitchers could start coming off the board in short order.

The good news for the Red Sox is there still are a lot of options to consider and chase in free agency and trades—at least in theory.

Right-handers Max Scherzer and James Shields remain readily available although both will cost Boston a pretty penny.

Scherzer is said to be seeking a $200 million contract, according to Jon Paul Morosi of Fox Sports, while Shields almost certainly will get a nine-figure deal of his own.

Considering the Red Sox reportedly came in with a final offer to Lester of six years and $135 million—or $20 million short of what he got from the Cubs, per Gordon Edes of ESPNBoston.com—it's fair to wonder whether Boston actually wants to meet such lofty asking prices.

The bad news? Boston needs more than just one starter—more like two or three—and the clock now is ticking a lot faster.

In case you've forgotten, here's a rundown of the Red Sox's projected starters, as listed on their own MLB.com depth chart:

Clay Buchholz14914.1
Joe Kelly481.9
Rubby De La Rosa281.2
Allen Webster180.2
Anthony Ranaudo70.2
Brandon Workman181.4

Aside from those top two free-agent arms, there's Brandon McCarthy and Ervin Santana, a pair of right-handers who aren't front-liners but who would provide some stability, which is something the Sox need as much as anything else.

Boston reportedly has made an offer to former Red Sox Justin Masterson, a bounce-back candidate after a disastrous, injury-ravaged 2014, according to Edes. But this is a team that needs a heck of a lot more reliability—and to put it simply, innings—to shore up a rotation that at the moment is as volatile and unproven as any in the entire sport.

The Red Sox have to do better than Justin Masterson, who turns 30 in March and posted a 5.88 ERA over 25 starts while dealing with injury in 2014.

That's why the Sox can't sit back and hope that, say, Japanese star Kenta Maeda gets posted by the Hiroshima Carp or that 39-year-old Hiroki Kuroda decides he's willing to give it one more year in MLB and would consider going to a new team.

After that, the free-agent market gets ugly really fast. Jake Peavy? Been there, done that. Edinson Volquez and Ryan Vogelsong? National League pitchers. Aaron Harang, Brett Anderson, Gavin Floyd and Brandon Morrow? Aging, injury-prone—or both.

Unless general manager Ben Cherington all of a sudden is going to change course and start throwing huge money at Scherzer or Shields, Boston's best hope at this stage is to go hard after any and all starters who might be available via trade.

Boston has been linked to Cole Hamels, and the Phillies ace may be its best option now.

Among others, that includes names like Johnny Cueto and Mat Latos of the Cincinnati Reds, Tyson Ross, Andrew Cashner and Ian Kennedy of the San Diego Padres and Doug Fister of the Washington Nationals.

Besides that batch, Boston already has been linked this offseason to the Detroit Tigers' Rick Porcello and Philadelphia Phillies' Cole Hamels.

There was mention of a potential trade built around Porcello and Yoenis Cespedes, per Jayson Stark of ESPN, and the Phillies have been eyeing some of the Red Sox's young talent.

Hamels may, in fact, be Boston's Plan B, according to Ken Rosenthal of Fox Sports.

Here's what Cherington had to say, via Ian Browne of MLB.com, about the need to add an arm:

"

I think we're in a position where we have position player strength and depth. We have resources, we have some financial flexibility. There's all sorts of different ways to build the pitching staff. We've been able to pursue all kinds of things. We don't feel constrained, other than just trying to find a deal that makes sense. That's the constraint—it's not one guy or the other. We're just still working towards deals that make sense.

"

To be clear, the Red Sox do have the pieces necessary to obtain a big-time starting pitcher or two. After inking Hanley Ramirez and Pablo Sandoval, the club currently has an excess of outfielders, cornermen and designated hitter types.

In addition to Cespedes, there's Mike Napoli, Allen Craig, Jackie Bradley Jr., Daniel Nava, Brock Holt and Will Middlebrooks.

Youngsters Mookie Betts and Rusney Castillo, whom the Sox would much rather hang onto as building blocks, also could come into play, especially if the price just went up on Hamels.

Boston also possesses one of the deepest farm systems around, with pitchers like Henry Owens, Matt Barnes, Eduardo Rodriguez and Brian Johnson as well as catching prospect Blake Swihart, third baseman Garin Cecchini and shortstop Deven Marrero. All of the above are just about big league ready.

But now that the dream of bringing back Lester has turned into the reality that Boston's former ace is headed to Chicago, the Red Sox will have to work even harder—and even faster—to ensure that they address a very shaky rotation.

The pieces seem to be in place to make a trade or signing or three, but until the Red Sox put them together, the 2015 rotation remains a huge puzzle. And Lester is no longer on the board.

Statistics are accurate through the 2014 season and courtesy of MLB.com, Baseball-Reference and FanGraphs unless otherwise noted.

To talk baseball or fantasy baseball, check in with me on Twitter: @JayCat11.

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