Pitching Around Some Trade Proposals While We Wait on Jon Lester

Maybe the question this offseason isn’t whether or not Pablo Sandoval was worth $95 million, but whether or not signing the new Red Sox third baseman was worth losing Jon Lester.

No, it wouldn’t be because of a financial cop-out by the Red Sox, already nearly $200 million deep in building the 2015 roster, but because Sandoval’s former team suddenly has a lot more cash to play with after failing to re-sign their popular Bay Area icon.

Lester continued his free agency tour on Monday, when he met with the San Francisco Giants, which has to be considered a major threat to Boston’s hopes to re-acquiring its one-time ace. It’s a quick hop over the Bay Bridge from where he spent most of his summer, he’d get to play in the best ballpark in the major leagues, wouldn’t have to deal with lineups including a designated hitter, and he’d join World Series hero Madison Bumgarner to create perhaps the most dangerous 1-2 punch in the National League.

If you’re Lester, it boils down to this; Boston (reportedly offering $110-$120 million over six years) is comfortable and the Chicago Cubs ($138, six years) present the ultimate challenge, but San Francisco arguably gives the lefty the best chance to fit the other three fingers on his throwing hand with some more World Series bling. Or you go to whomever is willing to give you the $150 million that you’re reportedly seeking.

That brings in the New York Yankee factor. Would anybody be surprised to see them – finally – throw their hat into the ring next week with an offer to trump them all at the Winter Meetings in San Diego?

But while Lester bides his time, Red Sox general manager Ben Cherington is forced to look at his starting pitching staff – with or without Lester – and gulp Bushmills neat. If Boston were to start 2015 with the lineup it has in place, which it won’t, you’re looking at a rotation anchored by Clay Buchholz (8-11 with a 5.34 ERA in 2014), Joe Kelly (4-2, 4.11 ERA in 10 games with Boston), and some combination of Rubby De La Rosa, Allen Webster, Anthony Renaldo, Brandon Workman, and perhaps Henry Owens filling things out.

That’s frightening, but not realistic. Even if the Sox end up losing out on Lester, they could still jump into the Max Scherzer sweepstakes or (shiver) overpay for James Shields to round out their rotation. That still leaves the house to be built from the foundation up with tools like Brandon McCarthy, Ervin Santana, Francisco Liriano, and Justin Masterson representing the second wave of options with varying degrees of welcomeness on the open market, which leads us to preview some of the wheeling and dealing that might be done in San Diego.

One of the latest ideas currently on the rumor market is the Red Sox’ interest in A’s starter Jeff Samardzija, the 29-year-old righty (30 in January) whom the Cubs traded to Oakland last July. He was only 7-13 last season between both clubs, but with a satisfying 2.99 ERA (2.83 in Chicago, 3.14 in Oakland). MassLive.com’s Jason Mastrodonato floats the idea of a package that includes Jackie Bradley, Jr., Brock Holt, and Ranaudo for the pending 2016 free agent.

As Mastrodonato points out, since 2011, Samardzija has the same ERA (3.61) as Lester with a higher strikeout rate, which places him in the category of under appreciated value that looks beyond his 36-48 career record. He’s expected to make nearly $10 million in salary arbitration this winter, which is a red flag as far as the tight-wallet A’s are concerned, even if GM Billy Beane did surrender two first-round picks in Addison Russell and Billy McKinney just last summer in his failed attempt to win it all in 2014.

The inclusion of Ranaudo in such a deal may give one pause, if only because the former first-round draft pick, who was 14-4 at Pawtucket last season, 4-3 in Boston with a 4.81 ERA, showed some flashes of promise in a handful of starts at the big league level last season (particularly in his big league debut against the Yankees and his season finale against the Tampa Bay Rays). He’s also 25, and perhaps on the cusp of putting it together. Ditto, Rubby De La Rosa. Is it worth shipping those kinds of guys out for one whom you’re not likely to re-sign to any semblance of a long-term deal at the age of 31? For Bradley, Holt, and say, Workman? Well, sure. In a flash. But the Red Sox are one of only a handful of teams vying for Samardzija this offseason, and it’s going to take more than that to satisfy Beane’s needs.

There’s the Cole Hamels thing, which I take it most Red Sox fans would be happy to leave at just that. Put aside Hamels’ unproven track record in the American League, which to be honest, is a bit irrelevant since the flip side is that he’s 54-42 with a 3.28 ERA in his career at Philadelphia’s Citizen’s Bank Park, one of the smallest bandboxes in the majors. Isn’t he a last-ditch option for Boston though? Not only will he cost $110 million when you tack on the fifth option year Hamels will demand in order to waive his no-trade clause, but also a package of top-tier prospects possibly including one of Xander Bogaerts or Mookie Betts. No. No, no, no. Are we clear on this?

Jordan Zimmerman might be a different story, though one you wouldn’t want to give too much up for without the assurance that the Washington Nationals righty might want to stick around long-term before he hits free agency in 2016. The right-hander was 14-5 with a 2.66 ERA last season with the Nationals, and was 12th among pitchers with a 4.88 WAR (for fairness’ sake, Hamels was fourth with a 6.62 WAR). But what’s the impetus for the Nationals to unload Zimmerman? They have the cash to sign him long-term, and probably will do so in lieu of risking their position atop the National League East. File under Boston daydream.

That brings us to the most likely trading pipeline in Cincinnati, though anyone other than 14-year-old Twitter sifters who thinks that the Reds would be down with trading Johnny Cueto straight up for Yoenis Cespedes needs to sober up. Cueto is also due to become a free agent in 2016, but is coming off a 20-6, 2.25 dominant campaign that landed him second in Cy Young Award voting. He missed significant stretched in 2010 and ’13 with injuries, so that’s a concern, but he’s also one of the more eclectic pitchers that could be dealt this winter and will be 29 by the start of the season.

FanGraphs Dave Cameron suggests that in addition to Cespedes, the Sox could send the Reds one of Ranaudo or Webster, and take on reliever Sean Marshall’s $6.75 million contract for next season. Marshall was abhorrent in 2014 (7.71 ERA in only 15 games), and shoulder injuries don’t suggest that he’ll regain the form that made him a bullpen threat only a few years ago. It still may be a risk worth taking in order to land Cueto, and a financial move the Red Sox can make that few other teams can bring to the Reds.

Failing that, the Sox could try and pry Mike Leake (11-13, 3.70 ERA in 2014) or Mat Latos (5-5 in ’14, following a 14-7, 3.16 season in 2013) from the Reds. Both Leake and Latos, both 27 by the time the season starts, are also free agents come 2016, which probably means one of the three is going to be playing elsewhere in 2015. The Sox could potentially get one of them for Cespedes, who looks like he’s on his way out the door with free agency under Jay-Z looming. Leake and Latos perhaps also represent better trade value in that the Sox could lock one or the other up for six years beyond 2015, and still get the pitcher in his prime seasons of ages 28-32 in the process.

Chris Sale? Not happening.

A lot of what the rotation projects out to be depends not only on the moves the Red Sox make over the next month, but whether or not the younger guys continue to develop. Owens, De La Rosa, Matt Barnes, Webster, Ranaudo, Eduardo Rodriguez, Brian Johnson, and the list goes on. There’s no room for all of them at the top, and even if there were, the unlikelihood that one-third of that group pans out to be viable starting pitchers in the majors. With so many pending free agents looking for a payday after their 2015 season, a handful of them won’t be here in a few weeks time.

Maybe Lester will finally make a decision by then, too.