So…Now What?

After a long wait, it’s official: John Lester is signing with the Chicago Cubs for the hefty price tag of $155 million spread out over six seasons (with a vesting option for a seventh year). He is not coming back to the Red Sox after all, not for the six year, $135 million final offer Boston made, which was $20 million less than the Cubs’ offer and $33 million less than San Francisco’s Godfather offer of 7/$168 mil. If you believe what the baseball community has been saying all along, and there’s no reason not to, this signing will finally open the flood gates on the starting pitching market and allow several more moves to be made.

Lester’s decision leaves the Sox with a starting rotation that, as of today, consists of Clay Buchholz, Joe Kelly, Rubby De La Rosa, and then two of the wildly underwhelming trio of Anthony Ranaudo, Allen Webster  and Brandon Workman. To be totally honest, I could replace everything in that previous sentence with the exception of the first five words with “in a tough spot”, because that’s precisely where the Red Sox stand right now with regards to their starting pitching. While they have addressed their flaccid lineup from last season with the acquisitions of Hanley Ramirez and Pablo Sandoval about two weeks and a half weeks ago, Boston’s rotation leaves much to be desired.

Before we get into what comes next for the Sox, it’s important to clarify that they brought this problem on themselves. All that Boston’s brass had to do was approach Lester with a reasonable offer in the spring, and all of this could have been avoided. Instead, Lester was offered the same amount of money that J.D. Drew signed for almost eight years ago. As Jeff Passan of Yahoo! Sports pointed out, had the Red Sox made relatively market competitive offer, there’s a good chance he would have re-signed. But they didn’t, he didn’t, and that’s how you get left with Clay Buchholz and his 5.34 ERA as your de facto ace.

Losing out on Lester means the Red Sox are losing out on a homegrown talent who spent eight and a half of his nine seasons with the club and was a part of two World Series championship teams. Sentimentalism aside, statically Lester is one of the best left-handers  in the game, a horse who has averaged 32 starts and 207 innings per season since 2008.

Lester enjoyed his best season in 2014, setting career bests in innings pitched, ERA, ERA+ (which adjusts for park factors), and strikeout to walk ratio. 2015 will be his age 31 season, meaning that the Cubs will have signed him through at least his age 37 season.

Assuming Lester can stay healthy (and he’s shown no reason why he can’t), this should be a solid deal for the Cubs, even though there will likely be a drop off in performance in the back half of the contract.

If nothing else, the Red Sox can take solace knowing that last season was the first season in which either Lester’s FIP or ERA was under 3.00. While Lester is a very good pitcher with terrific postseason performances who has been relatively consistent over the course of his career, last season stands out in some ways compared to past seasons. Whether Lester’s pinpoint control last season was the result of his maturation as a player and mastering of the cut fastball (a project that had been a few years in the making) or just an outlier only time will tell.

Regardless, there is no question that the Red Sox will sorely miss Lester’s steady hand in the rotation unless they can find a suitable replacement (or two). Fortunately, there are a few options for the club in both free agency and the trade market.

The most obvious candidate to fill the void left by Lester is Max Scherzer. The free agent right hander blossomed over the last couple seasons in Detroit, winning the 2013 Cy Young. Scherzer followed up his award-winning campaign with another excellent season in 2014, with a stat line that approached his career numbers from the previous year. While he would certainly be a welcome addition to a beleaguered group of starters, he also carries a much heavier price tag despite being only half a year younger than Lester. If the Red Sox weren’t willing to go over $135 million for the known commodity that Lester represented, it’s highly unlikely that they will be willing to pony up another $70 million for Scherzer.

A step down from Scherzer would be James Shields. The 32 year-old right hander will be entering his age 33 season in 2015, though he, like Lester, has proven to be both a workhorse and a highly effective pitcher. Since 2007 Shields has averaged 223 IP per season, and hasn’t thrown less than 203 innings in a season over that span. Mileage may be a concern here, though the Sox may be forced to bite the bullet and take that chance because, well, just look at the names I listed in the second paragraph of this column. Shields was reportedly going to sign soon after Lester’s decision was made, so we’ll have an answer as to whether the Red Sox are interested in the guy who beat them in Game 7 of the 2008 ALCS fairly soon.

After those two pitchers, the market becomes a lot more muddled. It is likely that the Red Sox will try to make moves on a reclamation project/low-end starter to try to fill out their rotation (aka the Edinson Volquez All-Stars). Boston has already reached out to this class of free agents, offering former member Justin Masterson (who they dealt away in 2009 as part of a year and a half Victor Martinez rental) a multi-year deal. Masterson struggled mightily last season, posting 5.88 ERA between the Indians and Cardinals while walking 4.8 batters per nine innings. Despite the sky-high ERA, Masterson’s FIP was only 4.50. While that’s not exactly a great number either, the fact that it is a good deal lower than his ERA points to some bad luck to go along with diminished control. The stats back this theory up: Cleveland was third to last in the AL in defensive efficiency and dead last in the AL in defensive runs saved. Masterson still struggled in St. Louis, one of the better defensive teams, but ultimately one could conceive of a scenario where Masterson returns to the effective pitcher he was in 2013.

Then of course, there’s trades. With Yoenis Cespedes both expendable and presenting the most value of the Red Sox outfielders, he has found himself at the center of a great deal of rumors ranging from the Mets (who weren’t interested after all) to the Reds (maybe interested?) to a Cespedes/De La Rosa to the Tigers for Rick Porcello (which, while floated out there, has been considered “not hot” by the Boston Herald’s Michael Silverman) to a Cespedes/Ian Kennedy swap with the Padres. Kennedy would be an interesting pickup; he won 21 games in 2011 with Arizona and last year benefited from the friendly confines of the spacious Petco Park while posting a career best 9.27 K/9. Jeff Samardzija was another attractive avenue, though the A’s already decided to partner up with some different Sox. The biggest potential trade would involve bringing the Phillies Cole Hamels to Boston, though that reportedly would require the Red Sox selling the farm. Hamels would be an ideal candidate to replace Lester as a bona fide left handed ace with playoff seasoning coming off another excellent campaign and with four years of team control at a reasonable rate. It is unlikely, however, that the Red Sox would be willing to budge on their stance of refusing to trade either Mookie Betts or Xander Bogaerts, making Hamels, like Scherzer, a pipe dream.

Regardless of the path the Red Sox do take, one thing is painfully clear: that lowballing Lester last spring was a dubious move at best, and one that will almost certainly come back to haunt them if they are unable to find a quality arm or two to help fill out their starting rotation. The options are out there, it will be up to Ben Cherington to take advantage.