Trading Jon Lester makes all kinds of sense. He's a free agent at the end of the season, the Red Sox aren't sure they'll commit the dollars necessary to keep him, he's not going to re-sign in Boston's exclusive October negotiating window, and he's far and away the most attractive pitching target on the July market now that David Price has been pulled back. Trading John Lackey, though, which the Sox are also entertaining, doesn't make anywhere near as much sense. In fact, unless someone were to offer a deal so stupidly lopsided in Boston's favor that the only thing worse would be for the Sox to turn it down, they should be holding on to John Lackey as tightly as they can.
Picture this: Jon Lester is traded and doesn't come back to Boston for 2015 and beyond. Or hell, maybe Lester isn't traded, but he doesn't re-sign, and all the Sox get for him is a compensation pick and its associated budget for the 2015 MLB Draft. Either way, a major void opens atop the Sox rotation, one that cannot be filled by Clay Buchholz -- the only major-league starting pitcher under contract for 2015 -- or any of the prospects or present-day rookies, no matter how many of them there are waiting for their turn. John Lackey is likely Boston's best starter in Lester's absence: if he's also gone, then the Sox' entire rotation is question marks.
Buchholz has incredible talent, but he's frustratingly inconsistent to the point where his ability to produce vanishes for months at a time. Between the injury history and his occasional inability to remember how or when to throw his change-up, he can't be relied upon as a top of the rotation arm -- that's coming from someone who has been sitting in Buchholz's corner since before he reached the majors. He'd be the top starter on the team barring a major transaction this winter, and that's a frightening proposition, both because you can't guarantee a major pitching acquisition like James Shields, Max Scherzer, or a Cole Hamels trade will happen, and because of what the Sox are left with if one does not.
A rotation could be cobbled together from Brandon Workman, Rubby De La Rosa, Anthony Ranaudo, and Allen Webster. It has the potential to be good, and might even be great if things go down all best-case scenario, but chances are much better that at least one of them would be a disappointment who mostly shows they belong in relief. Worst-case, three of them or all four of them prove as much, leading the Red Sox to hope that prospect lefties Henry Owens and Brian Johnson have progressed enough to jump to the majors, or that Matt Barnes has evolved enough at Triple-A to get his prospect shine back.
Henry Owens will be an answer eventually, but not yet. (Photo credit: Jerry Lai-USA TODAY Sports)
The point is that you just don't know, and there are too many warning signs out there for all four to be relied upon at once. De La Rosa needs more than just a plus change-up if he's going to be successful, so developing his slider to help setup the change and his high-end velocity is a must. Ranaudo might have solved his repertoire issues with the introduction of his own slider, but it and he have not been tested against big-league bats. Workman could be a successful fourth or fifth starter who can throw 200 innings, but his command needs to be more consistent, and we haven't actually seen him throw that many innings yet even if his build suggests it's an option. Webster has the plus pitches and the repertoire, but he's been a completely different pitcher in Triple-A than in the majors in a way that should make you uncomfortable about his future. Until he has an extended stint in a big-league rotation, it's hard to know if he's going to be be able to mix swing-and-miss with ground ball potential enough to survive in that role.
All four of these arms have talent and a potential future in a big-league rotation, but they also have questions that still need answering. Depending on those answers, they might all be bullpen arms: successful ones, mind you, but throwing future bullpen arms out there is not a way to build a competitive rotation. Keeping Lackey around, a veteran pitcher who you can reasonably predict going forward, helps lessen the pressure on the kids. It makes it easier to include any of the bunch in a trade for help elsewhere, and it keeps the Red Sox from feeling the pressure to promote Owens or Johnson or Barnes before they're ready next year, should an emergency arise or the bullpen suddenly become overpopulated with former prospects.
Plus, it's likely the Red Sox can bring Lackey in for well below market value if they want to have him stick around past 2015. Lackey has already hinted that he has to give pitching for just $500,000 -- a figure he's set to make thanks to an option triggered by his 2011 Tommy John surgery -- some serious thought. He'll be 36, the Red Sox will be coming off of a rough season, and he just might not want to be paid less than the kids he'd more than likely out pitch. It could all be a ploy to get a new deal for more guaranteed years and money on the table, but it's a ploy the Red Sox should fall for.
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The Red Sox could give Lackey any number of deals to make things right between both sides and keep them both happy going forward. They could tack two years on to his 2015 option for, let's say, $12.5 million each, giving Lackey a three-year, $25.5 million deal. It guarantees Lackey more money should something else go wrong health-wise -- without the kind of penalty for injury his previous deal featured -- but allows the Red Sox to hold on to a low average annual value for luxury tax purposes. They could also simply erase the $500,000 entirely and work out something like a three-year deal for $30 million, giving them a $10 million AAV. It would still pay Lackey well under market, but a $9.5 million raise in year one with another $20 million guaranteed for his age-37 and age-38 campaigns could be perfect.
WEEI's Alex Speier suggests a shorter tactic, with another year at Lackey's current $16.5 million price tag tacked on after the option. That would make for a two-year, $17 million deal, where Lackey knows he's got a bigger pay day waiting for him beyond 2015, and the Sox get to keep their payroll flexibility. Regardless of what the actual numbers end up being, this is a tactic the Sox should be taking.
It's likely it will be what they do, too. Putting Lackey out there makes sense because you never know which team desperate to make it to the playoffs is going to go all out on what is otherwise a pitching-thin market. There are few options available in the John Lackey mold, with the Mets' Bartolo Colon being one of the only others in that above-average, non-rental range. The Sox probably won't see a return that pushes them to move Lackey, though, because they don't have the same incentives to deal him that they do for Lester. Whether they are able to extend Lackey or not, it's probably for the best that he sticks around in the short term.