So, if you're making the decisions on 4 Yawkey Way, who are you willing to give up for a top-of-the-rotation starting pitcher? You have the cash to comfortably buy one -- Jon Lester, say, or Max Scherzer or James Shields. You have committed $105 million in salaries next season, but a lot of that money will come off the books in 2016, and you have only three arbitration-eligible players, which will help to tamp down costs, and you might be able to move some money in a trade or trades (Shane Victorino, Allen Craig).
But other teams are prepared to go dollar-to-dollar against you for the premium free agents, and you're looking not just for one top-of-the-rotation starter, but two. That means you'll probably be looking to trade for at least one pitcher, too, which means you'll have to dip into what appears to be the deepest talent pool of young prospects the Sox have had in some time.
Which begs the question again: To acquire a Cole Hamels or a Johnny Cueto or a Jeff Samardzija, who would you be willing to deal? Especially since the Phillies, Reds and Athletics, respectively, may decide they're better off holding on to what they have, unless they can extract a knock-your-socks-off return.
There is also this: Yes, Miami Marlins president David Samson declared this week that Giancarlo Stanton will be with the Marlins next season regardless of whether they can sign him to a long-term extension this winter, which Samson claims they will try to do. But what if the Marlins make the slugger available at the trading deadline next July, or next winter, when he will be a year away from free agency? How many assets do you need to save for that possibility?
It's pretty easy to figure out the Sox prospects who will top the list of Boston's prospective trading partners this winter: switch-hitting catcher Blake Swihart, ranked by SoxProspects.com as the team's No. 1 prospect; Mookie Betts, who shot up through the Sox system, added outfield to his résumé, and impressed one and all as a potential star in the making; one of three left-handers -- Henry Owens, Brian Johnson and Eduardo Rodriguez, all with a big-league ETA of 2016 at the latest; and shortstop Deven Marrero, an elite defender. Some team will probably aim even higher and ask for shortstop Xander Bogaerts.
The folks at SoxProspects.com would also advise you to consider two kids in the lower minors who rate very highly and undoubtedly have caught the attention of other scouts, as well: outfielder Manuel Margot and third baseman Rafael Devers. And the club has a boatload of other pitching prospects, all of whom have already logged big league time: Allen Webster, Anthony Ranaudo, Rubby De La Rosa, Brandon Workman and Matt Barnes. Take a look at some of the elite pitchers traded in the last five years -- Cliff Lee, Roy Halladay, David Price and James Shields, as well as the tandem the Cubs sent to Oakland this year at the July trading deadline, Samardzija and Jason Hammel -- and it's pretty clear the Sox must be prepared to part with at least three prospects, and possibly four.
Lee has been traded three times, and two of those deals were for four prospects, the other for three. The Indians traded him to the Phillies for two top pitching prospects, Carlos Carrasco and Jason Knapp, infielder Jason Donald and catcher Lou Marson. The Mariners gave up one former first-rounder (pitcher Phillippe Aumont) and two other players to get Lee from the Phillies, and then traded him to Texas for four players, including two former first-rounders -- Justin Smoak and Blake Beaven.
Samardzija and Hammel, acquired together from the Cubs, cost the Athletics their top overall prospect, shortstop Addison Russell, former No. 1 draft pick and top outfield prospect Billy McKinney, big league pitcher Dan Straily and a player to be named later. Price went to the Tigers from the Rays in a three-way deal that netted Tampa Bay a big leaguer starter in Drew Smyly and a former No. 1 draft pick in Nick Franklin.
Halladay, traded by the Jays to the Phillies in 2009, came at the price of two former No. 1 picks, pitcher Kyle Drabek and catcher Travis D'Arnaud, and a highly regarded minor league outfielder, Michael Taylor, who was flipped to Oakland for third baseman Brett Wallace. Tampa Bay dealt Shields and now-reliever Wade Davis to the Royals for outfielder Wil Myers, then regarded as one of the top five prospects in baseball, a top pitching prospect in Jake Odorizzi, and two other minor leaguers.
What is startling is how few of those prospects have panned out. To date, only Myers and Odorizzi have made a meaningful impact on the big league level, Odorizzi claiming a spot (31 starts) in the Rays' rotation, though Myers regressed considerably from his impressive rookie debut. The rest of the landscape is littered with busts, although Theo Epstein and Jed Hoyer of the Cubs hope Russell and McKinney reverse that trend.
But none of those deals extracted the kind of haul Cleveland's Mark Shapiro received in 2002 when he traded Bartolo Colon to the Montreal Expos for Cliff Lee, Brandon Phillips, Grady Sizemore and Lee Stevens as part of Montreal's going-out-of-business sale. Or what the Mariners got in 1998 when they traded Randy Johnson to Houston for Carlos Guillen, Freddy Garcia and John Halama.
So, is Hamels worth Swihart, the player the Phillies almost certainly would demand as the centerpiece of any deal? Swihart has been compared favorably to Buster Posey, the Giants' All-Star catcher. Is Cueto worth Betts, whose bright future is offset by the fact that the Sox have other outfielders for the immediate future and have Margot potentially on the horizon? The Phillies almost certainly want one of Boston's three lefty prospects to take Hamels' place, too. If Samardzija is the target, do you shoot for a bigger deal and see if Oakland would also move third baseman Josh Donaldson, which would cost you even more of the kids?
We've given you a list of players who could be traded by the Sox. For an elite pitcher, the Sox almost certainly would have to include such players as outfielder Jackie Bradley Jr., third basemen Will Middlebrooks and Garin Cecchini; shortstop Marrero; or one or two of the younger pitchers.
You're Ben Cherington. Are there any untouchables on your list? Who would you be willing to move? Take a look at our list of names, and vote accordingly. In our comments section, propose to us your best deal. Check out SoxProspects.com's Top 10 list. Tell us why your deal would work. We'll print the best responses.