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Dave Dombrowski has inherited far worse jobs and teams than that of the 2015 Red Sox, but he still has work to do in order to turn things around in Boston. That's part of why he didn't wait until the offseason to join the organization: getting a head start now on what the Red Sox have around, both in the majors and the minors, will be key to what Dombrowski spends his winter doing.
There are holes to fill, positions to sort out, and minor leaguers to evaluate. Dombrowski needs to get a sense of just who should stick around, who should go, and where everyone in between fits in. Let's take a look at the state of the Red Sox to see just what it is Dombrowski has to put on his to-do list now that he's stepped in as essentially the replacement of both Larry Lucchino and Ben Cherington.
Hire a general manager
Cherington has resigned, as he was going to be able to stay on as general manager but not the same kind of general manager he just was. The final call on everything is Dombrowski's, so while Cherington's voice still would have had value and weight, it would have been a demotion of sorts for him all the same. So, one of the first orders of business for Dombrowski is going to be finding someone who can add to the front office with their ideas who also does not mind that not everything they suggest will or can be enacted without the approval of the man who hires them.
This is how you end up with Frank Wren as a leading contender, as he probably isn't a great fit as a GM with limitless power, but with someone like Dombrowski around to keep his worst ideas in the idea stage, he has his uses. Wren did a solid job of building up the Braves' farm system while he was there, and he has a long history of working alongside Dombrowski in Montreal and Florida, so his name popping up makes sense on multiple levels.
Jerry Dipoto might be another candidate, as he is currently working with the Red Sox on an interim basis, and like Wren, might be better at his job with someone around to keep some of his ideas in check. He's a promising GM candidate who can likely get a job elsewhere, but he has a history in scouting with the Red Sox, and a homecoming of sorts working under Dombrowski as the more stats-oriented half of the front office could be beneficial to all parties.
Whoever it is, Dombrowski needs to find someone who can help compensate for his own weaknesses, just like Dombrowski can compensate for those of the person he hires.
Find a first baseman
The Red Sox need to figure out what they are doing at first base in 2016, as it could influence what they do at first base in the long run. We looked at the unexpected -- and somewhat uneasy -- importance of prospect Sam Travis to the Red Sox and their future at first base, and just because the executive has changed does not mean the situation is any different. He's a good prospect, one who might surprise a lot of people and carve out a career at first base, but the Red Sox need to find a solution for 2016 when Travis isn't ready, and might not want to bet on him. That last part could be even more true now that Cherington, who drafted Travis, is out.
So, what's the plan? Focus in-house, handing the job to Travis Shaw for a year if his 2015 performance continues to suggest that maybe he's better than he was given for. Shifting Hanley Ramirez to first base from left field, a plan that, while risky in a different way, is no less potentially problematic than entrusting the position to Shaw? Switching Pablo Sandoval to first in the hopes Ramirez can transition to third and succeed there more easily than he would at first?
Or is the answer to Boston's first base question outside the organization? Perhaps Chris Davis could be signed as a free agent after the Sox sort out their current roster crunch -- more on that later. Maybe Dombrowski's penchant for spending big has the Red Sox calling on, say, the Reds and Joey Votto, who is expensive and signed roughly for eternity but is also -- and this part is the key -- Joey Votto. Maybe they go smaller, focusing on a rental like Adam Lind to give Travis -- be it Shaw or Sam -- another year to see what they can do before committing anything significant to them.
Sort out Pablo Sandoval and Hanley Ramirez
It's unlikely that both Pablo Sandoval and Hanley Ramirez are finished as productive big-league players. With that being said, the Red Sox don't necessarily need to find themselves stuck with both if it turns out that they're in worst-case scenario mode forever. Figuring out which one the Red Sox should keep around for the duration of their contract is now Dombrowski's task, and many other roster questions can't be answered until this one is.
Sandoval is younger -- he just turned 29 this month, whereas Ramirez will be 32 before this year is over. Ramirez is owed fewer years and dollars, with three guaranteed seasons and $66 million still coming to him, while Sandoval is at four years and $75 million. Sandoval has an option for $17 million as well, with a $5 million buyout (factored into that $75 million), and while he's owed more in total money, his average annual value is lower: $19 million to $22 million. Ramirez does have a vesting option for 2019 at $22 million, but he needs to amass 1,050 plate appearances between 2017 and 2018 for that to happen.
Ramirez has the higher ceiling at the plate, and if David Ortiz retires after 2016 or 2017, the Red Sox just might get a few great seasons from Ramirez as the designated hitter. The problem is that his glove is capable of canceling out his bat entirely, and unless he's hitting like Manny Ramirez, that's not acceptable. Sandoval is streaky, but his defensive issues this year are a surprise and not necessarily permanent. His ceiling as a hitter is lower, but he's possibly the more complete player, as well as being younger.
Sandoval would continue at third base, where the Red Sox don't have an answer otherwise -- that's part of why they signed him in the first place, as Will Middlebrooks didn't work out (again) and Garin Cecchini had failed to convincingly throw his name in the mix. If Ramirez is dealt, the Red Sox could maybe run with an outfield that included Mookie Betts, Rusney Castillo, and Jackie Bradley Jr. That assumes, of course, that Bradley continues to hit and prove he's a capable big-league bat. Even if Bradley does not show enough competence, the Red Sox will have other options for the outfield that they could sign, options that would probably be a better use of their resources than Ramirez. That's not necessarily the case at third.
So, not to tell Dombrowski what to do before he's unpacked, but you're probably going to want to clear this up sooner than later.
Fix the rotation
Wade Miley has been the average starter the Red Sox need in the middle of their rotation, and Clay Buchholz, when healthy, is still setting down hitters with ease. Eduardo Rodriguez has scuffled at times, but he's all of 22 and a rookie -- the promise there is promise that does not exist in any other starter in the upper levels. Rick Porcello isn't going anywhere, so Dombrowski needs to figure out a way to account for Buchholz's health concerns, Rodriguez's youth, Miley's averageness, and the Porcello problem with just one rotation spot.
Finding a way to deal Miley while pulling in an upgrade for the rotation could help with this, as it would open up a second spot that Dombrowski could play with. If he doesn't want to go all-in right away with adding pitchers, Henry Owens could also fill in while Miley is dealt to be replaced by someone superior, but if that occurs, the Red Sox absolutely have to get a dependable ace and not just settle for a strong number two like Scott Kazmir or John Lackey.
This might be where the prospects come into play -- maybe Owens isn't even around any longer to be part of the conversation, as Dombrowski attempts to pry a cost-controlled ace from a team that can afford to dangle one in order to fill other holes on the roster and the farm. There are multiple ways Dombrowski can go about this, and it seems impossible he'd just give it another go with all the same players involved.
Make Joe Kelly a reliever
Dave Dombrowski has a reputation as a guy who can't build a bullpen, but he also has a reputation as a guy who can properly scout big-league players. As Dombrowski lacks the attachment to Kelly that Cherington and his staff had, maybe we'll finally get around to Kelly as a reliever, and two problems will be solved at once. Well, partially solved: the Red Sox bullpen probably needs more help than just Kelly.
Don't trade Yoan Moncada
Dombrowski has a reputation for trading prospects, and it's something Ben Cherington could have stood to do more of. If there is one thing Dombrowski should absolutely follow Cherington's lead in, though, it's in not dealing Yoan Moncada. Don't take this as prospect hugging or claiming everyone good has to stay: Moncada should be the lone untouchable in the system. Manuel Margot, Rafael Devers, Javier Guerra, anyone else should go in the right deal if it's going to make the Red Sox better.
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Moncada, though, might not be all that far off from the majors -- he's dominated Low-A since adjusting to coming stateside, and he has the tools and promise to make his way up most of the rest of the ladder next summer. Unless the Sox get a deal that they would be absolute fools for passing up on that involves Moncada, it's best he just continues on his merry way to Boston.
Figure out the value of the rest
Dombrowski (and interim manager Torey Lovullo) have to spend the rest of the season figuring out what all of these secondary pieces are best suited for. Is Travis Shaw a future starter at an infield corner, a bench player, or a Quad-A player who has just had a hot few weeks and will be exploited soon enough? What is Christian Vazquez's role going to be on the 2016 Red Sox, or Ryan Hanigan's? Who from the bullpen besides Junichi Tazawa and Koji Uehara should continue to be in the bullpen next summer? Is Alejandro De Aza someone the Sox should deal in August to a contender, or a player they should try to keep around for insurance purposes next year? If everyone is healthy, what is Brock Holt's regular role?
Should Brian Johnson cut his teeth in the majors as a reliever? What about Matt Barnes (again)? Edwin Escobar? How will the Hanley Ramirez situation be handled now that Cherington is gone? Bradley and Castillo still need regular at-bats, but dealing Hanley away is no sure thing, either, so can anything different even be done now?
Dombrowski has a whole bunch of players to familiarize himself with in a short amount of time, but that's why he's on the job in mid-August instead of after the season has ended. Changes might not be immediate, and they could be more all-encompassing than the above, but they are coming.