This will be an interesting storyline to follow throughout this offseason and during Spring Training. Right now, the Indians' goal is to get Danny Salazar healthy, while weighing whether it makes sense to tender him a contract through the arbitration process.
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Salazar avoided arbitration with a $5 million contract last season and -- considering he did not throw a pitch in the Majors in 2018 -- it stands to reason that his '19 salary would be in the same range. If the Indians think Salazar can contribute next season, then I would think that would be a worthwhile gamble, especially given the cost of pitching on the open market.
If Cleveland returns with its rotation intact, the cast is five strong between Corey Kluber, Carlos Carrasco, Trevor Bauer, Mike Clevinger and Shane Bieber. Adam Plutko is next in line at the moment. The depth behind that group is thin, making Salazar and fellow righty Cody Anderson potentially important alternatives. Anderson is coming back from Tommy John surgery (March 2017), but should be unrestricted come Spring Training.
During a season-end sit-down with reporters, manager Terry Francona noted that both Salazar and Anderson would head into the preseason with the plan of being built up as starting pitchers. Then, if there is a need in the bullpen, both right-handers could then be considered for that type of role. It is worth noting that Salazar has no Minor League options remaining, while Anderson has one.
Salazar underwent an arthroscopic debridement and bursectomy on his right shoulder on July 2 and, barring any further setbacks, could resume throwing by November. When he's been healthy, Salazar has boasted an elite fastball and split-change combination, making the righty one of baseball's best in terms of missing bats. If Cody Allen and Andrew Miller indeed leave via free agency, a healthy Salazar would be a very intriguing bullpen weapon.

Michael Brantley, Allen and Miller are the free agents that Cleveland will need to mull extending a one-year Qualifying Offer ($17.9 million for 2019) to this offseason. Given the season Brantley just turned in, I could see the Indians floating that one-year deal for the left fielder. The Indians rolled the dice on his $12 million club option last winter and Brantley posted 3.5 WAR (per Fangraphs). In terms of free-agent dollars, that showing was valued at $28 million, according to Fangraphs. The Indians have question marks at all three outfield spots, so trying to retain Brantley, who has been with Cleveland for parts of 10 seasons, makes a lot of sense.

Greg Allen can switch-hit, play all three outfield spots and offers speed, so I do think he fits the roster well as a fourth outfielder. As noted in the previous question, I also think it makes sense to try to retain Brantley. As for Leonys Martin, Cleveland needs to weigh whether going to arbitration with him makes sense, considering the serious health scare he had in the second half.
If Martin continues to recover well this winter, then keeping him in the fold via arbitration would seem like a logical decision. The extra year of control, after all, was a part of what made Martin an attractive acquisition for the Tribe. Bradley Zimmer (recovering from right shoulder surgery) might not be ready until mid-season and Tyler Naquin might be sliding to right field now that Lonnie Chisenhall is hitting free agency.
As for Andrew McCutchen, I like where your head's at, Tim. It's not a given that Cleveland will pick up Brandon Guyer's $3 million club option. If he is not retained, the Indians should target a right-handed complement for their outfield. McCutchen fits the mold, can offer depth at all three positions (while best utilized in the corners) and his 128 OPS+ against lefties indicates that he was 28 percent better than league average against left-handed pitching.

Given the subpar season he just had, Allen does not seem like a candidate for the one-year Qualifying Offer. It could also be risky to extend that offer to Miller, even though he seems like a safer bet to have teams overlook his health issues of '18 when considering a multi-year contract. Either way, it seems very unlikely either is back with Cleveland in 2019.

Disagree. Part of the reasoning behind acquiring Brad Hand and Adam Cimber was to guard against Allen and Miller leaving via free agency this offseason. It was not only with the 2018 postseason in mind. On top of that, Cleveland acquired Josh Donaldson for the stretch run and playoffs. That was the Tribe's "Machado," so to speak. Now, did Donaldson hit in October? No, he went 1-for-11, but the Tribe's lineup as a whole went ice cold against Houston's overpowering pitching. I liked how the Indians went about those trades. Alas, results do not always align with process.

First, let's run "VanBo" through the Terry Francona translator. That's the manager's nickname for hitting coach Ty Van Burkleo, who has held that role since Francona came to Cleveland in 2013. After the playoffs, Francona said Van Burkleo, along with the rest of the coaching staff, were in the plans for 2019, barring anyone leaving for jobs with another team.
Francona's reasoning for standing pat and standing by Van Burkleo was looking at the season's body of work -- not just three October losses. In the regular season, the Indians ranked third in the Majors with 818 runs scored, while ranking fourth overall in weighted on-base average (.330), fourth in OPS (.766), sixth in home runs (216) and tied for sixth in weighted runs created plus (105). Cleveland's strikeout rate as an offense (18.9 percent) was also the best in baseball in the regular season.

Well, as things currently stand, Jason Kipnis is set to earn $14.7 million in 2019 with Cleveland. If the Indians are unable to trade him this offseason -- the team nearly had a deal with the Mets last winter -- then the question will be how to handle Kipnis' place on the field. If Kipnis is in the plans for center, maybe the Indians won't tender a contract to Martin. If Brantley isn't in the plans, maybe Kipnis will slide over to left field.
Francona made a point in his season-end gathering to mention that the team needs to find a way to get a good look at Yandy Diaz in 2019. The easiest way to do that would be to hand him the keys to third base, meaning Jose Ramirez would stay put at second. That would seal Kipnis' fate as an outfielder, if he stays.