Updating the Hottest MLB Offseason Questions, Post-Winter Meetings

Rick Weiner@RickWeinerNYFeatured ColumnistDecember 12, 2014

Updating the Hottest MLB Offseason Questions, Post-Winter Meetings

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    USA TODAY Sports

    Well, that was fun.

    One of the most frenzied and hectic winter meetings in memory is in the books and in the process, we got answers to some of the hottest questions in baseball.

    Jon Lester decided against a reunion with the Boston Red Sox, signing instead with the Chicago Cubs, while the Los Angeles Dodgers found a taker for Matt Kemp and his burdensome contract. But with those answers come even more questions.

    Are the Cubs, Dodgers and Red Sox done dealing? Probably not. What's going to happen to the other two members of the "Big Three"? Have teams emerged from San Diego as clear favorites to win big in 2015?

    Let's take a look at the hottest questions yet to be answered as baseball gets back to doing business over the phone instead of in person.

Will the Phillies Continue to Sell off Pieces?

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    Denis Poroy/Getty Images

    While the deal is not yet official, Philadelphia took a big step in the right direction with its decision to trade longtime shortstop Jimmy Rollins to the Los Angeles Dodgers for a pair of young pitchers, per CSN Philadelphia's Jim Salisbury.

    But it's only the first step.

    Look, nobody expects general manager Ruben Amaro Jr. to actually find a sucker taker for Ryan Howard and the $60 million (at least) that remains on his deal, despite his statement on MLB Network that Howard "had a productive season in some ways."

    The same goes for the team's toxic closer, Jonathan Papelbon, who it appears has burned every possible bridge that leads out of Philly.

    But Cole Hamels remains a valuable trade chip despite the flurry of movement that we've seen on the pitching market over the past few days.

    The Phillies have lost some of their leverage in trade talks, given that Boston, Chicago and Los Angeles have gone elsewhere to bolster their rotations—a point that wasn't lost on David Murphy of the Philadelphia Daily News—but by the time Philadelphia is ready to contend again, Hamels won't be the pitcher he is today.

    Holding out for the massive return the Phillies have been waiting more than a year to receive does nothing to help them in the short term or the long term.

    The same goes for Chase Utley, who despite his no-trade clause and desire to remain in Philadelphia, was the subject of trade talks between the Phillies and Dodgers as well, according to Yahoo Sports' Tim Brown.

    Are the Phillies prepared to swallow their pride and take the next step? Or will they rest on their laurels and try to sell a frustrated fanbase on the premise that moving Rollins—and playing nothing but mediocre baseball—is good enough?

When Will Max Scherzer Find a New Home?

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    While much was made of the "Big Three" heading into the winter meetings, the reality is that Jon Lester and Max Scherzer were a level above the third member of the group, James Shields.

    Lester got his payday, signing a six-year, $155 million deal with the Chicago Cubs. Scherzer did not, and he remains available to any team that wants him.

    Scherzer and his agent, Scott Boras, believe he's worth $200 million, according to Fox Sports' Jon Paul Morosi, a figure reached by only one other pitcher, Clayton Kershaw. For as good as Scherzer is, he's not Kershaw.

    Whether it's because of the asking price, Boras' reputation or a combination of the two, there hasn't been a team definitively linked to the 2013 AL Cy Young Award winner, who—among starters with at least 60 starts over the past two seasons—has done a better job of missing bats than anyone.

    Still, Boras made it clear to a throng of media at the winter meetings, including MLive's Chris Iott, that neither he nor his client is in a rush:

    Max has given me kind of a laundry list of what his needs are, what his wants are. As to timeframe of these things, you can't tell, because these negotiations are largely owner decisions, owner-driven. I think every general manager in baseball wants Max Scherzer on their team.

    There's no doubt about that. It's not something you have to trade for. It's just really something that the owner has to decide what the economics are.

    San Francisco, which at one point seemed to be in the lead to sign Lester, has no intention of engaging Scherzer, sources tell Bay Area News Group's John Shea. Likewise, his former team, the Detroit Tigers, aren't trying to bring him back, team sources told Peter Gammons.

    New York seems like a logical landing spot, but the Yankees have shown no interest in getting involved with the highest-priced talent available this winter, something that we've not seen from the Bronx Bombers in the past. Boston, according to ESPN Boston's Gordon Edes, is taking a wait-and-see approach.

    If the big-market clubs aren't interested, will Boras and Scherzer stay the course and hold out for the megadeal they seek until sometime in January (or later), hoping something changes? 

    Will they rethink their strategy and take the best offer they can find, regardless of whether it's anywhere close to the $200 million that they had hoped for?

    Or could we see Scherzer go the Nelson Cruz route, signing a one-year deal to try his luck in what is expected to be a deep free-agent class of starters once again after the 2015 season?

Where Is James Shields Headed?

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    Matt Slocum/Associated Press

    While Scherzer is struggling to drum up serious interest, Shields is a different story.

    Both Gammons and Alex Pavlovic of the San Jose Mercury News say that the Giants want to add the 32-year-old alongside Madison Bumgarner at the top of their rotation.

    ESPN Los Angeles' Mark Saxon reported that buzz was building that the Dodgers might make a run at Shields—and while that was before the club signed Brandon McCarthy to a four-year, $48 million deal, would it shock anyone to see the Dodgers do just that?

    Edes says that the Red Sox met with Shields' agent, but there's no indication that the two sides exchanged numbers or that any substantive talks occurred.

    The Texas Rangers met with Shields in San Diego, but as GM Jon Daniels told MLB.com's T.R. Sullivan, his club won't be the one that signs him:

    I don't think it will come about. We wanted to be prepared if anything changes drastically. We enjoyed it, we like the guy a lot. In other circumstances we would like to have him. It was a function of him living out here so we took advantage of it.

    Clearly, teams believe that Shields will be far easier—and more affordable—to sign than Scherzer.

    Where he winds up, and whether he's the next big name to fall, are questions that still need to be answered. 

What Are the Royals Waiting For?

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    Charlie Riedel/Associated Press

    Speaking of Shields, one of the biggest questions heading into the offseason was how the defending AL champs, the Kansas City Royals, were going to replace the veteran atop the rotation.

    They lost out on a reunion with Ervin Santana, who signed with division rival Minnesota, and both Ross Detwiler and Justin Masterson, who they had checked in with, wound up elsewhere.

    To find that starter—or the power-hitting right fielder that they covet—the club is reportedly willing to trade one of its own "Big Three," the shutdown bullpen trio of Wade Davis, Kelvin Herrera or Greg Holland, sources tell ESPN's Jayson Stark.

    Considering how vitally important the team's ability to shorten games was to its success a year ago, moving any of the three seems like a terrible idea, despite their rising costs.

    Offensively, the club is gambling that Kendrys Morales can bounce back from an atrocious year split between Minnesota and Seattle and hoping that it'll come to an agreement with former Royal Melky Cabrera to play right field, per CBS Sports' Jon Heyman.

    Neither one is close to being what you'd call a sure thing, and the team's options if Cabrera doesn't sign—Nori Aoki, Colby Rasmus and Alex Rios—all come with significant holes in their game.

    While the rest of the division has gotten better in one way or another, the Royals have done nothing to build upon their remarkable run to the World Series. Which begs the question: What are they doing?

Are the Yankees Punting on 2015?

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    If nothing else, New York Yankees general manager Brian Cashman has a sense of humor.

    When informed that Scott Boras told reporters that the Yankees needed to sign his client, Max Scherzer, to have a "World Series-quality rotation," Cashman replied "Good, that means he likes the four we've got!" according to The Wall Street Journal's Daniel Barbarisi.

    Except Cashman and the Yankees won't be laughing if Masahiro Tanaka feels another twinge in his elbow, sidelining the Japanese phenom for any length of time. The rest of the team's rotation—CC Sabathia, Michael Pineda and Ivan Nova—isn't exactly what you'd call the picture of health or reliability.

    The additions of shortstop Didi Gregorius and reliever Andrew Miller were fine moves, but neither one is going to help solidify what, potentially, could be one of baseball's least-effective starting staffs.

    That the Yankees have avoided the likes of Scherzer, Jon Lester and James Shields is telling—or at least it should be. As Bleacher Report's Jason Catania noted earlier this month, the Yankees may be looking past the upcoming regular season:

    The biggest reason Cashman may be laying low this winter, however, is the quality and quantity of should-be readily available arms on the open market next year.

    If you think 2014's crop of free-agent pitchers is a good one, well, 2015's could be better. Much better.

    Here's a rundown of some of the more interesting hurlers in line to reach free agency after the season: David Price, Jordan Zimmermann, Johnny Cueto, Jeff Samardzija, Doug Fister, Hisashi Iwakuma, Mat Latos, Ian Kennedy, Rick Porcello, Scott Kazmir and Yovani Gallardo.

    Would you rather have Scherzer atop the rotation for roughly $200 million or two of those starters for slightly more? If we're being honest, the answer is the latter—and it's not really a tough decision.

    The Steinbrenner family has never told Cashman that he can't spend their money, and if he went to ownership asking for their blessing for him to sign Scherzer, they'd give it to him.

    But maybe, just maybe, the Yankees realize that, like Miller and Gregorius, adding Scherzer isn't going to be enough to make them one of the favorites to win it all in 2015.

    Could the Yankees be willing to sacrifice one more season without a playoff appearance to find more sustained success moving forward?

    It may not be as insane a premise as it seems.

Does the Road to the World Series Run Through Chicago?

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    Brian Kersey/Getty Images

    Besides the Dodgers, are there two teams that did more to improve themselves during the winter meetings than the Chicago Cubs and Chicago White Sox?

    The Cubs walked away with the player many considered to be the top talent available (Jon Lester), Jason Hammel, who enjoyed the best stretch of his career over the first half of the 2014 season in Chicago, and a two-time All-Star behind the plate in Miguel Montero.

    The White Sox landed former Cubs ace Jeff Samardzija, who slots in perfectly as a No. 2 behind Chris Sale and ahead of Jose Quintana in their rotation, the top closer on the market in David Robertson and a quality left-handed reliever in Dan Jennings.

    The buzz surrounding both teams is palpable.

    But both still have major questions about the back end of their respective rotations and holes to fill in their lineups. The Cubs are relying heavily on the continued development of youngsters Javier Baez, Jorge Soler and, before too long, Kris Bryant to help Montero and Anthony Rizzo power the offense.

    Across town, the White Sox are desperately trying to unload Dayan Viciedo, who Ryan Divish of The Seattle Times says is likely to be designated for assignment and ultimately put on waivers if they are unable to find a trade partner. Besides left field, the club has questions at second base, third base and behind the plate.

    There's no question that both teams will see marked improvement in their on-field performance in 2015 thanks to these additions.

    But have they done enough to vault from pretenders to contenders, much less the favorites in each league?


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