Winter Meetings Preview: Will Bryce Harper, Manny Machado Find New Homes This Week?

The Winter Meetings are kicking off on Monday in Las Vegas. What should we expect? SI's MLB experts have their daring predictions as the annual craziness commences.
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Every Major League team's front office brass has descended on Las Vegas for baseball's annual winter meetings, where the rumors will swirl and maybe, just maybe, some major transactions will occur. SI's resident baseball experts have gathered to make some predictions on what to expect during the most anticipated few days of every offseason. Will Bryce Harper and Manny Machado have new employers by week's end? Are there surprise trades brewing? We've got predictions. Now it's just time to wait and see.

Who will be the final two teams in contention for Bryce Harper? Has your predicted final destination changed?

Tom Verducci: Phillies and Giants. Yes, my predicted reunion with the Nationals is not happening. Washington had no real intention of keeping him, not with their window dressing offer on the last day of the season – knowing he was about to earn free agency status – and then saying, “We’re out.” Phillies.

Ben Reiter: The Yankees and Dodgers. I don’t think the game’s richest franchises will be able to pass on the chance to bid on a 26-year-old generational talent whose (many) best years likely remain ahead of him. And I’m sticking with the prediction I made in the Reiter 50: he’ll end up in pinstripes.

Emma Baccellieri: The Phillies and Dodgers. I’m still sticking with my initial prediction of Philadelphia, but I did originally believe that Washington would be hanging in there until the end with its attempt to re-sign him. The Nationals seem to have accepted their fate and moved on, however, by stocking up elsewhere.

Stephanie Apstein: Phillies and Padres. I’ve thought Phillies the whole way; they seem like the best mix of window and money. 

STAFF: Our Original Bryce Harper Predictions

Jon Tayler: Phillies and Nationals. Philadelphia was my original pick for Harper, and I still believe that’s where he’ll end up laying his perfectly coiffed head. I also think that his original team will be right there to the end, because any good drama needs that kind of tension. But with Washington dropping $140 million on Patrick Corbin and comforted by the presence of Juan Soto and Victor Robles, I see the Phillies coming out on top. Their need is greater, and their willingness to spend is, per owner John Middleton, stupider.

Jack Dickey: I predicted he’d wind up a Phillie (for 8 years, $250m), and I’ll stick to that because I’m stubborn. But I may have underrated the chances he sticks in D.C. on some bells-and-whistles’d-up contract. The fact that the Nats spent on Patrick Corbin (and deferred plenty of the money) makes the team more likely to go for Harper, not less. With Max Scherzer turning 35 next summer, third baseman Anthony Rendon under his last year of team control, and owner Ted Lerner just having turned 93, they very well may want to win now, future liabilities be damned. Shouldn’t they dangle a front-loaded eight- or nine-year deal with a pair of opt-outs after years two and three to Harper? And shouldn’t he accept? If he could get, say, $75 or $80 million total from Washington for the next two seasons and then hit free agency at 28, wouldn’t that be just as good as whatever megadeal he’d get elsewhere?


Who will be the final two teams in contention for Manny Machado? Has your predicted final destination changed?

Tom Verducci: Phillies and Yankees. Sign him up with New York, his preferred spot.

Ben Reiter: The Phillies and the White Sox. I think the White Sox will remain in play longer than many think, to try to add the player who would form the centerpiece of their rebuilding project. But I still think Machado ends up in Philadelphia—at third base, however, given the “stupid”-spending (their owner’s term) Phillies’ acquisition of shortstop Jean Segura.

Emma Baccellieri: The Yankees and Phillies. While I haven’t changed my thinking here, I’ve been a little surprised at how markedly different his approach has been from Harper, who’s been posting regularly on social media about what he’s up to and who he’s been seeing, along with steady media commentary from his agent, Scott Boras. Meanwhile, Machado’s been almost entirely silent, apart from one interview, in which he apologized for his postseason “hustle” comments. (Though, of course, it’s hard to say how much of that is actually a difference between Boras and Machado’s agent, Dan Lozano.)

Stephanie Apstein: Phillies and Yankees. The Phillies are ready to spend, and the Yankees are down a shortstop. 

Jon Tayler: Yankees and Phillies. I expect the Phillies to be in on everyone to the bitter end, and even with Jean Segura now manning shortstop, Machado still makes plenty of sense for them. But the way the Yankees have both kept their powder dry and missed out on Corbin makes me think that Machado will end up being their ultimate play. That was my prediction from the start, and with no big outlay for Corbin in the way, I think it’s still the way this ends: Johnny Hustle in the South Bronx.

STAFF: Our Original Manny Machado Predictions

Jack Dickey: I’d be stunned if the Phillies didn’t wind up with one of either Harper or Machado, but I’d also be stunned if they wound up with both. If Harper re-signs in D.C. or picks a dark-horse destination, Machado becomes a very good bet to come to Philly, even with Jean Segura having recently arrived from Seattle. If the Phillies get Harper, though, where does that leave Machado? To my eye, the star shortstop’s free-agent rollout hasn’t quite positioned him as the sort of player who could singlehandedly resurrect a franchise but rather as an elite hitter at a premium defensive position who could put a contender over the top; which teams feel he is worth splurging on, we’ll find out soon enough. I don’t think he’ll get an Eric-Hosmer-to-the-rebuilding-Padres-type deal, but then again he may not want one. If the Phillies pass, keep an eye on the Yankees or Dodgers. Neither team really needs another righty power bat (the Yankees especially), but Machado is special enough to nudge a team away from prudence.


Where will Craig Kimbrel sign?

Tom Verducci: He’s going back to Atlanta, but there is no six-year deal awaiting him anywhere.

Ben Reiter: Atlanta. He won’t get his preferred six years anywhere—not after a season in which his walk-rate spiked, including on the biggest of stages—but with the Red Sox seemingly out of contention, I believe he’s in for a homecoming with the Braves.

Emma Baccellieri: The Cardinals. They showed that they’re going for it by trading for Paul Goldschmidt; they’re reportedly interested in spending in free agency; and their bullpen certainly qualifies as an area in need.

Stephanie Apstein: The Braves. That division is getting tighter, and they know him well. 

Jon Tayler: Boston made re-signing Nate Eovaldi a priority over bringing back Kimbrel, and while there’s room for both, it feels like the Red Sox think they can live with or without their All-Star closer. Between that avenue possibly closing and Kimbrel’s reported desire for a six-year contract, I think he might linger on the market a while—certainly past the Winter Meetings. But if he does walk out of Las Vegas, unlike so many others, a richer man, my bet is that it’ll be the Phillies who pay him. Philadelphia was in on Edwin Diaz before the Mets got him, and the team desperately needs a true relief ace. Plus, the Phillies have the money and the payroll space to accommodate Kimbrel’s wants.

Jack Dickey: It looks like Nathan Eovaldi got the one “thank you for your valiant championship-season service” contract Boston will hand out; besides, once October rolled around, Kimbrel did more to harm the Sox’ title chances than to help them. So he’ll likely head elsewhere. The rumor that he’s seeking a six-year deal likely limits his suitors, especially since he turns 31 next season and recently wrapped what was by his standards a pedestrian year. I imagine he’ll sign for four or five in Atlanta or Philadelphia. Both teams need closers and are ready to spend.


Where will Dallas Keuchel sign?

Tom Verducci: Rockies. They've got two good starters (German Márquez, Kyle Freeland) and Keuchel will bolster that. 

Ben Reiter: Atlanta. They’re going for it, and Keuchel would immediately step in as the smart and steady bellcow of a young and talented staff.

Emma Baccellieri: The Astros re-sign him, I’ll say. With Charlie Morton likely to depart in free agency and Lance McCullers, Jr. out for the year with Tommy John, there’s more than enough room to bring him back on.

Stephanie Apstein: The Angels. He could stay in-division, and because he’s more of a finesse pitcher than a fireballer, he has a chance to be a lower-risk play for a team that has struggled to keep pitchers healthy. 

Jon Tayler: In terms of name value, Keuchel is the best starter left on the market, though I have a hard time seeing any of the contenders shelling out the millions it would cost for a veteran pitcher with declining stats and velocity. He makes more sense as an innings-eater with upside for a middle-tier team, and while there aren’t many of those left, the Angels fit the bill perfectly for him. Los Angeles always needs rotation help, and if nothing else, Keuchel can gobble up outs with the best of them.

Jack Dickey: Keuchel’s case is an unusual one. On the one hand, he feels undervalued by the market. You know what you’re getting with Keuchel: a wizard of weak contact who won’t strike many hitters out, but doesn’t need to. He threw 204.2 innings of 3.74 ERA ball for Houston in 2018—teammates Justin Verlander and Gerrit Cole got all the attention—and he’s not far removed from his 2015 Cy Young. On the other hand, on most contenders (which is to say, on the teams that will be players in free agency), he’d slot in as a #2 or #3 starter, and there’s only so much teams are inclined to spend on a non-ace. If he can be had for less than $100 million, he’d fit well with almost any team, but even at a higher price he’d be an especially meaningful upgrade for the Brewers or Braves. I’ll bet on Milwaukee.


Who will be the biggest free-agent bust?

Tom Verducci: Yasmani Grandal. Be cautious about a guy who loses his job in the postseason.

Ben Reiter: Patrick Corbin. The six years and $140 million that Washington just committed to a pitcher who had a 4.53 ERA between 2016 and `17—before a sparkling and exquisitely well-timed walk year—is … a lot.

Emma Baccellieri: A.J. Pollock. He’s not too far removed from his breakout performance in 2015, and he’s coming off his best season since then. But given his health history and his age, it’s easy to see a deal crumbling.

Stephanie Apstein: I don’t think Kimbrel will be a bust, but I can’t imagine a justification for the six-year deal he’s reportedly seeking. If he gets it, that will be a pretty clear overpay in my mind.

TAYLER: Goldschmidt Trade Reinforces All-or-Nothing Culture

Jon Tayler: Free agency came too late for A.J. Pollock, who entered it coming off two straight mediocre years offensively after missing nearly all of 2016 with an injury. When healthy, he’s been a star, but it looks increasingly like even when he’s capable of being on the field, the 2015 All-Star production may be a thing of the past. Someone will sign him hoping to capture that performance, and it’ll cost a fair amount, but they may end up sorely disappointed.

Jack Dickey: He’s already signed: Patrick Corbin. Everything about him feels walk-year-fluke-y to me—his 2018 success followed an ordinary 2017 and a wretched 2016. That he improved so dramatically because he became more of a junkballer might be a nice lesson for pitching coaches, but it’s not something that inspires much confidence about his future. Hitters can adjust to tweaked approaches. The nice thing for him about landing in D.C. is that he’ll spend at least the first three years of his deal sharing a rotation with Max Scherzer (with year one alongside Scherzer *and* Stephen Strasburg), meaning the expectations won’t be as high as they would have been had he signed with the Yankees. Still, $140 million is a fortune for a pitcher with so few bright spots on his résumé, and it won’t take long for the Nationals to wish they had spent their money on Keuchel instead.


Who will be the biggest free-agent bargain?

Tom Verducci: Wade Miley. He proved in the 2018 regular season and postseason that he's reliable rotation help.

Ben Reiter: Nelson Cruz. Over the past five years he’s slugged 15 more home runs than anyone else, 203.  Based on his WAR, he’s been worth an average of $31.14 million in each of those seasons.  Thanks to the fact that he’s limited to DH in an era in which clubs crave versatility, and to his age (38), he’ll be lucky to be paid a third of that in average annual value.  He’ll be a bargain no matter where he lands.

Emma Baccellieri: Wilson Ramos. Yasmani Grandal and J.T. Realmuto are grabbing all the attention for catchers, and Ramos’ injury record will reasonably be a strike against him—but he’s become one of the best offensive backstops in baseball, with decent defense, too.

Stephanie Apstein: At $17 million a year, Nathan Eovaldi isn’t a bargain, but if he stays healthy, that could be a real get for the Red Sox. 

Jon Tayler: Andrew McCutchen isn’t an MVP-caliber player any more, but the veteran proved he’s still got plenty left in his stick in a fine 2018 split between the Giants and Yankees. He’s a good choice for any team that needs a solid corner outfielder and is unlikely to cost too much in that capacity.

Jack Dickey: Manny Machado. Perhaps I’m underthinking this, but the number of shortstops and third basemen (assuming those are the positions to which he is limited) who can provide Machado-level value is astoundingly small. He’s right there with Francisco Lindor, Kris Bryant, and Nolan Arenado; he’s delivered six-fWAR seasons three of the past four years; he’s just 26 years old. He would make any team a ton better, and in a game with no luxury tax and no tanking, teams would be tripping over one another to guarantee Machado $400+ million. The way the market is going now, though, he may not crack $300 million. No tears should be shed for Machado; instead they should be shed for the poor Mets fans who have watched their Machado-needy team cheap out instead on a 36-year-old Robinson Cano and get away with it.


What team will be the most active?

Tom Verducci: ThePhillies. J.A. Happ, Manny Machado, Dallas Keuchel and more are all in play for them.

Ben Reiter: I have them signing Craig Kimbrel and Dallas Keuchel—in addition to their excellent signing of Josh Donaldson—so, the Braves.

Emma Baccellieri: The Mets. New GM Brodie van Wagenen has made it clear that he plans to remake the roster, and it seems likely that he goes after a catcher and an outfielder, at the least–and, uh, maybe still trades Noah Syndergaard?

Stephanie Apstein: The Mariners, of course. Jerry Dipoto makes a transaction nearly every time he draws breath. 

TAYLER: The Mariners Are the Latest Team to Choose Tanking, Not Competing

Jon Tayler: I’m really hoping we get an Ocean’s 11 remake this week with Jerry Dipoto as Danny Ocean—except instead of robbing a casino, he sneaks around and leaves his few remaining good players in the hotel rooms of contending teams. But there’s just not that much left for Seattle to do after it dumped so much of its roster over the last week. So let’s go with the Phillies, about whom you’re going to see so many cringeworthy “making bets/spending wild in Vegas” jokes.

Jack Dickey: The Phillies have already made a big move, trading for Segura, but I expect more where that came from. There’s a reason owner John Middleton promised profligacy: They have needs, they have cash, and they have been wandering in the desert for far too long.


What team should be the most aggressive?

Tom Verducci: TheGiants. They're the worst positioned team in NL West: they have an aging roster with long-term deals and thin farm system that needs to get younger and more athletic. This is also a team in serious need of outfield help. New team president Farhan Zaidi has a huge task ahead of him.

Ben Reiter: The Yankees. They have the young nucleus of a dynasty, and enough money to be stupid about spending it. They should be—a little stupid, anyway.

Emma Baccellieri: This one’s not particularly likely to actually happen, but Minnesota has a great reason to be aggressive. Cleveland seems to be operating under the reasonable assumption that it doesn’t have to do very much (or, really, anything) to win the division again. The Twins were the closest challenger last year, though, and they have enough young talent that it’s not hard to squint and see just a few necessary upgrades for them to put themselves in the conversation.

Stephanie Apstein: I think all the NL East teams other than the Marlins should be going for it this year. Especially if Harper leaves Washington, as predicted, anyone has a shot at that division. 

BACCELLIERI: The Phillies Should Get Spending ... and Soon

Jon Tayler: With the Mariners bowing out of contention for at least the next three or four years, there’s plenty of room for the Rays, Twins and Angels to take a step forward and significantly increase their playoff chances. I don’t expect anyone in that trio to do it, but all should be sniffing out trades and cozying up to free agents to take advantage of MLB’s continued plague of tankers not trying.

Jack Dickey: My pick is a team that has already been fairly active: the Cardinals. By landing Paul Goldschmidt for a trio of young players, St. Louis got one of the top hitters in baseball without subtracting anything from their 2019 core. It was a coup! The problem is that the Cardinals’ roster still doesn’t look quite right. The presumed Dexter Fowler/Jose Martinez right-field platoon is asking for trouble, plus there are holes where an ace and a closer should be. A little more roster-shuffling here would go a long way.


Who will be the highest-profile player to be traded?

Tom Verducci: Trevor Bauer. The Indians will be listening on Bauer and Corey Kluber, but it'll be Bauer who moves.

Ben Reiter: With Paul Goldschmidt already gone, I’m guessing it’ll be Trevor Bauer, who I’m considering somewhat higher-profile than the certain-to-move J.T. Realmuto.  Could he be the missing piece to the Yankees’ rotation?

Emma Baccellieri: Corey Kluber. Signing Carlos Carrasco to a lengthy and team-friendly extension seemed to telegraph Cleveland’s thinking here. Given the state of the AL Central, the team likely won’t have to try very hard to capture the division again, and it’s apparently taken that as a reason to strip back, rather than ramp up. By every indication, that would include moving its ace.

Stephanie Apstein: Felix Hernandez. The Mariners’ tear down is in full effect. 

Jon Tayler: With Carlos Carrasco now signed to an extension, it seems a lock that Cleveland will dump one of Corey Kluber or Trevor Bauer this winter—and probably sooner rather than later, as either is a better option than any free-agent starter still left. Kluber is the sexier name, though Bauer would be a strong addition for any contender as well. If nothing else, a trade of the latter would make for a fun couple of hours on Twitter as he reacts to his own deal.

Jack Dickey: Arizona spoiled some of the potential Vegas intrigue by dealing Goldschmidt—not anyone’s idea of a high-profile player, but a great one nonetheless—to St. Louis on Wednesday. So down the list we go. It’s hard to know exactly what the Indians are thinking in dangling Corey Kluber and Trevor Bauer; Cleveland had an easy path to the AL Central crown last year and, with a few bullpen upgrades, would project as the favorite in 2019. (Although the playoffs have delivered Cleveland a healthy share of heartbreak these last three seasons, it’s important to recall that short series are essentially a crapshoot.) Then again, maybe Cleveland is sweating its long-term future, and either pitcher would likely fetch strong prospects in return. Put me down for a Bauer trade. Where? The Yankees looked like a fit earlier in the offseason, though after trading for James Paxton they may no longer be one. Maybe the Brewers would see him as an ace, though they’re presently short on prospects. The Padres have the farm-system depth to pull off any trade, and they hope to contend in 2020 if not 2019, although Bauer’s stated intention to never sign an extension might scare them off.


A Bold Prediction

Tom Verducci: The Rays actually sign a big free agent: Nelson Cruz.

Ben Reiter: Even though execs have told me for months that Manny Machado is the better player, Bryce Harper will emerge with the bigger contract—by quite a bit (at least 10%).  Even in an analytics-driven age, Machado’s antics last season will end up costing him—rightly or wrongly—as fewer G.M.s will want to stake their careers and reputations on a player with such publicly recognized risks. It’s still humans who are making these decisions, after all.

Emma Baccellieri: Seattle Mariners GM Jerry Dipoto, having exhausted potential trades from the team’s core talent in its multi-layered rebuild, embarks on an unprecedented attempt to trade office supplies and ballpark equipment.

Stephanie Apstein: The White Sox will decide to pry their window open a year early and sign one of the mega free agents. 

Jon Tayler: Neither Harper nor Machado signs this week, and aside from a couple of trades, Winter Meetings sees little action with regards to available players. Save these predictions, because they’re going to have as much currency in mid-January as they are this week.

Jack Dickey: Miami will not trade J.T. Realmuto, since no organization will cough up its top 16 prospects and $150 million in exchange for the All-Star catcher. Derek Jeter will defend the team’s offseason intransigence, noting that the Marlins have upgraded their uniforms. In 2019, they will win 57 games but look cooler than ever while doing it.