Each MLB Team's Biggest Dilemma of the Upcoming Offseason
The hot-stove season will be here in no time, and with it will come tough decisions for every team in Major League Baseball.
What say we get ahead on breaking them down?
We're going to look at the biggest dilemma that each of MLB's 30 teams will be facing this winter. These run the gamut from how they should spend their money to which players require special attention to larger conceptual decisions about the future.
We'll go in alphabetical order by city.
Arizona Diamondbacks: To Re-Sign Free Agents, or to Extend Paul Goldschmidt?
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The Arizona Diamondbacks are just months away from watching Patrick Corbin, A.J. Pollock, Eduardo Escobar and other important pieces enter the free-agent market.
Meanwhile, they're also just a little over a year from watching Paul Goldschmidt do the same.
No thanks to Zack Greinke's massive contract and Yasmany Tomas' dead money, the D-backs probably can't hope to re-sign their biggest free agents and extend Goldschmidt this winter. They'll have to pick their battles.
The picture is further complicated by their contention window. If they look to spend big in free agency, they'll effectively be going all-in on a World Series run in 2019, the final year of Goldschmidt's contract. If they extend Goldschmidt, they'll be banking on him continuing to be a franchise centerpiece into his mid-30s.
Either way, the Diamondbacks can't avoid big risks this winter.
Atlanta Braves: Which Positions Should Get Pricey Upgrades?
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The Atlanta Braves have already re-established themselves as a force in the National League East. Their next step will be cementing their place through a busy offseason.
Since the Braves have only $51.2 million in guaranteed money for 2019, this will almost certainly involve a free-agent spending spree. And yet, they'll need to differentiate between where they could spend and where they should.
Do they sign a third baseman, or do they just pencil in top prospect Austin Riley? Do they spend on a veteran starting pitcher, or do they commit to filling out their rotation with their top pitching prospects? Do they spend on their bullpen, or do they keep spots open for whatever youngsters aren't up to the task of starting?
This is a good "problem" to have, but the Braves will still need to take their decisions seriously. Should they fumble their choices, some of their 2018 progress could be undone in 2019.
Baltimore Orioles: Where Does Their Rebuild Go from Here?
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More so than with other rebuilding teams, "now what?" is a good question for the Baltimore Orioles.
Although July trades of Manny Machado, Zach Britton, Brad Brach, Kevin Gausman and Jonathan Schoop outfitted the organization with prospect depth and international bonus pool money, Baltimore's farm system only improved to No. 20 in Bleacher Report's rankings. Trades of Dylan Bundy, Trey Mancini, Tim Beckham and Mychal Givens may be necessary to push it higher.
Before the Orioles can make a call on that, however, they must determine who's going to make the calls.
The contracts of general manager Dan Duquette and manager Buck Showalter are up at the end of 2018. If they go, it'll be time for a new direction. If they stay, so might the dysfunction that's clouded the organization.
In all, hard choices are still to come in Baltimore.
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Boston Red Sox: Can They Extend Any of Their Young Stars?
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The Boston Red Sox face the prospect of losing Craig Kimbrel to free agency and possibly David Price if he exercises his opt-out. After 2019, it'll be Chris Sale's and Rick Porcello's turn.
Nonetheless, arguably the Red Sox's top concern for the winter is locking up their young stars.
As of now, 2019 is set to be Xander Bogaerts' walk year. Mookie Betts and Jackie Bradley Jr. are ticketed for their walk years in 2020. Eduardo Rodriguez and Andrew Benintendi are further from free agency, but they're due for arbitration in 2019 and 2020, respectively.
As such, the Red Sox are no longer at a point where they can take their core homegrown talent for granted. They need to pony up with as many legitimate extension offers as they can.
Which leads to another dilemma: Given how crowded the Red Sox's long-term books already are, how far can they even go with extension offers?
Chicago Cubs: Should They Pick Up Cole Hamels' Option?
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When the Chicago Cubs acquired Cole Hamels from the Texas Rangers in July, it seemed like a given that they'd only be renting him for the rest of 2018. His $20 million option for 2019 was as good as declined.
But now that Hamels has returned to acehood by way of a 1.00 ERA through seven starts, suddenly things aren't so cut and dried. If there's any more where this is coming from, $20 million will ultimately be a small price to pay to keep him for another year.
However, the Cubs must also take into consideration that Hamels is going to turn 35 years old in December. Beyond that, they need to consider whether a payroll that's already bloated can handle an extra $20 million.
In either event, the Cubs are destined for a controversial decision.
Chicago White Sox: Is It Time to Spend?
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Suddenly, the Chicago White Sox are showing signs of life.
Much of it stems from young building blocks. Carlos Rodon, Lucas Giolito and the recently promoted Michael Kopech are pitching well. Meanwhile, Tim Anderson, Yolmer Sanchez and Matt Davidson have been hitting well.
There comes a time when rebuilding teams must decide whether they have a core of young talent that's good enough to be complemented with veterans. The Cubs started doing this when they signed Jon Lester after 2014. With plenty of money to spend, this winter could be the White Sox's turn to act.
Or, maybe it's too soon. The White Sox have only been successful over a small sample size, after all, and whatever additions they make this winter could be offset by losing Jose Abreu and Avisail Garcia to free agency after 2019.
The White Sox are thus in a position where they can be optimistic, but not reckless.
Cincinnati Reds: How Big Should They Go in Free Agency?
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There was a point when the Cincinnati Reds were playing so well under interim manager Jim Riggleman that they were openly talking about raising their payroll in 2019.
Then the inevitable cool-off came. The Reds went 9-19 in August, which put them deeper in the National League Central cellar.
Still, they may continue with their plan to raise payroll out of a desire to do something. Several years of rebuilding have thus far failed to turn them into a contender, so perhaps it's time for drastic measures.
But how drastic? If the Reds go small in free agency, it may not be good enough to make them relevant in the NL Central again. If they go big, they still might not be good enough and could find themselves anchored by multiple albatross contracts.
Ultimately, the Reds will have to find a happy medium between doing nothing and doing everything.
Cleveland Indians: Will This Be the Last Best Chance to Extend Francisco Lindor?
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The Cleveland Indians could lose Michael Brantley, Andrew Miller and Cody Allen to free agency this winter, but Francisco Lindor should be front and center in their offseason plans.
Sure, the superstar shortstop isn't due for free agency until after 2021. But this winter will bring his first trip through arbitration.
That should be the Indians' cue to get serious about extending Lindor. As in, more serious than they were when they made him a meager $100 million offer in 2017. At this point, the 24-year-old is worth at least twice that.
Rest assured, his price tag won't get any smaller as he gets closer to free agency. Likewise, his willingness to entertain an extension is likely to diminish as his checks get bigger and his date with free agency draws nearer.
Better get it done now, or else.
Colorado Rockies: Should They Spend on Nolan Arenado or Elsewhere?
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Speaking of franchise cornerstones who need immediate extension attention, the Colorado Rockies are nearly at the point of no return with Nolan Arenado.
The four-time All-Star and five-time Gold Glove winner is due for free agency after 2019, and he's only becoming more valuable with each passing season. The 27-year-old is becoming a better hitter with age, and this may be the year that he captures his first NL MVP.
The Rockies have a history of extending homegrown stars, and that could serve them well in negotiations with Arenado. But he's going to command by far the biggest contract in the team's history, and the timing for such a thing isn't exactly convenient.
After all, the Rockies are a contender that will have many other needs (outfield, second base, bullpen) to see to this winter. Even if it means losing Arenado after '19, they must determine whether they're better off spending their money on those.
Detroit Tigers: To Trade or to Extend Nicholas Castellanos?
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Despite some positive signs early on, it's become clear in recent months that the Detroit Tigers still have a ways to go with their rebuild.
So, get ready for the Nicholas Castellanos rumor mill to pick up again.
The 26-year-old is in the middle of a three-year run of sustained quality in the batter's box. Between that and his looming free agency after 2019, he's looked like an obvious trade candidate for a while now.
But it's not so straightforward. Castellanos doesn't offer much in the way of defense. And come the winter, the Tigers will be tasked with shopping him amid a market with plenty of right field alternatives in free agency, such as Bryce Harper, Andrew McCutchen and Nick Markakis.
Thus, there's the alternative: The Tigers can reopen extension talks that began in earnest December 2017. If they can't get anything for Castellanos, might as well keep him around for when things get good again.
Houston Astros: Will This Be the Last Best Chance to Extend Carlos Correa?
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As the Indians ponder an extension for Lindor, the Houston Astros must do the same for Carlos Correa.
Like Lindor, Correa isn't due for free agency until after 2021. But also like Lindor, he's heading into arbitration for the first time this winter.
Correa's agent, Greg Genske, made waves in 2017 when he said that his client would "never" do an early extension. However, circumstances look a little different now.
Correa has proved to be a target of the injury bug. He's also in the middle of the worst season of his career. So if the Astros come to him with anything close to market value, the 23-year-old could jump at the chance for long-term financial security.
There's a fine line here, though. The Astros can't go too big with an offer for Correa. And if they low-ball him, extension talks could be over for good.
Kansas City Royals: Can They Avoid Trading Danny Duffy and Whit Merrifield?
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Danny Duffy and Whit Merrifield looked like obvious trade chips for the summer trade season. Merrifield has emerged as one of the best second basemen in baseball since 2017. Duffy began 2018 slow but started getting back on track in late May.
And yet, the Kansas City Royals desired to trade neither Duffy nor Merrifield. Evidently, they wanted to have something to offer their fans in coming years.
However, they won't have much choice but to rethink their position this winter. They'll be coming off a disastrous season, and they'll have to know that there won't be any hope of improvement until they fix their dreadful farm system.
Rather than wait for future drafts and international signing periods, the Royals would be wise to kick-start a rebuild with a couple of blockbuster trades.
Los Angeles Angels: What of Albert Pujols?
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Technically, Albert Pujols' days with the Los Angeles Angels aren't yet numbered. His 10-year, $240 million contract runs all the way through 2021.
But that doesn't mean the Angels are obligated to keep employing him.
Alas, the legendary slugger isn't much of a slugger anymore. His offense has been on a steady downward trend for a decade, and he's no longer even an average hitter. He has just a .684 OPS since 2017.
Beyond that, the 38-year-old's body isn't as strong as it used to be. The knee surgery that's sidelined him for the rest of 2018 is only the latest in a long line of serious injuries that have taken their toll.
Mind you, letting Pujols go isn't such a simple move to make. The Angels would still have to pay him, and they would almost certainly have to deal with some public relations backlash. But since releasing him would more than likely be addition by subtraction on the field, they must take the idea seriously.
Los Angeles Dodgers: What of Clayton Kershaw?
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One way or another, the Los Angeles Dodgers will have a Clayton Kershaw conundrum this winter.
The three-time Cy Young Award winner can opt out of the final two years of his seven-year, $215 million contract. It once seemed like a foregone conclusion that he would, but the injuries and declining effectiveness that he's dealt with in recent seasons have upended that.
If Kershaw opt outs, however, the Dodgers' offseason will immediately become about whether to retain him. That will involve either handing him perhaps the biggest contract ever for a starting pitcher or making a surely unpopular call to let him go.
There's also a third possible outcome: Opt out or no opt out, Kershaw and the Dodgers can work out something mutually beneficial. Say, tacking a couple more years on to his current contract and calling it even.
Regardless, it'll be a fascinating situation to play out.
Miami Marlins: To Trade or to Keep J.T. Realmuto?
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J.T. Realmuto has been a regular in trade rumors ever since the Miami Marlins embarked on their latest fire sale last winter. But nearly a year later, he's still in Miami.
This makes some sense. If the Marlins want to have at least one star to offer their fans, it makes sense that it should be an up-and-coming superstar who's 27 years old and under team control through 2020. Realmuto isn't somebody they need to trade.
And yet, he is somebody that they arguably should trade.
Like the Royals, the Marlins are on a mission to build a contender from within. Also like the Royals, the Marlins have both a lousy major league roster and lousy farm system.
A trade of Realmuto would go a long way toward fixing the latter and, ultimately, the former. The Marlins won't have any choice but to reassess their willingness to do so this winter.
Milwaukee Brewers: How Should They Upgrade at Catcher?
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Apart from a few trade acquisitions (Gio Gonzalez, Curtis Granderson and possibly Mike Moustakas and Joakim Soria) who are arguably expendable, free agency won't open up any big holes in the Milwaukee Brewers.
So, they can focus on upgrading where they need to this winter. No position is more obviously in need than catcher, where the Brewers have lived with merely passable production out of Manny Pina and Erik Kratz.
How the Brewers should upgrade is a good question, however.
Option A is signing one of the top free agents on the market, such as Wilson Ramos or Yasmani Grandal. Option B is a trade, the best of which would be for J.T. Realmuto.
Milwaukee can't go wrong with any of those avenues. The only way it can is by doing nothing.
Minnesota Twins: To Retool or to Rebuild?
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The Minnesota Twins went for it this year after a surprise wild-card berth in 2017, but things fell apart early. This winter, they stand to watch Joe Mauer follow Brian Dozier, Eduardo Escobar, Lance Lynn, Zach Duke, Ryan Pressly and Fernando Rodney out the door.
The Twins will have to consider whether they should break up the band even further and commit to a full-on rebuild. They still have quite a few trade chips, after all. To name just a few: Jake Odorizzi, Kyle Gibson, Ervin Santana and Addison Reed, plus younger guys like Jose Berrios, Max Kepler, Miguel Sano, Eddie Rosario and Byron Buxton.
Or, the Twins could simply retool.
This is certainly the more likely route, if for no other reason than few of the aforementioned trade chips are at their peak value. Beyond that, a well-done shopping spree might indeed elevate them into the realm of wild-card contention.
New York Mets: How Aggressively Should They Pursue Upgrades?
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The New York Mets have already determined that Mickey Callaway will return as their manager. All they have to do now is determine what he has to play with next year.
In light of how bad their season has been and how weak their farm system is, the Mets should arguably spend the winter rebuilding. But that's not going to happen. With Jacob deGrom, Noah Syndergaard, Michael Conforto, Brandon Nimmo and Amed Rosario at the heart of a strong core, they have a little too much talent to punt on contending.
The Mets' real dilemma is how big they want to go in surrounding these cornerstones with enough complementary pieces to get the team back on track.
If they go really big, they risk bursting their already strained finances and having it all fall apart anyway. If they go too small, they risk staying stuck in place and merely delaying an inevitable rebuild.
New York Yankees: Should They Pass on Manny Machado and Bryce Harper?
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Beyond winning as many games as possible, staying under the luxury tax threshold is a top priority for the New York Yankees in 2018.
Since that effort is on track to be successful, their next step should be spending loads and loads of money in free agency. It just might not be on either Manny Machado or Bryce Harper.
The Yankees have long been mentioned as a likely destination for one or both of them, but the last two seasons have thrown these supposedly forgone conclusions for a loop. Where once the Yankees had questions at third base and right field, now they have Miguel Andujar and an Aaron Judge/Giancarlo Stanton tandem.
Thus, the Yankees may design to spend their riches on areas of actual need, such as their starting rotation.
Or, they could say "the hell with it" and go for Machado and/or Harper anyway. It's less a question of whether they can and more a question of whether they want to.
Oakland Athletics: Should They Spend on Khris Davis or Elsewhere?
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The Oakland Athletics have lived a charmed life this season, but they could find themselves at a crossroads this winter.
With Jed Lowrie, Jonathan Lucroy, Trevor Cahill, Brett Anderson, Jeurys Familia, Matt Joyce, Edwin Jackson and Shawn Kelley due for free agency, the A's are about to have a whole bunch of holes open up. They may have to commit their limited financial resources seeing to those.
Or, they could prioritize Khris Davis.
The slugger has already notched his third straight 40-homer season. A fourth in 2019 would allow him to springboard onto the open market with significant value.
But only if the A's don't extend him first. The idea has been on the table, and there appears to be mutual interest in it. Whether anything actually gets done may depend on how far beyond their comfort zone the A's are willing to go and, if they do, whether Davis deems even their best offer to be good enough.
Philadelphia Phillies: How Should They Spend Their Riches?
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The Philadelphia Phillies have probably overachieved this season, but don't think for a second that this means they're doomed to regress in 2019.
Since the Phillies are clearly done rebuilding, their next logical step is to start raising their payroll again. To that end, there's quite a bit of distance between the $95.3 million payroll they opened 2018 with and the $177.7 million payroll they peaked with back in 2014.
Really the only question is how the Phillies will invest their riches. They're going to be contenders for Manny Machado or Bryce Harper, if not both of them. Alternatively, they could sign just one of them and seek to spend their remaining dollars on other needs, such as rotation and bullpen depth.
Ultimately, the only way the Phillies can screw up the coming offseason is by putting unnecessary restrictions on themselves. They're the last team that should be outbid on something it wants this winter.
Pittsburgh Pirates: Should They Lock Up Jameson Taillon?
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Jordy Mercer is the Pittsburgh Pirates' only pending free agent, and he'll more than likely be replaced in-house by Kevin Newman, Cole Tucker or Kevin Kramer. If so, any one of them would take his place in a roster teeming with young, up-and-coming talent.
Perhaps the biggest offseason question for the Pirates is whether they'll lock up any of their youngsters. Of the bunch, nobody's a better candidate than Jameson Taillon.
When healthy, the 26-year-old has been one of the Pirates' most reliable starters over the last three seasons. And he's showing signs of getting even better, as he has a 2.84 ERA in his last 16 starts.
But since Taillon is only a year away from being arbitration-eligible, he may not be overly willing to take the first offer that comes across the table. Since he's a Tommy John survivor who isn't quite established as an ace yet, that could put the Pirates in a bind as to whether to up the ante.
San Diego Padres: Should They Continue to Spend?
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The San Diego Padres have been doing a lot of spending over the last two years. First, they extended Wil Myers for $83 million. After that, they signed Eric Hosmer for $144 million.
Nonetheless, they're on track for their worst season since 2008.
This might embolden them to keep spending this winter. They certainly wouldn't be in on top-tier guys, but perhaps they could push themselves for second-tier guys like Josh Donaldson or Dallas Keuchel. The idea would be to double down on using cash to strike a spark.
Or, they could simply wait on their young talent. Per B/R's rankings, the Padres have more of that in their farm system than any other team. And quite a few of their top prospects—namely: Fernando Tatis Jr., Francisco Mejia and Luis Urias—are ready for their MLB closeups.
If so, San Diego would flip the usual script on coming out of a rebuild by spending first and promoting second.
San Francisco Giants: Do They Need to Trade Before They Can Spend?
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It's not entirely clear where the San Francisco Giants stand in relation to the luxury tax threshold, but they've consistently acted like a team that wants to be under it. Assuming that mission is accomplished, an active offseason should ensue.
Still, the Giants may not be able to make any huge splashes unless they clear one or more of their big contracts. The most logical solution would be to trade Brandon Belt, whose first base job may be the best spot for a crumbling Buster Posey anyway.
And yet, it's not the most convenient time for a Belt trade. He's had some injury problems over the last two seasons. He's also been in a bad offensive slump since June. These things do not good trade value make.
If not Belt, the Giants may have to consider dealing Evan Longoria, Mark Melancon or even Brandon Crawford or Madison Bumgarner instead.
Seattle Mariners: What of Felix Hernandez?
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With respect to Nelson Cruz and his pending free agency, nobody will loom larger in the Seattle Mariners' offseason than Felix Hernandez.
In a cruel twist of fate, King Felix has been getting worse as the Mariners have been getting better. So it goes in 2018. As they seek a spot in the American League Wild Card Game, he's struggling with a career-worst 5.55 ERA.
The 32-year-old was briefly demoted to the bullpen in August. Although he made a quick return to the rotation, whatever signs of progress he's made have typically come paired with signs that his decline is permanent.
The Mariners still owe Hernandez $28.9 million after this season. They must determine if they're comfortable paying that much to a mere swingman or if they're better off eating that money and giving Hernandez's roster spot to someone else.
St. Louis Cardinals: What of Dexter Fowler?
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It's still 2018, but the St. Louis Cardinals have arranged a darn good outfield for 2019. It'll be Marcell Ozuna, Harrison Bader and Tyler O'Neill, with room for Jose Martinez, too.
The big question: Is there also room for Dexter Fowler?
The 32-year-old had sunk to the lowest point of his career even before a broken foot ended his season in August. He'd managed a .576 OPS and minus-1.4 wins above replacement on the field. Off the field, he reportedly feuded with former manager Mike Matheny and also found himself in the crosshairs of President of Baseball Operations John Mozeliak.
Fowler still has three years and $49.5 million remaining on his contract after 2018. The Cardinals must decide whether they want to give him a chance at salvaging that or if he's better off getting a change of scenery. If they go through Door No. 2, it'll probably only be via a bad contract swap.
Tampa Bay Rays: Do They Even Need to Do Anything?
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The Tampa Bay Rays have been one of baseball's hottest teams since August. And come winter, they'll have only two roster spots (those of Sergio Romo and Carlos Gomez) opened up by free agency. For that, they may stay in-house by plucking from their excellent farm system.
Otherwise, perhaps the only other item on the Rays' to-do list will be to upgrade at catcher. The position was in good hands when Wilson Ramos was in town, but now it's in the less capable hands of Jesus Sucre.
But because of the depth they have elsewhere in their lineup, this is less of a necessity and more of a luxury. The Rays also don't have many (if any) needs on the mound, where they have more than enough capable arms on which their "opener" strategy can continue thriving.
So as much as any team, the Rays may be comfortable sitting out the offseason.
Texas Rangers: What of Adrian Beltre?
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Adrian Beltre is nearing the end of his storied career. But if he does return in 2019, his only stipulation is that it will be with the Texas Rangers or nobody.
"If I'm going to play next year, I want it to be here," Beltre told Evan Grant of the Dallas Morning News.
It's a big if, however. Beltre has never seemed especially gung-ho on returning in 2019. He seemed even less so in August, when ongoing issues with his legs led him to wonder aloud: "Is it worth it to fight back?"
Not to be lost amid all of this is another possibility. Even if Beltre decides he does want to continue with the Rangers, perhaps the feeling won't be mutual.
After all, they do have a rebuild to carry on with. It might be better for them to cut the cord with the 39-year-old Beltre sooner rather than later.
Toronto Blue Jays: To Retool or to Rebuild?
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The Toronto Blue Jays have already purged numerous veterans, including 2015 American League MVP Josh Donaldson. According to Ken Rosenthal of The Athletic, manager John Gibbons is probably next.
These are familiar trappings of a team that's going into a rebuild, and the Blue Jays certainly could lean in to that destiny this winter. After sacking Gibbons, Marcus Stroman, Aaron Sanchez, Justin Smoak, Kendrys Morales and Kevin Pillar are additional trade chips they might cash in.
This may not be a foregone conclusion, however.
Whereas teams typically start rebuilding as a means to build a foundation of young talent, the Blue Jays are already equipped to build one. Stroman and Sanchez are still young, and the team's up-and-coming prospects include Vladimir Guerrero Jr., Bo Bichette, Danny Jansen and Anthony Alford.
Between their presence and all the money the Blue Jays have cleared in recent months, they could be in for a more active and aggressive offseason than you'd think.
Washington Nationals: How Far Should They Go to Keep Harper?
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The Washington Nationals are headed for an important offseason. They have many roster spots to fill or fix, and they must also decide whether to continue with embattled manager Dave Martinez.
But, let's not kid ourselves. The guy in the middle of everything will be Bryce Harper.
The relationship between Harper and the Nationals won't necessarily end when he becomes a free agent. The Nats can afford to re-sign him. And even after having endured seven largely frustrating seasons in Washington, he may not find a better place to chase a World Series ring.
And yet, the Nationals will face the same conundrum as everyone else: In the pursuit of Harper, how far is too far?
For while he's an amazing talent who's still only 25 years old, he's also been a favorite of the injury bug and a notoriously inconsistent hitter. Dropping several hundred million dollars on him would come with a great deal of risk. And with top prospect Victor Robles ready to step in, the Nats have an excuse not to take it.
Stats courtesy of Baseball Reference.
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