Each MLB Team's Biggest Dilemma of the 2019-20 Offseason

Zachary D. Rymer@zachrymerMLB Lead WriterSeptember 4, 2019

Each MLB Team's Biggest Dilemma of the 2019-20 Offseason

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    Will the Cleveland Indians keep Francisco Lindor?
    Will the Cleveland Indians keep Francisco Lindor?Paul Sancya/Associated Press

    Decisions, decisions. Major League Baseball teams have to make them all the time, but perhaps the toughest choices come during the winter.

    We've gotten ahead of them by pinpointing the biggest dilemma each team will face in the 2019-2020 offseason. These cover difficult calls that teams will have to make regarding trades, signings and, in some cases, the general direction they want to go in.

    We'll go division by division, starting in the American League East and ending in the National League West.

American League East

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    Mookie Betts
    Mookie BettsMichael Dwyer/Associated Press

    Baltimore Orioles: What Should They Do with Chris Davis?

    Whatever hopes the Baltimore Orioles had that Chris Davis would pull out of his brutal 2018 slump in 2019 have been dashed. 

    The 33-year-old former slugger has only improved from a .539 OPS to a .577 OPS. He's also gone from minus-2.8 wins above replacement to minus-1.1, according to Baseball Reference. The Orioles surely expected more when they inked him to a seven-year, $161 million deal in 2016.

    Baltimore won't get out of the $69 million it owes Davis through 2022, so the only question is if he's even worth a roster spot. In other words: Is the team ready to admit defeat by releasing him and swallowing his remaining contract?


    Boston Red Sox: What Should They Do with Mookie Betts?

    The upcoming hot-stove season will be critical for the Boston Red Sox. And more so than that of J.D. Martinez, chief among their predicaments will be the fate of Mookie Betts.

    The Red Sox's efforts to extend the 2018 AL MVP have thus far been met with resistance. With free agency looming after 2020, it's doubtful Betts will alter his position unless the Red Sox top the $200 million offer they made to him after 2017.

    According to Jon Paul Morosi of Fox Sports, it's not out of the question that the Red Sox will give up and trade Betts this winter. Barring an extension, the only alternative would be to keep him and hope for some kind of last hurrah in 2020.


    New York Yankees: Who's on Third?

    Given how swimmingly things have gone without Giancarlo Stanton, perhaps the New York Yankees will weigh unloading him and as much of his $325 million contract as they can.

    But rather than sell low on Stanton, the Yankees might prefer to keep the 2017 NL MVP and see if he can bounce back in 2020. After all, they can afford to carry him.

    In lieu of the Stanton question, the situation at third base might be the Yankees' biggest conundrum this winter. Will they assume a strong recovery from shoulder surgery for Miguel Andujar? Or will they buy into Gio Urshela's breakout and shop Andujar on the trade market?


    Tampa Bay Rays: What Can They Afford to Do?

    Granted, what the Tampa Bay Rays can afford to do is always a good question in any given offseason.

    Yet it will be an especially pressing question this winter. The Rays don't have a lot of salary set to come off their books. Meanwhile, notables such as Tyler Glasnow, Tommy Pham and Mike Zunino will be due raises in arbitration, and the salaries of Kevin Kiermaier, Blake Snell and Brandon Lowe will escalate.

    But as they did with their two-year, $30 million deal with Charlie Morton last winter, the Rays might have some surprises in them. They'll have an influx of spending money at their disposal if they hammer out a new local TV contract.


    Toronto Blue Jays: Is It Time to Add Yet?

    The Toronto Blue Jays have had a rough go of things since back-to-back trips to the American League Championship Series in 2015 and 2016. However, things have lately been looking up.

    In Vladimir Guerrero Jr., Cavan Biggio, Bo Bichette and Lourdes Gurriel Jr., the Blue Jays have established a young, exciting offensive core. Nate Pearson, who's MLB.com's No. 13 prospect, should take the lead in their rotation sometime in 2020.

    The future isn't quite now for the Blue Jays, but it might be close enough for them to consider spending on veteran talent this winter. It's either that or a few more months of rebuilding, which could be a tough sell for their fanbase.

American League Central

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    Francisco Lindor
    Francisco LindorMary Altaffer/Associated Press

    Chicago White Sox: Is It Time to Go Big?

    The Chicago White Sox were linked to Bryce Harper, Manny Machado and other high-profile free agents on last winter's market. Yet they didn't make any seismic moves.

    That was understandable. Though the White Sox had money to spend and a prospect base worthy of big dreams, they were also coming off a 100-loss season. It was a bit soon for them to force their way out of their rebuild.

    Fast-forward to now, and Tim Anderson, Yoan Moncada and Lucas Giolito are entrenched as stars, while Eloy Jimenez may not be far from that status. Between this and their largely clean long-term books, the White Sox have every excuse to spend. The only question is whether they will.


    Cleveland Indians: What Should They Do with Francisco Lindor?

    Despite spending all of last winter cutting payroll and trading Trevor Bauer in July, the Cleveland Indians are in line to make the playoffs.

    Even still, their payroll will be a central story yet again this winter. Will their lean 2019 spending give way to a heftier payroll for 2020? Or will they stick with their penny-pinching approach?

    If the Indians opt for the latter, Francisco Lindor may hit the trading block. Since an extension for the superstar shortstop seems out of the question, the Indians may prefer to cash in his value rather than pay him huge raises via arbitration in 2020 and 2021.


    Detroit Tigers: Where Does Their Rebuild Go Next?

    The bad news is that the 2019 Detroit Tigers are worse than the clubs that lost 98 games in 2017 and 2018. The corresponding good news should be that at least their farm system is in good shape.

    In actuality, it's merely MLB's No. 13 system. If the Tigers want to accelerate their rebuild, they need to push it as close to No. 1 as they can.

    But how? The best trade chip they have left is left-hander Matthew Boyd, but he's done nothing but damage to his value over the last three months. If the Tigers can't get a haul for him this winter, they might not get one at all.


    Kansas City Royals: Will New Ownership Mean a New Direction?

    They may be on track for a second straight 100-loss season, but at least the Kansas City Royals are about to take on new management. 

    Assuming the rest of MLB's owners sign off on it, ownership of the Royals will pass from David Glass to John Sherman, a Kansas City native who's presently a minority owner of the Indians. The estimated cost: $1 billion.

    What will happen after that is anyone's guess. With help from a new local TV deal, Sherman could put some money into the Royals. Or he could facilitate a top-to-bottom restructuring of the club's front office and roster. Or maybe something in between. 


    Minnesota Twins: Should They Spend on Stars or Depth?

    It's looking more and more like the Minnesota Twins will win their first AL Central title since 2010. The next step will involve going as deep into the postseason as they can.

    Come the winter, it will presumably be time for the Twins to double down. Their successful 2018 will be an ideal excuse to spend big bucks, and they'll have plenty of holes to fill with Jake Odorizzi, Kyle Gibson, Jonathan Schoop, Michael Pineda and Jason Castro due for free agency.

    How the Twins should spend will be the interesting part. They could aim for superstars such as Gerrit Cole and Anthony Rendon. Alternatively, they might aim lower and prioritize more of a depth-based approach.

American League West

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    Michael Wyke/Associated Press

    Houston Astros: Should They Re-Sign or Replace Gerrit Cole?

    The Houston Astros have a bunch of players set to hit free agency this winter, but none bigger than Gerrit Cole.

    The 28-year-old was a reclamation project when the Astros acquired him from the Pittsburgh Pirates in 2018. All he's done since is post a 2.84 ERA and strike out 13.0 batters per nine innings. In all likelihood, he's in line for a $200 million contract.

    The Astros should be able to afford a contract of that size, but they might determine they don't have to. Instead, they might favor a pursuit of another reclamation project who could be turned into a superstar starter.


    Los Angeles Angels: How Can They Fix Their Starting Rotation?

    It's almost impressive that the Los Angeles Angels are even 65-74. By all rights, they should have been sunk by a starting rotation that's experienced hardship upon hardship en route to its 5.34 ERA.

    Fixing said rotation will be the Angels' top priority this winter. But they don't have many prospects to deal or much money coming off their books.

    That could force the Angels to clear payroll, perhaps by rejecting Kole Calhoun's $14 million option or trading the bad contracts belonging to Zack Cozart, Justin Upton and Albert Pujols. In lieu of that, they might simply spend beyond their comfort zone and hope it pays off.


    Oakland Athletics: What Can They Afford to Do?

    The Oakland Athletics' reputation as one of baseball's cheapest teams precedes them, but their payroll for 2019 is the highest in their history.

    The A's might not have much choice but to keep it up in 2020. They only have a handful of players coming off their books, and arbitration raises could easily account for savings from that.

    This raises the question of how the A's will fill their needs. They could dig deeper into their pockets or perhaps keep their payroll steady by shedding salaries via non-tenders and trades. Either way, they'll have tough calls to make.


    Seattle Mariners: Where Does Their Rebuild Go Next?

    The Seattle Mariners could have started a full-on rebuild last winter, but they tried to have it both ways by making deals that benefited both their farm system and their major league roster.

    The early results are mixed. On one hand is a farm system that's one of baseball's 10 best. On the other is a flop of a major league team that needs fixing.

    The Mariners have transitioned into more of a classic rebuild by trading Edwin Encarnacion, Jay Bruce and Mike Leake. The next step could involve further trades of Mitch Haniger and Domingo Santana. Or, it might involve a second whack at last winter's have-it-both-ways approach.


    Texas Rangers: What Should They Do with Rougned Odor and Nomar Mazara?

    The Texas Rangers have made surprising progress in 2019 after they dropped 95 games in 2018. From here, they may only continue to rise up the AL West.

    But they might have some dead weight to shed in the persons of Rougned Odor and Nomar Mazara. Both were once billed as cornerstones. But neither has lived up to expectations, and they've hit bottom with a combined minus-0.4 WAR in 2019.

    Evan Grant of the Dallas Morning News and Levi Weaver of The Athletic touched on the uncertain futures of both players. The Rangers' choices may come down to selling low on both in trades or keeping them and hoping against hope for the best.

National League East

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    Anthony Rendon
    Anthony RendonJustin K. Aller/Getty Images

    Atlanta Braves: Should They Spend on Stars or Depth?

    The Atlanta Braves should soon wrap up a second straight NL East championship. After that, they'll embark on a winter in which they'll have a ton of holes to fill thanks to free agency.

    Hypothetically, the Braves could make big signings to fill some holes and stay in house to fill the others. Particularly with regard to pitching, there's a variety of talent in their fourth-ranked farm system.

    Yet it's also possible the Braves will prefer a repeat of what they did last winter. Though they had plenty of money to spend, they focused on adding depth through short-term, low-risk deals. They may reason that if that could work once, it might work again.


    Miami Marlins: Where Does Their Rebuild Go Next?

    The Miami Marlins have done nothing but shed talent since Bruce Sherman and Derek Jeter took over in 2017. Yet all it's gotten them is diminishing attendance and a farm system that's not as good as it should be.

    Miami's system is presently ranked No. 10 in MLB. Like the Tigers, the Marlins' only hope of pulling out of their rebuild any time soon is moving their system as close to No. 1 as possible.

    Also like the Tigers, however, the Marlins have largely run out of valuable trade chips. Their only recourse may be to dangle players who have actual long-term value, such as breakout lefty Caleb Smith.


    New York Mets: What Should They Do with Yoenis Cespedes?

    Yoenis Cespedes hasn't played a game for the New York Mets since July 20, 2018, and a combination of surgeries on both heels and a broken ankle will sideline him for all of 2019.

    Because Cespedes, 33, suffered his ankle injury in a non-baseball activity at his Florida ranch, there's been talk about the Mets possibly voiding the remainder of his four-year, $110 million contract and recouping his $29.5 million salary for 2020. 

    That may be a long shot, but the Mets could seek to keep Cespedes out of the picture for 2020 anyway. They might continue to collect insurance money by keeping him on the injured list, or potentially look to release him or buy him out.


    Philadelphia Phillies: How Can They Fix Their Pitching?

    The Philadelphia Phillies have arguably underachieved, but the alternative take is that they've done well in putting up a winning record despite a negative run differential.

    For the Phillies to clear a path to better things in 2020 and beyond, they'll need more from their Bryce Harper-led offense. But more so than that, they'll need better pitching from a staff that's been largely unreliable outside ace Aaron Nola and closer Hector Neris.

    Trouble is, the Phillies have a middling farm system and a bloated payroll. Whether it's cutting salaries, spending beyond their comfort zone or sacrificing valuable prospects, their quest for pitching will require some tough calls this winter.


    Washington Nationals: Should They Re-Sign or Replace Anthony Rendon?

    The Washington Nationals tried to sign Anthony Rendon to a contract extension in spring training, but those talks never got close to a done deal.

    All Rendon has done since then is put together a walk year for the ages with career highs in OPS (1.054) and home runs (32), and his 6.1 WAR puts him on track to top his previous high of 6.6. The 29-year-old now looks like a shoo-in for a $200 million contract on the open market.

    The Nats can probably afford such a pact, but it would mean adding yet another long-term megadeal to their books. Instead, they might consider alternatives such as a shorter deal for Josh Donaldson or a blockbuster trade for, say, Kris Bryant.

National League Central

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    Theo Epstein and Joe Maddon
    Theo Epstein and Joe MaddonDylan Buell/Getty Images

    Chicago Cubs: Are Big Changes Inevitable?

    In July, Chicago Cubs president of baseball operations Theo Epstein declared "a ton of change" was in order if the club didn't turn things around.

    The Cubs are firmly in second place in the NL Central race. After disappointing turns in 2017 and 2018, this is the clearest sign yet that the dynasty they thought they were building in 2016 won't come together.

    A rebuild won't be on the table this winter, but the Cubs could consider a retooling. At the least, manager Joe Maddon figures to be shown the door. Beyond that, the Cubs will also have to consider trading some of their ostensible building blocks, up to and including Bryant.


    Cincinnati Reds: How Do They Fix Their Offense?

    If nothing else, the Cincinnati Reds will come out of 2019 with a drastically improved starting rotation. It's gone from a 5.02 ERA in 2018 to a 4.05 ERA this season, and Luis Castillo, Sonny Gray, Trevor Bauer and Anthony DeSclafani are all due back in 2020.

    The Reds have struggled, however, because their offense hasn't kept up with the times. Only three NL clubs have averaged fewer runs per game.

    The Reds will only make progress in 2020 if they fix this problem. Assuming they don't want to subtract any more from a farm system that's already fading, they might have to invest more than usual in free agency.


    Milwaukee Brewers: How Do They Fix Their Starting Rotation?

    It's a minor miracle that the Milwaukee Brewers have a winning record in spite of their minus-38 run differential. For that, they mostly have reigning NL MVP Christian Yelich to thank.

    But while Yelich will be back to lead their offense in 2020, the Brewers can't take much for granted with a rotation that's lucky to have even a 4.67 ERA. They may need to find as many as three starters to slot in behind Brandon Woodruff and Zach Davies.

    Unfortunately for the Brewers, their farm system has been picked clean, and the free-agent market won't have much to offer. Solving their rotation puzzle will require creativity.


    Pittsburgh Pirates: Time to Blow It Up?

    The Pittsburgh Pirates were only 2.5 games out of first place at the All-Star break. But ever since, they've sunk to the bottom of the NL Central with a 16-33 record.

    Injuries have contributed to the Pirates' demise, but that gets at how ill equipped they were for contention in the first place. This team has precious few major league stars, and there aren't many more within their 18th-ranked farm system.

    The Pirates could boot up a rebuild this winter, perhaps by trading ace closer Felipe Vazquez and slugger Josh Bell. It's either that, or they commit to what would seem to be an impossible retooling job.


    St. Louis Cardinals: Should They Re-Sign or Replace Marcell Ozuna?

    It's been a struggle for the St. Louis Cardinals to generate offense in 2019, but they've at least been able to count on Marcell Ozuna. He's bounced back from a rough 2018 with an .846 OPS and 25 homers.

    Unfortunately for the Cardinals, Ozuna is due for free agency. And given how little talent will be available this winter, the market for him could lead to a bidding war that exceeds his practical value.

    The Cards are bound to be involved in some capacity, but there might come a point when they're comfortable falling back on their many in-house options. Between Tyler O'Neill, Randy Arozarena and Dylan Carlson, they have plenty of young outfielders waiting for their shot.

National League West

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    Hyun-Jin Ryu
    Hyun-Jin RyuMark J. Terrill/Associated Press

    Arizona Diamondbacks: What Comes Next?

    The Arizona Diamondbacks are on track to emerge from 2019 with a winning record and, mainly by way of their Zack Greinke blockbuster, baseball's No. 3 farm system.

    The D-backs' next step could involve treading even further into rebuilding territory. If they were to move, say, David Peralta, Robbie Ray and Nick Ahmed, their farm system could take over the No. 1 slot in MLB.

    If the Snakes don't want to do that, well, their only alternative might be loading up for 2020. Because if they don't get it done next season, their books will be so clean that embracing a rebuild will be less of a choice and more of a necessity.


    Colorado Rockies: How Do They Fix Their Offense?

    After winning 91 games in 2018, the Colorado Rockies haven't had enough pitching to sustain themselves in 2019. They've posted a 5.69 ERA and sunk to last place in the NL West.

    However, pitching will always be a struggle for a team that has to play half its games in Denver. What's harder to excuse is how much trouble the Rockies have had with their offense over the last two seasons. Their 2019 attack, in particular, is one of the worst in franchise history.

    If the Rockies won't rebuild, they must start getting back on track by adding hitters. But due to their bloated payroll and diminished farm system, it'll require some cleverness.


    Los Angeles Dodgers: Should They Re-Sign or Replace Hyun-Jin Ryu?

    Though longtime Los Angeles Dodgers ace Clayton Kershaw has partially regained his vintage form this season, fellow southpaw Hyun-Jin Ryu has stolen the spotlight with an MLB-best 2.35 ERA.

    In so doing, Ryu has lined himself up for a significant free-agent payday. And unlike last year, the Dodgers can't lure him back or hinder his market with a qualifying offer. New rules prohibit players from receiving more than one of those.

    If the Dodgers want Ryu back for 2020 and beyond, they'll have to pay up. Rather than give in, it's possible they'll sign a lower-risk starter or perhaps hand Ryu's spot to young lefty Julio Urias.


    San Diego Padres: How Can They Add an Ace?

    The San Diego Padres haven't made much of a secret of their desire to add an ace starter over the last couple of years, but their efforts have been fruitless.

    Still, they aren't likely to stop trying. With Manny Machado, Fernando Tatis Jr., Hunter Renfroe and Eric Hosmer established as core stars, a top-of-the-rotation starter may be the only thing standing between the Padres and real contention in the NL West.

    How they'll prefer to get one is the question. Unless the Padres can jettison Wil Myers' albatross contract, trading from their No. 1 farm system may be their only practical option.


    San Francisco Giants: Time to Blow It Up?

    It's to the San Francisco Giants' credit that they've played as well as they have. But by not trading Madison Bumgarner and Will Smith at the deadline, they didn't do their rebuild timeline any favors.

    With Bumgarner and Smith now ticketed for free agency, the Giants are heading toward an offseason in which their best trade chips will all come tied to problematic contracts. Namely: Buster Posey, Johnny Cueto, Jeff Samardzija, Brandon Belt, Brandon Crawford and Evan Longoria.

    More so than if they should, whether the Giants even can trade these guys is a good question. Save for Samardzija, it might be better for the Giants to keep playing them and try to boost their farm system in other ways.


    Stats courtesy of Baseball Reference and FanGraphs.