Every MLB Team's Biggest Dilemma of the 2020 Offseason

The 2020 Major League Baseball unfolded in fewer than three months, and it'll only be a couple weeks before the league moves into its 2020-21 offseason.

It's not going to be an easy one for any team.

We've gone through and highlighted the single biggest dilemma that each team will face this winter. These cover big-picture matters such as which directions organizations should even be going in. There are also more specific issues relating to which players might be re-signed, extended or traded.

We'll proceed in alphabetical order by city. 

After an 85-win effort in 2019, the Arizona Diamondbacks went into 2020 with the playoffs in sight.

Instead, they sunk to last place in the National League West and offloaded Starling Marte and Archie Bradley along the way. And given the size and poor returns of Madison Bumgarner's $85 million deal, they could be wary of free agency this winter.

The Snakes might, however, put themselves in the blockbuster trade market. Their farm system is the eighth-best in MLB and contains pieces (i.e., outfielders Kristian Robinson and Alek Thomas) that would interest sellers.

The alternative would be for the D-backs to simply wait for their top prospects to arrive. But since they're more of a win-now team, they would potentially live to regret that.

Atlanta has a World Series to pursue in the next few weeks, but it will soon have a Marcell Ozuna-sized hole in its lineup.

The veteran outfielder came to Atlanta on a one-year, $18 million deal in January. The club was gambling that Ozuna was better than he showed in two years with the St. Louis Cardinals, wherein he only managed a 107 OPS+.

It paid off. Ozuna played in all 60 of Atlanta's games and put up a 175 OPS+ and NL-high marks with 18 home runs and 56 runs batted in. As a result, he'll be one of the winter market's most coveted free agents.

Atlanta might be able to re-sign Ozuna. But if his price tag climbs into the nine-figure range, the organization's spending history suggests it would pivot to other options.

Despite their 25-35 record, the Baltimore Orioles might be satisfied with how their rebuild progressed in 2020. They may even feel comfortable investing in free agents in the not-too-distant future.

It seems likely, however, that the O's won't make that leap until next offseason. If anything, this winter will be more about deciding which veterans they should cut loose.

Namely, Chris Davis.

He played in only 16 games this season, yet still lowed his rWAR total since 2017 to an ugly minus-6.3. Even if Baltimore can't get out of paying him the $46 million he's owed through 2022, it can at least free up the roster spot that's being wasted on the once-great slugger.

Just two years after they won 108 games and the World Series, the Boston Red Sox traded Mookie Betts and plummeted to last place in the American League East in 2020.

Now they need a new manager, and their list of free agents includes longtime center fielder Jackie Bradley Jr. In theory, the totality of all this puts Boston squarely in the rebuilding camp.

But in Rafael Devers, Xander Bogaerts, Alex Verdugo and Bobby Dalbec, the Red Sox have an exciting offensive core already in place. And for 2021, they can look forward to having Chris Sale and Eduardo Rodriguez back healthy, as well as anticipating potential bounce-back years by J.D. Martinez and Andrew Benintendi.

Factoring in the club's reset luxury-tax penalties, the Red Sox should arguably favor an aggressive way forward this winter.

Even though they won the NL Central, the Chicago Cubs spent most of 2020 below .500 and were promptly swept out of the postseason by the Miami Marlins.

It's been three years since the Cubs last won a playoff game, and the one run that they scored against Miami was emblematic of the offensive issues they've been having. Accordingly, they're obviously in need of a shakeup.

Yet president of baseball operations Theo Epstein almost certainly won't instigate a rebuild while he has only one year left on his contract. Likewise, Kris Bryant, Javier Baez and Kyle Schwarber might not be tradable on account of their poor 2020 seasons and looming free agency after 2021.

The Cubs would thus seem to have two options for the winter: do nothing or go all-in on a last hurrah in 2021.

Unlike their neighbors on the North Side, the Chicago White Sox must be thrilled with their 2020 season.

They won more games than the Cubs, and the amount of youth and talent that they have on both sides of the ball leaves little doubt that they're only getting started as a contender. What's more, they don't figure to have many major needs this winter.

The big one, though, will be at closer. Alex Colome played the role marvelously in 2020, finishing with a 0.81 ERA in 21 appearances. But after the World Series, he'll become a free agent.

The White Sox could simply re-sign Colome. Health permitting, they might otherwise pass his role to fireballing left-hander Garrett Crochet or seek a replacement in free agency or on the trade market.

The Cincinnati Reds made the playoffs, but the zero runs that they scored against Atlanta in the Wild Card Round reflected the all-or-nothing nature of their offense.

Yet the Reds will surely focus their energy on pitching this winter. Specifically, on the massive void that's about to be left by Trevor Bauer's free agency.

Following a deadline-day trade, Bauer initially flopped with Cincinnati last year with a 6.39 ERA in 10 outings. Then in 2020, he made himself the front-runner for the NL Cy Young Award with a 1.73 ERA and 100 strikeouts in 11 starts.

After previously saying he's only going to sign one-year deals, Bauer recently expressed a willingness to entertain long-term offers in September. If he indeed pursues one of those, the Reds will likely have to find someone else to take his place.

This season netted Cleveland its fourth trip to the postseason in the last five years, during which Francisco Lindor has become one of baseball's brightest stars.

Yet next season is slated to be Lindor's last before free agency, and the odds of Cleveland making him an extension offer to his liking are basically nil. Hence why a trade of the superstar shortstop seems inevitable.

However, Cleveland doesn't have to trade him. And in the wake of a season in which he posted a career-low 102 OPS+, his value on the winter market might not be what they hope.

If so, Cleveland will have to make a choice: sell low on Lindor, or keep him and try to make the most of his final season under team control.

We could say that the Colorado Rockies are in the same boat with Nolan Arenado as Cleveland with Lindor, but it's not that simple.

While Cleveland is a contender that should probably keep Lindor, the Rockies are a pretender that frankly should be open to moving Arenado. Indeed, the man himself clearly isn't happy (see: here and here) with the state of the franchise.

Trouble is, Arenado's contract pays out $199 million through 2026. It also has a no-trade clause and an opt-out after 2021, both of which further complicate his trade value.

What's more, Arenado is coming off a season in which a shoulder injury contributed to an 84 OPS+. So even if the Rockies can trade him this winter, they might get less than they would have liked.

Following Ron Gardenhire's sudden retirement in September, the Detroit Tigers must first determine who their next manager will be.

Whoever it is, Detroit's next skipper will be tasked with guiding the team out of its rebuild. What's less clear, though, is exactly when the Tigers are planning on contending again.

They've been the worst team in MLB over the last four seasons, and their efforts to establish a foundation for a consistent winner still need work. It's good that they have baseball's No. 6 farm system. But apart from shortstop Willi Castro, the Tigers are thus far short on homegrown stars.

Perhaps the Tigers will attempt to force the issue with a big signing or two anyway. Otherwise, it figures to be a quiet winter in Detroit.

The Houston Astros had a difficult regular season, ultimately finishing two games under .500. But in the postseason, they've looked more like the juggernaut that tore up the competition between 2017 and 2019.

One way or another, however, the Astros will be in for a dramatic winter. Three of their top outfielders are due for free agency, including Michael Brantley and George Springer.

Because he turns 34 next May, the Astros might be able to bring Brantley back at a reasonable price. But Springer? Not so much. He's 31 years old, but his career 131 OPS+ and .930 OPS in the postseason will make him one of the market's most coveted free agents. 

If the Astros can't bring back Springer, they'll have to tab someone else to fill his ample shoes.

Like the Tigers, the Kansas City Royals are rebuilding in hopes of climbing up the AL Central ranks in the near future.

The difference is that the Royals could hypothetically speed up their rebuild—i.e., add more prospects to their ninth-ranked farm system—through trades this winter.

For instance, Jorge Soler, Salvador Perez and Danny Duffy are only under Kansas City's control through 2021. There's also All-Star utility man Whit Merrifield, whose club-friendly deal is guaranteed through 2022 with an option for 2023.

The catch is that the Royals have thus far resisted doing a tear-it-down, build-it-back-up style of rebuild. If they stay this course and hold on to those four guys this winter, they'd be running the risk of their trade value depreciating in 2021.

First, the Los Angeles Angels need to hire a new general manager after firing Billy Eppler. Then, their new GM will have to find an everyday shortstop and improve the club's woeful pitching.

The new GM will also have a difficult call to make on Albert Pujols.

The easy thing would be to let the future Hall of Famer serve out the final season of his 10-year, $240 million contract in 2021. But that would mean saving a roster spot for a 41-year-old (as of January 16) who's posted minus-0.8 rWAR since 2017.

It's also doubtful that Pujols can close the 34-homer gap between him and Alex Rodriguez for fourth place on the all-time list. So as much as it would hurt, the Angels wouldn't be losing much if they simply released Pujols this winter.

The Los Angeles Dodgers began the 2020 season as the de facto favorite to win the World Series, and they have thus far looked the part every step of the way.

Whenever their journey ends, it could also be the end of the line for Justin Turner in a Dodgers uniform. He's due to become a free agent after the World Series, and he'll turn 36 on November 23.

The Dodgers might simply install an incumbent such as Edwin Rios (who's fresh off a breakout season) at third base. Or, they might pursue a trade for a name-brand star like Kris Bryant or Nolan Arenado.

There's also, of course, the possibility they'll bring Turner back on a short-term pact. Though he's getting up there in years, he continued hitting in 2020 to the tune of a 135 OPS+.

At least in baseball, there was no greater surprise than the Miami Marlins this year.

They lost 105 games in 2019, and their 2020 season seemed doomed when they dealt with a coronavirus outbreak early on. But mainly with the help of their exciting young pitchers, they won 31 games and made the playoffs anyway.

For their next move, the Marlins might just sit back and wait for the other top prospects from their No. 3 farm system to join the party in the majors.

Yet that same farm system might allow the Marlins to make some blockbuster trades. Likewise, the cleanliness of their long-term books could put them in the market for big-name free agents. Either way, it's ultimately a question of whether they're ready to make some noise this winter.

Even though they made the playoffs anyway, not much went right for the Milwaukee Brewers as they racked up a 29-33 overall record this season.

In response, the Brewers might be willing to upgrade themselves through free agency. But if it's trades they fancy, their 26th-ranked farm system wouldn't be much help.

Milwaukee might have more luck landing a haul in a trade of All-Star closer Josh Hader. That would also mean saving some money, as he scored a $4.1 million salary in the first of four trips through arbitration this year.

Trouble is, Hader is coming off a year in which his ERA, walk and strikeout rates and velocity all regressed. Such things lend credence to the idea of holding on to him through at least next year's trade deadline.

The Minnesota Twins won the AL Central this season, but their offense let them down in the regular season and especially in the postseason.

Nelson Cruz, however, has nothing to apologize for. After blasting 41 homers in 2019, he hit 16 homers with a 169 OPS+ in 2020. He also drove in both of Minnesota's two runs in the Wild Card Round against Houston.

Though Cruz will soon be a free agent, the Twins want him back, and he wants to be back. 

Yet it would be understandable if the Twins didn't want to give him a raise on his $12 million salary for 2020. As great as Cruz has been for them, he'll turn 41 years old next July. Even he might not be able to keep slugging at that age.

For various reasons, the New York Mets just didn't have the depth to keep up as they sunk to fourth place in the NL East. But going forward, there is one major silver lining.

The team's ownership is about to pass from the Wilpon family to Steve Cohen. Given how deep the latter's pockets go, the days of the Mets not having payrolls worthy of New York are likely over.

Ah, but who will be in charge of running the club's baseball operations?

That task presently belongs to general manager Brodie Van Wagenen, who's overseen a respectable 112-110 record in two seasons. Yet he's also had some misfires (see: the Robinson Cano/Edwin Diaz trade) and generally hasn't run the smoothest ship (see: the Yoenis Cespedes mess), so a change may indeed be in order.

The New York Yankees offense made plenty of noise in the postseason, but the struggles of pitchers not named Gerrit Cole ultimately contributed to an early exit from October.

The good news is that the Yankees will soon have a chance to remake their starting rotation. Come the conclusion of the World Series, Masahiro Tanaka, J.A. Happ and James Paxton will all be free agents.

However, having as many as three rotation slots to fill is also the bad news. The Yankees likewise don't know when Luis Severino, who had Tommy John surgery in February, will be back in 2021.

The Yankees might be able to sign Trevor Bauer, who cheekily teased his interest in joining the club on Wednesday. But even if they do, they'll still need bodies for their starting rotation.

The A's made the playoffs for a third straight season and even managed to win a series this time around. But on Thursday, their season ended when Houston dispatched them from the American League Division Series.

Before long, the A's will stand to lose star shortstop Marcus Semien and ace closer Liam Hendriks to free agency. The latter is likely a goner no matter what. The former? Maybe not.

After finishing third in the AL MVP voting on the strength of 8.9 rWAR in 2019, Semien regressed and had maybe his worst offensive season so far in 2020. The experience might make him amenable to a one-year pillow deal the likes of which even Oakland might be able to afford.

If not, the A's will have to dig up a new everyday shortstop.

After Matt Klentak stepped down, the Philadelphia Phillies are unexpectedly in the market for a general manager. 

Whoever they hire will have one task above all: bring back J.T. Realmuto.

He was arguably the best catcher in baseball when the Phillies traded for him in February 2019. The "arguably" is now no longer necessary. Realmuto's combination of offensive and defensive skills have contributed to 5.6 rWAR since 2019. That's easily the best mark among catchers.

If the Phillies are willing to cut a nine-figure check, the Realmuto sweepstakes might be theirs to win. If not, they'll face the oh-so-difficult challenge of replacing him.

After a 93-loss season in 2019, the Pittsburgh Pirates cleaned house in hopes of getting back on track in 2020. Instead, they posted an MLB-worst 19-41 record.

Considering how they also have the league's No. 16 farm system, the Pirates are clearly in need of a proper rebuild. So in all likelihood, they'll be in sell mode this winter.

Pitchers like Joe Musgrove, Chris Stratton and Chad Kuhl figure to draw interest. Teams are also bound to come sniffing after slugger Josh Bell and second baseman Adam Frazier.

But with those latter two, specifically, there is a question of whether Pittsburgh's trade chips might appreciate in value next season. Short of closer Richard Rodriguez, there isn't actually much for the team to sell high on this offseason.

Even though they couldn't get past the Dodgers in the National League Division Series, the San Diego Padres will walk away from 2020 feeling confident in their status as a rising superpower.

What's more, they aren't due to suffer catastrophic losses in free agency. If anything, arguably San Diego's top priority this winter should be extending superstar shortstop Fernando Tatis Jr.

He's under their control through 2024. But when looking at his 154 OPS+ and 6.7 rWAR through his first 143 games, the team should surely want to keep him for far longer.

Yet if Ronald Acuna Jr.'s contract is any indication, it could cost the Padres nine figures to extend the 21-year-old Tatis. That's assuming he's even willing to sign now, which he may not be.

From one perspective, the San Francisco Giants aren't done rebuilding.

They're coming off a fourth straight losing season, and their farm system is still only the 14th-best in MLB even despite the presence of uber-catcher Joey Bart. They might be best served selling this winter, specifically if they make Johnny Cueto and Brandon Belt available.

From another perspective, though, the Giants are indeed ready for a next step. After all, they barely missed the playoffs in going 29-31 this year. And while they still have plenty of big salaries on their books now, there isn't much there after 2021.

So this winter, maybe the Giants should think big and put themselves in the market for brand-name free agents who could help them contend in the near and distant future.

Were the Seattle Mariners as good as their 27-33 record in 2020? Probably not, but their season was nonetheless a fitting tease of their bright future.

The Mariners got good pitching out of Marco Gonzales and Justus Sheffield, and Kyle Lewis, Dylan Moore and Ty France look like offensive stars worth building around. Before long, the latter group will also be joined by super-prospect Jarred Kelenic.

He had a .904 OPS, 23 homers and 20 stolen bases as a mere 19-year-old in the minors last season. This year, he further impressed the Mariners with his work at the alternate site.

There's little question that Kelenic will be a part of the Mariners in 2021. If there is a question, it's only whether the team will risk another Evan White and extend Kelenic before he even debuts.

The St. Louis Cardinals' season ended with a loss to the Padres in the Wild Card Round. Up next may be the end of an era.

Yadier Molina, who's been catching for the Cardinals since 2004, is a free agent this winter. So is Adam Wainright, who's been pitching for them since 2005.

For his part, Molina has said he wants to keep playing for another two years. Wainwright's plans for his future aren't as clear, but he did indicate to Ken Rosenthal of The Athletic in May that 2020 won't be his last year.

There would therefore seem to be a window for the Cardinals to bring back both players. But since Molina and Wainwright are 38 and 39, respectively, whether the Cardinals should re-sign them is ripe for debate.

After finishing the regular season with the best record in the American League, the Tampa Bay Rays have only dug in as a World Series contender in the postseason.

Moreover, most of these Rays won't be going anywhere this winter. Apart from left-handed reliever Aaron Loup, they don't have anyone ticketed for free agency.

However, that's contingent on how they value veteran right-hander Charlie Morton. If it's as a top-of-the-rotation starter, then they'll surely pick up his $15 million option for 2021.

Then again, maybe not. Morton turns 37 years old on November 12, and he's coming off a year in which his ERA and strikeout rate regressed from their 2019 peaks. The Rays may take such things as signs that they're better off letting him go.

After a productive 2019 season, the Texas Rangers came into this year with good intentions. Alas, all sorts of hell paved the way to a last-place finish.

Because the Rangers also have one of baseball's worst farm systems, it's hard to see what good would come from staying the course this winter. They ought to sell, whether it means trading ace Lance Lynn or even slugger Joey Gallo.

Gallo is 26 years old and under team control through 2022. And while he's mainly known for his humongous power, he's also a good athlete who's displayed superstar upside.

But after teasing said upside with 3.1 rWAR in only 70 games in 2019, Gallo slipped to 1.2 rWAR in 2020. The Rangers may want to wait until after he revitalizes his value to trade him.

Right on schedule, the Toronto Blue Jays arrived and made the playoffs in 2020. Now they just need to reinforce their position as a rising power.

This is going to require filling a few holes over the winter, as Taijuan Walker, Ken Giles, Robbie Ray, Matt Shoemaker and Jonathan Villar are due for free agency. While they're at it, the Jays might also consider extending some of their core stars.

First in line are Teoscar Hernandez, Lourdes Gurriel Jr., Bo Bichette, Cavan Biggio and Rowdy Tellez. To one degree or another, each enjoyed a breakout season in 2020.

Or, it could mean chancing it on Vladimir Guerrero Jr., who's yet to really live up to the hype that accompanied him when he was MLB's No. 1 prospect. In any case, Toronto has options aplenty.

Following their triumph in the 2019 World Series, the 2020 season just never really came together for the Washington Nationals.

Still, this offseason will surely be more about retooling than rebuilding. The Nats figure to be in the market for both pitching and offensive upgrades, specifically an impact right-handed hitter for the latter.

Washington's top priority, though, should be making Juan Soto a National for life. Per his 151 OPS+, the 21-year-old is one of the greatest young hitters the sport has ever seen. And he's only getting better, as he led MLB in on-base (.490) and slugging percentage (.695) in 2020.

Soto is due for free agency after 2024. The closer the Nats let him get to that occasion, the harder it may be to get him to sign on the dotted line.

Stats courtesy of Baseball Reference and FanGraphs