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For example, the Boston Red Sox's Mookie Betts conundrum.
For example, the Boston Red Sox's Mookie Betts conundrum.Billie Weiss/Boston Red Sox/Getty Images

One Make-or-Break 2019-20 Offseason Decision Each MLB Team Faces

Zachary D. RymerOct 2, 2019

Once a little thing called the Major League Baseball postseason is out of the way, the 2019-20 offseason will open up. Every team will do its best not to screw it up.

We've highlighted one specific decision that looms especially large over each team's winter dealings. These involve potential trades, signings and more general strategies that could make or break their future fortunes.

In other words, we looked past front-office and managerial openings and focused strictly on matters pertaining to on-field personnel. Who teams choose to call the shots is certainly important, but games are won or lost on the strength of those clubs' rosters.

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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Vladimir Guerrero Jr.
Vladimir Guerrero Jr.

Baltimore Orioles: How to Handle Trey Mancini's Breakout

Though the Baltimore Orioles didn't repeat last year's 115-loss flop, that they only improved to 108 losses makes it clear their rebuild still has a long way to go.

A central question for now is how Trey Mancini fits into their plans for the future. The 27-year-old slugger's value is at an all-time high in the wake of his career-best .899 OPS and 35 home runs. He's also under club control for three more years.

The Orioles could extend, trade or do nothing with Mancini. All three decisions come with some risk, but none more so than Door No. 3. If the Orioles walk through it, they might watch Mancini regress and nix any possibility of a blockbuster deal.

Boston Red Sox: Whether to Trade Mookie Betts

According to Alex Speier of the Boston Globe, Boston Red Sox president Sam Kennedy said Monday that fitting both Mookie Betts and J.D. Martinez into the team's 2020 budget will be "difficult."

The Red Sox may not have a choice with Martinez, who might forgo the opt-out clause in his contract. But since Betts, who will turn 27 on Monday, seems to have no interest in an extension, the Red Sox have to either trade him now or keep him—and likely pay him a $30 million salary for his walk year in 2020.

If the Red Sox can't leverage a favorable offer for the 2018 American League MVP, they'll have to choose between cutting his salary via a trade or keeping him and going for next season. In any case, they'll have to determine just how much one of the very best players in MLB is worth to them.

New York Yankees: How to Handle Their Starting Rotation

Regardless of how their playoff journey pans out, the New York Yankees must decide whether a starting rotation that posted a 4.51 ERA in the regular season needs upgrading.

If they lean toward the affirmative, Gerrit Cole, Hyun-Jin Ryu, Madison Bumgarner, Zack Wheeler and potentially Stephen Strasburg (who has an opt-out) will be there for the taking on the open market. The Yankees should be able to afford any one of them.

Alternatively, they could do nothing and move forward with Luis Severino, Masahiro Tanaka, James Paxton, J.A. Happ and either Domingo German or top prospect Deivi Garcia. Though that wouldn't be the worst plan, the Yankees would invariably be risking more of the same in 2020.

Tampa Bay Rays: How They Should Add Power

The Tampa Bay Rays were good enough at pitching, fielding and situational hitting to make their way to October, but they struggled to keep pace in the league's extraordinary home run revolution.

Rather than risk a repeat of that in 2020, the Rays could favor adding power. The question, of course, is what they can afford to do. With little salary set to come off their books, they may have to non-tender Mike Zunino, Matt Duffy and Jesus Aguilar to clear space.

Even then, the Rays may be limited to bargain-bin shopping in free agency. Their best hope of a substantial upgrade might require sacrificing some of their considerable prospect depth on the trade market. That's never an easy call for cash-strapped teams such as the Rays.

Toronto Blue Jays: Whether to Extend Their Young Core Stars

Despite the Toronto Blue Jays' 95 losses, their season may be fondly remembered in Toronto as the one in which the rebuild began bearing fruit.

Specifically, rookie hitters Vladimir Guerrero Jr., Cavan Biggio and Bo Bichette look like keepers. Instead of letting them play out their remaining years of club control, perhaps the Blue Jays will make like the Atlanta Braves with Ronald Acuna Jr. and Ozzie Albies and lock them up for the long haul right now.

If the Blue Jays don't want to do that or are rebuffed by each player's reps, it may not be long before they're bemoaning the financial flexibility they could have had if only they'd signed Guerrero, Biggio and Bichette to club-friendly deals when they had the chance.

American League Central

2 of 6
Francisco Lindor
Francisco Lindor

Chicago White Sox: Whether to Extend Yoan Moncada and Lucas Giolito

The Chicago White Sox will almost certainly re-sign veteran slugger Jose Abreu. Beyond that, they face a dilemma as to whether they should go all-in on trying to contend.

If they'd rather wait, the contract statuses of third baseman Yoan Moncada and right-hander Lucas Giolito will emerge as their top concerns. Both established themselves as rising stars in 2019, so the White Sox must consider extending them like they've already done with Tim Anderson and Eloy Jimenez.

Since both Moncada, 24, and Giolito, 25, are due for arbitration in 2021, this may be the White Sox's last best chance to get good deals.

Cleveland Indians: Whether to Trade Francisco Lindor

Though the clock isn't ticking as loudly as it is with Mookie Betts, the Cleveland Indians will face their own trade dilemma with regard to superstar Francisco Lindor.

According to Baseball Reference, the 25-year-old leads all shortstops with 28.6 wins above replacement since 2015. Between that and his two remaining years of club control, the Indians have a pair of very good reasons to keep him far from the trading block.

Trouble is, they also have a tight payroll and middling farm system. Even if they clear room for Lindor's likely $20 million salary by forgoing options on Corey Kluber and Jason Kipnis, they may still be tempted to trade him if the right offer comes along.

Detroit Tigers: Whether to Trade Matthew Boyd

The Detroit Tigers are coming off a year in which they lost 114 games and allowed 333 more runs than they scored. Suffice it to say there isn't anything they can do to return to contention in 2020.

The Tigers can only find ways to inch forward with their rebuild. On that front, left-hander Matthew Boyd is the only trade chip of note they have left. He's fresh off striking out 238 batters in 185.1 innings, and he's under club control through 2022.

But since the 28-year-old also posted a 4.56 ERA and surrendered an AL-high 39 homers, the Tigers might wait and see if he can push his value higher with a more complete breakout in 2020. The downside to this plan is the threat of Boyd's getting hit even harder and his value going kaput.

Kansas City Royals: How to Handle Jorge Soler's Breakout

The Kansas City Royals may have endured a second straight 100-loss season, but at least Jorge Soler found his calling. The 27-year-old slugged an AL-high 48 long balls.

Now comes the tricky part. Soler is all but certain to opt out of his contract and into arbitration, which would line him up for a raise on the $4.7 million he'd otherwise be owed in 2020. He would also be due for free agency after 2021.

The Royals' options are to stay the course with Soler or to extend or trade him. With the latter two, there's the matter of whether Soler is more valuable to a homer-starved franchise such as the Royals than he is to other teams in this homer-saturated era.

Minnesota Twins: How to Fill Out Their Starting Rotation

The Minnesota Twins are proof that when you hit more home runs than any team in MLB history, you only need so much help from your pitching staff. Their hurlers posted a modest 4.18 ERA, which ranked ninth in MLB.

Yet the Twins won't be able to sit back and wait for this formula to play out all over again in 2020. With Jake Odorizzi, Kyle Gibson and Michael Pineda reaching free agency, their starting rotation will have some big holes in need of filling.

How the Twins fill them will be the interesting part. With plenty of empty space in their long-term books, they could favor signings. With bountiful talent in their farm system, they could just as easily favor trades. In any case, they won't have an excuse for a disappointing haul of arms.

American League West

3 of 6
Matt Chapman and Matt Olson
Matt Chapman and Matt Olson

Houston Astros: Whether to Re-Sign or Try to Replace Gerrit Cole

His postseason story has yet to be written, but Gerrit Cole can boast of producing an all-time-great walk year. He led the AL with a 2.50 ERA and recorded the highest strikeout rate in MLB history (13.8 K/9).

The unfortunate part for the Houston Astros is that re-signing Cole is likely to cost them between $200 and $250 million. Another is that if they spend that kind of money on him, they'll only have so much left for the other pitching holes they must fill.

The alternative would be to let the 29-year-old ace go and replace him with a pitcher who has similar upside. Naturally, this will be much easier said than done.

Los Angeles Angels: Whether to Splurge for an Ace or Depth

The Los Angeles Angels can look forward to Shohei Ohtani's return to the mound in 2020. Yet Andrew Heaney and Griffin Canning may be the only other locks for their rotation, and neither resembles an ace.

Fortunately for the Angels, there will be upgrades aplenty available on the open market. There should also be a few on the trade market, perhaps including New York Mets flamethrower Noah Syndergaard.

Trouble is, the Angels are saddled with a handful of expensive contracts and a farm system that has little talent outside of presumably untouchable outfielder Jo Adell. They therefore may face the difficult task of using their limited resources on one big catch or several smaller catches.

Oakland Athletics: Whether to Extend Matt Chapman and Matt Olson

The Oakland Athletics could lose one major free agent (Tanner Roark), and they might have to make some difficult non-tenders (Blake Treinen and Marcus Semien), but they're otherwise set up well.

As such, there may be no time like the near future to approach Matt Chapman and Matt Olson about extensions. They stand as arguably baseball's best corner infield duo following their combined 72 home runs and 11.8 WAR in the regular season.

But since big-money extensions are a rarity in Oakland, the A's may have to choose one or another. And that's assuming Chapman, 26, and Olson, 25, aren't already looking forward to arbitration in 2021 and free agency after 2023.

Seattle Mariners: Whether to Trade Mitch Haniger

Seattle Mariners general manager Jerry Dipoto is going to make trades. It's just what he does.

Yet even "Trader Jerry" faces a tough call with Mitch Haniger. The club is rebuilding, and he's due for arbitration in 2020, so now is seemingly a good time to cash in the 2018 All-Star. But on another hand, the 28-year-old is coming off a season that was difficult even before he ruptured a testicle.

Haniger's talent and three remaining years of club control might make it possible for Dipoto to find a good offer anyway. If not, Dipoto will have to risk seeing what happens with Haniger's trade value in 2020.

Texas Rangers: Which Stars to Acquire for Their New Stadium

Though Globe Life Park in Arlington is even younger than 25-year-old star Joey Gallo, the Texas Rangers are preparing to move into a new stadium in 2020 anyway.

Ballpark-related quibbles aside, the Rangers figure to actively shop for star talent worthy of their new home. And in the wake of a respectable 78-win season, there's a decent chance the right selections will lead them back to contention in 2020.

Ah, but which players are the right choices? The Rangers probably can't have, say, Gerrit Cole and Anthony Rendon. And if they fail to sign even one of them, they'll have to scramble to pick up what pieces they can elsewhere on the market.

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National League East

4 of 6
Anthony Rendon
Anthony Rendon

Atlanta Braves: Whether to Re-Sign or Replace Josh Donaldson

With a 97-win campaign, the Braves are going into the postseason as a World Series contender. But free agency will open many holes in their roster.

None will be bigger than the one at third base, which is occupied by Josh Donaldson. Following two straight injury-marred seasons, the 33-year-old bounced back in 2019 with a .900 OPS and 37 long balls. To boot, he resembled his old MVP-winning self in an outstanding second half.

According to Gabriel Burns of the Atlanta Journal-Constitution, Donaldson and the Braves have mutual interest in a reunion. But it would be costly, so the Braves will have to pick between writing a big check and trusting young slugger Austin Riley to replace Donaldson.

Miami Marlins: Whether to Extend Brian Anderson

The Miami Marlins have trended as expected since dealing Christian Yelich, Giancarlo Stanton and Marcell Ozuna after the 2017 season. But if nothing else, at least they're building an elite farm system.

While the Marlins wait to harvest fruit from said system, the best thing they can do now is ensure Brian Anderson is still around when the tide finally turns. The 26-year-old isn't a superstar by any means, but he's easily been Miami's best player over the last two seasons.

Anderson won't be a free agent until after 2023. But with his first year of arbitration eligibility due up in 2021, the clock is ticking for the Marlins to sign him to a club-friendly extension.

New York Mets: Whether to Trust Edwin Diaz

Despite myriad challenges along the way, the Mets won a respectable 86 games this season. What's more, their roster looks pretty good for the immediate future.

Even still, New York is probably only so comfortable with a bullpen that held it back with a 4.99 ERA and negative win probability added. Alleged ace closer Edwin Diaz, who saved 57 games in 2018, was particularly bad to the tune of a 5.59 ERA and 15 homers allowed.

Yet Diaz is only 25, and his velocity readings were par for the course. Hence the Mets' big conundrum with their bullpen: Do they proactively upgrade it or trust that all problems will be solved by Diaz's reverting back to his All-Star form?

Philadelphia Phillies: Where a Big Splash Is Needed Most

The Philadelphia Phillies made a noble effort to build a contender last offseason, but a combination of injuries and disappointing seasons resulted in a .500 flop in 2019.

With so much already invested in the team, the Phillies don't have much choice but to keep pushing the envelope. They also have needs all over their roster, most notably in the rotation, bullpen and at second and third base.

But since they're beset by a bloated payroll and a weak farm system, the Phillies may have to settle for making one big splash and picking their battles elsewhere. How they approach these efforts will determine whether improvement is in the cards.

Washington Nationals: Whether to Re-Sign or Replace Anthony Rendon and Stephen Strasburg

The Washington Nationals were one of the best teams in baseball from May 24, and they're now fresh off a win in the NL Wild Card Game that was, well, wild. 

But before long, 29-year-old star Anthony Rendon will become a free agent after October. According to Jon Paul Morosi of MLB.com, there's also a likelihood that 31-year-old ace Stephen Strasburg will use his opt-out to follow Rendon out the door.

Per Barry Svrluga of the Washington Post, the Nationals have already offered Rendon a $210-215 million contract. However, they probably can't do a deal like that and sign Strasburg at his market value. They'll likely have to choose one and replace the other.

National League Central

5 of 6
Kris Bryant
Kris Bryant

Chicago Cubs: Everything, but Specifically Whether to Trade Kris Bryant

Coming off an 84-win season that all but killed their plans for a dynasty, the Chicago Cubs are heading into their most consequential offseason since...well, maybe ever.

Which is to say that every decision they make will matter, yet they face especially difficult choices with regard to potential roster turnover. They may find it necessary to trade some of their core stars, up to and including 27-year-old third baseman Kris Bryant.

A deal would save the Cubs from raises on the 2016 National League MVP's $12.9 million salary via arbitration in 2020 and 2021 and could net a much-needed haul of young talent. It's either that or the Cubs can keep Bryant and hope he continues as their best player.

Cincinnati Reds: Whether to Sign or Trade for Offensive Upgrades

The Cincinnati Reds barely improved from 95 losses in 2018 to 87 losses this season, but they don't have much choice but to keep pushing forward with their effort to contend.

To that end, they need more firepower for an offense that finished 12th in the NL in runs per game. A left-handed complement for righty slugger Eugenio Suarez would be ideal, but the Reds might gain just as much from spreading several good hitters around their lineup.

However, the Reds are already spending big, and their farm system is trending backward. So whether they sign or trade for offensive upgrades, they'll pretty much be going all-in for 2020.

Milwaukee Brewers: Whether to Re-Sign or Replace Yasmani Grandal and Mike Moustakas

Losing Christian Yelich for the season on Sept. 10 should have doomed the Milwaukee Brewers. Instead, it's a feat that they even made it as far as the NL Wild Card Game.

Before long, however, the Brewers will almost certainly get a rude awakening when catcher Yasmani Grandal and third baseman Mike Moustakas decline their mutual options for 2020.

The two sluggers combined to hit 63 homers while earning a total of $23 million in 2019. The Brewers will have to pay a lot more to retain both or hope to re-sign one and find a suitable replacement for the other. Either way, a return to October will be in the balance.

Pittsburgh Pirates: Whether to Trade Josh Bell

After a 93-loss season that was made worse by inner turmoil, the Pittsburgh Pirates seem to have no other recourse than to enter into a rebuild.

The only question is how far they'll take it. For instance, trading center fielder Starling Marte seems to be a no-brainer. But if the Pirates decide a more drastic shift in direction is warranted, they'll put slugging first baseman Josh Bell on the block.

The 27-year-old's value is at its peak after his career bests in OPS (.936) and homers (37) and with his club control through 2022. But if the Pirates listen to their pride and hold on to Bell, they'll be risking his value descending and further ruin befalling the franchise.

St. Louis Cardinals: Whether to Trust Paul Goldschmidt and Matt Carpenter

What makes the St. Louis Cardinals' surge to the NL Central championship all the more impressive is that they featured a below-average offense.

No matter what happens in October, this is something the Cardinals must have on their minds. The problem will certainly be compounded by Marcell Ozuna's free agency. If he walks, the Cardinals will be saying goodbye to an .804 OPS and 29 long balls.

Yet the team's willingness to upgrade could be tied to its degree of confidence that Paul Goldschmidt and Matt Carpenter can hit more like they did in 2018 than in 2019. If they do, the Cardinals could get away without any upgrades. If not, they won't be so fortunate.

National League West

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Cody Bellinger
Cody Bellinger

Arizona Diamondbacks: Whether to Extend Nick Ahmed

The Arizona Diamondbacks were surprisingly competitive en route to 85 wins. Now the question is whether they'll lean in to contending or get ahead on dealing their many post-2020 free agents.

Even if the D-backs opt for the latter, they may have second thoughts about trading Nick Ahmed. The 29-year-old is a Gold Glove-winning shortstop and an improving hitter as well as a leader in the clubhouse, according to Jack Magruder of Forbes.

Because of the latter quality, Ahmed likely has more value to the Diamondbacks than he does to any other team on the trade market. If so, now would be the best time to sign him to an extension that locks him down as a core member of the team.

Colorado Rockies: Whether to Trade Nolan Arenado

The Colorado Rockies are reeling from an ugly 91-loss season. Meanwhile, they also have a heavy payroll and a diminished farm system.

In the face of these issues, the Rockies might not have an easy path back to the quality of life they enjoyed amid back-to-back postseason trips in 2017 and 2018. At worst, no such road exists, and the only thing they can do is rebuild.

Their nuclear option is trading superstar third baseman Nolan Arenado while his recently signed $260 million contract still looks like a fair deal. Alternatively, the Rockies can take all the money from their new TV pact and push their payroll even higher, which would only heighten their bust potential.

Los Angeles Dodgers: Whether to Extend Cody Bellinger

Nobody had a bigger hand in the Los Angeles Dodgers' 106-win season than Cody Bellinger. He's the likely NL MVP on the strength of a 1.035 OPS, 47 homers and MLB-best 9.0 WAR.

Couple that performance with Bellinger's history-making rookie season and the fact that he's still only 24 years old, and L.A. has every reason to want to keep him in Dodger blue for the rest of his career. The first step in that direction involves offering him a long-term contract extension.

Though Bellinger isn't due for free agency until after 2023, he's up for his first trip through arbitration in 2020. If the Dodgers dawdle on making him a fair offer, he may bet on himself with a huge free-agent payday in his sights.

San Diego Padres: Whether to Sign or Trade for an Ace

The San Diego Padres have issued $527 million to Wil Myers, Eric Hosmer and Manny Machado over the last three years, but they're only making incremental progress on the field.

If the Padres are going to make a quantum leap in 2020, they need an ace starter to lead the vanguard. Their pitching staff isn't short on intriguing talent, yet it still largely struggled with a 4.66 ERA in 2019.

Signing one, however, may be difficult precisely because of the aforementioned contracts. The Padres can otherwise dangle talent from their No. 1 farm system on the trade market, but an apparent shortage of options makes it look like a seller's market. They'll have to stretch their resources either way.

San Francisco Giants: How to Handle Mike Yastrzemski's Breakout

Though the San Francisco Giants played better than expected in 2019, they still have a payroll full of albatrosses and will likely lose star lefties Madison Bumgarner and Will Smith to free agency.

But even if the Giants enter a rebuild, they likely can't do much besides shed payroll. Unless, perhaps, they put rookie outfielder Mike Yastrzemski on the trading block in hopes of cashing in his breakout (.852 OPS and 21 homers).

A trade of Yastrzemski might indeed benefit the Giants' steadily improving farm system. But if the organization would rather throw its fans a bone, it could always keep Carl Yastrzemski's grandson around as the central attraction for the lean years that lie ahead. An extension might even be in order.

Stats courtesy of Baseball Reference and FanGraphs.

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