Predicting Each MLB Team's Most Nightmarish Contract by 2020

Zachary D. Rymer@zachrymerMLB Lead WriterSeptember 14, 2018

Predicting Each MLB Team's Most Nightmarish Contract by 2020

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    The biggest Major League Baseball contracts tend to age like...well, whatever the opposite of a fine wine is.

    So, it shouldn't be too hard to project which deals will be haunting teams a couple of years from now.

    We're going to predict each team's biggest nightmare contract by the year 2020. Some of these are active deals that are either already kaput or trending that way. Others are deals that could be signed in the near future and go bad in short order.

    We'll proceed in alphabetical order by city.

Arizona Diamondbacks: A.J. Pollock

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    Zack Greinke is aging too well to fear for the remainder of his $206.5 million contract. Yasmany Tomas' $68.5 million deal is already dead money, and 2020 will be the year it ends.

    Which brings us to A.J. Pollock.

    Along with Patrick Corbin and Eduardo Escobar, the center fielder is one of three major players the D-backs stand to lose to free agency this winter. Pollock is the best bet to be re-signed. There's mutual fondness between him and the team. Beyond that, Arizona doesn't have an in-house replacement lined up.

    But while Pollock is still a useful player now, his offense and defense have fallen from their 2014-15 peaks. He'll also be 31 in December, so he's at an age when what athleticism he still has could go at any moment.

    Pollock is basically the anti-Lorenzo Cain. His contract will play out as such.

Atlanta Braves: Craig Kimbrel

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    The Atlanta Braves have only one big-money contract on their books for 2020, and it belongs to the ever-reliable Freddie Freeman. Around him will be a ton of young, cheap talent.

    If the Braves are going to have a bad contract by 2020, chances are it'll belong to a free agent brought in to complement their current core. To this end, Craig Kimbrel is a possibility.

    Braves general manager Alex Anthopoulos has hinted to the media he'll have interest in bringing the 30-year-old closer back to Atlanta. His return would mark an ideal addition for a bullpen that lacks a relief ace. And thanks to their new ballpark and years of saving up, the Braves should be able to afford an Aroldis Chapman- or Kenley Jansen-sized contract. 

    However, it can't be ignored that Kimbrel's fastball velocity is down in 2018. If that's the start of a trend, his knack for eluding contact could also go. Then his home run and walk rates would become much bigger concerns. 

Baltimore Orioles: Chris Davis

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    The Baltimore Orioles could actually be hurt less by Chris Davis' contract in 2020 than they have been in 2018.

    This might seem impossible, given that Davis has been baseball's worst everyday player to the tune of minus-2.3 wins above replacement, according to Baseball Reference. If they were to simply stop playing him, it would be addition by subtraction.

    But short of Davis voluntarily retiring or some other team taking him on in a bad contract swap, the Orioles can't get out of paying the 32-year-old. That'll be a major inconvenience not only in 2020, but also for two more years afterward. His pact runs through 2022.

    The only way this deal can be salvaged is if Davis finds his power again. In light of his age and how his power has been trending, that's not happening.

Boston Red Sox: David Price

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    David Price can opt out of his seven-year, $217 million contract with the Boston Red Sox this winter. Since he's been pitching like his former Cy Young Award-winning self of late, perhaps he will.

    But don't count on it, the man himself told Christopher Smith of Price says he wants to "continue to be good here."

    Beyond that, Price is 33, and there are already red flags planted in his left elbow. It's doubtful that the free market would offer more than the $127 million he'll make in the final four years of his Red Sox deal.

    For their part, though, the Red Sox may be hoping that Price opts out anyway. The alternative is paying him an awful lot of money to either get hurt or to have his margin for error become smaller as his fastball velocity continues to decline.

    In either event, they'll be paying ace money for a non-ace.

Chicago Cubs: Yu Darvish

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    It's hard to think highly of a six-year, $126 million contract that's already a disaster in year one.

    Yu Darvish managed only a 4.95 ERA in his first eight starts for the Chicago Cubs. Then he vanished onto the disabled list with an elbow injury that ultimately ended his season

    This is not the first time that Darvish's right arm has broken down. Because he's a 32-year-old with over 2,100 professional innings on his arm, nor is it likely to be the last. And even if he stays healthy, his days as a power pitcher are probably numbered.

    Mind you, the Cubs should also be worried about how Jason Heyward's and Jon Lester's contracts will look in 2020. But the former should still have defense going for him, while the latter will be in the final guaranteed year of his deal.

Chicago White Sox: Matt Harvey

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    Tim Anderson's dirt-cheap salary is the only guaranteed money on the Chicago White Sox's 2020 books. And with their rebuild in the "not quite done" phase, it may be another year before they spend big in free agency.

    So...[/shrugs]...Matt Harvey?

    The 29-year-old right-hander has reclaimed some value since hopping from the New York Mets to the Cincinnati Reds in May, but not enough to be anything more than a free-agent upside play.

    With James Shields set to leave, the White Sox are one team that may be interested. They're building their rotation around power arms. And as's Dayn Perry noted when Harvey was in limbo in May, White Sox pitching coach Don Cooper has a track record of repairing broken veterans. 

    Still, Harvey could struggle to live up to even a modest multiyear deal. The fastball velocity that he's found in Cincinnati is still nothing like what he had at his peak. If that's a problem in the National League, it would be a worse one in the American League.

Cincinnati Reds: Joey Votto

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    No matter what the Reds do in coming years, Joey Votto's 10-year, $225 million contract will continue to lord over their payroll.

    That hasn't been much of a problem to this point. The Reds have lost many games in recent years, but Votto has carried on as one of the best pure hitters in baseball history. To wit, 2018 should be his third straight and seventh overall season as the NL's on-base percentage leader.

    Votto just turned 35, however, and there are ways in which he's already looking his age. Worst of all, his power has finally declined below the MLB average. Without that, he can't be an elite hitter no matter how high his OBP goes.

    Votto's durability is also worth worrying about. If years and years as an iron man can finally get to Miguel Cabrera, they could get to Votto, too.

Cleveland Indians: Michael Brantley

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    With Michael Brantley, Andrew Miller, Cody Allen, the newly acquired Josh Donaldson and many more set for free agency, the Cleveland Indians are ticketed for a busy offseason.

    If one of their pending free agents is a good bet to come back—and add to their relatively light 2020 commitments—Brantley's the guy. Cleveland can't afford to lose the best piece from its outfield, and his injury history should open an opportunity to re-sign him for a relative discount.

    But since he's already 31 now, Brantley is never going to be far beyond the clutches of the injury bug. It wouldn't be the biggest shock if he spent the bulk of a new contract on the disabled list.

    If the DL doesn't get Brantley, declining athleticism might. He's already a below-average runner whose defense comes with red flags. If his power also goes, even his excellent feel for hitting won't be enough to save him.

Colorado Rockies: Ian Desmond

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    For now, the Colorado Rockies are to be commended for being on the doorstep of the playoffs despite getting down years from three big-money players: Ian Desmond, Wade Davis and Charlie Blackmon.

    They may not be so lucky in the future, however. Particularly not where Desmond is concerned.

    His five-year, $70 million contract went bust right away in 2017, as he debuted with minus-1.1 WAR. So it goes in 2018, in which he's improved to only minus-0.7 WAR.

    In fairness to Desmond, he's hit well for the bulk of 2018. He's nonetheless settled into a life as a below-average hitter, no thanks to an absurdly high ground-ball rate. He's also a player without a true home on defense.

    Throw in how Desmond will turn 33 on Sept. 20, and it's impossible to see his future as anything other than bleak.

Detroit Tigers: Miguel Cabrera

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    The Detroit Tigers are stuck with two big contracts as they seek to rebuild, but there is some good news: Jordan Zimmermann's deal will be in its final year come 2020.

    Miguel Cabrera's eight-year, $240 million contract, however, isn't due to end until 2023.

    It was easy to predict calamity for Miggy's contract even as soon as he signed it back in 2014. He was coming off his second straight AL MVP, but he was past 30 with some injury red flags, and his deal wouldn't kick in until 2016.

    In fairness to Cabrera, that '16 season was yet another brilliant one in what should be a Hall of Fame career. But he's put up just a .754 OPS in 168 games since then. When 2019 comes around, he'll be 35 years old and looking to bounce back from season-ending biceps surgery.

    Cabrera is too good a hitter to completely fall off the radar. Nonetheless, he's already fading on it.

Houston Astros: Dallas Keuchel

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    The Houston Astros stand to lose Dallas Keuchel and Charlie Morton to free agency. They can commit one of their spots to top prospect Forrest Whitley, but re-signing one of them is sure to be a priority.

    If nothing else, Keuchel (30) has youth on Morton (34). And while he'll be able to market himself as the 2015 AL Cy Young Award winner, assorted questions about what's befallen him since then could push him back to a safe port in Houston, which is due enough salary relief to afford, say, a $20-million-per-year contract.

    The Astros will regret that, however, as questions about Keuchel's last three years are well-founded.

    He's had some injuries, for one thing. For another, his velocity has decreased and made a rise in contact unavoidable. In two of the last three years, alarmingly little of that contact has been on the ground.

    Keuchel may be able to get Jake Arrieta money as a free agent. If his issues persist, he wouldn't earn it as well as Arrieta has so far.

Kansas City Royals: Ian Kennedy

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    The Kansas City Royals are still in the early stages of their rebuild, so it's possible that trades will take Danny Duffy's and/or Salvador Perez's big-money contracts off their 2020 books.

    They're not going to be able to rid themselves of Ian Kennedy, however.

    The 33-year-old righty started his five-year, $70 million contract off strong with a 3.68 ERA in 33 starts in 2016. He's slumped to a 5.20 ERA over 49 starts since then. This year, he suffered an oblique injury that sidelined him for two months.

    The Royals may have only been attracted to Kennedy in the first place because they figured that Kauffman Stadium could curb his home run problem. Alas, it hasn't. Between that, his age and his heavy workload history, it'll be nigh impossible to move him in a bad contract swap.

    On the bright side, 2020 will mark the final year of his deal.

Los Angeles Angels: Albert Pujols

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    Unfortunately for the Los Angeles Angels, the end of Albert Pujols' days as a useful player has come much sooner than the end of his 10-year, $240 million contract.

    Pujols still has three years left on his deal after 2018. There's zero chance that he'll earn his keep in those three years, simply based on three facts:

    • His bat is dead
    • His body is broken
    • He's 38 years old

    The only question is if the Angels can bring themselves to keep playing Pujols. It's either that or aim for addition by subtraction, which they could achieve by letting him go and signing even a bargain-barrel first baseman (e.g., Lucas Duda).

    But unless he does them a solid by retiring, the Angels can't get out of paying Pujols. One way or another, they'll pay him $87 million for nothing through 2021.

Los Angeles Dodgers: Clayton Kershaw

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    Because he can opt out of his seven-year, $215 million contract, there's technically a chance Clayton Kershaw and the Los Angeles Dodgers part ways this winter.

    But realistically? Less so. After running into injury and performance issues in recent years, Kershaw may not say no to the $70 million he's due in 2019 and 2020. Even if he does, the Dodgers are sure to find a way to keep the modern-day Sandy Koufax in town.

    In either event, Kershaw will be making too much money to possibly live up to in 2020.

    Although no pitcher was even close to Kershaw's level between 2011 and 2015, injuries have limited him to only 70 starts in three years since. He does have a 2.15 ERA in these starts, but that obscures declining stuff and, with it, a declining strikeout rate.

    Kershaw still has the goods to be an ace. Just not one that's as priceless as he is peerless.

Miami Marlins: Wei-Yin Chen

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    The Miami Marlins got rid of pretty much all their big contracts last winter. With a ways still to go in their rebuild, it's bound to be a while before they seek to add any big contracts.

    But then there's the one which they can neither hope to jettison nor hope to reap benefits from: Wei-Yin Chen.

    Chen was signed by the pre-Derek Jeter Marlins regime for five years and $80 million in January 2016. His contract seemed steep even at the time, and Chen immediately flopped with a 4.96 ERA over 22 starts. In 2017 and 2018, he's stayed flopped with a 4.52 ERA over 32 appearances.

    The 33-year-old's elbow is damaged goods, and what had been a strong ability to rack up more strikeouts than walks is gone. With these things have gone any hope of him being a useful asset. And since he still has $44 million headed his way, he's all but immovable.

Milwaukee Brewers: Ryan Braun

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    The Milwaukee Brewers will have at least three big-money players on their books in 2020: Ryan Braun, Lorenzo Cain and Christian Yelich.

    Even now, one of these things is not like the other two.

    Braun was en route to winning the NL MVP award in April 2011 when the Brewers signed him to a second contract extension, which would pay him $105 million between 2016 and 2020. In seven seasons since then, however, he's dealt with performance-enhancing drug controversies, injuries and declining production.

    In 2018, Braun has finally ceased to be even a "good" player. Although he plays a decent left field, his glovework has been undercut by roughly average offense and little activity on the basepaths.

    If this is Braun's reality at 34, his reality at 36 isn't going to be any better.

Minnesota Twins: Daniel Murphy

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    The Minnesota Twins don't have any guaranteed money on their 2020 books. And due to the fragility of their immediate contention chances, they probably won't be looking to bloat any time soon.

    But if nothing else, they'll have money with which to lure a replacement for Joe Mauer at first base this winter. The Wild Guess Meter points to Daniel Murphy, a professional hitter who has no business playing second base anymore, in a multiyear deal will be their ideal play.

    At least in theory. In reality? Less so.

    Murphy was one of baseball's elite hitters between the fall of 2015 and 2017, but then came microfracture surgery on his right knee last October. He hasn't been the same hitter in his return, in large part because his hard-hit rate has cratered.

    At 33, Murphy may be too old to recover from these trials.

New York Mets: Yoenis Cespedes

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    The New York Mets will still be paying Yoenis Cespedes, Jay Bruce and (with help from insurance) David Wright in 2020. It's more than a safe guess that none of them will be worth it.

    But if it's a question of which will be the biggest drag on the team's payroll, well, only one of them will be making $29.5 million: Cespedes.

    To give Cespedes his due, he's been a boon to the Mets when he's been able to suit up. He has an .890 OPS and 74 home runs in 308 games with the team since 2015. 

    Staying healthy, however, has been the hard part for the 32-year-old. And never more so than now. The surgery that he had on both of his heels in July will require eight-to-10 months of recovery time.

    There goes a chunk of Cespedes' 2019 season, and probably whatever hope he had of ever resembling his vintage five-tool self ever again. 

New York Yankees: Patrick Corbin

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    The New York Yankees already have plenty of guaranteed money on their 2020 books. More will be added this winter when they celebrate getting under the luxury tax with a massive spending spree.

    With J.A. Happ, CC Sabathia and Lance Lynn due to enter the open market, the Yankees' top priority will be signing a starting pitcher. They should be able to conjure a $100 million contract for Corbin, who grew up a Yankee fan and still appreciates the team.

    Trouble is, Corbin's fastball velocity is already way down. That doesn't portend good things for a possible move to the AL East, which could straighten out his home-run-per-fly-ball rate in a hurry.

    And whereas Jacoby Ellsbury and Masahiro Tanaka will be in their final guaranteed years, 2020 probably won't even mark the midpoint of a deal for Corbin.

Oakland Athletics: Nathan Eovaldi

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    With Trevor Cahill, Brett Anderson and Edwin Jackson ticketed for free agency and Sean Manaea due to miss all of 2019 recovering from shoulder surgery, the Oakland A's will need starters this winter.

    These are the A's we're talking about, so the top free-agent starters can be ruled out. But their need is so strong that they may not have much choice but to extend themselves for a relatively expensive upside play.

    To pull a name out of a hat, Nathan Eovaldi could be a match. Although there haven't been many bright spots in his career, the promise of a breakout still exists because of his youth (he's 28) and upper-90s fastball. Perhaps the A's will deem these things worthy of a multiyear gamble.

    But at this point, it's hard to imagine any team cracking Eovaldi's code. He has a big arm, yet he's had a hard time racking up strikeouts and keeping hard contact at bay. Hence his relative shortage of bright spots to this point—and probably forever after.

Philadelphia Phillies: Andrew Miller

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    How will the Philadelphia Phillies respond to their late-season swoon? Probably by going full John Hammond and sparing no expense in free agency.

    After opening 2018 with just a $95.3 million payroll, the Phillies can easily sign Machado or Harper. They're also sure to be in the market for a relief ace. If they do indeed sign Machado or Harper, they might bypass a megadeal for Kimbrel and settle for the market's next-best thing: Andrew Miller.

    If so, they'll regret it.

    Miller dominated with a 1.72 ERA between 2014 and 2017. But he's 33 now, and he's looked it in 2018. Injuries have limited him to 29 good-not-great appearances, and there's no longer anything special about his fastball velocity or his control.

    The Phillies would be banking on a return to good health and productivity with a multiyear deal for Miller. Neither would be assured.

Pittsburgh Pirates: Chris Archer

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    The Pittsburgh Pirates don't have to pay Chris Archer beyond 2019. He'll only stick around for 2020 and/or 2021 if they exercise his options.

    Still, it's a safe bet that they'll take their shots. Those two options are worth only $20 million total. And after giving up Tyler Glasnow, Austin Meadows and Shane Baz to get Archer, the Pirates will surely want as many chances as possible to get their money's worth out of him.

    Trouble is, Archer's devolution seems irreversible.

    The hard-throwing righty was really good between 2013 and 2015, but he has just a 4.17 ERA since 2016 for good reasons. His fastball is no longer faster than all other heaters by a significant margin, and it shows. Since 2016, hitters have consistently slugged over .500 against it. 

    Because Archer will turn 30 on Sept. 26, any notions of him finding more velocity are pure fantasy.

San Diego Padres: Eric Hosmer

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    Eric Hosmer was a frustratingly inconsistent player in seven seasons with the Royals, but that didn't stop the San Diego Padres from signing him to an eight-year, $144 million contract.

    One year in, it doesn't look like Hosmer has any plans to stop being frustratingly inconsistent.

    Hosmer has just a .713 OPS and 16 home runs in his debut season as a Padre. And in keeping with tradition, the metrics still aren't sure what to make of his defense.

    Since Hosmer is still only 28, one can hope that he diagnoses what's wrong and snaps out of it. But his defense seems to be an unsolvable Rubik's Cube, and his offense is beset by a mix of old (ground balls) and new (strikeouts) problems.

    In short, the biggest contract in San Diego's history belongs to a deeply flawed player.

San Francisco Giants: Johnny Cueto

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    The San Francisco Giants are obligated to pay Buster Posey, Johnny Cueto, Jeff Samardzija, Brandon Belt, Brandon Crawford, Evan Longoria and Mark Melancon over $125 million in 2020.

    That's a lot of money for players who are past their primes right now. But if one player must be singled out as the biggest potential waste, it should be Cueto.

    His $21.8 million salary will be topped only by Posey's $22.2 million payout, and Cueto will be owed the same figure in 2021. He faces a particularly tall order in earning that money.

    After undergoing Tommy John surgery in August, it's not guaranteed that the veteran righty will even pitch in 2019. In 2020, he'll be 34 years old and four years removed from his last season as an ace-caliber pitcher.

    Combine all these things together, and there's not much room for optimism.

Seattle Mariners: Kyle Seager

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    Robinson Cano's 10-year, $240 million contract will only be in its seventh year come 2020. In light of his age (35) and recent PED suspension, that should set off some alarm bells.

    But Cano may not be doomed. Unlike Pujols, Cano is aging fairly well on offense. Plus, an inevitable transition to a full-time first base/DH role should keep him healthy.

    Kyle Seager, on the other hand, truly is getting worse as he gets deeper into his seven-year, $100 million contract.

    After averaging 4.7 WAR per year between 2012 and 2016, the 30-year-old has mustered a total of 3.3 WAR since 2017. His bat has sunk to a .665 OPS in 2018. Per the metrics, his glovework might also be on thin ice.

    If things continue in this fashion, it'll become tougher for the Seattle Mariners to salvage anything from his contract.

St. Louis Cardinals: Dexter Fowler

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    The best way the St. Louis Cardinals can avoid further disappointment with Dexter Fowler is by moving him in a bad contract swap this winter.

    This could actually be doable. Fowler was still hitting at a high level as recently as 2017. If he were to get back to that, the $49.5 million he's owed through 2021 would be money well spent.

    And yet, there will be complications abound in marketing Fowler. The broken foot that ended his season in August is only the latest in a long line of injuries. Before that, he had been mired in a catastrophic slump that lowered his OPS all the way to .576.

    If the Cards can't move Fowler this winter, they may have wasted their last good chance to do so. Rather than bounce back in 2019, the 32-year-old could go right back to being an injured, unproductive mess. That would doom him to remaining an albatross in St. Louis.

Tampa Bay Rays: Kevin Kiermaier

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    Kevin Kiermaier "wins" by default.

    His six-year, $53 million contract accounts for the only guaranteed money the Tampa Bay Rays have on their books past 2018. Since they're fully loaded with talented players who are both young and cheap, they have no immediate need to add sizable contracts.

    As for Kiermaier, the Rays know they can count on him to play excellent defense. It says enough that no other center fielder is even close to matching his 98 defensive runs saved since 2015.

    Instead, the Rays must worry about the 28-year-old's health and offensive productivity. Injuries have limited him to 281 games over the last three seasons. And this year, he's slumped to a .671 OPS.

    Any more of this, and the final four years of Kiermaier's deal will be rough.

Texas Rangers: Elvis Andrus

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    The Texas Rangers can't feel too great about having Shin-Soo Choo, Mike Minor, Rougned Odor and Elvis Andrus on their books through 2020.

    But at least the first two will be in their final guaranteed seasons, while the third is a 24-year-old who's remembered how to be a productive hitter in 2018.

    This leaves Andrus, who's unlikely to exercise the opt-out in an eight-year, $120 million contract that runs through 2022. 

    That's no surprise, given that this has been one of his least productive seasons. Because Andrus' 2018 woes can't be separated from a fluky broken elbow that he suffered in April, it's within reason that he'll get back on track in 2019.

    Yet, it's not certain. Andrus is now on the wrong side of 30 and past his athletic peak. In light of his history at the plate before 2016 and 2017, his return to below-average hitting in 2018 ought to raise a skeptical eyebrow regarding his future.

Toronto Blue Jays: Troy Tulowitzki

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    When or even if Troy Tulowitzki will play again are good questions, but this much is certain: He'll still be on the Toronto Blue Jays' payroll in 2020.

    That'll be the final season of the six-year, $118 million extension he signed with the Rockies in 2010, when he was smack in the middle of a reign as arguably baseball's best shortstop.

    But those days were on the wane by the time Tulo got traded to the Blue Jays in 2015, and the wane has continued unabated. He mustered 3.4 WAR in 197 games in 2016 and 2017, and he's missed 2018 while recovering from surgery on both heels.

    The 33-year-old has vowed to return as Toronto's shortstop, but his age and injury history will make that difficult. What hope he has of being useful again rests in his bat. Considering the modest .751 OPS it's produced since 2015, that also looks like a long shot.

Washington Nationals: Stephen Strasburg

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    The Washington Nationals will have to pay Max Scherzer $42.1 million per year from 2019 to 2021. That's a lot of money, so it's a good thing he's Max Scherzer.

    By comparison, paying Stephen Strasburg $138.3 million through 2023 is a lot less appetizing.

    The Nationals knew about Strasburg's injury proclivity when they extended his contract in 2016, and the fates haven't made them look wise in retrospect. Shoulder inflammation has limited the righty to 19 starts this season, which will be his fourth straight of fewer than 30 outings.

    On top of that, the 30-year-old has posted a pedestrian 3.87 ERA when he has been healthy. Home runs are back to being a problem. When (not "if") age starts to rob him of his fastball velocity, that problem will get worse, and other issues will probably keep it company.


    Stats are accurate through Wednesday, Sept. 12, and are courtesy of Baseball Reference and FanGraphs.