MLB Players Who Can Earn Themselves Huge Paydays Down the Stretch

Zachary D. Rymer@zachrymerMLB Lead WriterAugust 29, 2017

MLB Players Who Can Earn Themselves Huge Paydays Down the Stretch

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    Ross D. Franklin/Associated Press

    The postseason isn't the only thing players will be playing for as the 2017 Major League Baseball season winds down. Some should also have massive paydays in their sights.

    The list isn't entirely composed of upcoming free agents. They take up only three slots, with the other five being players who could sign contract extensions with the teams they're already on.

    The list is also exclusive for guys who actually have something left to prove. Players like J.D. Martinez, Eric Hosmer, Mike Moustakas and Wade Davis have strong track records and have been good from day one this season. The stretch run shouldn't make or break their earning power.

    That's it for the ground rules. Beginning with the three upcoming free agents, let's get to it.

Justin Upton, Detroit Tigers

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    Offseason Status: Can Opt Out of 6-Year, $132.75M Contract

    Justin Upton can opt out of the four years and $88.5 million remaining on his contract, but he's signaling that he'll cross that bridge when he gets to it.

    "I can't make a decision on that right now, so that doesn't affect me right now," the left fielder told MLB.com's Jason Beck. "It's always nice to have options, but I think it's more interesting to you guys than it is to me."

    Granted, $88.5 million is no small sum. But the 11-year veteran is on a Detroit Tigers team that's going nowhere. He's also still just 30 years old and pushing for new career highs in OPS (.913) and home runs (28 so far). These are good reasons for him to seek greener grass and greater riches this winter.

    The greater riches part isn't a given, however. As Dave Cameron covered at FanGraphs, the free-agent market has soured on power-centric players like Upton. Thus, his earning power must not be overestimated.

    To this end, a strong finish can only help. Such a thing could cement his 2017 season as his best yet as well as one of his most consistent. Given that inconsistency has long been a knock against Upton, that alone could earn him an extra dollar or two.

Jake Arrieta, Chicago Cubs

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    Offseason Status: Free Agent

    Jake Arrieta broke out as an ace in 2014, won the National League Cy Young in 2015 and helped the Chicago Cubs win the World Series in 2016. He's cloaked in all the trappings of a big-money pitcher.

    But with his free agency now just months away, the sky no longer seems to be the limit for his earning power. He has himself to blame for that, as he violated the terms of his ace status with a full year of mediocre pitching with a 4.55 ERA in 32 starts across 2016 and 2017.

    Arrieta and agent Scott Boras have had a six- or seven-year deal in mind, according to a June report from Jon Heyman of FanRag Sports. However, a rival executive floated five years as a more reasonable figure, per Heyman.

    Although that did sound appropriate at the time, Arrieta has since resumed pitching like an ace. He has a 1.85 ERA over his last 10 starts, making him one of MLB's elite second-half pitchers.

    Another month of that would jack up the 31-year-old's price tag. He could jack it up even further if he improves on his up-and-down postseason track record in October. Ultimately, a six- or seven-year deal could be well within reason.


    Follow Arrieta and the Cubs all season with the B/R app.


Yu Darvish, Los Angeles Dodgers

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    Offseason Status: Free Agent

    Yu Darvish doesn't need to worry about getting paid this winter. He'll be arguably the best free agent available, so it's going to happen.

    Yet it's also possible to imagine his stock being even higher.

    With a 3.41 ERA and an MLB-best strikeout rate in 126 major league starts since 2012, Darvish has been quite good when he's been able to pitch.

    One catch, of course, is that he isn't always able to pitch. He missed 2015 recovering from Tommy John surgery and is gunning for just his second season of 30-plus starts. And since he only recently came off the disabled list, it's going to be close.

    There are also nits to pick with Darvish's pitching ability. He's mostly been good, but 2013 remains his only Cy Young-caliber season. Even this year, his 3.88 ERA over 160 innings make him an also-ran in wins above replacement.

    Nonetheless, the 31-year-old is a lock for a contract worth well over $100 million. If he were to polish off his 2017 numbers with a hot stretch in September and then prove himself as a formidable postseason weapon in October, his price tag would climb closer to $200 million.

Dallas Keuchel, Houston Astros

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    Offseason Status: 3rd-Year Arbitration-Eligible

    Dallas Keuchel is just a year away from free agency. But if he gets there, he'll be sharing a crowded market with Bryce Harper, Manny Machado, Josh Donaldson and possibly Clayton Kershaw.

    Beyond the risk of being somebody's Plan C, D or E on one of the best free-agent markets ever, Keuchel also has his longevity to worry about. He's only been a major leaguer for six years, but he's already pushing 30. And he's lost significant time to injuries over the last two seasons.

    These things make him a candidate to strike while the iron is hot this winter. In the meantime, he must heat the iron as much as possible.

    The left-hander began the year looking like his Cy Young-winning self again, but has only recently gotten back on track following a lengthy stay on the DL with a bad shoulder. He has a 1.31 ERA over his last three starts. More of the same in September and October would further salvage his season.

    Then getting paid would just be a matter of waiting for the Houston Astros, who have few long-term salary commitments, to come to the table. Ultimately, the two sides could come together on a nine-figure contract.

Anthony Rendon, Washington Nationals

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    Offseason Status: 2nd-Year Arbitration-Eligible

    Don't count on the Washington Nationals extending Harper this winter. He's already signed for 2018 and will have a shot at a record contract the following winter. He's as good as gone.

    Anthony Rendon is a different story. The 27-year-old doesn't have Harper's upside, but WAR shows he's been nearly as valuable to the Nationals since 2014. That speaks to his underrated skill set and consistency.

    Plus, Rendon has fewer reasons than Harper to hold out for free agency.

    Certainly the biggest is that he's still a good way away from it. This winter will bring his third trip through arbitration, but he's not due to hit the market until after 2019. Given that he's struggled with injuries, that presents a big target for the injury bug to aim at.

    Meanwhile, Rendon must show the Nationals why he's a good guy to lock up. He's already done a heck of a job of that in carving out a career-best .943 OPS and 22 homers. But since August has been his worst month, he has redemption to seek in September and October.

    If all goes well, he could target a $100 million deal in extension talks. If Kyle Seager is worth that, then so is Rendon.

Xander Bogaerts, Boston Red Sox

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    Michael Dwyer/Associated Press

    Offseason Status: 2nd-Year Arbitration-Eligible

    Xander Bogaerts has this much in common with Rendon: He's a star on a rich team that has growing incentive to lock him up.

    As is typical of Scott Boras' clients, Bogaerts wasn't keen on signing an extension when he was headed into his first arbitration dance earlier this year. But he at least left the door open.

    "If the right deal presents, obviously you're going to get something done," Bogaerts said, per ESPN.com's Scott Lauber.

    Bogaerts is headed for his second dance with arbitration this winter, and is ticketed for free agency after 2019. So, he could have more leeway to extract the "right deal" from the Boston Red Sox.

    The "could" is necessary because Bogaerts must first improve his stock. He began 2017 looking like the star shortstop he was in 2015 and 2016, but then injured his hand and got mired in a bad slump.

    The 24-year-old has finally begun to snap out of it with an .899 OPS over his last 14 games. More of that in September and October would give him the leverage he needs to blow away the recent extensions of fellow shortstops Jean Segura and Brandon Crawford.

Mookie Betts, Boston Red Sox

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    Offseason Status: 1st-Year Arbitration-Eligible

    As much as the Red Sox would like to lock up Bogaerts, they'd love to sign Mookie Betts.

    He's also 24 and, unlike Bogaerts, is one of the very best players in MLB. The right fielder was the MVP runner-up to Mike Trout last season. He's also the runner-up to Trout in WAR compiled since 2015.

    However, Betts has gotten a reality check this season. His excellent defense and baserunning have kept his overall value afloat, but his OPS has fallen from .897 to .783. He's yet to hit the peaks he reached last year and has been slumping hard in recent weeks (.231 BA, .663 OPS in August).

    There's no time like the present for Betts to get hot again. His bat can help stabilize a Boston offense that could use more stability for the purpose of wrapping up the AL East. After that, the postseason would present an opportunity to carry the team even further.

    According to Heyman, the Red Sox approached Betts about an extension last winter, only to be shot down. With plenty of production in his wake, his first year of arbitration on deck and free agency three years away, his increased leverage for a megadeal could change his attitude this winter.

Kris Bryant, Chicago Cubs

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    Offseason Status: 1st-Year Arbitration-Eligible

    The Kris Bryant Payday Watch has been on since he debuted on April 17, 2015. The drama only heightened as he gathered a Rookie of the Year, an MVP and a World Series ring.

    Nonetheless, it was too soon for the Cubs to extend him last winter. They did make a run at it, according to Tom Verducci of Sports Illustrated, but his source said they "got nowhere."

    Simply being a Boras client makes Bryant a hard get for an extension. And if Boras is going to sign a client to an extension, it's not going to be while until said client isn't yet arbitration eligible.

    That's at least one thing that will change this winter, as Bryant will be eligible for the first of four arbitration years. That will up his negotiating leverage by default.

    And while the 25-year-old's value is already sky-high, there's room for him to send it even higher. A red-hot showing in September and October would do two things: make his 2017 season arguably even better than his MVP-winning 2016 season and help him shake his well-deserved reputation as an unclutch hitter.

    If Bryant can do that, there will be nothing left for him to prove. If he and the Cubs were to sit down and try to make music on a long-term deal, the end result could be something epic.

            

    Data courtesy of Baseball Reference and FanGraphs. Stats are updated through games played on Monday, Aug. 28. 

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