Every MLB Team's Biggest Free-Agency Fail of the Past Decade

Jacob Shafer@@jacobshaferFeatured ColumnistDecember 21, 2017

Every MLB Team's Biggest Free-Agency Fail of the Past Decade

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    Carlos Osorio/Associated Press

    It's a cruel, unavoidable fact of the MLB offseason: Every year, some teams fail in free agency.

    That can mean not signing a player. It can also mean doling out a terrible contract.

    While we await the latest hot-stove chatter, let's focus on the latter category and dredge up each franchise's biggest free-agency fail of the past decade. A few things to keep in mind:

    • We're looking at every offseason since 2007-08, so ugly moves made before then don't count.
    • Production versus money spent is paramount. But we're also considering the optics of each signing, aka how much sense (or lack of sense) it made at the time. From there, we're adding a dusting of hindsight-aided subjectivity. This isn't simply a calculation of stats to dollars.
    • In some cases, the contract in question has run its tragic course. In others, there's a chance for redemption.

Arizona Diamondbacks: INF/OF Yasmany Tomas

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    Rick Scuteri/Associated Press

    The contract: Six years, $68.5 million, signed in November 2014

    The aftermath: The Arizona Diamondbacks hoped they were getting a powerful lineup anchor to pair with first baseman Paul Goldschmidt when they signed Cuban slugger Yasmany Tomas prior to the 2015 campaign.

    Tomas showed flashes in 2016 when he hit 31 home runs and posted an .820 OPS. Overall, though, the 27-year-old owns a pedestrian .268/.307/.462 slash line and suffered a series of injuries in 2017 that culminated in season-ending core surgery.

    There's time for Tomas to rebound. If he doesn't, the D-backs will burn $46 million over the next three seasons (assuming Tomas exercises his player options after the 2018 and 2019 seasons) on a big-swinging bust.

Atlanta Braves: LF/CF/RF Melvin Upton

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    Mike Zarrilli/Getty Images

    The contract: Five years, $75.3 million, signed in November 2012

    The aftermath: When the Atlanta Braves signed Melvin Upton in November 2012, he was still known as B.J. and was coming off a season in which he hit a career-high 28 home runs and stole 31 bases for the Tampa Bay Rays.

    Upton's first season in Atlanta was an unmitigated disaster, as he hit just .184 with a paltry .557 OPS. Those totals rose only slightly to .208 and .620 in 2014, and Upton was traded that winter to the San Diego Padres as a throw-in with closer Craig Kimbrel.

    The Braves managed to shed a healthy chunk of Upton's salary, a decent consolation in the wake of a dreadful deal.

Baltimore Orioles: 1B/OF Chris Davis

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    Gail Burton/Associated Press

    The contract: Seven years, $161 million, signed in January 2016

    The aftermath: The Baltimore Orioles opened their wallet wide in the winter of 2015-16 to bring back slugger Chris Davis, who had paced baseball with 47 home runs the previous season.

    It seemed like an overpay at the time with the Orioles largely bidding against themselves, as Sporting News' Jesse Spector snarkily pointed out. 

    It's gone from overpay to albatross, as Davis slashed .221/.332/.459 in 2016 and .215/.309/.423 in 2017. Last season, amid the game's power explosion, he hit a relatively modest 26 home runs. 

    Just imagine what he'll be doing in 2022, when he'll turn 36 and the O's will pay him $23 million. Or, if you're a Baltimore fan with a weak stomach, don't.

Boston Red Sox: 3B Pablo Sandoval

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    Patrick Semansky/Associated Press

    The contract: Five years, $95 million, signed in November 2014

    The aftermath: Pablo Sandoval's Boston Red Sox career was light on production and heavy on disappointment. 

    Yeah, sorry, weight jokes are easy.

    In 161 games spread over parts of three injury-plagued seasons with Boston, Sandoval slashed .237/.286/.360 with 14 home runs before the Sox cut him loose. Now, the team will pay Sandoval more than $40 million over the next three seasons to play for someone else—or not at all.

    His isn't the only awful contract the Sox handed out over the past decade. They gave seven years and $142 million to Carl Crawford in December 2010 and seven years and $72.5 million to Rusney Castillo in August 2014.

    The fact that Sandoval's deal is still the worst says it all.

Chicago Cubs: RF Jason Heyward

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    Patrick Smith/Getty Images

    The contract: Eight years, $184 million, signed in December 2015

    The aftermath: The Chicago Cubs won the World Series the season after they signed Jason Heyward. He's won two Gold Gloves for his play in right field with the Cubbies.

    So what makes this a fail?

    How about this: Heyward has hit a combined 18 home runs in his two go-rounds with Chicago while posting a .669 OPS. Those would be solid totals for a utility infielder. For a corner outfielder making more than $20 million annually, they're subpar to say the least.

    Heyward can opt out of his contract after the 2018 season. Unless his offensive output dramatically improves, he'll remain on the North Side and curtail the Cubs' payroll for years to come.

Chicago White Sox: 1B/OF/DH Adam Dunn

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    Ted S. Warren/Associated Press

    The contract: Four years, $56 million, signed in December 2010

    The aftermath: The Chicago White Sox knew they were getting a one-dimensional slugger when they inked Adam Dunn. What they didn't count on was his failing to slug.

    In 2011, the first year after Chicago handed him more than $50 million, Dunn hit .159 with a scant 11 home runs in 122 games. He rebounded the following year to club 41 homers, though he also led MLB with 222 strikeouts.

    By the time White Sox cut bait and traded Dunn to the Oakland A's in 2014, he'd amassed a zero-dimensional .201/.321/.410 slash line on the South Side.  

Cincinnati Reds: RHP Jonathan Broxton

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    Joe Robbins/Getty Images

    The contract: Three years, $21 million, signed in November 2012

    The aftermath: The Cincinnati Reds acquired Jonathan Broxton from the Kansas City Royals at the 2012 trade deadline, and the big right-hander posted a 2.82 ERA in 25 appearances. 

    The Reds re-signed him to a lucrative pact that winter, and the results were less than pretty.

    Broxton posted a 4.11 ERA in a wobbly 2013 season and was traded the next year at the waiver deadline to the Milwaukee Brewers after blowing six of 13 save opportunities with Cincinnati, though he did secure 21 holds.

Cleveland Indians: RF/1B Nick Swisher

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    Jason Miller/Getty Images

    The contract: Four years, $56 million, signed in December 2012

    The aftermath: Nick Swisher was one of the game's more reliable switch-hitters when the Cleveland Indians signed him to a then-franchise-record contract prior to the 2013 season.

    He'd hit 20 or more home runs in eight straight campaigns and had posted an .837 OPS the previous year with the New York Yankees. He was also 32 years old, an age when many players' skills begin to erode.

    Erode they did, as Swisher hit .228 with an anemic .377 slugging percentage in two-plus seasons with Cleveland before being traded to the Braves along with Michael Bourn in August 2015.

Colorado Rockies: INF/OF Ian Desmond

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    Alex Gallardo/Associated Press

    The contract: Five years, $70 million, signed in December 2016

    The aftermath: The jury is still out on the deal between Ian Desmond and the Colorado Rockies, but the early returns aren't great.

    In his first season with Colorado, Desmond was hampered by injury and hit only seven home runs with a .701 OPS in 95 contests despite playing his home games at Coors Field. 

    He'll have a starting job in 2018 at either first base or in the outfield and a chance to restore his value. For now, a contract FanGraphs' Dave Cameron panned at the time looks worse than ever.

Detroit Tigers: 1B/DH Prince Fielder

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    Ben Margot/Associated Press

    The contract: Nine years, $214 million, signed in January 2012

    The aftermath: When Prince Fielder inked a massive, nine-figure contract with the Detroit Tigers prior to the 2012 season, it looked like he'd follow in his father Cecil's slugging footsteps as the face of the franchise. 

    The younger Fielder did make a pair of All-Star teams and had a top-10 American League MVP finish in two seasons with Detroit, but he was traded to the Texas Rangers in November 2013.

    In a sense, the Tigers dodged a bullet. They got three mostly productive seasons out of Kinsler and shed the bulk of Fielder's remaining contract. Fielder, meanwhile, saw his production plummet with Texas and retired because of a neck injury in 2016.

    Detroit has made other regrettable moves in the interim, including signing right-hander Jordan Zimmermann for five years and $110 million only to see him post a 5.60 ERA.

    Big picture, however, the Fielder megadeal didn't work out for anyone involved. 

Houston Astros: INF Kaz Matsui

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    Bob Levey/Getty Images

    The contract: Three years, $16.5 million, signed in December 2007

    The aftermath: The Carlos Lee boondoggle occurred in the 2006-07 offseason, one year prior to our cutoff. So we turn to a lower-profile yet still unsuccessful Houston Astros signing: Kaz Matsui.

    The Japanese middle infielder acquitted himself capably in the first year of his Astros contract, hitting .293 with 20 stolen bases, though he was limited to 96 games.

    After that, his production tumbled. In 2010, he slashed .141/.197/.155 and was given his release, to use one of professional sports' cruelest euphemisms. 

Kansas City Royals: RF Jose Guillen

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    The contract: Three years, $36 million, signed in December 2007

    The aftermath: Jose Guillen hit .290 with 23 home runs for the Seattle Mariners in 2007 and earned a three-year deal from the Kansas City Royals that winter.

    Guillen hit 20 home runs with 97 RBI in his first year with Kansas City but managed only nine homers with a .242/.314/.367 slash line the following season. 

    In 2010, he was traded to the San Francisco Giants and was linked to performance-enhancing drugs. 

    Add his reputation as a hotheaded clubhouse malcontent, and Guillen's K.C. contract was the opposite of money well spent.

    It's possible the four-year, $72 million pact the Royals gave Alex Gordon will be worse in the end, but for now we're giving the ignoble nod to Guillen. 

Los Angeles Angels: 1B/DH Albert Pujols

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    The contract: Ten years, $254 million, signed in December 2011

    The aftermath: If he retired today, Albert Pujols would be a Hall of Fame lock. Unfortunately for the Los Angeles Angels, all his best years were with the St. Louis Cardinals.

    In 11 seasons with the Cards, Pujols won three NL MVP Awards and made nine All-Star teams. That's when the Halos signed him to one of the most lucrative deals in MLB history.

    Since arriving in Southern California, Pujols has slashed .262/.319/.459 and has failed to post higher than a .790 OPS since 2012.

    The Angels will pay him $114 million through 2021, followed by a 10-year, $10 million personal-services contract. 

    If you think the 37-year-old is a budgetary drag now, just wait.

Los Angeles Dodgers: CF Andruw Jones

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    Kevork Djansezian/Associated Press

    The contract: Two years, $36.2 million, signed in December 2007

    The aftermath: The Los Angeles Dodgers gave a lot of bad contracts to fading veterans during the reign of general manager Ned Colletti. The two-year deal he handed Andruw Jones might be the most egregious. 

    For the sky-high sum of $18.5 million per season, Jones hit .158 with 12 extra-base hits in 75 games in 2008, underwent knee surgery and was released prior to the 2009 season.

    "Obviously this is a disappointing day for both us and Andruw," Colletti said at the time, per CBS Sports' Mike Axisa, a contender for understatement of the decade.

Miami Marlins: LHP Wei-Yin Chen

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    The contract: Five years, $80 million, signed in January 2016 

    The aftermath: The Miami Marlins are shedding salary under their new ownership group fronted by Derek Jeter. One contract Jeter and Co. won't be able to move is Wei-Yin Chen's.

    Inked prior to the 2016 season, Chen's deal will pay him $10 million in 2018, $20 million in 2019 and $22 million in 2020, with a $16 million vesting option for 2021.

    Chen got the deal from Miami after posting a 3.34 ERA in 191.1 innings for the Baltimore Orioles in 2015, though his 4.16 FIP indicated a degree of luck. 

    Since joining the Fish, the 32-year-old right-hander has posted a 4.72 ERA and was limited to 33 innings last season while battling elbow issues. 

Milwaukee Brewers: RHP Eric Gagne

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    Al Behrman/Associated Press

    The contract: One year, $10 million, signed in December 2007

    The aftermath: Eric Gagne was the best closer in baseball in the early 2000s and won an NL Cy Young Award with the Dodgers in 2003.

    His 2008 season ended on a down note, as he posted a 6.75 ERA in 20 games with the Red Sox after a trade from the Texas Rangers.

    The Milwaukee Brewers handed him a $10 million deal anyway. Shortly thereafter, Gagne was named as a performance-enhancing drug user in the infamous Mitchell Report. 

    He then followed with a 5.44 ERA and seven blown saves in 17 chances. Inexplicably, the Brewers offered Gagne a minor league contract the following year, but the bespectacled right-hander failed to make the Opening Day roster.

Minnesota Twins: 1B/DH ByungHo Park

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    Jim Mone/Associated Press

    The contract: Four years, $12 million plus a $12.8 million posting fee, signed in December 2015

    The aftermath: The small-market Minnesota Twins made a splash on the international scene when they won the bidding for Korean slugger ByungHo Park.

    Park hit 210 home runs and posted a .951 OPS in 868 games with the Korea Baseball Organization but couldn't translate his success stateside. In 62 games with the Twins, he slashed .191/.275/.409 and was released in November.

    Per Mike Berardino of the Pioneer Press, Minnesota will pay Park $1.4 million in 2018 and shed the remaining $5.1 million he was owed over the next two seasons. 

    That's better than paying the full contract but a whole lot less than the Twinkies were hoping for. 

New York Mets: LF Jason Bay

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    Ronald C. Modra/Sports Imagery/Getty Images

    The contract: Four years, $66 million, signed in January 2010

    The aftermath: Jason Bay was a three-time All-Star and 2004 AL Rookie of the Year winner when the New York Mets signed him.

    Once he arrived in Queens, Bay's numbers cratered. He hit .259 with a .749 OPS in his first season with the Mets, hit .245 with a .703 OPS the following year and hit .165 with a .536 OPS in 2012 before agreeing to an early contract termination.

    "I still feel I have plenty to give to this game and that I can play baseball at a high level," Bay said in a statement at the time, per MLB.com's Anthony DiComo. "But after serious consideration, both sides agree that we would benefit from a fresh start."

    The following season, Bay hit .204 with a .393 slugging percentage for the Mariners and never played another MLB inning.

New York Yankees: CF Jacoby Ellsbury

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    Bill Kostroun/Associated Press

    The contract: Seven years, $153 million, signed in December 2013

    The aftermath: After seven strong seasons with the Red Sox, Jacoby Ellsbury signed with the New York Yankees prior to the 2013 season.

    At the time, it seemed like a classic Evil Empire move, snatching a star away from a hated rival for gobs of cash. The signing has mostly blown up in New York's face.

    Ellsbury has shown occasional flashes of his former All-Star self in the Bronx, but he's never hit more than 16 home runs while posting a ho-hum .716 OPS.

    Now, with the acquisition of Giancarlo Stanton, Ellsbury is buried on the Yanks' depth chart. If they can't trade him, they could end up paying the 34-year-old $21 million-plus annually through 2020 to be a fourth or fifth outfielder. 

Oakland Athletics: 1B/DH Billy Butler

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    The contract: Three years, $30 million, signed in November 2014

    The aftermath: A three-year commitment at an average annual value of $10 million is a lot of coin for the tiny-budgeted Oakland Athletics.

    They gave it to Billy Butler before the 2014 season, and it came back to bite them.

    Butler hit .295 with an .808 OPS in eight seasons with the Royals, but those numbers dropped to .258 and .719 with the A's, who released him in 2016 after he got into a fight with teammate Danny Valencia and suffered a concussion.

Philadelphia Phillies: RHP Jonathan Papelbon

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    Julie Jacobson/Associated Press

    The contract: Four years, $50 million, signed in November 2011

    The aftermath: Jonathan Papelbon wasn't bad during his time with the Philadelphia Phillies. The right-hander made two All-Star teams, notched 123 saves and posted a 2.31 ERA in three-plus seasons with the Phils.

    But his contract, the largest ever for a relief pitcher at the time, was the exact wrong move for Philadelphia. 

    The Phillies' window of contention had slammed shut prior to the 2012 season. Instead of spending lavishly on a closer, they should have been rebuilding.

    Sure enough, they never finished better than .500 with the mercurial Papelbon on the roster and traded him to the Washington Nationals in 2015.

Pittsburgh Pirates: C Rod Barajas

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    Gene J. Puskar/Associated Press

    The contract: One year, $4 million, signed in November 2011

    The aftermath: In the scheme of things, a one-year contract for a middling catcher for under $5 million doesn't rate as a huge fail.

    The Pittsburgh Pirates aren't in the habit of handing out massive deals, however, so the Rod Barajas signing makes the cut. 

    The Bucs tapped Barajas to be their everyday backstop prior to the 2012 season and made him, at the time, the sixth-highest-paid player on the team.  

    Barajas "rewarded" Pittsburgh by hitting .206 with a .283 on-base percentage and throwing out an embarrassing 6 percent of would-be base stealers. 

    He never played for the Pirates—or any other MLB team—again.

St. Louis Cardinals: RHP Mike Leake

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    Gary Landers/Associated Press

    The contract: Five years, $80 million, signed in December 2015

    The aftermath: The St. Louis Cardinals gave Mike Leake the biggest contract for a pitcher in franchise history prior to the 2016 campaign.

    The right-hander went 16-24 with a 4.46 ERA in 330.2 innings with St. Louis before a trade to the Seattle Mariners last season. 

    In exchange, the Cards got minor league infielder Rayder Ascanio, who hit .213 across three minor league levels in 2017. The team also surrendered $17 million along with $750,000 in international cap space. 

    Leake posted a 2.53 ERA in five starts with Seattle, suggesting he could rebound in the Pacific Northwest. If he does, it will only add a layer of regret for St. Louis.

San Diego Padres: RHP James Shields

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    The contract: Four years, $75 million, signed in February 2015

    The aftermath: The San Diego Padres were going for it when they signed right-hander James Shields to a franchise-record contract in February 2015.

    Shields was coming off eight straight 200-plus-inning seasons and had just guided the Kansas City Royals to a World Series berth.

    In a season and change with the Friars, Shields posted a 4.00 ERA and 4.45 FIP and was dealt to the White Sox in 2016 along with $22 million.

    It was a necessary move as San Diego shifted into rebuild mode, but it was also a black eye for general manager A.J. Preller and his brain trust. 

San Francisco Giants: CF Aaron Rowand

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    Brad Mangin/Getty Images

    The contract: Five years, $60 million, signed in December 2007

    The aftermath: Barry Zito signed his infamous seven-year, $126 million contract during the 2006-07 offseason and at least contributed to the San Francisco Giants' 2012 championship.

    Aaron Rowand, on the other hand, was a smoldering tire fire in the post-Barry-Bonds, pre-even-year-title era.

    Rowand hit .309 with 27 home runs and won a Gold Glove for the Phillies in 2007. That led to a handsome deal with the Giants, for whom he slashed .253/.310/.394.

    He got a ring in 2010 despite minimal contributions and was released in September 2011, which was his final major league season. 

Seattle Mariners: INF/OF Chone Figgins

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    Duane Burleson/Associated Press

    The contract: Four years, $36 million, signed in December 2009

    The aftermath: Chone Figgins hit .298 with 42 stolen bases and 6.9 fWAR for the Angels in 2009. That winter, the Mariners signed him away from their division rival.

    Figgins was coming off easily the best campaign of his career and entering his age-32 season. He took a steep dive in Seattle, where he hit .227 and posted minus-1.1 fWAR over three seasons and was demoted to utility status before the M's cut him loose.

    After a fruitless stint with the Dodgers in 2014, his MLB career was over.

Tampa Bay Rays: 1B Carlos Pena

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    Tony Gutierrez/Associated Press

    The contract: One year, $7.25 million, signed in January 2012

    The aftermath: Carlos Pena had a productive run with the Tampa Bay Rays from 2007 to 2010, as he won a Gold Glove and had a pair of top-10 AL MVP finishes.

    After Pena spent a season with the Chicago Cubs in 2011, the Rays brought him back on a one-year deal that chewed up a significant portion of their limited budget.

    Pena proved the old saying about how you can't go home again with a .197 average and .684 OPS. In 2015, he signed an honorary contract to retire as a member of the Rays, but it didn't fully erase the sting of that ill-fated 2012 pact.

Texas Rangers: RF/DH Shin-Soo Choo

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    Tony Gutierrez/Associated Press

    The contract: Seven years, $130 million, signed in December 2013

    The aftermath: Shin-Soo Choo hasn't been an unmitigated disaster since the Texas Rangers signed him prior to the 2014 season.

    He's posted a scant 5.1 fWAR, however, while putting up a .779 OPS. For a guy making superstar money, that's meh bordering on bleh.

    The Rangers will pay the 35-year-old Choo $62 million through 2020, and their odds of getting above-average production are marginal at best.

Toronto Blue Jays: RF Jose Bautista

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    Eric Christian Smith/Associated Press

    The contract: One year, $18 million, signed in January 2017

    The aftermath: Jose Bautista has an indelible place in Toronto Blue Jays lore. His prodigious power and bat-flipping antics defined the Jays' return to relevance. 

    Sadly, an awful 2017 season tarnished his Toronto legacy.

    After the Blue Jays brought him back on a hefty one-year deal, Bautista slashed .203/.308/.366 and posted minus-0.5 fWAR as the team slid to fourth place in the AL East. The club declined his $17.5 million option for 2018.

    Fans north of the border will remember Joey Bats fondly, but they'd do well to forget his dismal swan song.

Washington Nationals: C Matt Wieters

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    Mark Tenally/Associated Press

    The contract: Two years, $21 million, signed in February 2017

    The aftermath: In February 2017, with spring training approaching and the Washington Nationals in need of a catcher, the club gave Matt Wieters a contract worth $10.5 million with a player option for a second year at the same rate.

    After hitting .225 and rating as the 11th-worst pitch-framer in the game, per StatCorner, Wieters unsurprisingly opted in for 2018.

    A turnaround is possible, but the 31-year-old's numbers have been trending downward since 2015, which doesn't bode well for him or the Nats.


    All statistics and contract information courtesy of Baseball Reference and FanGraphs unless otherwise noted.