Every MLB Team's Toughest Dilemma of the 2021 Offseason

Brandon Scott@@brandonkscottFeatured Columnist IOctober 22, 2021

Every MLB Team's Toughest Dilemma of the 2021 Offseason

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    The World Series begins in less than a week, and three days after that's over, MLB free agency begins in earnest. 

    Non-contending teams are already mulling over their offseason decisions and what's most important for them to take steps to compete for a pennant. 

    Even teams still in the mix for a World Series title have difficult decisions to make this offseason. 

    So with that, let's take a look at each team's toughest dilemma this offseason. Every team is different, as will the focus of their respective dilemma, whether it's free-agent spending or addressing a specific area of the group. 

Arizona Diamondbacks: How to Fix the Bullpen?

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    For the past two seasons, the D-backs' bullpen has been a major weakness for the team.  

    In 2021, Arizona relievers had the highest xFIP (4.98), according to FanGraphs. They also had the third-highest ERA in baseball. 

    Diamondbacks general manager Mike Hazen lamented earlier this month with Arizona Sports' Bickley & Marotta about losing more than 30 one-run games. Hazen wants to add some power arms to the bullpen and will search the free-agent market to do so. 

    Another idea is letting young starting pitching prospects get their feet wet in the big league bullpen.

Atlanta: Uncertainty in the Outfield

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    Atlanta deserves credit for adjusting on the fly and piecing together a productive outfield, even if they have made some defensive sacrifices. 

    Eddie Rosario and Joc Pederson were traded to Atlanta for their bats but have been adequate in the field. Adam Duvall's departure lasted about five months, as Atlanta promptly brought him back in a trade with the Miami Marlins for outfield depth.

    The team could not have anticipated Ronald Acuna Jr.'s torn ACL suffered in July, or Marcell Ozuna going on administrative leave because of legal issues related to domestic violence. 

    Both players are signed to long-term deals, but when will they be back, and how does Atlanta go about replacing them the way it did this season?

    Rosario will be an unrestricted free agent. Pederson and Duvall both have mutual options on their deals.

Baltimore Orioles: Whether to Trade Trey Mancini, Cedric Mullins or John Means?

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    Expect the Baltimore Orioles to make a lot of moves just to field a 40-man roster next season. They don't have a single player signed to a guaranteed contract for 2022, though Baltimore has young talent and several prospects it will want to protect from the Rule 5 draft. 

    Conventional wisdom might say Trey Mancini, Cedric Mullins and John Means are foundational pieces. Baltimore's reluctance to move any of them at the trade deadline this year might affirm this idea. 

    Mancini, who returned this season after having colon cancer, turns 30 before Opening Day. He is one of the longest-tenured players on the team, widely respected for both what he does on the field and his clubhouse leadership.

    Yet there is no word on an extension for Mancini, whose contract expires after 2022. The right trade package could entice Baltimore to deal Mullins, and whether to trade Means comes down to the intention of paying a high figure once he becomes expensive.

Boston Red Sox: How Aggressive to Be in Free Agency?

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    Whether now is the time for Boston to spend heavily in free agency is something its front office has to reckon with after this postseason run is finished. 

    How hard does Chief Baseball Officer Chaim Bloom try to retain their own free agents like Eduardo Rodriguez, J.D. Martinez, Kyle Schwarber and Christian Vazquez? Or does he pursue others like Robbie Ray, Max Scherzer and Marcus Semien?

    It feels like the Red Sox are playing mind games with their fans. They traded Mookie Betts a year after winning the World Series, and a more frugal rebuild, with Bloom's Tampa Bay Rays background, was supposed to ensue. 

    A year later and they're back to competing for another World Series, but it's still unclear how much Boston's brass is willing to spend.

Chicago Cubs: Where to Begin?

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    Jed Hoyer's buzz words recently have been "thoughtful" and "intelligent." This is a team that wants to spend on free agents and faces pressure from its fanbase to do so. 

    Hoyer has also talked about how the best organizations build from within and has cautioned against relying too much on free agency. 

    The Cubs' 2016 World Series championship was built with the right mix of young, affordable talent still under team control and free-agent signings to help solidify the roster. 

    They are essentially starting from scratch on the North Side. If Hoyer's logic holds, the Cubs have work to do with drafting and player development, much less free agency. 

    MLB Pipeline ranks the Cubs' farm system at 18th in baseball. 

    "Ultimately, that'll be the key to this next wave of success," Hoyer told reporters at a press conference introducing new general manager Carter Hawkins. "We have to do a great job of player development over the next three to five years. Obviously, that was a huge part of my focus in this hire."

Chicago White Sox: How to Address an Identity Crisis?

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    It's fascinating to consider the White Sox's best attribute proved to be a fatal flaw in the postseason: starting pitching. 

    This was the best rotation in the American League in the regular season. But against Houston in the ALDS, the White Sox did not get quality from Lance Lynn, Lucas Giolito, Dylan Cease or Carlos Rodon. One of them, Dallas Keuchel, did not even make the ALDS roster.

    Only Rodon is a free agent this offseason, and the ascension of Michael Kopech from the bullpen to the rotation has long been forecasted. Except the White Sox probably want to retain Rodon and find a way to trade Keuchel, who was a disappointment in his second season with the squad. 

    Easier said than done, though. 

    The White Sox are already built to win the American League Central and at least see the postseason, but it's a mystery exactly how they take the next step beyond what they have been the past two seasons.

Cincinnati Reds: Can They Trade a Veteran Pitcher for an Outfielder?

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    The Reds are not likely to spend the money necessary to fix all of their problems, which exist primarily in the outfield and bullpen. 

    Where they do have a surplus of talent is in their starting pitching, both on the major league roster and in prospects. Cincinnati has to determine how much their best prospects—pitchers Nick Lodolo and Hunter Greene—factor into their 2022 plans. 

    If Lodolo and/or Greene are ready to contribute to the Reds' rotation, that opens up the possibility of moving Sonny Gray or Luis Castillo to free up money. Or, Cincinnati could pick up Wade Miley's club option for $10 million and see what the 34-year-old garners on the trade market. 

    Also, how do the Reds replace Nick Castellanos if opts out of his contract?

    The Reds are trying to find a creative way to improve this roster without spending much more than their already top-10 payroll.

Cleveland: Whether to Spend?

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    Cleveland spent the past two seasons slashing its payroll, and now, after a disappointing 2021, the question is "to what end?"

    Whether to pick up the club options for Roberto Perez and Jose Ramirez is something President of Baseball Operations Chris Antonetti has to decide. 

    Perez, Cleveland's beloved All-Star third baseman, has a club option for $11 million, and it's hard to imagine it not being picked up, even if it's only later used to engineer a trade. 

    Picking up the $7 million club option for Ramirez is a bit more complicated, considering his dip in production over the past two seasons. But he could also be used as a trade chip at some point. 

    The AL Central appears to belong to the White Sox, but Cleveland could compete again in this new Guardians era if willing to spend.

Colorado Rockies: What Is Life After Trevor Story?

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    Almost assuredly the Rockies are losing their All-Star shortstop, just a year after trading away franchise icon Nolan Arenado (who they are still paying). 

    Trevor Story is a free agent this offseason. Re-signing him seems highly unlikely, and not moving him by the trade deadline seems like an egregious error by this organization.

    It is time to turn over a new leaf, with Story on his way out and Bill Schmidt stepping up from scouting director to general manager. 

    How Schmidt approaches turning around a consistently low-70-win squad has Rockies fans on the edge of their seats.

    As The Athletic's Nick Groke put it, "They are either building or falling apart."

Detroit Tigers: Are They in the Free Agent SS Market?

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    The Tigers gave Willi Castro a look at shortstop this year. Castro will have a role on this team, but they are looking elsewhere at shortstop. 

    That brings up one of the deepest and more impressive free-agent classes at that position in a while. The obvious connection is between Tigers manager A.J. Hinch and free-agent-to-be Carlos Correa from their days together in Houston. 

    While that connection is strong, Correa has made it clear he will not sell himself short. So unless the Tigers are ready to outbid the larger markets, they will have to look at whether Marcus Semien or Trevor Story could be options. 

    Here is what Tigers general manager Al Avila said earlier this month about spending, per MLB.com:

    "I will caution: This is not going to be spending like a drunken sailor," Avila said. "This is going to be a very measured process. We're going to make sure that whatever decisions we make, free agency-wise, that it doesn't sink this organization for years to come, but it builds this organization for years to come."

Houston Astros: Whether to Re-Sign Carlos Correa?

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    Nothing matters more for the Astros this offseason than what happens with Carlos Correa, whether they up the ante from their spring training negotiations, or go in a different direction. 

    Their infield with Correa at shortstop, Alex Bregman at third base, Jose Altuve at second and Yuli Gurriel at first has played in more postseason games together than any four teammates in MLB history. 

    It is a historic run the Astros are on, advancing to five straight American League Championship Series with this group. Correa is the only one of these core players set to hit free agency and has proven to be the best among them. 

    General manager James Click comes from the Tampa Bay Rays organization, which fields contenders without dishing out exorbitant contracts. Correa, though, is looking for a 10-plus-year deal in the vein of his friend Francisco Lindor. 

    Something has to give, or the Astros are losing franchise icons George Springer and Correa in back-to-back offseasons.

Kansas City Royals: How to Configure a Crowded Infield?

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    Top prospect Bobby Witt Jr. is ready to make his big league debut. If he is anywhere near as good in the Majors, the Royals are inserting a star into their lineup.

    How they navigate this crowded infield will be interesting, though. There is Witt, who can play shortstop, third base and second base. There is Nicky Lopez, who proved himself at shortstop this season. 

    There is also Adalberto Mondesi, who was solid at third base toward the end of the season, and Whit Merrifield, who wants to continue playing second.

    Do the Royals keep Lopez at shortstop, Merrifield at second, and allow Mondesi to be their utility player in both the infield and outfield? And will any of this be enough for Kansas City to compete in the AL Central?

Los Angeles Angels: How to Fill out Their Starting Rotation?

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    Another offseason, another Angels team in desperate need of pitching.

    It is a constant theme for the Angels, and this offseason will be no different. Fortunately for theM, the free-agent starting pitching market should be a healthy one. 

    As previously mentioned, Max Scherzer, Robbie Ray and Carlos Rodon are among those who should be available. Los Angeles could also take a shot at Marcus Stroman or Kevin Gausman. The bullpen also needs help.

    However it goes, the Angels cannot expect to compete in the AL West with this pitching staff, which finished with the fourth-worst ERA in the American League (4.69).

Los Angeles Dodgers: Who to Keep?

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    The Dodgers as we know them could very well be in the midst of their last hurrah.

    Corey Seager, Chris Taylor, Clayton Kershaw, Kenley Jansen are all free agents. There is also that Max Scherzer guy we keep talking about, who will be on the market. 

    The Dodgers are not keeping all of these players. They are probably saying goodbye to at least half, if not all of them. But can they keep any? Do they want to?

    One of the calling cards of this Dodgers run has been their embarrassment of riches when it comes to positional depth. Just look at what Kike Hernandez is doing in Boston and Joc Pederson in Atlanta. These were rotational players for the Dodgers before they left in free agency after their World Series title last year. 

    The position players are likely gone, so do the Dodgers just write Scherzer a blank check? Could they perhaps keep Taylor?

Miami Marlins: Who to Trade?

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    The Marlins boast a ton of young, quality starting pitching. Trevor Rogers' performance trailed off toward the end of the season, but he showed ace potential early.

    They also have Sandy Alcantara, Jesus Luzardo, Edward Cabrera, Sixto Sanchez and veteran pitcher Pablo Lopez. 

    What the Marlins are lacking in the way of becoming a legitimate contender is hitting. How much hitting they could get from dealing any or a combination of these arms is unclear, but it's what they have most of to offer. 

    The expectation in Miami this season was to be competitive following their playoff appearance in the pandemic-shortened 2020. But as Rogers characterized it, 2021 was a failure (67-95). 

    Marlins CEO Derek Jeter and general manager Kim Ng have said to anticipate an active offseason, with more money to spend on free agents. 

    That would help, as would making the most of a starter surplus.

Milwaukee Brewers: How to Fix Christian Yelich?

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    If the Brewers are going anywhere any time soon, they have to get more from their best player. No one seems to have an explanation for why Christian Yelich's performance has dipped over the past two seasons. 

    His lasting image of 2021 will probably be striking out looking with the Brewers' tying run at first base to end the NLDS against Atlanta. Yelich hit .248 with just nine home runs and 51 RBI over 117 games.

    The Brewers offense is underwhelming enough without Yelich being a shell of himself. They were shut out twice in the four NLDS games against Atlanta, collectively hitting just .192 and striking out 48 times.

    Yelich alone cannot overcome all of the Brewers' offensive shortcomings. But with his salary rising to $26 million as the seven-year contract extension kicks in, Milwaukee needs more production from its star.

Minnesota Twins: Who Will Pitch?

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    In some ways, this is a rotation starting from scratch. The only two starters Minnesota can pencil in for next season are Bailey Ober and Joe Ryan, both young, promising pitchers with just 119 innings of MLB experience combined.

    The Twins entered this season with Jose Berrios and Kenta Maeda at the top of their rotation. Then Berrios was traded to the Toronto Blue Jays and Maeda needed Tommy John surgery in the summer. 

    Michael Pineda, the Twins' third starter, will be a free agent.

    Minnesota also traded and released its older starters in J.A. Happ and Matt Shoemaker, leaving a gaping hole in the rotation.

    The Twins' most recent success has been directly tied to solid pitching. 

    If they want to threaten the White Sox in the AL Central, the Twins have to find pitching somewhere.

New York Mets: Who Is Their Leader?

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    The Mets are in the mix for the most dysfunctional franchise in baseball. Searching for a third general manager in less than a year and a fourth manager in the last five years is not an ideal way to run an organization.

    Yet, here the Mets are. Priority No. 1 is solidifying leadership and figuring out who will make future baseball decisions, much less what those actual decisions will be. 

    Do they rehire Carlos Beltran, who never got the chance to prove himself as a manager before being fired because of his connections to the Astros' sign-stealing scandal? Or is being tied to a scandal not what new ownership wants in its next manager?

    On the field, the Mets must decide whether to keep trade-deadline acquisition Javier Baez. Francisco Lindor has said the two feed off each other as middle infielders and could form an impressive double-play combination for years to come.

New York Yankees: How to Get Their Groove Back?

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    The first thing for the Yankees was moving on from hitting coaches Marcus Thames and P.J. Pilittere and third base coach Phil Nevin.

    Is that enough to fix the offense, or will more significant moves be made?

    The Bombers were not good enough offensively throughout the season and were far too streaky to be considered reliable. That has to be disappointing when you consider who is in the lineup and how much they spend on the team. 

    The Yanks put up just 711 runs, and their plus-46 run differential was far below the AL's division winners. The Rays were plus-206, the Astros were plus-205 and the White Sox were plus-160. 

    Tampa hit the same number of home runs as the Yankees (222) but scored 146 more runs. 

    New York can close the gap by simply realizing its potential at the plate. The rotation after Gerrit Cole has to get better, and Cole himself can't have another postseason performance like the wild card against Boston.

Oakland Athletics: Prioritizing in-House Free Agents?

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    The A's have 10 upcoming free agents, which includes Starling Marte, who they traded for midseason, as well as Mark Canha, Josh Harrison, Yan Gomes and Yusmeiro Petit.

    How many of these players can Oakland retain, and is it enough to make up the difference with the Seattle Mariners, an ascending team which finished ahead of the A's in the AL West?

    Their stars will get raises through arbitration this offseason. That's Matt Chapman and Matt Olson, and their starting pitchers Chris Bassitt, Sean Manaea and Frankie Montas.

    "I think the idea is, obviously, we have some significant players that are important to this club right now, going forward that still have service time with us," Executive Vice President of Baseball Operations Billy Beane told reporters earlier this month. "It really depends on the level of our payroll, to be totally frank with you.

    "And where we are as a club, too. Sometimes moves aren't made just because of payroll. They're made because we need to make some changes for the long term. Those discussions will be part of our next couple of weeks."

Philadelphia Phillies: Where Is Bryce Harper’s Help?

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    Aside from Bryce Harper's MVP-caliber performance in right field, the Phillies have been underwhelming in the outfield. Harper is carrying them, and as great as he is, it won't be enough. 

    The 2021 season was a step in the right direction for Philly. The team finished above .500 for the first time in a decade, and Harper's season was encouraging. 

    But the Phillies have played 13 different center fielders since Odubel Herrera's domestic violence suspension in 2019. 

    In 2021, they produced a sad .230/.298/.363 slash line. Phillies center fielders combined for the second-fewest home runs and RBI. 

    They likely have openings in center and left field if the Phillies decline Andrew McCutchen's $15 million team option. 

    Harper needs help out there.

Pittsburgh Pirates: Whether to Spend?

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    With one of the top-ranked farm systems in baseball, it does seem Pittsburgh is on track in its rebuild. Another 100-loss season is a hard sell to fans, but what if that's in the Pirates' best interest?

    Not just in a tanking sort of way, but to allow younger players to develop with as much experience as possible. Pirates general manager Ben Cherington has said they should be "incredibly busy" this offseason in exploring trade and free-agent opportunities. 

    "But we need to do that in a way that fits with the strategy," Cherington said, per The Athletic's Rob Biertempfel. "Much of our success will need to be driven by improvement from young players. The last thing we want to do is make a decision that would unintentionally get in the way of a young player's opportunity."

    There is money to spend in Pittsburgh. Next year, the Pirates are on track to spend about $43 million.

San Diego Padres: More Depth in the Lineup?

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    The Padres swung for the moon over the past year. They extended 22-year-old Fernando Tatis Jr. through his mid-30s. They traded for Yu Darvish and Blake Snell last December and Joe Musgrove in January.   

    This was supposed to be the year San Diego knocked down the door to threaten the Los Angeles Dodgers in the NL West. For a time, it seemed like they might do it. 

    Then there was the epic collapse to end the season when health failed them and their lineup proved to be top-heavy. 

    The Padres have to get better past Tatis, Manny Machado, Jake Cronenworth, Trent Grisham and Adam Frazier. They don't have the depth to survive injuries, making them vulnerable to another letdown like 2021.

San Francisco Giants: Who Pitches After Logan Webb?

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    There are four giant holes in San Francisco's rotation next year. Logan Webb looks like an ace, and he's not going anywhere, but beyond that, there are no guarantees. 

    Kevin Gausman, Anthony DeSclafani and Alex Wood are all eligible for free agency this offseason. Johnny Cueto is likely headed toward a buyout, which could pay him $5 million rather than his $22 million club option for next year. 

    So that makes starting pitching a top priority for Giants President of Baseball Operations Farhan Zaidi. Will the Giants land more gems in free agency? Could they retain Gausman? Maybe both?

    The Giants posted the third-lowest WHIP and fifth-lowest ERA in 2021, but it's unclear what that looks like in 2022. 

    Figuring it out is just as if not more important than signing Kris Bryant.

Seattle Mariners: How Much to Spend and for Who?

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    A foundation has been built in Seattle, and the Mariners appear to have a bright future. They are coming off a 90-win season and fought for a playoff spot until the final days of the regular season. Their farm system ranks second. 

    Now feels like the time to strike with a free-agent splash. 

    President of Baseball Operations Jerry Dipoto says he has the green light from ownership to increase payroll, and that he intends to do so with an impact infield bat. They also want to add to their starting pitching. 

    They should make runs at Trevor Story, Kris Bryant and Carlos Correa. On the pitching side, target Carlos Rodon, or anyone from the Giants' expiring rotation.

St. Louis Cardinals: Exploring the Historic Shortstop Market?

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    Edmundo Sosa was a pleasant surprise for the Cardinals this season after Paul DeJong underperformed. St. Louis the past two seasons has added first baseman Paul Goldschmidt and third baseman Nolan Arenado to the corner infield spots. Second baseman Tommy Edman is a star in the making. 

    That leaves a potential opening at shortstop with this historic free-agent class everyone keeps talking about. Could Arenado and Trevor Story reunite in St. Louis?

    Could it be Corey Seager's future home? 

    The Cardinals could use his left-handed bat, though he would likely command more money than they have ever offered in free agency. They could also move Edman to shortstop and figure out something else at second base.

Tampa Bay Rays: Whether to Trade Tyler Glasnow?

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    Tyler Glasnow is the Rays' best pitcher, and he's arbitration-eligible for the next two years. But he is going to miss all of next season to recover from Tommy John surgery, which he underwent in August. 

    The Rays would have to give Glasnow a slight raise for a season in which he won't play, and the only guarantee would be the season he returns from surgery, likely with a well-managed workload.

    This question comes down to what their plan is for Glasnow—if the Rays believe him to be their ace for years to come, or whether it's smarter to move him sooner rather than later to a team that really wants him for 2023.

Texas Rangers: What If They Swing and Miss?

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    President of Baseball Operations Jon Daniels echoed what many executives have said since their season ended—the club plans to be active and aggressive in free agency. No one is going to come out and just say "We're cheap; we don't want free agents."

    But the Rangers are serious about craving a star. Daniels said there's nobody they will rule out because of a perceived price tag, so expect Texas to throw money at high-profile free agents at every position. 

    The dilemma is what happens if they swing and miss? What if that marquee free agent does not arrive in Arlington?

    After a 102-loss season, the Rangers are in full rebuild mode. They want to make Texas a contender again through both player development and free agency. 

    The farm system ranks 11th, per MLB Pipeline, but it would be a massive disappointment if they come up empty on the open market.

Toronto Blue Jays: Bringing Back Robbie Ray or Marcus Semien?

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    When Robbie Ray re-signed with Toronto for 2021 on a one-year, $8 million contract, it was not with the expectation he would have one of the best pitching seasons in the game. 

    Ray was supposed to be the No. 3 or No. 4 starter, providing some depth in the rotation for a budding young squad. Turns out he put up a Cy Young-worthy season and, at age 30, is sure to command a lot of money on the free-agent market. 

    Marcus Semien, 31, will also generate a lot of interest after his All-Star season with Toronto.

    So it's a good thing the Blue Jays have money to spend. Ray was a major factor in them being in the postseason picture. Semien led MLB with 86 extra-base hits.

    They already have a promising young core, but finding a way to keep one of these vets seems like a solid idea.

Washington Nationals: Is Victor Robles Still Part of the Future?

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    Management has been adamant publicly about not giving up on the 24-year-old center fielder after regressing since the Nationals' World Series title in 2019. 

    Victor Robles slashed .203/.310/.295 with a .605 OPS in 107 games for the Nationals this year before he was sent down to Triple-A, where he thrived. He finished the season batting .301 with four homers, eight doubles, eight RBI, six stolen bases and a .936 OPS over 23 games with the Rochester Red Wings. 

    His replacement, Lane Thomas (acquired via trade from the St. Louis Cardinals), performed well in Robles' absence. Thomas slashed .270/.364/.489 with 48 hits, 14 doubles, seven home runs and 27 RBI after the Jon Lester trade. 

    Since Robles performed how they envisioned in Triple-A, he will have an opportunity to compete for the job with Thomas in spring training.

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