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Each MLB Team's Most Gut-Wrenching Offseason Decision

Robert KnapelJun 7, 2018

Each MLB team will have at least one difficult decision to make this winter. For some teams, it's in regards to what players they should sign, and for some others, it surrounds whether they should trade away one of their top players.

Some of these gut-wrenching decisions may be unpopular with fans, but they could be the right moves. A year from now, it will be easy to look back on some of these decisions and scratch your head.

There are teams that need to make decisions almost immediately, while others can sit back and think about their difficult choices for months.

Arizona Diamondbacks

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Justin Upton is one of the most promising players in baseball. He is in his mid-20s, and he has already shown that he can be a 20/20 player. However, the Arizona Diamondbacks may trade him.

According to Nick Piecoro of the Arizona Republic, it currently seems likely that Upton will remain with the Diamondbacks. A number of teams should call the Diamondbacks about the young star, though, and they may be torn about dealing him.

Atlanta Braves

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How can a team replace a player who has been the face of its franchise for the past two decades? It is certainly not easy, and the Atlanta Braves will need to figure it out this winter.

Chipper Jones will not be back next season, and the Braves need to find a new third baseman. They brought in Juan Francisco last year, but the team may not feel comfortable with him starting.

Baltimore Orioles

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Following their impressive season, in which they reached the postseason for the first time in more than a decade, the Baltimore Orioles will have some interesting decisions to make this winter.

Baltimore needs to improve its starting rotation and figure out how much money it will spend on starters. The Orioles could try for a top-end starter, which would prevent them from improving in other areas, or they could go after a middle-of-the-rotation starter and spend the rest of their money elsewhere.

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Boston Red Sox

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The Boston Red Sox freed up a lot of salary this year when they traded Adrian Gonzalez, Josh Beckett and Carl Crawford to the Los Angeles Dodgers. Now, they have a lot of available cash to spend.

Boston will need to make a decision regarding whether it should reallocate that capital this year by going after big-name free agents or whether it should focus more on the future. The second option may not be very popular in a major market like Boston.

Chicago Cubs

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Matt Garza's injury has likely forced the Chicago Cubs' hand. It hurt his trade value to some extent, and GM Jed Hoyer has said that he expects Garza to be a member of the Cubs in 2013 (h/t Paul Sullivan of the Chicago Tribune).

The Cubs are building for the future, and holding on to Garza seems to be more of a short-term solution. It would likely be in the Cubs' best interests to deal Garza for prospects this winter.

Chicago White Sox

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The Chicago White Sox have already gotten one difficult decision out of the way by signing Jake Peavy to a two-year deal (h/t Scott Powers of ESPN Chicago).

Catcher A.J. Pierzynski is set to become a free agent this winter. He has been an important part of the White Sox's lineup for years, and the team needs to decide if he's worth the price tag.

Cincinnati Reds

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Ryan Ludwick was incredible during the second half of the season, hitting .309 with 14 home runs and 46 RBI.

After turning down his mutual option, Ludwick will become a free agent. This means his price is going to go up, and the Cincinnati Reds need to decide if he's worth what other teams are willing to pay him.

Cleveland Indians

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After struggling in 2012, the Cleveland Indians will try to turn things around in 2013. The Indians may also decide to rebuild in 2013.

Jon Heyman of CBS Sports has mentioned that the Indians could look to trade Shin-Soo Choo this winter since they will not have much of a chance of re-signing him. This decision will be a difficult one for the Indians to make, but it is likely the right move.

Colorado Rockies

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While the Colorado Rockies have the core to contend in 2013, their supporting cast needs to pick things up. The Rockies will need to greatly improve their starting rotation in 2013 if they want to make the postseason.

However, signing a few free-agent pitchers would prevent a number of the Rockies young starters from getting the MLB exposure that they need. This makes the decision a fairly difficult one.

Detroit Tigers

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Detroit Tigers owner Mike Ilitch wants to win a World Series, and that will have a big impact on their offseason (h/t Bob Wojnowski of the Detroit News). Ilitch has a lot of money to spend, and he will need to decide if potentially mortgaging the Tigers future is worth a bolstered attempt at a World Series ring.

If Ilitch decides to go all in, then he could pursue an outfielder such as Josh Hamilton, Michael Bourn or B.J. Upton.

Houston Astros

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Moving to the American League will present some new challenges for the Houston Astros. They are in the middle of the rebuilding process and are moving into a more difficult division.

Houston made Jed Lowrie available during the summer, but the team could not make a deal with anyone (h/t Danny Knobler of CBS Sports). Lowrie is one of the team's best players, and Houston may look to move him once again this winter.

Kansas City Royals

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It's seemed like it could be the Kansas City Royals' year to finally break through the past couple of seasons. That has not happened yet, but it could in 2013.

Kansas City has already added Ervin Santana this winter (h/t Alden Gonzalez of MLB.com), and that seems to indicate that the Royals will make a big push this winter.

The Royals need to open their checkbook to bring in a few new players, but they may chose to wait until their current roster improves.

Los Angeles Angels

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After their big spending offseason last year, the Los Angeles Angels failed to reach the playoffs. They will need to spend big money to improve their pitching staff as well.

Zack Greinke is the top starter available this winter, and the Angels would like to retain him. Their division rivals, the Texas Rangers, could go after him as well and start a bidding war.

The Angels need to decide quickly what the maximum contract they're willing to give Greinke is.

Los Angeles Dodgers

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The Los Angeles Dodgers do not have many areas that they need to improve this winter thanks to all of the trades they made during the year. However, they do need a few more starters behind Clayton Kershaw.

Los Angeles' difficult decision will be determining what starters they should go after. The Dodgers could try to acquire expensive top-of-the-rotation pitchers, or they could go after more affordable starters who have the potential to pitch above expectations.

Miami Marlins

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Spending the big bucks has not normally been the Miami Marlins' approach to the offseason. They decided to try it during the 2012 offseason, but it did not end well, as the Marlins had a bit of a fire sale during the summer.

As the Marlins look to improve and continue to draw more fans to their ballpark, they'll need to decide how to approach the winter and how much money to spend.

Milwuakee Brewers

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Although the Milwaukee Brewers were not willing to spend the money on Prince Fielder this past offseason, they may be willing to give a player a big contract this winter.

Jon Heyman of CBS Sports reports that the Brewers have a serious interest in pursuing Josh Hamilton. This may be an unlikely scenario, but it will be a difficult decision for the Brewers to make if they have the chance to get involved in the bidding.

Minnesota Twins

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Scott Baker has put up some good numbers for the Minnesota Twins when he's been healthy during the past few years. The Twins declined his option this winter and are trying to re-sign him (h/t Joe Christiansen of the Star-Tribune).

That decision is not particular gut-wrenching at the moment, but it could become a difficult one if other teams are willing to give him a multi-year deal.

New York Mets

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Letting Jose Reyes walk last offseason certainly stung for the New York Mets and their fans. The move signaled that the Mets may not be contenders soon.

R.A. Dickey has one more year left on his deal with the Mets, and the team will have some difficult decisions to make if they can't sign him to an extension. Anthony DiComo of MLB.com has suggested that the Mets could deal Dickey this winter if they don't give him a long-term deal.

New York Yankees

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Alex Rodriguez was absolutely miserable for the New York Yankees during the 2012 postseason. With a number of years and millions of dollars left on his contract, Rodriguez is a hard player to deal.

Jon Heyman of CBS Sports has reported that no teams have been in touch with the Yankees about Rodriguez yet. If the Yankees do find a suitor, they will need to eat some of Rodriguez's contract. The tough decision will be how much the Yankees are willing to pay to get rid of A-Rod.

Oakland Athletics

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Few teams in the MLB were a bigger surprise in 2012 than the Oakland Athletics. They'll be looking to repeat as a playoff team in 2013, and their offseason will have a big say in that.

Oakland acquired Stephen Drew midseason and is considering retaining him (h/t Joe Stiglich of the Mercury News). Drew will not be cheap, though, since he is one of the best shortstops on the market. And if Drew gets away, the Athletics may have a tough time finding a shortstop.

Philadelphia Phillies

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Even with a late-season run, the Philadelphia Phillies were unable to reach the postseason in 2012. But they will look to improve their outfield to get back there in 2013.

Philadelphia may need to acquire two outfielders, so the Phillies need to decide if they want to go with a top-tier guy and an in-house option or if they will go after two mid-tier guys such as Shane Victorino and Angel Pagan.

Pittsburgh Pirates

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The Pittsburgh Pirates are getting closer and closer to finishing above .500. With a few minor moves, they could finally break that barrier.

Pittsburgh does not have a lot of money to spend during the free agency period, so it will need to get creative to improve the team. Each move the Pirates make will be important, because with every player they sign, another option is potentially eliminated.

San Diego Padres

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Earlier this year it seemed like trading Chase Headley would be the biggest decision that the San Diego Padres faced during the 2013 offseason. Now, their plans have seemingly changed.

The Padres' new ownership wants to try to sign Headley to an extension (h/t Bill Center of the San Diego Union-Tribune). This will be a very interesting decision because Headley is coming off a career year and it is uncertain if he will be able to repeat that level of production.

San Francisco Giants

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The San Francisco Giants are the defending world champions, but that doesn't mean they have an easy offseason in front of them.

Their most interesting decision surrounds Tim Lincecum.

He makes too much money to remain a reliever, so the options are to start him or trade him. A number of teams could come calling for Lincecum if he is made available. Dealing the two-time Cy Young Award winner would be a difficult pill to swallow for Giants fans.

Seattle Mariners

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Competing in the American League West will not be easy over the next few years with all of the talent that the Los Angeles Angles, Texas Rangers and Oakland Athletics have, but the Seattle Mariners have a solid core and should be a borderline division contender.

Seattle may consider dealing one of its top pitching prospects for more talent in other areas. According to Jeff Baker of the Seattle Times, the Kansas City Royals have been heavily scouting James Paxton. Dealing a prospect of Paxton's caliber would be a gut-wrenching move for the Mariners.

St. Louis Cardinals

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Lance Berkman's 2012 season was a big disappointment because of injuries. As a result, Berkman is leaning toward retirement, but he may come back (h/t Joe Strauss of the St. Louis Post-Dispatch).

The St. Louis Cardinals got a great year out of Berkman in 2011, and they could look to see if he has one more solid season left in him.

St. Louis will have a difficult decision to make in regards to whether Berkman can fit in the lineup.

Tampa Bay Rays

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The Tampa Bay Rays have never been a team that's able to put together a massive payroll. That means that they'll need to let players like B.J. Upton walk when they become free agents.

Tampa Bay will need to find a way to replace Upton and potentially Carlos Pena with the limited money that it will have available. Finding the right players will be difficult, but if the Rays make the right moves, they could be back in the playoffs the next year.

Texas Rangers

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Josh Hamilton has been a superstar since he joined the Texas Rangers, and he even picked up an AL MVP award when he was with the team. Hamilton is a big reason why the Rangers have reached two World Series in the past three years.

Now, Hamilton is the top position player on the free-agent market. Letting him go would be very difficult, but the Rangers might need to do it if another team offers him a deal with an average annual value of more than $20 million.

Toronto Blue Jays

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Every team needs a good manager. The Toronto Blue Jays just sent John Farrell to the Boston Red Sox in return for Mike Aviles, and now they need to find a new manager.

There are a number of managerial options out there, but choosing one will be no easy feat. Sandy Alomar Jr. and Manny Acta could be solid choices for the Blue Jays, but they won't know if they made the right decision until the 2013 season has ended (h/t Tony Care of CBC Sports).

Washington Nationals

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The Washington Nationals' offseason could very easily be determined by what happens with Adam LaRoche. He wants to stay with the team, and the Nationals want to re-sign him, but if they don't, they could find themselves looking for a first baseman or an outfielder (h/t Adam Kilgore of The Washington Post).

This is not necessarily a bad thing for the Nationals, as it would allow them to pursue Michael Bourn or B.J. Upton. Those moves could help improve the Nationals' 2013 World Series chances.

Chapman's Game-Saving Play 😱

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