Every MLB Team's Biggest Mistake Made This Offseason

Ely SussmanCorrespondent IJanuary 30, 2013

Every MLB Team's Biggest Mistake Made This Offseason

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    MLB teams make countless decisions over the course of the offseason, and not all of them can be resounding successes. These are the mistakes they will eventually regret.

    While many seem guilty of irresponsibly spending on free agents, others deserve reprimand for not pulling the trigger. In several instances, general managers missed out on great opportunities by second-guessing themselves.

    The 2013 regular season will expose the following errors.

Arizona Diamondbacks: Trading Justin Upton for Weak Package

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    The Arizona Diamondbacks cannot be reprimanded for trading Justin Upton. They identified him as a poor fit for their clubhouse and organization and had a surplus of outfielders to fill the void.

    But as ESPN Insider Keith Law thoroughly explains, this agreement was pretty unbalanced.

    Martin Prado is an impending free agent who reportedly seeks at least $12 million annually on a contract extension. Randall Delgado has MLB experience, though there's skepticism as to whether or not he can lead a rotation without a breaking ball to miss more bats. Moreover, none of the prospects coming to the desert are even sure-fire MLB regulars.

Atlanta Braves: Claiming Jordan Schafer off Waivers

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    Jordan Schafer's days in the Atlanta Braves organization might be numbered following the Justin Upton trade.

    But why did the team pick him up at all?

    Craig Calcaterra of NBC Sports had the same question back in November.

Baltimore Orioles: Non-Tendering Mark Reynolds

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    The Baltimore Orioles gave the other 29 MLB teams opportunities to speak with Mark Reynolds, and now he's gone.

    Declining his $11 million club option was a no-brainer, but the O's should have been content to offer him arbitration at a significantly lower price.

    Now, spring training is only a couple weeks away, and the team has very few places to turn for a middle-of-the-order hitter.

Boston Red Sox: Signing Stephen Drew

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    Homegrown shortstop Jose Iglesias has looked totally over-matched at the plate in limited MLB opportunities, and Xander Bogaerts isn't ready to debut. The Boston Red Sox were right to sign a veteran shortstop.

    With that said, Stephen Drew is the wrong fit.

    The team has guaranteed him $9.5 million when similar stopgaps like Yuniesky Betancourt and Alex Gonzalez were available at dramatically lower prices.

    If the money had gone toward starting pitching, perhaps the Red Sox could have signed Anibal Sanchez instead of Ryan Dempster.

Chicago Cubs: Signing Carlos Villanueva

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    There comes a point where enough is enough.

    The Chicago Cubs have splurged on the free-agent market, mainly to bolster their starting rotation. Scott Baker and Scott Feldman each received one-year contracts so that they may be flipped for prospects over the summer. Edwin Jackson is a long-term piece who inked a four-year deal.

    Carlos Villanueva got $10 million to join the rotation mix.

    It's a hefty price to pay a homer-prone right-hander with 56 career starts. Plus, his presence blocks Chicago's cheap internal candidates.

Chicago White Sox: Guaranteeing Three Years to Jeff Keppinger

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    Jeff Keppinger was a smart addition for the Chicago White Sox, as he provides similar overall value to Kevin Youkilis at one-third the salary. Contact ability helps manufacture runs, and his positional versatility could become very important further down the road.

    It's risky nonetheless to make a three-year guarantee to someone who has never played 140 games in any season.

Cincinnati Reds: Moving Aroldis Chapman to Starting Rotation

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    A dominant starter is worth much more than a dominant closer, so you can't blame the Cincinnati Reds for trying Aroldis Chapman in a larger role.

    But it's going to be a rough transition for him.

    The Cuban Missile will need to refine a tertiary pitch to mix in with his fastball and slider. He also has a tendency to nibble during plate appearances ("wasting" pitches), which will limit him to a short outings in the rotation.

    Making this decision led the Reds to overpay for Jonathan Broxton.

Cleveland Indians: Paying Big Bucks for Nick Swisher

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    Ohio native Nick Swisher is powerful, consistent, lovable, enthusiastic...and expensive. Very expensive, especially for a small-market team like the Cleveland Indians.

    They will be hard-pressed to build a deep and talented roster around Nick Swisher's $56 million deal.

    A shorter commitment to Torii Hunter or Ryan Ludwick would have made more sense considering Cleveland's payroll limitations.

Colorado Rockies: Re-Signing Jeff Francis

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    Factoring in ballpark conditions, Jeff Francis had a mediocre 86 ERA+ last summer and owns a 89 ERA+ since 2008.

    Why does he deserve a major league deal?

    The Colorado Rockies need to make wholesale changes to their pitching staff. This familiar face is not part of the solution.

Detroit Tigers: Choosing Prospect Bruce Rondon over Established MLB Reliever

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    Bruce Rondon has pitched just eight innings about the Double-A level, but the Detroit Tigers insist that he is ready to close out games in the majors.

    Jose Valverde clearly wasn't the right man for the ninth-inning job. Still, it's risky to replace him internally.

Houston Astros: Moving Wilton Lopez

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    General manager Jeff Luhnow is under the absurd impression that starting pitcher Alex White still has "a great future in front of him," reports Brian T. Smith of the Houston Chronicle. That belief compelled him to trade away the team's best reliever.

    Wilton Lopez was first-time arbitration eligible following a brilliant season. The move would have made some sense had the Houston Astros signed a cheaper closer to fill his shoes.

    Alas, they proceeded to pay $2 million for Jose Veras (1.51 WHIP in 2012), while Lopez settled for a one-year, $1.76 million deal with the Colorado Rockies.

Kansas City Royals: Re-Signing Jeremy Guthrie

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    Jeremy Guthrie spent the majority of 2012 performing poorly at high altitude, but the Kansas City Royals didn't hold that against him in contract negotiations. They were only concerned with retaining the late-season version who maintained a 3.16 earned run average in the American League and pitched six-and-a-half innings per start.

    His game plan suits Kauffman Stadium, but left-handed power hitters have always given him trouble. Right on cue, Victor Martinez will return from a torn ACL, Justin Morneau is going through a normal, healthy offseason and entering his walk year and Nick Swisher has signed with the Cleveland Indians.

    The AL Central should be a nightmare for Guthrie, and the Royals will be largely disappointed in their investment over the next three years.

Los Angeles Angels: Adding Tommy Hanson

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    Entering the offseason, the Los Angeles Angels' rotation was in terrible condition. After a flurry of moves, unfortunately, the outlook isn't much brighter.

    Acquiring Tommy Hanson was particularly ill-advised because he has trended in the wrong direction since debuting with the Atlanta Braves in 2009. Though the 26-year-old continues to get plenty of strikeouts, he fails to stick around into the later innings (one complete game in 108 career starts).

    The Angels exchanged Jordan Walden for Hanson in a move that comprises their bullpen depth.

    Projected closer Ryan Madson continues to rehab from Tommy John surgery, and new setup man Sean Burnett is coming off a minor elbow procedure of his own. Preserving leads could be a problem early on if neither return to 100 percent.

Los Angeles Dodgers: Extending Brandon League

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    Brandon League fooled the Los Angeles Dodgers by making the final two months prior to free agency the finest of his career. League had never previously pitched at Dodger Stadium, but he recorded some clutch saves down the stretch as interim closer.

    In reality, he's somewhat of a questionable fit.

    League—whose success hinges on inducing ground balls—only has half an infield he can trust. Between Luis Cruz, Dee Gordon and Hanley Ramirez, the left side doesn't inspire much confidence.

    According to Ken Gurnick of MLB.com, L.A. wants Scott Rolen to tighten up the defense. However, the accomplished third baseman would play sparingly, even if he avoided injury.

    Pre-arbitration-eligible Kenley Jansen should be on the mound when the leverage is highest.

Miami Marlins: Consenting to 12-Player Blockbuster

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    At first, negotiations with Toronto Blue Jays general manager Alex Anthopoulos centered around Josh Johnson. Moving him alone might have angered Miami Marlins fans, but with the right-hander entering an expensive walk year, they would've understood.

    However, the Fish alienated what remained of their small following by dumping Emilio Bonifacio, Mark Buehrle and Jose Reyes. Their contracts were back-loaded yet affordable for a franchise profiting off a new ballpark and line of apparel.

    Though surrendering star players is never popular, it can be wise if the exchange includes elite prospects.

    It doesn't seem that any of the seven newcomers have All-Star potential. Justin Nicolino, 21, owns gaudy minor league stats, but you won't find anyone who expects him to be an MLB ace with such an ordinary repertoire.

    Convinced that the team doesn't care about competing, a lot of former supporters will stay away from Marlins Park in 2013.

Milwaukee Brewers: Conceding to Boston Red Sox in Ryan Dempster Bidding War

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    This winter, Ryan Dempster sought the most lucrative multi-year deal available. He received the best offer from the Boston Red Sox, who guaranteed him $26.5 million through 2014.

    The Milwaukee Brewers had a bizarre fascination with him. GM Doug Melvin actually told Tom Haudricourt of the Milwaukee Journal Sentinel that they wouldn't pursue any other free-agent starting pitchers.

    He has stayed true to his word, which leaves a host of inexperienced internal candidates to battle for rotation spots behind Yovani Gallardo and Chris Narveson.

    If Dempster was the only available arm that Milwaukee trusted, why didn't the front office make a more tempting offer?

    Missing out has left the Brewers ill-prepared for the season.

Minnesota Twins: Signing Kevin Correia

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    The Minnesota Twins have committed to overhauling their starting rotation.

    They dealt outfielders Ben Revere and Denard Span and received Alex Meyer, Vance Worley and Trevor May—a serviceable arm for 2013 and two future major league pitchers with high ceilings.

    In free agency, the Twins inked Rich Harden and Mike Pelfrey to low-risk deals as they attempted to come back from serious injuries.

    The only thing missing was an eight-figure commitment to an established, top-tier guy.

    Inexplicably, Minnesota deemed Kevin Correia worthy of two years and $10 million.

    Correia owns one of baseball's lowest strikeout rates, despite spending the first decade of his career in the National League. The 32-year-old has one season of 30-plus starts and none above 200 innings pitched.

    The team's biggest addition was probably its most useless.

New York Mets: Reaching Early Expiration Agreement with Jason Bay

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    Jason Bay will still get every cent of his contract, but the New York Mets decided that paying it all on time is too tough to swallow.

    By deferring the $21 million, the team was presumably going to spend more on the 2013 team. It's been nearly three months since the agreement, and Shaun Marcum is the only free agent to sign a major league contract with New York.

    Meanwhile, the Mets don't have any established, right-handed-hitting outfielders.

New York Yankees: Letting Russell Martin Leave

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    For two years, Russell Martin was a very adequate starting catcher for the New York Yankees. He's both an athletic defender and above-average power source.

    The soon-to-be 30-year-old sought a slight pay raise in free agency this offseason and got it from the Pittsburgh Pirates. The Yankees reportedly had serious interest, but weren't willing to match the $17 million offer.

    His departure leaves them with an unexciting competition between Francisco Cervelli, Chris Stewart and prospect Austin Romine.

Oakland Athletics: Dealing Cliff Pennington for Chris Young

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    At the time, the Oakland Athletics probably had confidence that they would re-sign shortstop Stephen Drew.

    Instead, Hiroyuki Nakajima got the opportunity, even though he has zero MLB experience.

    There doesn't seem to be space for Chris Young in the crowded outfield, and the A's are on the hook for $8 million of his 2013 salary. And with Cliff Pennington gone, Oakland will have trouble filling in for Nakajima should he underachieve.

Philadelphia Phillies: Acquiring Michael Young

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    Few full-time third basemen were available in free agency, and hardly any could be acquired via trade.

    So the Philadelphia Phillies settled for Michael Young.

    He has played just 65 games there since 2011 and has been very mediocre defensively. Young's hitting skills seem to be fading at age 36, as he set career lows in home runs and OPS last summer.

    Philly received surprisingly strong production from Kevin Frandsen's right-handed bat in 2012. Pursuing a platoon partner like Eric Chavez seemed like a more sensible choice.

    Instead, this team sacrificed two relievers and remains on the hook for $6 million of Young's salary.

Pittsburgh Pirates: Signing Francisco Liriano

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    The Pittsburgh Pirates wisely sought a veteran to solidify the back end of their rotation.

    Francisco Liriano isn't the right fit.

    Much like Tommy Hanson, he is a strikeout artist who works inefficiently. Going from the AL to the NL generally helps starters, but facing shorter lineups won't help Liriano if his struggles to find the plate persist.

    Agent Greg Genske looks like a genius for getting the southpaw a multi-year deal in light of an offseason arm injury.

San Diego Padres: Backing out of Edwin Jackson Sweepstakes

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    A San Diego Padres source told ESPN.com's Jim Bowden that the team was aiming toward signing Edwin Jackson to a three-year deal.

    Of course, the 29-year-old ultimately went elsewhere for more guaranteed money.

    San Diego was foolish to shy away from a long-term commitment. Aside from Tommy John survivor Cory Luebke, the Padres don't have any starting pitchers in their future plans.

    It has otherwise been a quiet offseason for a club that's seemingly over-matched in the NL West.

San Francisco Giants: Re-Signing Angel Pagan

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    GM Brian Sabean spoils his own players, either in the form of premature contract extensions or lucrative free-agent contracts.

    He brought back Jeremy Affeldt and Marco Scutaro on three-year deals. Overpaying was somewhat acceptable in those cases because there wasn't much else available at either of their positions.

    Locking up Angel Pagan for $40 million, however, is tougher to justify.

    The San Francisco Giants had ample payroll to use, and Michael Bourn, B.J. Upton and Shane Victorino were on the market. Each of them is better established at the major league level.

Seattle Mariners: Passive Approach to Felix Hernandez Extension Talks

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    In practically every case, MLB teams try to sign players to short contracts. That way, they don't wind up overpaying for declining or injured individuals.

    Felix Hernandez is an exceptional case, however.

    The Seattle Mariners must make it their top priority to lock in the ultra-durable perennial All-Star to a long deal. In the coming months, Clayton Kershaw and Justin Verlander will change the market with massive extensions of their own.

    Jon Heyman of CBS Sports reports that the M's have only proposed to add four years to his existing contract this point. 

St. Louis Cardinals: Guaranteeing Three Years for Randy Choate

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    The St. Louis Cardinals overpaid for the left-handed specialist that had been eluding them.

    Randy Choate pitches almost exclusively with the platoon advantage, which means very brief appearances.

    St. Louis also has to worry about him regressing in his age-37 season.

Tampa Bay Rays: Signing Kelly Johnson

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    The Tampa Bay Rays seemingly had their 25-man roster set up prior to this surprise signing.

    Kelly Johnson's .225/.313/.365 batting line last season wasn't enough to land him an everyday job in 2013. Instead, Ken Rosenthal of Fox Sports has learned that he'll alternate between second base and the outfield.

    The unofficial deal is presumably a cheap one, but it doesn't necessarily make Tampa Bay more competitive.

Texas Rangers: Overpaying for Lance Berkman

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    Lance Berkman isn't particularly motivated to play at this stage of his career. He has a championship (from the 2011 St. Louis Cardinals) and was prepared to retire if the right offer didn't come along.

    With great power and plate discipline, he should be able to live up to the $11 million contract if healthy.

    But that's a big "if" for a veteran coming off multiple knee surgeries.

    The Texas Rangers have a surplus of desirable prospects who could have been packaged together to acquire a healthier, hungrier power bat of the Giancarlo Stanton/Justin Upton ilk.

Toronto Blue Jays: Not Trying to Trade Adam Lind

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    GM Alex Anthopoulos expressed his disappointment in first baseman/designated hitter Adam Lind last September, according to Chris Toman of MLB.com. He insisted that changes were coming to the organization and that the 29-year-old was essentially on the hot seat.

    We've witnessed the front office revamp Toronto's roster and make it a serious contender, yet Lind remains.

    Moving him early in the winter to a desperate suitor would have allowed the Blue Jays to search for upgrades in free agency. Now it's too late—the market is all dried up.

Washington Nationals: Non-Tendering John Lannan

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    Paying upward of $5 million for a sixth starter isn't ideal, but at least John Lannan was somebody the Washington Nationals could trust to fill in if need be. He became a free agent at the non-tender deadline and promptly joined the division rival Philadelphia Phillies.

    On paper, the Nats look like World Series favorites.

    For the time being, though, they seem unprepared to handle a major injury to any rotation member.