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Every MLB Team's Biggest Offseason Regret

Joel ReuterFeatured ColumnistMay 15, 2012

Every MLB Team's Biggest Offseason Regret

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    Roughly a month and a half into the baseball season, we have a good gauge on what teams and players to watch this season and we can begin analyzing how certain offseason decisions worked out for teams.

    Whether it was signing or trading for someone, or in the end not signing or trading someone, now is the time when teams begin to second guess the decisions they made this winter.

    So with that in mind, here is a look at each team's biggest offseason regret as of right now.

Baltimore Orioles: Signing Tsuyoshi Wada

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    Wada was one of two Japanese pitchers the Orioles signed this offseason, the other being Wei-Yin Chen (3-0, 2.68 ERA), who has been a solid part of the big-league rotation.

    Wada on the other hand struggled to a 9.00 ERA in five spring training innings and was sent to Triple-A where he allowed six earned runs over 2.1 innings in his only start before going down with an arm injury.

    The injury required Tommy John surgery, and he will miss the rest of the season and perhaps the start of next season. In the end, the two-year, $8.15 million contract they signed him to could come and go without him making a big-league appearance.

Boston Red Sox: Not Signing a Starting Pitcher

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    This offseason, the Red Sox kicked the tires on a number of starting pitchers but in the end they decided to sign a bevy of low-cost veterans to provide rotational depth.

    Aaron Cook, Vicente Padilla, Carlos Silva and Ross Ohlendorf were signed to minor league deals but in the end the two open rotation spots went to Felix Doubront and Daniel Bard.

    That duo has been up and down—as has the entire rotation—and in the end it likely would have been wise for the Red Sox to add at least one more proven veteran arm to the front of their rotation.

New York Yankees: Trading for Michael Pineda

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    In need of starting pitching depth after relying on veterans Bartolo Colon and Freddy Garcia last season, the Yankees dealt top prospect Jesus Montero to the offense-starved Mariners for Michael Pineda.

    An All-Star as a rookie, Pineda went 9-10 with a 3.74 ERA as a 22-year-old rookie and it looked to be a trade that greatly benefited both sides. 

    So far, Montero has been solid hitting .262, five HR, 17 RBI, and at 22 years old, he has the makings of a future superstar.

    Pineda, on the other hand, saw his 2012 season end before it even started as he will be shelved for the season with a torn labrum.

    There is certainly time for this trade to turn around in the Yankees' favor, but as of now they are no doubt regretting it.

Tampa Bay Rays: Not Upgrading at Catcher/Second Base

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    The Rays have been among the league's best teams so far this season, compiling a 22-14 record as they have once again benefited from terrific starting pitching.

    Many believed they would use their wealth of young starting pitching to fill glaring holes at catcher and shortstop, but instead they entered the season with well below-average options.

    Jose Molina (.210 BA) and Sean Rodriguez (.228 BA) have both performed as expected and one has to wonder how much better the team would be if they had upgraded at those positions.

Toronto Blue Jays: Not Making a Splash Signing

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    As the Blue Jays continue their ascent to relevancy in the AL East, many expected them to make a splash this offseason.

    Whether it was signing Prince Fielder or Albert Pujols to anchor the lineup, or making the winning bid to negotiate with Yu Darvish, they were expected to make some sort of game-changing addition by many experts.

    Instead, the team more or less stood pat and now they find themselves right in the thick of things in the AL East to the point that a big addition may have been enough to push them over the top.

    Granted they are building up their team from within, and keeping a reasonable payroll while they do it, but they likely at least partially regret not adding a big name.

Chicago White Sox: Not Re-Signing Mark Buehrle

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    After 12 seasons and 161 wins as a member of the White Sox, Mark Buehrle hit the free-agent market this offseason and eventually signed a four-year, $58 million contract with the Marlins.

    Expected to be in a rebuilding season, the White Sox have shown flashes of being a solid team this season. Had they seen that coming, they likely would have at least made a play to bring back Buehrle.

    Not only was he an effective and durable starter, but Buehrle was also a fan favorite in Chicago and they have no doubt given second thought to not bringing him back.

Cleveland Indians: Re-Signing Grady Sizemore

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    Once a budding superstar following three straight 20-20 seasons, capped by a 33 HR/38 SB season in 2008, Grady Sizemore has fallen off drastically since that season.

    He has appeared in just 210 games over the past three season, posting a .234 BA, 28 HR, 109 RBI line over that span, and that was enough for the Indians to decline his $9 million option this offseason.

    However, the team brought him back on a one-year, $5 million contract that included $4 million in incentives, but a back injury and subsequent back surgery has kept him off the field indefinitely.

Detroit Tigers: Not Moving Jacob Turner

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    With the signing of Prince Fielder this offseason, the Tigers immediately moved into the ranks of the American League's elite.

    However, they still look as though they are a notch below the Rangers and the incredibly deep AL East, and that may not have been the case had the made a big trade this offseason.

    The team was willing to move top prospect Jacob Turner for the right package, but they did not peruse anything all that strongly.

    Would they have been able to land someone like Matt Garza with a package built around Turner? We may never know but chances are they wish they would have tried a little harder, especially following the emergence of fellow pitching prospect Drew Smyly (1.59 ERA, 34 IP).

Kansas City Royals: Not Adding a Front-of-the-Rotation Starter

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    The Royals are off to a disappointing start this season after showing signs of taking the next step last year, and that is due in large part to their starting pitching.

    While their young offensive core is coming together and continues to improve, the starting rotation is made up of a number of borderline starters.

    They acquired Jonathan Sanchez (6.75 ERA) from the Giants this offseason, but he has struggled and is now on the disabled list and no one in the rotation has an ERA under 4.50.

Minnesota Twins: Letting Michael Cuddyer and Jason Kubel Walk

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    Last season at the deadline, the Twins made the surprising decision not to be sellers and held onto free-agent-to-be outfielders Jason Kubel and Michael Cuddyer.

    In the end, the team was unable to re-sign either player as Kubel joined the Diamondbacks and Cuddyer joined the Rockies.

    The team did add Josh Willingham to take over in right field, but with a .238 team batting average, they could use all the offense they can get. Not bringing back those two guys, or at least one of them, was a questionable move by the team.

Los Angeles Angels: Signing Albert Pujols

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    It took a 10-year, $240 million deal, but the Angels surprised the baseball world when they landed Albert Pujols this offseason and immediately became a trendy pick to win it all.

    However, Pujols has struggled like never before and he currently has a line of .196 BA, one HR, 12 RBI through his first 138 at-bats.

    The contract was expected to be a bad one over the final five seasons or so, but the trade-off was that the team would be a contender now. Instead, they have struggled to a 15-20 record and have seen their prize acquisition stumble out of the gates.

Oakland Athletics: Trading Gio Gonzalez

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    Another season, another crop of veterans dealt away for prospects in Oakland as the team traded young starters Gio Gonzalez and Trevor Cahill as well as closer Andrew Bailey.

    It landed them four solid prospects, but in the end trading Gonzalez was a head-scratching move, as the Nationals immediately locked him up with a very reasonable five-year, $42 million deal.

    He has rewarded them with a 4-1, 1.94 ERA, 50 Ks, 41.2 IP line through his first seven starts as he has been one of the top starters in baseball.

Seattle Mariners: Not Signing Prince Fielder

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    The Mariners have played solid baseball off and on this season on their way to a 16-20 start, and it is their offense that continues to hold them back as they are hitting .235 collectively.

    Without question, Prince Fielder was the biggest question mark free agent of the offseason and he took longer to sign than the other big names on the market.

    While little to no one saw him going to the Tigers, many thought the Mariners would be his eventual destination. That did not come to pass, and the Mariners could no doubt use the offensive boost Fielder would have given them right about now.

Texas Rangers: Not Locking Up Josh Hamilton

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    This offseason saw the Rangers sign Yu Darvish to a six-year, $60 million deal that also included a $51.7 million posting fee. They also re-signed Ian Kinsler to a five-year, $75 million extension.

    However, absent from their moves was an extension for free-agent-to-be Josh Hamilton, as the team decided to wait and see what happened this season regarding his production and health before making a decision.

    A .402 BA, 18 HR, 44 RBI start later and his value has likely increased from what the Rangers could have signed him for this winter, and he will only get more expensive if he continues to produce like he has.

Atlanta Braves: Not Trading Jair Jurrjens

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    The market value for good starting pitching was high this offseason, as teams gave up loaded prospect packages to acquire the likes of Mat Latos, Gio Gonzalez and Trevor Cahill.

    That led to a number of other pitchers rumored to be moving while their value was high, and chief among them was 26-year-old All-Star Jair Jurrjens.

    With a good deal of young pitching depth and Jurrjens headed for another raise in his final year of arbitration eligibility, moving him made sense. In the end though, the team chose to hold onto him.

    A 9.37 ERA over 16.1 innings in his first four starts earned him a demotion to Triple-A, and his value is now a shell of what it once was even if the team wanted to trade him.

Miami Marlins: Signing Heath Bell

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    With the ushering in of their new ballpark, the Marlins made a bevy of moves this offseason, signing Jose Reyes, Mark Buehrle and Heath Bell as free agents and trading for Carlos Zambrano and new manager Ozzie Guillen.

    Those moves have netted mixed levels of success, but the Bell signing has been without a doubt the worst as he has converted just 3-of-7 save chances and has a 10.03 ERA.

    That after saving 132 games over the past three seasons while pitching for the Padres, and with a three-year, $27 million commitment to him, Bell could be a mistake the Marlins are not able to soon forget.

New York Mets: Relying on Frank Francisco to Close Games

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    The Mets have been one of the surprise teams of the year so far, with a 19-15 record. Despite a relatively quiet offseason that saw them lose star shortstop Jose Reyes and gain little to nothing, they have been impressive.

    The one move that stands out as a mistake was signing Frank Francisco to be the team's closer. The 32-year-old had converted just 49-of-70 save chances for his career entering the season, yet he was brought on to man the ninth inning.

    With a 8.59 ERA, two blown saves and three losses, it has been a rough start to the season for Francisco and he may soon lose his job to Jon Rauch, Bobby Parnell or someone else entirely.

Philadelphia Phillies: Not Adding More Offense

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    With Ryan Howard expected to miss the first several months of the season and Chase Utley injured early in spring training and out indefinitely, the Phillies offense has struggled mightily this season.

    In the offseason, they signed Ty Wigginton and Jim Thome to help hold down the fort at first base, and Juan Pierre was signed as a minor league free agent, but little else was done to improve an aging and injured offense.

    As a result, the Phillies find themselves with a losing record, unable to match their terrific starting pitching with a passable offense and they desperately need Howard and Utley to return.

Washington Nationals: Nothing

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    Things could not have gone better for the Nationals to this point from a player standpoint, as they were able to cope with the loss of Ryan Zimmerman and continue to win without Michael Morse.

    Bryce Harper has shown flashes of the hype, and the pitching staff has been out of their minds as a collective unit.

    So to this point, the Nationals have no reason to be anything but pleased with their offseason decisions. I guess that makes up for last offseason when they shelled out a seven-year, $126 million contract to role-player Jayson Werth.

Chicago Cubs: Trading for Ian Stewart

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    After hitting 43 home runs and driving in 131 runs combined in 2009 and 2010, Stewart had a disastrous 2011 season that saw him hit just .156 and spend much of the season in the minors.

    The Cubs took a chance on him bouncing back, trading Tyler Colvin and DJ LeMahieu to the Rockies for the 27-year-old and plugging him into an everyday role.

    So far, he has responded by hitting .193, four HR, 12 RBI, while Colvin has hit .328, three HR, 11 RBI as the Rockies' fourth outfielder.

Cincinnati Reds: Signing Ryan Madson

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    In his first season as a full-time closer, Madson saved 32 games and posted a 2.37 ERA, before hitting the free-agent market this winter.

    Unable to find a multi-year deal to his liking, he signed a one-year contract worth $8.5 million with the Reds in hopes of performing for a multi-year deal next year.

    Madson was signed to replace the departed Francisco Cordero in Cincinnati, but a spring injury led to Tommy John surgery. Chances are he will never set foot on the field as a member of the Cincinnati Reds.

    That has forced fellow offseason acquisition Sean Marshall into the closer's role and weakened the entire bullpen as a result.

Houston Astros: Nothing

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    The Astros did exactly what they should have this winter, as they avoided spending money on the free-agent market and remained committed to rebuilding.

    They entertained offers for the likes of Wandy Rodriguez, Brett Myers and Carlos Lee, and those guys will continue to be available all season long, but for now the Astros are far outplaying expectations.

    That said, there is no reason those three guys should still be in Houston after the trade deadline, as the team should be able to net some decent prospects in return for them.

Milwaukee Brewers: Signing Aramis Ramirez for Three Years

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    In the wake of Prince Fielder departing and with a hole at third base, the signing of Aramis Ramirez made plenty of sense for the Brewers this offseason.

    Coming off of a .306 BA, 26 HR, 93 RBI season, Ramirez was far and away the best third baseman on the market.

    However, he is also 34 years old and just two years removed from a .241 BA, 25 HR, 83 RBI season, and so far in 2012 he has looked more like his 2010 self in hitting .230, two HR, 19 RBI.

    If this were a one-year deal it would not be so bad, but the fact that he is signed for the next two seasons at $13 million per season is the part of this deal the Brewers may now be regretting.

Pittsburgh Pirates: Signing Clint Barmes

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    After suffering through season after season of Ronny Cedeno at shortstop, the Pirates massively overpaid for Clint Barmes, inking him to a two-year, $10.5 million contract this winter.

    He had a solid 2011 season, as he hit .244, 12 HR, 39 RBI and posted a 3.1 WAR, but at 33 years old and with far less impressive career averages, the signing was a head-scratcher at that price.

    And he has proved the doubters right, with a .162 BA, two HR, six RBI line thus far in 2012.

St. Louis Cardinals: Nothing

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    The Cardinals dealt with losing one of the greatest players of all time the winter after winning the World Series, yet they still hold a 20-15 record and sit in first place in the NL Central.

    Lance Berkman was re-signed, as was deadline-acquisition Rafael Furcal. Outfielder Carlos Beltran was brought in to replace some of the production that left with Pujols.

    While Berkman has been hurt much of the year, Furcal (.383 BA, 25 R) and Beltran (.298 BA, 13 HR, 32 RBI) have carried the offense and the Cardinals look as good as ever top to bottom.

Arizona Diamondbacks: Not Signing a Replacement Shortstop

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    When shortstop Stephen Drew went down with a fractured ankle last July, Willie Bloomquist filled in admirably as he hit .266 with 20 steals while playing terrific defense at shortstop.

    The team also acquired John McDonald from the Blue Jays at the deadline for insurance, and this offseason brought both Bloomquist and McDonald back to bridge the gap until Drew returns.

    However, Bloomquist has struggled (.219 BA) and there is no real timetable on when Drew will return at this point. Cody Ransom (.317 BA, four HR, 12 RBI) has seen some time there recently, but he is better suited playing third base.

    In an offseason where a number of veteran shortstops were available for relatively cheap, such as Alex Gonzalez, Yuniesky Betancourt, Jamey Carroll and Jerry Hairston Jr. among others, the Diamondbacks would have been wise to ink one of those guys, as Bloomquist is best off as a utility player, not an everyday starter.

Colorado Rockies: Not Finding a Staff Ace

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    Since trading Ubaldo Jimenez to the Indians at the deadline last season, the Rockies have been without a staff ace. While they acquired a number of pitchers this offseason, none really fits the bill.

    Jeremy Guthrie, Guillermo Moscoso, Josh Outman, Zach Putnam, Tyler Chatwood and Jamie Moyer were all brought in this offseason and thus far the 49-year-old Moyer (1-3, 4.66 ERA, seven starts) has been the best of the bunch.

    The team has a lot of top-end young talent in guys like Drew Pomeranz, Alex White and Christian Friedrich, but for now they will continue to struggle with a staff full of bottom-of-the-rotation guys.

Los Angeles Dodgers: Nothing

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    Much like the Nationals, the Dodgers should be nothing but pleased with their offseason as they not only helped fill out their roster with veterans like Mark Ellis, Jerry Hairston Jr, Chris Capuano and Aaron Harang, but they also locked up superstar Matt Kemp through 2019.

    The team is thriving with a 23-11 record, and while there are still holes in left field and at third base, that is by no fault of what the team did this past offseason.

    Expect one or both of those issues to be addressed at the deadline, and making a decision regarding Andre Ethier to be the big decision of this coming offseason.

San Diego Padres: Trading Away Anthony Rizzo

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    The Padres pulled off a huge coup when they acquired four quality young players from the Reds in exchange for starter Mat Latos. Among those players was first baseman Yonder Alonso. 

    The acquisition of Alonso made top prospect Anthony Rizzo expendable in the Padres' minds and they sent him to the Cubs for reliever Andrew Cashner.

    Both Alonso (.293 BA, 10 RBI) and Cashner (3.45 ERA, 15.2 IP) have been solid this year, but Rizzo has all the makings of a future star in the middle of the Cubs' order and he is currently hitting .351, 11 HR, 34 RBI through 134 Triple-A at bats.

    He may have been expendable for the Padres, but you have to think they could have gotten significantly more than they did for him.

San Francisco Giants: Ignoring the Middle Infield Situation

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    The Giants have developed a reputation as a team with a dynamite pitching staff and an anemic offense over the past few years, and that has been the case again this year.

    While there are a number of holes in their lineup, none is more gaping than the middle infield situation where Brandon Crawford (.208 BA) and Emmanuel Burriss (.231 BA) are currently the starters.

    Ryan Theriot (.179 BA) was signed to add depth, but the team did little else to address the situation. While Freddy Sanchez should be back at some time this season, there is still no reason any big-league club should pencil in Brandon Crawford's name as their everyday shortstop.

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