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Ruben Amaro's 25 Biggest Fails as GM of the Philadelphia Phillies

Greg PintoCorrespondent IDecember 22, 2016

Ruben Amaro's 25 Biggest Fails as GM of the Philadelphia Phillies

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    The Philadelphia Phillies are having the kind of season that puts the word "failure" in perspective.

    To be out of the postseason race in the month of August after having the expectations of a World Series contender in spring training is simply inexcusable for the team with the highest payroll in the National League.

    Of course, when you devote that kind of money to build a winner and it doesn't win, the blame falls on the general manager, tasked with putting that team together. For the Phillies, that man has been Ruben Amaro Jr. since November 1, 2008.

    It has been an interesting ride for Amaro thus far. He took over the organization's front office at the peak of its success—the day after the Phillies paraded down Broad Street to celebrate just their second championship.

    The four seasons that followed could be described as a "fall from grace." The Phillies made it back to the World Series in 2009, but lost. In 2010, they were expelled from the National League Championship Series. The next season, they made an even earlier exit.

    In 2012, making the postseason would be nothing short of a miracle.

    While you shouldn't put too much stock in that decline, it is symbolic of Amaro's tenure as the general manager. Although he has had his share of successes, he has had his share of failures as well, and that's how the Phillies wound up in this position.

    Let's take a look at the 25 biggest failures of Amaro's tenure.

The Castillo Experiment

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    It may not have been his worst move, but it was certainly one of the most curious.

    With Chase Utley on the disabled list for the foreseeable future at the beginning of 2011, Ruben Amaro Jr. brought in a former enemy: Luis Castillo.

    Needless to say, bringing in the former Florida Marlins and New York Mets second baseman wasn't a popular decision among the Phillies' fanbase.

    After scuffling in spring training, Castillo was released by the Phillies after just nine days.

Losing Quintin Berry on Waivers

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    Given the lack of quality positional prospects in the Phillies' system, you would think that Ruben Amaro Jr. would hold on to guys with upside.

    You can add outfielder Quintin Berry to that list. Amaro gets a bit of slack on this one because Berry wasn't showing many signs of life in the Phillies' system.

    The Phillies wound up designating Berry for assignment in July of 2010 and the San Diego Padres made sure he didn't clear waivers.

    This year Berry's having a breakout season for the Detroit Tigers.

Brandon Moss Walks

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    Brandon Moss had quite a season in 2011.

    Though he didn't join the Phillies until after rosters expanded in September, Moss went on a tear for the Phillies' Triple-A affiliate, posting a slash line of .275/.368/.509 with 23 home runs.

    Couple that with the Phillies' monetary restrictions coming into the 2012 season, and you would think that the club had found itself some serious left-handed pop on the cheap.

    Not so fast.

    The Phillies let Moss slip away following the 2011 season. He signed with the Oakland Athletics, where he's already hit 11 home runs this season despite starting the year in Triple-A.

The Jim Thome Experiment

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    Full disclosure: I was a big fan of this move. It just didn't work out.

    If the Phillies were lacking anything in 2011, it was power off the bench. By the end of the season, Ross Gload's hip was so frayed that he could barely swing a bat, let alone hit for power.

    So Ruben Amaro Jr. spent most of the offseason rejuvenating his bench. That included the signing of a familiar face in Jim Thome.

    The idea was for Thome to be the club's primary pinch-hitter while starting at first base at least once a week in Ryan Howard's absence to stay sharp.

    Obviously, that never happened, as Thome just couldn't handle the strain. The Phillies eventually abandoned the experiment by sending him to the Baltimore Orioles for a pair of prospects.

Brian Schneider's Deal(s)

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    In hindsight, bringing Brian Schneider into the fold was probably a good decision by the Phillies' front office. He's a consummate professional and clearly knows how to call a game. Having a veteran backup is never a bad idea. 

    That doesn't mean that the Phillies signed him to a pair of good deals.

    Prior to the 2010 season, the Phillies inked Schneider to a two-year deal. Again, he's a solid backup, but why commit to two years? That will be a recurring theme.

    When that deal expired following 2011, the Phillies re-signed Schneider to a one-year deal that could wind up being worth $1 million. I'd rather have Erik Kratz for the league minimum.

The Dontrelle Willis Experiment

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    In theory, this was a pretty good idea.

    Believe it or not, it wasn't all that long ago that Dontrelle Willis was dominating the competition as a member of the Florida Marlins. His subsequent fall from grace was certainly surprising.

    However, one area of his game that always remained consistent was his success against left-handed hitters. The Phillies decided to try to tap into that success by converting him into a left-handed specialist.

    The experiment didn't last long.

    Willis struggled early in the spring and then couldn't pitch on back-to-back days, citing soreness in his arm. He wanted to be a starter. The Phillies eventually wound up releasing him and he signed with the Baltimore Orioles.

Jason Jaramillo to the Pirates for Ronny Paulino

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    This is one that never made much sense to me.

    Coming through the system, Jason Jaramillo was a solid prospect. No one thought that he'd be an All-Star, but he always seemed like a solid bet to develop into a pretty good backup guy.

    The Phillies, apparently, couldn't wait for that. They traded him to the Pittsburgh Pirates for a guy that was already a backup catcher: Ronny Paulino.

    Of course, Paulino didn't even survive spring training. They would flip him to the San Francisco Giants for left-handed reliever Jack Taschner.

Dr. Jekyll and Mr. Qualls

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    Baseball can be a funny sport.

    Heading into the regular season, I thought that this was one of Ruben Amaro Jr.'s best moves.

    It was no secret that the club's bullpen, outside of Jonathan Papelbon, was going to be relatively inexperienced, and he was able to sign a veteran right-handed reliever Chad Qualls on the cheap just before spring training.

    But Qualls would eventually implode, and the Phillies wound up designating him for assignment.

    The New York Yankees must have seen something they liked in Qualls. They worked out a trade for the right-handed reliever before the Phillies could release him.

    Then again, the Yankees eventually sent him to the Pittsburgh Pirates at the trade deadline.

Lendy Castillo Left off 40-Man Roster

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    Lendy Castillo isn't much of a household name, but the right-handed pitcher was developing into a solid prospect. Of course, prospects that develop this slowly always come with a risk.

    After Castillo spent several years in the Phillies' system, the club found itself stuck between a rock and a hard place. They had two options: Add him to the 40-man roster or risk losing him in the Rule 5 Draft.

    They chose the latter.

    The rebuilding Chicago Cubs jumped at the chance to acquire Castillo. He hasn't pitched much in the MLB this season (or well, for that matter) and is dealing with a groin injury. But scouts believe he'll become a solid reliever.

The Release of Ryan Vogelsong

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    Every now and then, a good player slips through the cracks. That's exactly what happened to the Phillies when they cut ties with right-handed pitcher Ryan Vogelsong.

    A former fifth-round pick by the San Francisco Giants, Vogelsong struggled early in his career and wound up bouncing around the league, spending a majority of his career in the Pittsburgh Pirates' system.

    But even the Pirates would tire of waiting for him to come around. Vogelsong would wind up playing in Japan before returning to the United States. The Kutztown University graduate would end up signing with the Phillies in 2010.

    The Phillies tried him as a starter and a reliever before releasing him from Triple-A mid-season. He hooked on with the Los Angeles Angels of Anaheim for the remainder of 2010 before signing with the Giants in 2011.

    The rest is history.

    Vogelsong followed up his All-Star campaign in 2011 with a Cy Young-caliber season in 2012.

Jamie Moyer's Two-Year Deal

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    Look, I understand that Jamie Moyer is a unique case. But when is it ever a good idea to sign a 45-year-old pitcher to a two-year deal?

    Given the results, I'm going to go with "never." 

    Undoubtedly, the Phillies were feeling a little giddy heading into the offseason following the 2008 campaign that ended with a parade down Broad Street. At the time, Ruben Amaro Jr. was giving away multi-year deals like candy.

    One of those deals went to the left-handed Moyer, who inked a two-year contract worth $13 million prior to the 2009 season.

    A one-year deal would have been sweet for the Phillies. Moyer won 12 games and certainly helped in the development of a relatively young pitching staff.

    The next season wasn't as good. Moyer only made 19 starts before suffering an injury and undergoing Tommy John surgery. Amaro's "extra free-agent year" strikes again. More on that in a bit.

Scott Podsednik to the Red Sox

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    Ruben Amaro Jr. has only completed three full seasons as the Phillies' general manager, and when you look at the results, it is hard to argue with his success.

    Three seasons, three trips to the postseason.

    Of course, a couple of years from now we'll probably look back on his tenure and be a bit more cynical about it. Part of the reason is Amaro's tendency to shell out big money and nice prospects for big-name players while cheaper guys rot away in Triple-A.

    You can count Scott Podsednik among them. After losing a spring position battle to Juan Pierre, the Phillies sent Podsednik to Triple-A. He wasn't a member of the Lehigh Valley IronPigs for long this season.

    The Phillies would eventually deal him to the Boston Red Sox for cash considerations. In 70 plate appearances for the Sox, Podsednik hit .387 and posted an OPS of .893.

    At the trade deadline, the Sox sent him to the Arizona Diamondbacks as part of a deal for reliever Craig Breslow.

    Does that sound like something the Phillies need?

The Release of Jason Grilli

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    Do you think that Ruben Amaro Jr. has ever stared out at his bullpen from his luxury suite this season and wished he had Jason Grilli?

    That could have been the case last season. Grilli spent most of the first half of the year pitching for the Phillies' Triple-A affiliate before he forced the Phillies to make a decision.

    Grilli had an opt-out clause in his contract that allowed him to void his contract with the Phillies if an MLB team would add him to their major league roster. The Pittsburgh Pirates wanted to do just that.

    Of course, the Phillies could have erased that opt-out clause by promoting him to the MLB. However, they decided that they were comfortable with their bullpen and let Grilli go to the Pirates.

    Grilli has since appeared in 71 games for the Pirates and posted an ERA of 2.09.

Jose Contreras' Two-Year Deal

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    Jose Contreras' Phillies career has been a game of what I like to call "Good Deal, Bad Deal."

    Contreras first joined the Phillies on a one-year deal prior to the 2010 season. At that point, he hadn't been a reliever for long after just having converted the year before as a member of the Colorado Rockies. But he posted an ERA of 3.34 and showed signs of promise.

    So what does Ruben Amaro Jr. do? Well, he did the same thing he's done for every aging veteran he's ever called on the phone. He signed him to a multi-year deal.

    That's right. Amaro signed a 39-year-old reliever to a two-year deal. How did that work out for the Phillies, you ask? Well, he missed nearly all of the 2011 season after undergoing exploratory surgery and will miss the remainder of the 2012 season after tearing his ulnar collateral ligament and undergoing Tommy John surgery at the age of 40.

    The first deal was a good one. The second? Not so much.

Danys Baez's Two-Year Deal

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    What do you think inspires a major league general manager to give a guy like Danys Baez a two-year deal?

    We're not talking about a big-time arm here. Signed prior to the 2010 season, Baez was coming off a deal with the Baltimore Orioles in which he got lit up year-in and year-out.

    Sure, a guy like Baez could be a solid veteran option. He's not going to be dominant, but he was switching leagues, so there was some hope.

    But why would you guarantee a 32-year-old pitcher with a career ERA north of four two years on a contract? It just never made sense.

    Of course, Baez was terrible during his Phillies tenure. He pitched in 80 games and posted an ERA of 5.81.

J.C. Romero's Three-Year Deal

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    The Phillies signed J.C. Romero to a minor league contract during the 2007 season and it proved to be one of their best moves of the season.

    Of course, that was a move orchestrated by Hall of Fame executive Pat Gillick, not Ruben Amaro Jr.

    Amaro would get his chance to follow in his predecessor's footsteps after the season when Romero reached free agency. However, instead of signing Romero to a one-year deal as is commonplace for most relievers, Amaro threw extra years at him.

    The Phillies and Romero agreed to a three-year deal. That's right. Three years for a left-handed specialist.

    The 2008 season worked out pretty well for all parties involved. The Phillies won the World Series and Romero was a huge part of the reason why the Phillies' bullpen was so successful.

    The rest of the contract was dreadful. Romero battled with injuries and inconsistency, and was suspended for 50 games after a positive drug test.

Charlie Manuel's New Deal

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    Ruben Amaro Jr.'s strange tendency to give out too many guaranteed years on contracts does not end with the players. In fact, you could make a strong argument that he made a mistake by signing Charlie Manuel to a new, two-year deal during the 2011 season before his contract had run out.

    Of course, at that point in time, things were going well for the Phillies. The manager's flaws were covered up by an elite pitching staff that would go into the record books as one of the greatest of all time. That Phillies team would win more games than any other in franchise history.

    Now, however, we can look back on that contract extension and wonder if Manuel was the right guy for the job through 2013, especially with Ryne Sandberg waiting in the wings.

Jonathan Papelbon's Four-Year Deal

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    The need for a team to have an elite closer to pitch the ninth inning is understandable.

    That's what won the Phillies the World Series in 2008. Brad Lidge was perfect that year, but in each season after that, he struggled. As a result, the Phillies struggled.

    So, to replace Lidge, the Phillies wanted a guy with a good medical history and a history of dominance against tough competition. No one fit that bill better than former Boston Red Sox's closer Jonathan Papelbon. Admittedly, he was a good fit for the club.

    The real question is whether he is worth a four-year, $50 million contract. The short answer is "no."

    That's not a knock against Papelbon, who has been as advertised in 2012. How do you justify making a commitment of that size (the largest ever for a reliever) to a man who has never eclipsed the 70 innings- pitched mark in a single season?

    Papelbon is a good fit for the Phillies. It's the contract that's not. That was the mistake.

Raul Ibanez's Three-Year Deal

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    Pat Burrell's farewell tour ended in the best way possible: A World Series ring and a trip down Broad Street.

    However, it was no secret that the Phillies had been eyeing a replacement to take over in left field for quite a while and let Burrell walk in the offseason.

    Ruben Amaro Jr. went after an interesting name that season. There were a few options, but he wanted the guy that had managed to hit 23 home runs in the spacious Safeco Field in 2008. That man, of course, was Raul Ibanez.

    Amaro inked him to a three-year deal worth $31.5 million and critics jumped all over the deal, believing that it was too long and for too much money.

    Ibanez would go on to make his critics them look silly midway through 2009. But the critics would get the last laugh. Ibanez was terrible for the last two-and-a-half seasons of his contract and only once hit more than the 23 home runs he hit in his final season as a Seattle Mariner.

    His defense was shoddy and his bat never lived up to the contract.

Placido Polanco's Three-Year Deal

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    A year after signing Raul Ibanez, Ruben Amaro Jr. made a curious decision when he signed former Detroit Tigers' second baseman Placido Polanco to a three-year deal to fill his hole at third base.

    The funniest part of the deal in hindsight is that people were most concerned about whether Polanco could make the switch from second to third base. He wound up doing that with ease, becoming a Gold Glove defender.

    But age and injury would sap the life out of his bat. The contact hitter never eclipsed the .300 mark for the Phillies.

Cliff Lee to the Mariners

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    The Phillies were cheap for a long time. As a result, they would spend decades in the National League's cellar (in some way, shape or form).

    They finally broke that mold in the latter half of the 2000s and would eventually go on to win five consecutive National League East titles. But that didn't mean that the "cheap Phillies" tag would not eventually rear its head.

    The Phillies acquired Cliff Lee from the Cleveland Indians for an inexpensive package of prospects in 2009 and he was set to make just $9 million in 2010. That's pennies on the dollar for an ace-caliber pitcher.

    But he wasn't the guy the Phillies wanted at the time. They wanted Roy Halladay, then of the Toronto Blue Jays. So Toronto sent the 32-year-old Halladay to Phillies for three minor leaguers: catcher Travis d'Arnaud, right-hander Kyle Drabek and outfielder Michael Taylor.

    And Lee was shipped out to the Seattle Mariners for prospects Phillippe Aumont, Tyson Gillies and J.C. Ramirez.

    Of course, the Lee trade would come back to bite the Phillies. The prospects they acquired from the Blue Jays did not pan out. And during the middle of the 2010 season, the Phillies found themselves in need of an upgrade in the starting rotation and sent three more prospects to the Houston Astros for Roy Oswalt.

Roy Oswalt to the Phillies

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    The 2010 season turned out to be interesting in more ways than one for the Phillies.

    After trading Cliff Lee to the Seattle Mariners and acquiring Roy Halladay from the Toronto Blue Jays during the offseason, the Phillies liked their starting pitching a lot heading into 2010. 

    But as it always seems to be the case in baseball, the starting rotation had some unforeseen struggles, namely Cole Hamels in the first half, before he started using his cutter in earnest.

    So, at the trade deadline, Ruben Amaro Jr. landed one of the two best starting pitchers available in Houston Astros' ace Roy Oswalt.

    The price was steep. Though many saw Phillies' starter J.A. Happ as the centerpiece, the two prospects in the deal were the players the Astros were really after.

    They acquired outfielder Anthony Gose (who was later flipped to the Blue Jays) and shortstop Jonathan Villar in the deal, both of whom are now among their respective team's top-10 prospects.

    Oswalt certainly gave the Phillies' a boost in 2010, but he was a disaster in 2011 when he couldn't stay healthy or be effective.

Cliff Lee's Five-Year Deal

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    There is no doubt that the Phillies are a better team with Cliff Lee in their starting rotation. It is impossible to add a pitcher of Lee's caliber—a former Cy Young Award winner—and not become a better team.

    It isn't Lee that's hurting the Phillies right now. It's the mammoth contract that Ruben Amaro Jr. gave to him.

    When Lee signed his new five-year, $120 million deal before the 2011 season, there is no doubt that Phillies fans were happy to have their prodigal son back. However, critics couldn't help but look at the deal with an eyebrow raised.

    Signed through his age-36 season, Lee is guaranteed $132.5 million, which includes the buyout for his 2016 club option. Of course, if Lee isn't on the disabled list with a left arm or shoulder injury in 2015, that $27.5 million option becomes guaranteed anyway.

    Lee is a great pitcher. That's not in question. However, you have to wonder if the Phillies would have been better off spreading the wealth around the rest of the roster instead of investing in a starting pitcher who  will be well into his 30s by the time the contract expires.

Hunter Pence to the Phillies

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    The Phillies paid a hefty price for Hunter Pence.

    Sure, you could look back on the 2011 season and say that Pence was the right player at the right time. They needed to make a splash and add a right-handed bat with power. That was obvious.

    With Ben Francisco and Domonic Brown flopping around in right field, the Phillies needed a right-handed bat to hold off the competition. They were a legitimate contender in need of an upgrade and Pence was arguably the most appealing bat on the market.

    But the price was steep.

    The Phillies sent their top positional and pitching prospects to the Houston Astros in Jonathan Singleton and Jarred Cosart, respectively. This deal came after the Phillies emptied their farm system in trades for Cliff Lee, Roy Halladay and Roy Oswalt.

    Singleton and Cosart would go on to become two of the game's best prospects. Pence would spend just a season in Philadelphia before being moved at the 2012 trade deadline to the San Francisco Giants.

Ryan Howard's Five-Year Deal

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    Ouch.

    This is one that I'll never fully understand. The Phillies approached Ryan Howard's contract situation rather curiously. In 2009, the team agreed to a new deal with Howard for three years and $54 million. After watching what Howard did in the years leading up to his new deal, that's not bad.

    However, a little more than a year later, the Phillies would agree to yet another contract extension with their slugging first baseman, and this one left people scratching their heads big-time.

    Ruben Amaro Jr. and the big-bodied first baseman agreed to a five-year, $125 million deal that would keep Howard in Philadelphia until, at least, the end of the 2016 season. The Phillies also hold a club option for 2017 that's attached to a $10 million buyout.

    The new extension came despite Howard's declining production and the availability of free agents Albert Pujols and Prince Fielder, two of the best first basemen in the game, after the 2011 season.

    Now, you tell me who you'd rather throw the money at.

    To make matters worse, Howard tore his Achilles tendon following the 2011 season and missed the first half of the 2012 campaign.

    You think Amaro wants a do-over?

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