Philadelphia Phillies: 5 Potential Roadblocks in the Phillies' Offseason Plans

Alec Snyder@@alec_snyder62Contributor IIINovember 30, 2011

Philadelphia Phillies: 5 Potential Roadblocks in the Phillies' Offseason Plans

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    Phillies GM Ruben Amaro, Jr. has quite a bit on his plate this offseason. Having already signed a veteran closer in Jonathan Papelbon, Amaro has one less obligation to worry about.

    However, he's still got a few more positions to settle: shortstop, another pinch hitter or two, and a left-handed reliever. Amaro could also look to sign a starting left fielder if he feels that John Mayberry Jr. can't get the job done, or he could sign another starting pitcher if he feels that the rotation is lacking.

    The offseason is still just beginning. With the kickoff of the annual Winter Meetings next week in Dallas, there will be signings galore, and most of the remaining free agents will have found their new (or former) team.

    The biggest question is not who Amaro could sign, but what could prevent him from doing so for specific players. Signing higher profile free agents, such as Jimmy Rollins, will have more obstacles. Others may have a slight obstacle. Nevertheless, Amaro will have to work around any given roadblocks, and he'll have to settle with the fact that not every deal he wants to do will get done.

    But what sorts of roadblocks could persist? In this slideshow, we'll discuss some of the potential targets or target positions for which Amaro may pursue players and what could prevent him from getting who he wants.

Jimmy Rollins' Contract Demands

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    Jimmy Rollins has been the starting shortstop of the Philadelphia Phillies for the last 11 years. In that time span, he's endeared himself to Phillies fans, whether for his leadership in the clubhouse, his accurate declarations that the Phillies were the team to beat, or maybe for his upbeat personality.

    In the meantime, Rollins has also become one of the best all-around shortstops in the game. He peaked in offensive production in 2007 when he won the NL MVP award. Rollins has remained one of the premier defensive shortstops in baseball. While 2011 was an improvement for Rollins on his seasons since his MVP season of 2007, it still wasn't great by any standards.

    In 142 games this year, Rollins hit .268 with 63 RBI, 16 home runs, and a .736 OPS last year, which still makes him one of the top free agents on the market this offseason.

    Behind Jose Reyes, there is little depth available at shortstop via free agency. That's where Rollins comes in. Since Rollins is by far the best available free-agent shortstop behind Reyes, he'll command a hefty contract.

    Although there are many disparities between the Phillies and Rollins as to what he should receive on his next deal, it's practically etched in stone that Rollins will command more three years and more than $10 million per season.

    Beyond that is difficult to predict. Rollins has consistently stated that he wishes to obtain a five-year contract, and the least he'll settle for is a four-year deal with a fifth-year player option. The Phillies, on the other hand, are willing to give him three years with a fourth-year option, preferably a club or mutual option. As for exactly how much they're willing to pay him, that's hard to foresee.

    It's difficult to imagine Rollins in any uniform other than that of the Phillies, and Rollins himself has said that. However, he's also stated that he's not taking any hometown discount. If the market is right for Rollins, he'll get his five-year contract.

    Whether it will be with the Phils is a different question, but it could definitely prove to be an obstacle in their negotiations should Rollins refuse to relent from his contract demands.

Minimal Production from Minor League Shortstops

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    Let's assume for a moment that Ruben Amaro has no intention of re-signing Rollins, or that he signs elsewhere. Should such an event occur, Amaro could look at someone else in the free agent market to play shortstop, such as Rafael Furcal or Cesar Izturis. Then again, he could also look within the organization for a replacement for Rollins.

    The primary candidate to take the place of Rollins from within the farm system would be Freddy Galvis. Galvis is the Phillies' top shortstop prospect and winner of the 2011 Paul Owens Award, given to the Phillies' top offensive minor leaguer in the previous season.

    The problem with Galvis is that he's had his fair share of struggles already following the season. Sent to the Venezuelan Winter League (VWL) to hone his offense, Galvis ended up having an injury scare when a ganglion cyst was discovered on his wrist. Upon returning to the VWL, his offensive production still took a hit, with Galvis hitting just .204 with a .578 OPS in just 113 plate appearances.

    Galvis' defense isn't an issue, having been compared to that of Rollins, but if his offense doesn't increase, then he isn't worth much.

    The other in-house candidates, Wilson Valdez and Michael Martinez, haven't done much at the plate either. Both hitting in the Dominican Winter League, Valdez has hit just .238 with two home runs, and Martinez has batted an atrocious .096 with a .301 OPS.

    It doesn't get much worse that that, folks.

    With the lack of hitting by the Phillies' organizational candidates to play shortstop, it just goes to show how much Rollins is needed. Unless the Phillies plan on making a run at Jose Reyes, there is little hope for them at shortstop if Rollins walks.

Michael Cuddyer's Age and Asking Price

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    There's little doubt that Michael Cuddyer fits the bill for the Phillies. He can play adequate defense at a multitude of positions, and he's an above average right-handed bat that can hit lefties well.

    The biggest problem with Cuddyer for the Phillies is his age. He's 33 years old. For a player like him, who's easily going to get a three-year deal over $30 million, it's a little dangerous offering that kind of money.

    The Phillies have done riskier business before. They signed then-36-year-old outfielder Raul Ibanez to a three-year, $31.5 million deal, but that was Ruben Amaro's first signing as Phillies general manager. Whether he'll make a mistake signing like that here on out is unclear, though the Jon Papelbon signing could become a problem if his performance declines in the next few years.

    However, Cuddyer's a little different than Ibanez. He can play not only left field, but also right field, first base, second base, and third base While his defense at any given position isn't fantastic, it's far better than what Ibanez or Howard could provide.

    As we've also covered, he's a right-handed bat who can hit southpaws, something the Phillies have needed for quite some time. Cuddyer hits for average with moderate power and would be a welcome addition in the Phillies lineup.

    If the Phillies did sign Cuddyer, where he would play could be an issue. With Ryan Howard out due to his torn Achilles, the issue isn't as prominent. Cuddyer could play in either left field or at first base, with John Mayberry, Jr. playing whichever position Cuddyer isn't.

    However, when Howard does return, would Cuddyer start in left field with Mayberry as the Phils' primary backup outfielder? Or would Placido Polanco become the backup infielder with Cuddyer starting at third base?

    These questions can't be answered yet because Cuddyer isn't yet a Phillie. Will he become one at all now? It's not nearly as likely as it was maybe a month ago, but since then the Phils have traded for Ty Wigginton, who in many aspects is a poor man's Cuddyer.

    But a bench with Cuddyer and Wigginton would be incredible, and the versatility and offense that those two could combine to provide could be pretty awesome.

    If Cuddyer signed a two-year deal, the Phillies could pay him more over the course of the deal. It really isn't the money that's preventing a Cuddyer signing, but rather the age. They do go hand in hand. If Cuddyer takes less money and/or fewer years, a deal could occur. Until it does, Cuddyer's age and asking price provide an obstacle to any potential signing.

Jonathan Papelbon's Contract

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    Speaking of Jonathan Papelbon, his contract signing could become more of a burden for the Phillies than benefit before it even kicks in.

    Papelbon came from the Boston Red Sox as an established closer in the difficult AL East. Having handled the pressure of pitching on one of baseball's biggest stages at Fenway Park, Papelbon will theoretically handle the pressure of pitching at Citizens Bank Park with ease, right?

    Maybe. Papelbon's weakness is that he allows a ton of fly balls At a hitter's park in Citizens Bank Park, some of those fly balls could become home runs if they carry far enough. Whether that will be an issue has yet to be seen, but it is an issue on paper.

    What could prove to be a bigger issue than that is Papelbon's contract. When the Phillies signed Papelbon, they inked him to a record-setting four-year, $50 million deal, the most money ever for a relief pitcher.

    Although he agreed to take $11 million in his first year of the contract to give the team more payroll flexibility, it isn't much, and the only thing that could increase it would be either dumping contracts or signing front-loaded deals.

    If any were to occur, the latter would be more likely, yet it doesn't seem like the Phillies, which have signed multiple back-loaded contracts recently, have any intentions of doing so.

    Papelbon has arguably deserved the money he's due to receive. He's been the fastest closer to reach 200 saves, has kept runs low and racked up the strikeouts. He's also performed well in the postseason, posting a 1.00 ERA. It doesn't get much better than that.

    In the end, the biggest issue could be the Phillies' lack of ability to sign or trade for whom they desire in the next few years. Even though Papelbon's contract isn't fully to blame, it contributes to the overall issue that may persist for the Philies in the future: lack of payroll flexibility.

    Since the new collective bargaining agreement doesn't raise the luxury tax like it had in years prior, it may become even more difficult for the Phillies to stay under the $178 million threshold.

New Collective Bargaining Agreement

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    In addition to Papelbon's new deal, the new collective bargaining agreement could prevent the Phillies from going after some big name free agents in addition to Papelbon.

    Why?

    With the new CBA being ratified last week, the Phillies' signing of Papelbon is not retroactive, meaning that they still must surrender a first-round pick to the Red Sox due to the rules of the now-obsolete Elias Rankings.

    Papelbon, who was a Type-A free agent according to those rankings, required his signing team to surrender a draft pick under the rules of the old CBA.

    However, the new CBA declares only a small list of free agents in the category of compensation-eligible, meaning that only five or six free agents out of the bunch will cost their signing teams a draft pick that will now be slotted one pick after that of the player's former team.

    If the Phillies wanted to pursue someone like C.J. Wilson, he would cost the team a draft pick. The Phillies, having already surrendered a first-round pick, would be held even more accountable for signing a top-tier free agent.

    While it's not necessarily fair that the Phillies would not have their first round pick returned to them, they did sign the deal before the new CBA, so it could have been expected.

    In addition, as was lightly discussed last slide, the new CBA is keeping the luxury tax threshold at $178 million. Prior to this year, the luxury tax, which was established prior to the 2003 season, increased by roughly $6-8 million per season. For next season, the luxury tax will remain the same as last season.

    This could affect the Phillies' plans in a few ways. Signing both a Rollins and a Cuddyer-type free agent will likely be impossible, in addition to the fact that another reliever and/or bench bat is still needed. With the Phillies' priority being Rollins, Cuddyer would likely be the player who would have to look elsewhere for a deal.

    Additionally, future trades involving salary commitments will be less frequent for the Phillies. They will most likely not be able to trade for a player of All-Star caliber who's either due a raise through a previously-signed contract or through arbitration, should they sign Rollins, Cuddyer, or both.

    Then again, the Phillies could ignore the luxury tax threshold and become the first NL team to pay it since its creation. It would be surprising to see the Phillies be willing to spend that much money, but stranger things have happened.