5 Potential Deals Ruben Amaro Jr. Should Propose at the Deadline

Alec Snyder@@alec_snyder62Contributor IIIMay 16, 2014

5 Potential Deals Ruben Amaro Jr. Should Propose at the Deadline

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    Concerning the Philadelphia Phillies, there is good and bad news. The good news is that they are only 4.5 games out of first place in the NL East. The bad news? They're dead last in the division at 17-21, have lost three straight and are 3-7 in their last 10 games. One more note: They're 6-11 at home.

    In order to make one last run at the playoffs, Phillies general manager Ruben Amaro Jr. was supposed to improve the team over the offseason in its most-needed areas. Marlon Byrd was not the worst pickup he could have made, but there was better out there. Carlos Ruiz was overpaid. And Brad Lincoln being the most significant bullpen addition Amaro made in the offseason speaks for itself.

    Amaro needs to focus on the future. The window has closed, and it's time to accept that fact. What may hinder him from doing so, though, is the amount of money tied up to the Phillies' most attractive trade pieces. Most, if not all, of the Phillies' best trade chips are due guaranteed money in 2015, if not beyond.

    However, it's time that Amaro and the Phillies front office get creative and make some trades that go against their self-imposed rules. That means eating salary when necessary. And it will be necessary for many players.

    While it's too early to speculate on who the Phillies would get in return in a hypothetical fire sale, here is the framework for five deals Amaro should propose come the July 31 trade deadline.

A.J. Burnett to Baltimore Orioles

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    Offseason chatter aside, this is a trade that just makes sense.

    When A.J. Burnett signed with the Phillies in mid-February—rather late in the offseason—it came as a slight surprise. The more natural fits were Pittsburgh, where he had pitched for the last two seasons, and Baltimore, which is closer to his Maryland home.

    Burnett opted instead to take the best of both worlds and settle at a midpoint. Playing relatively close to Baltimore yet making a significant paycheck is a move few could argue with. But could a team like Baltimore have interest now?

    If the Phillies ate some of the remainder of the $16 million due to Burnett on the season come July, a deal could be struck. Who the Orioles would trade is anyone's guess—and would also depend on the salary eaten by the Phillies—but the organization's top prospects are rather pitcher-heavy. That could bode well for the Phillies, who need some organizational pitching depth in the worst way.

    With a 4.19 rotation ERA on the season, Baltimore could use an ace. A.J. Burnett could be the closest they come to acquiring one. Amaro should strike on this opportunity, especially while Burnett's hernia still isn't a major issue.

Kyle Kendrick to New York Yankees

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    Kyle Kendrick has long been one of the Phillies' biggest wild cards. Now in his last year before free agency, Kendrick is looking to make himself noticed so he can land a decent contract in the offseason.

    While Kendrick will never command top dollar, he's good as a dependable arm to pitch every fifth day. He's never spent a day of his life on the disabled list, and although he doesn't always provide the best outing, Kendrick doesn't always lose a game single-handedly, either.

    Considering that Kendrick is a sinker-baller and the New York Yankees play in a hitter-friendly park, a trade involving this framework makes perfect sense for all parties. The Phillies would get the rest of Kendrick's salary off their hands, Kendrick would be a much-needed addition for the Yankees' injured rotation and Brian Cashman would not need to worry about long-term cash considerations due to Kendrick's impending free agency.

    This would not be the flashiest move for Amaro to make, and it wouldn't net the best prospect package in return. But it would get something in return for a pitcher who may or may not be likely to come back to the Phillies after 2014.

Cliff Lee to Texas Rangers

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    It's been a perfect trade match for years, and there's even better reason to suggest this trade now.

    Cliff Lee signed with the Phillies before the 2011 season on a five-year, $120 million contract. At the time, the only finalists known to the public were the New York Yankees and Texas Rangers, the latter of which had traded for Lee in the second half of the 2010 season.

    Lee spurning both teams to return to Philadelphia was a feel-good story—if you were a Phillies fan, that is. He came back to win a World Series ring with the Phils along with the rest of the four-headed monster that was the 2011 rotation.

    But Lee never won his ring in Philadelphia. The Phillies haven't even made the playoffs since Lee's first season back. Isn't it time to give him a shot at winning it all with someone else?

    The Rangers are simply the best fit. With a rotation spearheaded by Yu Darvish and Colby Lewis, the need may not seem obvious. However, news emerged (per NBC Sports) on May 14 that both Martin Perez and Matt Harrison's seasons were in jeopardy. Perez likely needs Tommy John surgery; as for Harrison, his career is in jeopardy due to a displaced vertebra and nerve irritation in his spine.

    With sketchy options already supporting the Rangers' starting staff, Lee might be a necessity if they want to emerge from fourth place in the AL West. Lee could push them over the top, and the Phillies would get a nice prospect package in return regardless of salary considerations. Amaro needs to call Rangers GM Jon Daniels and hit the ground running on a Lee trade soon.

Jonathan Papelbon to Los Angeles Angels

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    Jonathan Papelbon's contract—and personalityhas been a bit ridiculous in Philadelphia. Signed to the largest deal in history for a reliever, Papelbon continues to make $13 million a year to close out games for the Phillies. While Papelbon seemed ready for collapse midway through 2013, he's done a nice job holding down the ninth inning.

    However, Papelbon is a luxury on a team like the Phillies that doesn't need to be dedicating $13 million a year to one bullpen pitcher. He'd be better off pitching for a team that could use his services and is on the fringe of contention. Enter the Los Angeles Angels.

    Every year since their spending spree after the 2011 season, it's seemed like the Angels have been one move or injury away from possible contention. In 2012, Mike Trout had a breakout rookie season, but Albert Pujols was hurt and did not live up to expectations when he played. Come 2013, Josh Hamilton faltered with his new team, while Jered Weaver's velocity woes caught up to him.

    This season, the bullpen has been the Angels' Achilles' heel, and there's been little they've tried to do to stop the bleeding. With a 4.34 ERA despite decent names such as Ernesto Frieri, Kevin Jepsen and Joe Smith, a change has to be made. Yes, Smith's done a decent job as the closer in Frieri's place, but it's practically a given that Frieri will get his shot again at the ninth inning role.

    Papelbon would end the dispute in Los Angeles. The Angels have the financial capability to take on a decent portion of his salary, and they would get a top-notch closer in return. Granted, the Phillies' return would be lackluster since the Angels have one of baseball's worst farm systems, but they would at least get Papelbon off their hands.

    With Papelbon pitching as well as he ever has in a Phillies uniform, the time is now for Amaro to maximize his value and trade him.

Chase Utley to San Francisco Giants

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    Chase Utley being traded to a California team seemed like a decent possibility in 2013. When he and the Phillies agreed to a two-year contract extension in early August, though, all bets were off.

    The California team at that time was the Los Angeles Dodgers. Now, however, the San Francisco Giants are more in need of an upgrade at second base, and they may be willing to acquire a player like Utley should he be willing to waive his 10-and-5 rights to go there.

    What's appealing about the Giants from a contention standpoint is their two World Series in the last five years in addition to rather consistent October play. Even when they haven't made the playoffs, the Giants have come close in recent years, 2011 aside.

    Right now, the Giants' most glaring weakness is at second base. Brandon Hicks had a hot stretch in mid-April, but he fell out of it soon after and is no guarantee to produce for the remainder of the season.

    Utley, on the other hand, is a guarantee to hit at least around .280 with 15-20 home runs if he's healthy. So far in 2014, health hasn't been a problem, and as a result, Utley's batted as if it was 2009.

    Utley's value will never again be as high as it is now, and Amaro should carefully consider trading him. Yes, the move would come without fan support, but if Amaro finally decides to dedicate himself to the future, he should trade Utley without thinking twice about it.