The Philadelphia Phillies have quite a few holes to fill on their roster before next season.
General manager Ruben Amaro Jr. is looking for two outfielders—one of whom should be a center fielder, and probably a right-handed bat. The Phillies also need a third baseman and could use another reliever for their bullpen.
Amaro could address all of those needs on the free-agent market. Outfielders like Michael Bourn and B.J. Upton would fit well in the Philadelphia lineup. Kevin Youkilis would give the Phillies a suitable third baseman. And plenty of relievers are available to help shore up the corps of middle relievers.
But that would get expensive. Big spending doesn't fit into Amaro's current plan, as he's been quite public about getting the Phillies' payroll underneath the $178 million luxury-tax threshold for 2013. Presumably, he wants the team under the $189 million luxury-tax limit for 2014 as well.
To patch up every hole on his roster without incurring MLB's luxury tax, Amaro will probably have to make some trades to get what he needs. That would almost surely mean tapping into his team's greatest strength: starting pitching.
But does Amaro really want to do that? The trio of Roy Halladay, Cliff Lee and Cole Hamels atop the Phillies rotation is what sets them apart from their NL East rivals. Starting pitching will likely be what pushes Philadelphia back into playoff and division-title contention next season.
Though that part of the team is a strength, is there enough depth to use in trade? If the Phillies weaken their starting rotation yet bolster other parts of the roster, does that ultimately even out? Or would Amaro be making a mistake by undercutting the advantage he has over division and league rivals?
The most tradeable commodity Amaro has is left-hander Cliff Lee. Plenty of teams checked in on him around the trade deadline this year, but it was never really clear whether or not the Phillies were looking to deal him away.
Amaro certainly had an opportunity to trade Lee to the Los Angeles Dodgers in early August. The Phillies put Lee on waivers, and the Dodgers won the claim for him.
Philadelphia could have either tried to work out a trade, though the Dodgers likely wouldn't have given up much because they would have taken on up to $102.5 million remaining on Lee's contract. Amaro could have also decided to just let Lee go on waivers, dumping his salary without getting anything in return.
Instead, the Phillies held on to Lee. Perhaps Amaro never had an intention of trading Lee and wanted him to be a part of their rotation for 2013 and beyond. Or the Philadelphia GM figured he could find a far better deal with more time—and more teams—to negotiate with during the offseason.
However, does that deal really exist?
Perhaps a trade with the Texas Rangers, built around third-base prospect Mike Olt and pitcher Martin Perez, would work for the Phillies. Then Amaro could get his outfielders in free agency.
The Arizona Diamondbacks could be another possibility, with Justin Upton going to the Phillies and taking one of those corner outfield openings. But D-Backs owner Ken Kendrick was rather vocal about not wanting a pitcher on the wrong side of 30 years old who's owed up to $100 million.
Could the Colorado Rockies present another option? The Atlanta Braves have shown interest in center fielder Dexter Fowler. Why couldn't the Phillies get in that mix, especially with the Rockies reportedly seeking pitching in return? The Braves probably have better arms to offer, however.
Of course, the Dodgers are still out there. But does GM Ned Colletti really have anything the Phillies are looking for in return?
He dealt two of his best pitching prospects—Allen Webster and Nathan Eovaldi—in trades for Adrian Gonzalez (and others) and Hanley Ramirez. Would Colletti really want to trade any others when he can sign Zack Greinke, Anibal Sanchez or Ryu Hyun-jin? Andre Ethier could be included, but do the Phillies want another left-handed bat?
The best argument for trading Lee to the Dodgers could be shedding his salary and using his $25 million salary for this season (and the next two, plus a team option) to help fill those holes in the outfield and at third base.
Amaro also has some pitching prospects he could use in a deal. Trevor May, Jesse Biddle and Jonathan Pettibone are among the Phillies' top four prospects, according to Baseball America. Could those young arms—along with pitchers with major league experience, like Vance Worley and Kyle Kendrick—be used to get someone like Chase Headley from the San Diego Padres?
But the Phillies need arms for the back end of their starting rotation as well. If Amaro deals away pitchers who could be the team's fourth and fifth starters, who fills those roles next season? Isn't trading talent for established veterans what got the Phillies into their current predicament?
Are such trades worth doing again if it gets Philadelphia back into playoff contention? Is dealing off some of the future the price that has to be paid for getting an outfielder or third baseman who could be a cornerstone player for years to come?
What looks like a surplus can become a weakness quickly. The Phillies rotation doesn't look nearly as imposing or competitive with the Braves or Washington Nationals in the NL East if they break up the Halladay-Lee-Hamels triumvirate. Amaro arguably has more holes to fill if he trades starting pitching away too.
Obviously, Amaro should explore every option available. But he is in the fortunate position of being able to take care of his team's needs on the free-agent market this winter. The question is how much that might cost the Phillies.
Another question might be how valuable a pitching staff is if the lineup can't score any runs to help the team win. That's the dilemma the Phillies and Amaro face this winter.
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