Matching up the Red Sox and Phillies for a Cliff Lee trade is a simple task. Boston has had interest in the left-hander before, and are still in need of pitching with uncertainty surrounding the health of their own ace, Clay Buchholz, and a sore groin that's plagued Ryan Dempster at times in 2013. The Phillies could very well keep Lee, but he might be at his best for the organization as a trade chip that general manager Ruben Amaro can cash in, with the idea being he represents their best chance at restocking the minors or big-league team with talented youth.
Leading in to Wednesday's non-waiver trade deadline, the Red Sox are shopping for pitching, and the Phillies are listening for Lee offers. It seems like a pretty natural pairing, as Boston has the prospects to bring in Lee, who is under contract for this year and two more, in addition to a 2016 option -- acquiring him would help maintain that balance of playing for now but also looking to the future, as he would be a part of both squads. His presence would easily justify dealing some of the Sox' pitching prospect depth, as, if Cliff Lee is in the rotation for up to three more years, that's one less spot that said prospect could take up.
The only real question is what a deal for Cliff Lee could look like. It's very difficult to gauge what Amaro and the Phillies would want, as it's clear they need to feel like they can't say no to a trade in order to move him, but given Amaro's history with prospects, what he feels he can't say no to might be a lot different than what you'd expect. For example, the last time Amaro dealt Lee, he acquired Tyson Gillies, Phillippe Amount, and J.C. Ramirez. That was back in late-2009, and Lee didn't have a major contract keeping the prospect haul down -- Amaro simply whiffed on the return, and did so before hindsight came into play. With hindsight, it looks even worse.
Still, even if we acknowledge that Amaro might deal Lee for a little less than one would expect, that doesn't mean the Sox would give up nothing of value. Their system is stacked, and Lee is a commodity that a few teams will be chasing for the next few days: Boston is going to have to pay up to win this one.
Top prospect Xander Bogaerts is likely off the table. This might disappoint some Phillies fans, but he's a top-five prospect and shortstop, and Lee is still owed $50 million after 2013, as well as a $12.5 million buyout on his 2016 option, one that could vest automatically if Lee throws 200 innings in 2015 or 400 combined between 2014 and 2015 -- that's a lot to ask a team to take on in salary, in addition to losing out on the best prospect they've had in at least a decade. Plus, it's unlikely any team with a prospect as good as Bogaerts is going to be seriously in on Lee, lessening the need for the Sox to go that far in their own discussions.
If the Sox hold Bogaerts out of negotiations, that means they will need to emphasize quantity without skimping on the quality in order to keep the Phillies on the phone. They have plenty of both, though, leading us to a list of names that could entice Amaro to pull the trigger. Could some combination of these players get a deal done for Lee?
Will Middlebrooks, 3B
He's not a prospect, but Middlebrooks is a player the Phillies had have interest in before, back when the Red Sox were attempting to move Kevin Youkilis out of town in 2012. He's back in the minors after a rough start, and while he hasn't torn them up just yet, he's making incremental gains with his strikeout rate in his quest to consistently find good pitches to hit. There's still a lot of talent here, and at a position where there is suddenly very little outside help available for teams looking for an upgrade at the hot corner. Given he's not a free agent until 2019 at the earliest, and won't even be arbitration-eligible until 2015 at the earliest, he might as well be a prospect still, especially since he's all of 24 years old.
Boston can afford to move him because they have Xander Bogaerts and Garin Cecchini in the system -- Bogaerts might already be ahead of him on the depth chart, or could be shortly, and Cecchini isn't far behind given his breakout campaign. Middlebrooks is absolutely worth the risk to a team like the Phillies, who traded for Michael Young this past winter in order to have something with a pulse playing third base. Even if all Middlebrooks does is hit for around the league average while playing above-average defense, he's going to be useful at his cost. He's obviously not the centerpiece in any Lee deal, however, and would have to be packaged with a couple other prospects.
Anthony Ranaudo, RHP
Ranaudo might be the easiest of Boston's starting pitching prospects to give up, but don't confuse that for a lack of potential. What makes him movable for the Sox is that he's in Double-A and requires a 40-man spot after this season in order to avoid the Rule 5 draft. The Sox have a slew of starting prospects in Triple-A (as well as Brandon Workman in the majors), Matt Barnes working things out in Double-A but without the ticking of the Rule 5 clock, and then they have another wave further off in the distance that includes names like Henry Owens. They do not lack for pitching prospects, and Ranaudo is just sort of caught in the middle at a time when a roster decision will need to be made to preserve his place.
He has a 2.80 ERA in Double-A this season, with 2.5 times as many strikeouts as walks in 103 innings. He made his first Futures Game this year, and while he didn't do well, it means little in the grand scheme of prospect evaluation. He's a starter with mid-rotation potential, and while he's certainly not going to replace Lee's projected 2014 production, he could get to the majors fairly quickly next year, so long as he's healthy. Like Middlebrooks, the appeal here would be having a close-to-ready, inexpensive piece to plug holes on the roster in a meaningful way.
Jackie Bradley Jr., CF
It's difficult to picture the Red Sox dealing Bradley in a Cliff Lee deal, but if the Phillies are willing to absorb at least half of the money in the deal -- including the 2016 option should it come up -- then it becomes easier to envision. Bradley's value lies in both his potential and his timing, as he's slated to be called up after Jacoby Ellsbury walks as a free agent. If Boston can clear a massive chunk of Lee's salary from the books for each of the next three years, though, it's easier to believe they would be able to retain Ellsbury on a deal that paid him $16-18 million per year.
This is a risky proposition, of course, as it relies on Ellsbury choosing Boston in the off-season -- that makes it unlikely, even if it is plausible. For that reason, Bradley Jr., while not off the table entirely, is teetering off the edge.
Allen Webster, RHP
Webster has plenty of promise, with those who love him thinking he can be more than a mid-rotation arm if he gets his command together. He's not quite big-league ready yet, as evidenced by his tours of duty at the level in conjunction with what has been an up-and-down first stint at Triple-A. He's still all of 23, though, so there's time for him to continue to develop and become a productive member of big-league society.
The Sox have less reason to bet on Webster if they can acquire Lee, however, much like the Phillies have less reason to hold on to Lee if they can roll the dice on arms like Webster's. In a trade scenario that very likely could hold out on both Bogaerts and Bradley, Webster might be the name that headlines a trade.
Deven Marrero, SS
Like Middlebrooks, Marrero isn't going to be the centerpiece of any Lee trade. However, he's unlikely to have much of a career in Boston unless Bogaerts moves off of shortstop and Jose Iglesias either fails or is sent packing. Even if this were to occur, the Sox still have Jose Vinicio and Tzu-Wei Lin at short behind Marrero in the system, and someone like second baseman Mookie Betts could conceivably shift back there if there was a sudden hole in the pipeline. Anything could happen, but there's plenty of cushion for any blow that comes from dealing Boston's first-round pick from 2012.
Marrero's numbers might not jump off the page, but considering he's a shortstop prospect in his first full season in a league with an unimpressive-looking average line, he's doing fine. Plus, the real selling point on Marrero is his glove, which projects to be plus in the majors at a premium defensive position. In the right deal, Boston should absolutely move him, and it doesn't get much more right than Cliff Lee.
There are other pieces the Sox could move, too, as final additions to a deal that could very well focus on quantity. They are overflowing with inexpensive relief options like Jose De La Torre and Alex Wilson that might appeal to the Phils. Bryce Brentz is sitting on the minor-league disabled list and is out for the year, but his power and arm might intrigue Amaro. Michael Almanzar isn't an impressive defensive third baseman, but he could have the bat for the position, is just 22, and needs to be placed on the 40-man before the November Rule 5 draft deadline. None of these players could swing the deal as a major piece, but if Boston wants to send a package like Ranaudo, Middlebrooks, and Marrero for Lee, with the Phillies contributing some money, they might be what dots those i's on a trade proposal.
Admittedly, all of this could be for naught: the Phillies might refuse any deal that doesn't include Bogaerts, Bradley, or even Garin Cecchini, rendering this exercise pointless. We'll know soon enough in the next few days, though, as it's almost assured these two will be linked once more before the trade deadline, just in case there's something to be worked out.
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