Phil Rogers of the Trib brought us this nugget of information buried deep in his column about ranking the rotations in baseball (The Cubs tied for 9th).

If the Red Sox wind up with Matt Holliday or Jason Bay, the Cubs immediately would make a major effort to land Jacoby Ellsbury to fill their center field/leadoff hole, according to sources.

That scenario helps explain why the Cubs have been so patient in studying their options. The best way to do such a trade might be for GM Jim Hendry to facilitate a three-team deal that sends first baseman Adrian Gonzalez from the Padres to the Red Sox by packaging a group of prospects, possibly including one or two of their top ones, such as third baseman Josh Vitters, shortstop Hak-Ju Lee and pitchers Andrew Cashner and Jay Jackson.

~ Phil Rogers (Chicago Tribune – 12/27/09)

He also mentioned in another column that same day (why he didn’t combine them I have no idea), that perhaps Fernando Perez of the Rays might be a good fit. So we get two new names to throw into the mix with Rick Ankiel and Marlon Byrd and I’d like to see what your feelings are on all four names.

It’s weird, because if this rumor is true, we should actually be cheering for a team like the Red Sox to get richer. We should actually pull for them to add a stud like Gonzalez to play 1B for them and a huge bat like Holliday in the OF so we can pick off some of the excess goodness. It’s as if we’re homeless and the Sox would essentially let us eat off the fruit that falls off the tree. Let me tell you this: Jacoby Ellsbury would be some mighty sweet fruit. The question then becomes “How much talent are you willing to part with to get him”.

Cincinnati Reds v Boston Red Sox
Jacoby Ellsbury makes a catch (Picapp)

If we look at the four names Rogers mentions above and add to it a guy like Starlin Castro to it, we have to ask the question of if we’d be willing to part with two of those names to get Ellsbury. It’s important to keep Vitters based on Ramirez’s health of late and the lack of depth in the system at the position. That leaves the two SS and two Pitchers. I’d package one of each to get Ellsbury with my preference being to include Cashner and Lee, despite the fact that I think both have the higher ceiling. I like Cashner, but he projects at as a bullpen arm in my book, while Jackson should be able to start. Lee probably have a better skill set than Castro, but the fact that we’ve only seen one year of him at such a low level means I’d rather take a chance with the lower ceiling (although not much lower) of Castro. My guess is those two names might be good enough to get him, considering the Sox would have a major logjam in the OF.

Personally, I don’t consider Perez a major option unless his price tag is very cheap. A name I’d look at is Desmond Jennings, who has a lot better skill set than Perez and seems to be a better option to succeed at the Major League level because of the fact that he’s been more successful in the minors and isn’t coming off shoulder surgery like Perez is.

Looking at the three major sources I consult on prospects we get the following on Jennings at the start of 2009

Deric McKamey – “Lean/athletic OF with plus speed and impressive on-base skills, priming himself for a leadoff role. Possesses solid bat speed, with projectable power. Plus range and average arm strength make him solid in CF. Missed most of season (2008) due to shoulder surgery and a strained back”

Baseball America – “…has exceptional speed and the discerning eye to become a prototypical leadoff hitter and center fielder. His strike-zone judgment rates among the best in the system. While he has some pop and the ability to drive the ball in the gaps, he knows his role and focuses on getting on base. He covers a wide swath in center and has an average arm.”

John Sickels – “…has what you need in a leadoff man: lots of speed, good strike-zone judgment, fine OBP skills, and enough pop in his bat to keep the pitchers honest. His arm was weak even before the injury, so his throwing won’t be an asset but otherwise his defense is very good.”

I’m not sure if he’d truly be available for a reasonable price, but he’s a name I’d rather see Jim Hendry look at. I believe the Rays may look at him in CF for 2010, which also might mean someone like B.J. Upton may be available after a down year in 2009.

Rays Index chimed in about the matter via e-mail:

Perez is tough. On the one hand, the Rays don’t have a spot for him on the big league roster, and there will be one or two outfielders in triple-A ahead of him on the organizational depth chart. At 27, he probably is no longer part of the Rays future. He just never learned to hit from the left side of the plate as well as the Rays had hoped. Towards the end of ’09 he was almost exclusively bunting when he faced right-handed pitchers. But the Rays also still have two minor league options on Perez and they know he can contribute if needed, so there is no need to move him. Therefore the Rays aren’t going to give him up for a bag of balls even if there isn’t a need for him in the foreseeable future. My guess is that it would take a legitimate big league prospect. Otherwise, why not keep him around for depth and insurance? If that prospect played catcher, first base or pitcher, they are more likely to listen. In all likelihood, the Rays will want a guy in single-A or double-A. A catcher or a pitcher that projects well to the big leagues and is not on the 40-man roster. But is Perez worth a legit catching or pitching prospect? I doubt it. So what about young, cheap power arm that can contribute in the bullpen this season?

That being said, Perez can be an everyday big league outfielder. He might struggle against righties. But even if he bunts every time he faces a righty, he could still get on base at a .330 clip based on his speed and ability to draw a walk.

Jennings: The Rays will never say a player is untouchable. I mean, everybody has a price. But the price for Jennings will be very high. He is a legit top 5 prospect with all the tools. Unlike Perez, there is a need in the foreseeable future for Jennings, assuming the Rays cannot resign Carl Crawford after the season (or trade him before then). So if the Cubs (or another team) wants to try and pry Jennings away it would probably take a young, cheap player that can contribute at the big league level this season and is a considerable upgrade over the player currently in that position. And the only spots that can stand to use an upgrade are catcher and the bullpen. And the Rays aren’t giving up a top prospect for a relief pitcher. Do the Cubs have a Buster Posey or Matt Wieters laying around?

It’s still a weird situation to be in for this team. There is a good chance we may go into the season with a rather putrid situation at CF or a potentially big impact type player in Ellsbury manning the position. Should be an interesting next month or so.

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Joe Aiello is the founder of View From the Bleachers and one of the lead writers as well as host of VFTB Radio. Growing up in Chicago, he fondly remembers attending games in the bleachers before that was the popular thing to do. Currently Joe resides in North Carolina with his wife and three kids. Connect with Joe via Twitter / Facebook / E-mail