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Is Now The Right Time For The Cubs To Deal Starlin Castro?

The Padres have a need and a desire. The Cubs have a shortstop. Could A.J. Preller and Theo Epstein have a conversation?

Rick Scuteri-USA TODAY Sports

It's no secret that I have often suggested that the Cubs should seek to trade shortstop Starlin Castro while his value is high. This has less to do with any frustration I may feel toward Castro himself than it does with my overwhelming preference for Addison Russell and my desire to see Javier Baez get a boatload of 2015 Major League plate appearances as he continues his adjustment to the top level.

But this isn't a story about me. This is a story about Buster Olney, A.J. Preller, and the alignment of stars.

I do not have access to ESPN Insider, but I do read quite regularly. A recent MLBTR post included this nugget:

The shortstop position is an obvious area to watch for the Cubs, but [Buster] Olney says (in the [below]-linked piece) that it may not all be positive. Starlin Castro has proven he can hit, but Olney says there are real concerns about how committed he is to grinding things out on defense. Chicago informed other teams this winter that it was open to trade scenarios involving the 25-year-old.

If you have Insider access and want to read Olney's full musing, here you go.

On the whole, none of this is all that surprising to hear. The Cubs have three Major League caliber shortstops within a couple of months of being ready for full-time gigs at that level. That's not a tenable situation long-term. We've long debated which shortstop should be dealt, if any, but that's not exactly the point of this post either.

Earlier Tuesday, USA Today's Bob Nightengale revealed that the all-in San Diego Padres are not all that enthused about going through the 2015 season with Alexi Amarista and Clint Barmes fighting for plate appearances at the shortstop position. That's hardly a surprise. Speculation immediately turned to a couple of shortstops, including Troy Tulowitzki, Andrelton Simmons, and, most relevant for our purposes, Castro.

The most likely scenario here remains that the Padres will give it a go for a few months before pulling the trigger on any deals. However, another big move for a team that has completely reshaped itself this year is hardly out of the question. If we've learned anything about baseball over the past six months, it is that Pads general manager A.J. Preller is never done dealing.

But what about Theo Epstein? The Jon Lester signing flipped the switch in Chicago as the Cubs shifted from years of basement dwelling and prospect collecting to actually attempting to win at the Major League level. Most of us expect a competitive team with a genuine chance to play meaningful October baseball. Trading Castro would be a blow to the club's chance to compete, even if the primary blowback would seem to be emotional.

Then again, Epstein has arguably the longest leash of any executive in baseball (except for Ruben Amaro, Jr. -- I don't think Amaro can do anything to get himself fired at this point). With continuous contention expected in 2016 and onward, a Castro deal may represent Epstein's last opportunity to cash in on the desperation of another club. I would be surprised if Epstein was willing to trade Castro for a prospect-only return.

With all of that in mind, let's take a peek at what kinds of deals the Cubs could put together with the Padres that may actually be palatable to the Cubs' 2015 interests and beyond. I'll start with my least favorite proposal and end with my favorite.

Proposal #3
Padres Get: SS Starlin Castro, 1B Kyle Parker
Rockies Get: C Austin Hedges, OF Hunter Renfroe, 3B Mike Olt
Cubs Get: 3B Nolan Arenado

The Padres get their shortstop and a possible bench bat for their stretch run. The Rockies turn one plus youngster into two as they continue their rebuild. And the Cubs convert one left-side infielder with a good bat and a mediocre glove into one with an average bat and a vacuum attached to his hand.

I both like Arenado and am worried by him. He crushes lefties at Coors Field. Other than that, he's a below-average offensive player thus far. Then again, the floor is very high given his incredible defensive work at third base. If the bat takes another step, he may reach star territory. If not, he's still a good piece.

Proposal #2
Padres Get: SS Starlin Castro, SP Rob Zastryzny
Phillies Get: C Austin Hedges, OF Hunter Renfroe, SP Travis Wood, OF Billy McKinney
Cubs Get: SP Cole Hamels

The Padres again get their shortstop and a sweetener. The Phillies get a top-25 prospect (Hedges), a top-50 prospect (Renfroe), a top-100 prospect (McKinney), a flippable rebound candidate (Wood), and a huge pile of cash to spend in the near future. The Cubs get their third ace.

Proposal #1
Padres Get: SS Starlin Castro, SP Taylor Guerrieri
Rays Get: C Austin Hedges, OF Hunter Renfroe
Cubs Get: SP Chris Archer

The simplest deal of the trio. The Padres get their shortstop and a very talented, very troubled sweeter in Guerrieri. The Rays get two big building blocks at positions of desperate need while dealing from a strength. And the Cubs turn a good, 25-year-old shortstop on a team-friendly deal into a good, 26.5-year-old starting pitcher on a team-friendlier deal. Assuming all of the options are exercised on both deals, Castro is controllable for $59 million through 2020 whereas Archer is controllable for just $42.25 million through 2021.

What Does it All Mean?
Trading Castro remains a very real possibility, though the timing here is less than ideal. However, the Cubs could presumably eke a few weeks out of Jonathan Herrera or Arismendy Alcantara at shortstop until Baez or even Russell is ready to man the position. Further, while the Cubs would admittedly open up a short-term hole at shortstop, they could use this deal to plug a longer-term hole in the rotation or at the hot corner. The conversion of one nugget of 2015 Major League talent into another, different nugget of 2015 talent should make such a deal much more palatable to all parties involved.

The Rockies, Phillies, and Rays are by no means an exclusive list of potential trade partners. The Diamondbacks could get involved, though they lack attractive Major League pieces unless the Cubs are willing to take a bit of a gamble on Archie Bradley. I mean no disrespect to Billy Beane; If he wants to get involved, the Athletics will get involved. And the Braves could certainly enter the fray as well.

Regardless, if the Cubs are looking for the right time to deal Starlin, the iron is smoldering. There's a hungry, willing buyer in San Diego with just enough pieces left to make a major move, something that the Cubs could put to their advantage by converting one long-term piece into another more needed long-term piece.

So, would you do it? Would you be willing to work out a deal that sent Castro to the Padres? And if so, would you consider any of the deals proposed above? Feel free to shoot out some ideas below.