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Do The Cubs Have Trading Troubles?

The Cubs haven't made a trade since "the big one" July 4. Why?

Wesley Wright could be traded soon
Wesley Wright could be traded soon
Charles LeClaire-USA TODAY Sports

As BCB's Rob Huff has been writing specific trade deadline articles, I've been trying to avoid duplication. However, there is a story that I feel needs to be written regarding the Cubs' silence since the blockbuster two weeks ago. It's a bit convoluted, which should surprise none of you. And, to be told properly, it requires a story as an introduction. It's a story of an historic Cubs trade. By comparing the story to the present reality, the deafening silence might be explained.

A number of years ago, the Cubs were eliminated from serious contention well before the trade deadline. As it happens, they had a pitcher and an infielder who intrigued one of the playoff-contending teams. Both were having decent-to-good seasons, and were some of the better available options for contenders as the deadline loomed. The general manager for the team wanting the reliever was savvy, and had decent trade chips, some of them major-league ready. The Cubs had a few spots on their roster that needed instant improvement. Not only did the parent club have no long-term answers at some of the spots, their upper minors had no solid answers either. The opposing GM reached into his system depth.

The Cubs were looking for young pitchers. The team in question had a good reputation for developing pitchers and three young pitchers in their system who the Cubs thought could fill holes in their rotation, either then, or soon. One of the pitchers they were looking at had solid minor-league numbers and was lefthanded; a second, just 21, looked like he'd be good very quickly, and the third, a former second-round pick, was having a solid if unspectacular year in Double-A. The naysayers claimed none of these guys were really any good, despite their youth, and the Cubs would never get anything out of them.

The deadline loomed and the Cubs opted to trade for the three prospects. The naysayers had them nailed pretty accurately; combined, they made 28 starts for the Cubs and not one of them was even in the organization two years later. On the other hand, the players acquired did a solid job helping the contender to the LCS and the World Series. The rich got richer.

(In case you want specifics, I am talking here about a deal the Cubs made at the trading deadline, July 31, 1999. You can see the details here.)


These days, the Cubs are again facing another October of no meaningful baseball. They have up to three relievers a team might want in exchange. However, this time around, things are a bit different. While the parent club still has some holes, trading has been more difficult to execute. With minor leaguers Kris Bryant, Javier Baez, and others champing at the bit in Triple-A Iowa and elsewhere, there is no compelling reason to jump after guys who have unsuccessfully burned a few minor league options.

While it might be possible to upgrade over a few rostered outfielders or infielders, players such as Ryan Kalish, Matt Szczur, and Logan Watkins are "in line" for September opportunities, if only to see if they belong on the 2015 and 2016 40-man roster. While a team might want to trade a Triple-A guy with the baseball value of some chip dip that might have been outside of refrigeration for too long, Theo Epstein wants "something else" in exchange.

The closer to the major leagues a prospect is, the more certain, or at least expected, the return is. As Epstein is more than willing to minimize the current aspect for a more patient approach, much of the talent he gets in trade tends to be more down-the-ladder than MLB-ready. None of this should be news to most BCB readers.

This article, as well as providing me an opportunity to rattle off a bit of history, notes what is currently "far off" for the Cubs. I am limiting the discussion entirely to A-Ball, in either Daytona or Kane County. This is a list of 25 rather intriguing players on just those teams.

Starting pitchers: Paul Blackburn, Daury Torrez, Jen-Ho Tseng, Duane Underwood, Juan Paniagua, Felix Pena, Tayler Scott, Rob Zastryzny, Nathan Dorris, Tyler Skulina

Catchers: Willson Contreras, Kyle Schwarber, Will Remillard, Ben Carhart

Infielders: Dan Vogelbach, Carlos Penalver, Marco Hernandez, Jeimer Candelario, Gioskar Amaya, Jordan Hankins

Outfielders: Billy McKinney, Albert Almora, Bijan Rademacher, Jake Hannemann, Trey Martin


When a team tries to make a play for one of the Cubs relievers, they are in a tight spot. They aren't going to offer their top prospect for (for instance) Wesley Wright. Nor should they. However, when they want to offer something of value, Epstein generally busts out a list similar to this. When trying to impress an executive like Epstein, you aren't trying to improve upon his utility infielder, seventh reliever, or third catcher in Kane County or Daytona. You have to show that you are materially improving his  talent pipeline.

That is becoming harder to do.

When the Jeff Samardzija trade was made, at some point, Athletics GM Billy Beane likely was trying to find the third piece in the trade. With Samardzija and Jason Hammel already on the table, along with Addison Russell and Dan Straily, the question became: What else will be needed? Likely, around that point, a list similar to this came out. Beane wanted to toss off a down-the-list prospect, and Epstein said that the guy that was just mentioned wasn't materially better than someone the Cubs already had.

Eventually, it had to become Billy McKinney, or no trade.

If a team wants something from Epstein for Wright, James Russell, or anyone else, coming back in return has to be something 'materially better' than something already on hand. Maybe it will be a first baseman far better than Jacob Rogers, or a second baseman quite a bit better than Daniel Lockhart, both Kane County hitters. Or a pitcher much better than Daytona's Tayler Scott or Felix Pena. Maybe an outfielder far better than Trey Martin.

Most teams have guys better than those guys in their pipeline in A-Ball. However, they don't necessarily have them in abundance. To get one of the Cubs spare parts, something of value will have to be surrendered, and with the Cubs system deep in the upper and lower minors, that is a tough task for a rival GM to pull off. For a reliever or a spare part hitter, especially. And no, I don't expect a team to offer a fourth outfielder for a reliever, as then, they'd have to go out and replace the fourth-outfielder type anyway. Even if Epstein wanted to make the trade. A team looking at the post-season is trying to upgrade their roster, not gamble on where their next injury will be.

Either way, I expect there will be trades. Teams want as much late July depth as possible, and the Cubs are willing to make deals. Too many other teams are teetering on contention, and don't necessarily want to throw in the towel yet. Some of the trades will get less traditional. On Saturday, as I understand it, the equity draft will take place, awarding twelve trade-eligible picks to small-market teams. Some of the winners of these draft selections may be interested in swapping them.

The way I figure it, players like Russell, Wright, Chris Coghlan, and any others might be bartered as 1 WAR players for the last two months. If a rival exec thinks they aren't worth that much, then the argument could be made, why the heck do you want them if the aren't worth a late win or so. Then, the question becomes, at what point do equity picks become worth a WAR? I'm not sure on that one. If needed, the Cubs could flip some international free agency currency along in exchange, as well, to sweeten the pot.

In the end, I think the Royals or Brewers could blink, as they both might be receiving equity picks. Even if they don't have anyone in their pipeline to materially improve Daytona or Kane County, those picks are very important to the current administration. Possibly, more than they should be. Depending on where any acquired picks fall, they may be being acquired to be surrendered in free agency, as adding a big-name free agent might cost the Cubs said equity pick.

Not many people would be terribly disheartened to surrender a pick acquired for a reliever and a current outfleider as compensation for Jon Lester.

I would really enjoy seeing a trade with Milwaukee. Their lead in the division disappeared quicker than a plate of homemade chocolate-chip cookies at snack time. They have been terrible with drafting talent recently. And, this may be their last shot in the near future, as their minor league system lacks many marquee names, in part to their poor drafting recently. Having a Milwaukee selection in June would be fun, as would adding a Lester or Johnny Cueto, and surrendering their selection as compensation.

Trades will happen, and I expect discussions to begin in earnest again after the equity draft. The players being acquired recently, including ex-Cubs pitcher Rich Hill twice, have been less-than-exciting. The eight-man bullpen has made Wright, Russell, and Pedro Strop look somewhat better than they probably are. And, someone will jump, leaving the Cubs a mild hole in the bullpen this off-season, that they will likely fill like they did last year -- with an option like Wright, on a team-friendly deal.

Depending on who gets traded, and how they perform, it may even be the guy they trade in the next two weeks. The team that wants them so much down the stretch, might not really want them over the long winter. And it would be so-very-Theo to trade a reliever for a draft pick, spend the draft pick as compensation for a big-name starter, and re-sign the reliever for another go-around next year.

Or, they could keep the talent around for next year, and listen to the GMs in the league fuss that the prices were too steep. As Epstein and crew howl with laughter as their bullpen or bench hitters keep them out of the playoffs.