Chicago Cubs: When to Trade Bryan LaHair and Ryan Dempster

Frank Sinatra released a song in 1966 that can summarize multiple Cubs seasons. The song title also gives eloquent reason for the Cubs to trade some players now rather than waiting until the July trade deadline.

The song? “That’s Life.”

There is a line from that song which could define the predicament the Cubs are currently in: riding high in April; shot down in May.

We have all seen the surprise starts to the season by both Bryan LaHair and Ryan Dempster, both playing at a level which few believe they can sustain for very long—riding high in April. Therefore, the Cubs would be wise to sell while their stock is up.

However, there are two sides of the coin on waiting until the deadline to trade LaHair and Dempster—a positive and a negative. There is no “Two-Face” coin in the equation.

One side of the coin is if—and that is a big if—Dempster and LaHair can continue their statistical paces through July. Both would bring in much greater value in the quantity and quality of prospects received in a trade than if they were dealt now.

Three possible AL World Series representatives—the panicky Yankees and Red Sox, along with the Tigers—have seen their starting rotations struggle early in the season. The bidding war for Dempster could bring in some serious young talent in return for the surprise ace.

LaHair will be in a similar situation when placed on the trading block.

The Cleveland Indians need a production upgrade at first base so they can continue to pose a threat to Detroit in the AL Central. There may be interest in a Major League-ready alternative if they decide Matt LaPorta is not it.

There is also need regarding the Rangers with Mitch Moreland and the Giants with Aubrey Huff.

But what if Dempster and LaHair do not continue their unexpected performances?  What if they are bitten by the injury bug?

The other side of the coin indeed has more variables that could work against the Cubs.

If the Cubs do decide to wait until the deadline in hopes that the pair can continue to produce, they take the gamble that the odds of the coin landing tails will go higher and higher. 

If the duo falters and their production returns to normal levels—shot down in May—then their trading value in July will be less than what the Cubs could get by trading them now.

They could see the starting pitching staffs of the aforementioned teams could improve, leaving them not looking for a No. 2 or 3 starter, but rather a No. 4, thus downgrading their trade proposals regarding Dempster.

For LaHair, the market could all but dry up if his numbers plunge to average levels. If the starting first basemen for those interested teams begin to perform, those teams will have the option to stick with whom they have regardless.

If this occurs, those teams’ trade scope would shift from a starting first baseman to a back up, thus offering less when considering a trade for LaHair.

The Cubs cannot place their hopes on Dempster and LaHair to continue to perform the way they have so the club can demand higher prospects come the deadline.

They need to get what they can for the pair now, because there are too many variables that could dampen their trade value if the organization decides to wait until July 31.

If the Cubs wait too long, another line from “That’s Life” could rear its ugly head:  if there’s nothin’ shakin’ come this here July, [they're] gonna roll [themselves] up in a big ball, and die.