Most Cub fans are well-aware of the heavy burden some of Jim Hendry’s larger, longer contracts present to the team.  In simple terms, the highest-paid Cubs (Soriano and Zambrano) are the ones most fans would like to see traded away.  But their contracts are essentially untradeable, because they’re so heavily back-loaded, paying the highest salaries at the end of the deals.  In Soriano’s case in particular, his salary has continued to climb while his production withers, progressing from a minor annoyance to a massive laughingstock across the league.  Some writers list it as the worst-ever for the Cubs—others say it’s the worst in league history.

So let’s face it, Cub fans—short of some clever dealing*, both those guys are staying in Chicago for the foreseeable future.  What’s less apparent—and potentially more damaging for the Cubs long-term—is the next tier of back-loaded contracts Hendry has given out, and what they mean to the team’s ability to retain their veteran players.

*Don’t hold your breath—Hendry’s still our GM for the time being.  His cleverness is limited to turning batting practice hugs into national headlines and using spare buttons to pay for snacks from the office vending machines.

Carlos Pena is one example.  He signed with the Cubs this past offseason for a staggering $10 million—staggering because he’s a ten-year veteran with a career batting average of .239, coming off a contract season where he managed to hit only .196.  Across the league, it was considered a bizarre amount to pay, even if half of it is deferred until 2012.

Fast forward to this week, and it looks like Pena might be starting to live up to his offensive potential.  His long fly balls are making it into the stands, and his glove is covering up for inexperience elsewhere in the infield.  Add in his growing reputation as a quality teammate and clubhouse leader, and he has many Cubs fans wondering if he can stick around beyond this one season.

Ah, but there’s the problem.  Any extension talks with Pena start at that $10 million price tag.  By the numbers, Pena is probably a good value somewhere between $6-7 million.  If he really does like Chicago and day baseball as much as reported, he might be willing to give the Cubs a discount in return for more years, but it’s doubtful it will bring the overall price to within a reasonable range**.  What’s more, how many years can you safely commit to a thirty-three-year-old veteran before the discount you get isn’t worth the money you’re saving?  Ideally, you’d want to sign him for one or two more years, but at the price you’d likely have to pay—plus the $5 million you already owe him for this year—it’s not worth the production he’d bring to the lineup.

**That doesn’t mean I think Pena is the villain here—far from it.  Just look at it from his perspective: if the Cubs are happy enough with his performance this season to want to resign him, why would he come back for substantially less than what they’re already paying him?  The same is true for you—you wouldn’t take significantly less money next year to do the same job you’re doing now, no matter how many years you were promised.  Would you?  Nope.  I wouldn’t either.

Carlos Marmol’s three-year, $20 million contract presents an even stickier situation for the Cubs down the road.  This season he’s making just over $3 million—a bargain price for one of the best closers in the game.  But next year his salary jumps to $7 million, and the year after that the Cubs will pay him just under $10 million.  That means when it comes time to negotiate his next contract or any extension, the base salary you’re working from is that $10 million price tag.  By then, Marmol will be over thirty, and the combination of age and cost might force the Cubs to trade him away or let him wade into free agency, still well in the midst of his prime.

The same question of resign-ability is looming over Ryan Dempster and Aramis Ramirez this season.  Both have options for next year—Dempster has a player option***, while the club has the option in Ramirez’s contract.  Both are fairly beloved, long-term Cubs who have professed a desire to stay with the team to the end of their careers.  But in both cases, their back-loaded contracts put the starting price for negotiations at an unreasonably high level—Dempster is making $13.5 million this year, while Ramirez makes $16 million.  By maxing out the tail end of their deals, Hendry has inadvertently**** guaranteed that one or the other—and possibly both—will be playing in different uniforms next season.

***I can’t speak for Dempster, but I think he would waive his $14 million option for next year to extend his deal with the Cubs.  And it wouldn’t be the first time he financially sacrificed for the sake of the team—he deferred $3 million of his contract back in 2010.  Much like Kerry Wood, I get the sense that Dempster is the rare veteran who would make a large financial sacrifice to keep playing where he wants to play.  I just don’t think the Cubs can afford to bank on that kind of benevolence, and with Hendry in charge, they are.

****Not sure why I’m giving Hendry the benefit of the doubt there.  The truth is that his pattern as a GM has been pretty focused on the supposed needs of the moment, with little regard for the future.  His track record is full of half-measures, band-aid signings, and short-term self-preservation—the Soriano signing is just one example.  He’s not what I would call a “planner.”  If I had to guess, I’d say he probably buys a whole lot of stuff from the Home Shopping Network.

Bottom line, the Cubs have roughly $50 million coming off the books at the end of the season.  Most of that money will go to resign current Cubs***** and reel in key free agents******.  Can the Cubs trust Jim Hendry to use that money wisely to piece together a roster and rebuild a winner?  His track record says no.

*****Possibly a combination of Garza, Wood, Pena, or Dempster, and raises for the handful of arbitration-eligible players we have.

******Please, please… not Pujols or Fielder.  Neither of them solves any of the Cubs’ primary problems.  And if the worst should happen and Hendry keeps his job through the offseason, both of them are prime targets for one of his patented, massively back-loaded deals.

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