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When Tom Ricketts purchased the Cubs at the end of the 2009 season, he spoke openly about how important it was for him to bring a title to the North Side of Chicago. That’s certainly possible, but previous moves by general manager Jim Hendry have handcuffed the team on a nearly unprecedented level. The contract situation Ricketts inherits is among the worst in baseball history, akin to him assuming somebody else’s poker hand and he’s all in, needing some help on the river.

Entering 2010, the Cubs have more than $125 million committed to just 11 players, including eight earning more than $10 million. That leaves a team that opened 2009 with a club-record payroll of $137 million almost already there again with 14 contracts still left to fulfill, nine of which could get locked up in the arbitration process. The $125 million figure doesn’t lead baseball, as the Yankees and Red Sox surpass it, but what makes situation so uniquely bad is that many of the contracts are for underperforming players, with Hendry’ propensity for handing out no-trade clauses like they were lollipops further constraining future personnel decisions, including at the July 31 non-waiver trading deadline should the Cubs contend.

Here’s a look at the eight big deals that are weighing down the Cubs, courtesy of our own Jeff Euston of Cot’s Contracts fame:

1. Alfonso Soriano, LF*
2010 salary: $18 million
Further commitment: $72 million for 2011-14

Coming off his worst season, Soriano actually gets a raise in 2010, with a good chance to be the team’s highest-paid player for the next five years. While Soriano has not been awful overall, he has hit .275/.328/.508 for the Cubs. As a point of reference, the MarlinsCody Ross has been an exact match (.276/.333/.503) over the same stretch. Soriano still certainly has the ability to be a good player, but nobody would give him a deal anywhere close to five years and $90 million at this point.

2. Carlos Zambrano, RHP*
2010 salary: $17.875 million
Further commitment: $35.875 million for 2011-12 with a vesting option for 2013 that will be difficult to reach.

Zambrano is paid like an ace, but hasn’t pitched like one for the past two years, as he is usually beset by minor dings here and there, with the annual emotional blowup now becoming downright predictable. Like Soriano, he is good, but that doesn’t mean he’s not overpaid.

3. Aramis Ramirez, 3B*
2010: salary: $15.75 million
Further commitment: $14.6 million player option for 2011, $16 million team option for 2012

Ramirez is worth every penny when he is healthy, yet he’s averaged less than 130 games a year over the past five seasons, including just 82 last year.

4. Kosuke Fukudome, OF*
2010 salary: $13 million
Further commitment: $13.5 million for 2011

One of the biggest stars in Japan, Fukudome was expected to be a middle-of-the-order run producer and center fielder, but instead, has given the Cubs fourth-outfielder production. That mistake costs roughly half of the Marlins’ payroll for each of the next two years.

5. Ryan Dempster, RHP
2010 salary: $12.5 million
Further commitment: $13.5 million in 2011, $14 million player option for 2012

While the Cubs did a dangerous thing by giving Dempster a four-year deal coming off a career year, it worked out in the first season as Dempster actually out-pitched Zambrano in 2009 with a VORP of 30.3, compared to the Big Z’s 27.7.

6. Derrek Lee, 1B*
2010 salary: $13 million
Further commitment: None

Worth every penny.

7. Ted Lilly, LHP*
2010 contract: $12 million
Further commitment: None

Lilly has gone from an above-average lefty to one of the better ones in the game, and while he turns 35 before the 2011 season, another strong showing this year could lead to a considerable salary bump next year.

8. Carlos Silva, RHP
2010 salary: $11.5 million
Further commitment: $11.5 million in 2011, $2 million buyout in 2012

In fairness, the Cubs are responsible for “just” $6 million this year and $8 million next, as the Mariners, whose previous administration was dumb enough to give the fat strike-thrower this deal in the first place, will pick up $9 million. Even the $16 million the Cubs are responsible for is wasted money, a leftover sunk cost that serves as a two-year reminder of the Milton Bradley mistake.


*: The players marked with an asterisk have a contract clause preventing the Cubs from trading them, although Ramirez’ only applies through 2010.

So not only did the Cubs give these contracts, they’re stuck with them. On the financial side, they don’t have the dollar flexibility needed to add talent for the stretch run, and on the flip side, should things go horribly wrong and the Cubs find themselves out of contention, they’ll have veterans around with no ability to trade them to acquire help in building for the future because of the no-trade clauses. Hendry’s club-crippling addiction to such clauses even applies to the draft: as if Jeff Samardzija‘s ridiculous deal to steer him away from football doesn’t already generate snickers from other teams, he too cannot be dealt.

This isn’t the say all is lost, even though just Lee and Lilly come off the books at the end of this season, still leaving the Cubs committed for more than $100 million for just nine players. We’re talking about a team that finished in second place in the National League Central last season, 7 ½ games out of a playoff spots, in a year where everything that could go wrong, did. The Cubs are already an economic cash cow, as Wrigley Field doubles as a tourist attraction and they are one of the few franchises with little correlation between win-loss record and attendance. A World Series title would turn them into a true economic monster, as winning forgives everything, both in terms of fan sentiment and economic struggles.

Which brings us to one last contract, that of Hendry. He signed a four-year contract extension following the 2008 season. He has four years to get that river card to come up in the form of a World Series or he’ll be someone coming off the Cubs’ books in 2012.

A version of this story originally appeared on ESPN Insider Insider.