In his complaint, Bennett claims that he is due record and song royalties, both for the time he was in the band as well as after. He also alleges that he is owed compensation for his appearance in the 2002 DVD, "I'm Trying To Break Your Heart."
I will admit being partial, as I am a huge fan of both Wilco and Tweedy. I will also acknowledge that I have no familiarity with the facts surrounding Bennett's complaint or the relationship of the parties. However, based solely on what Bennett submits in his complaint, it appears that he is desperate and is likely to lose.
As an initial matter, Bennett alleges that he is a beneficiary to a written agreement to which he is neither a party nor (it appears) an intended third-party beneficiary. While this is by no means fatal, it certainly is not a hallmark of a strong case.
Bennett states that he is a songwriter and entitled to royalties under the agreement that he didn't sign. That provision provides, in part: "In the event that a song is wholly owned by one Member, the non-owning Members shall be entitled to an aggregate 15% of the income generated by sales and performances of the Group's recordings of the song earned during each non-owning Member's Term."
Bennett seems to admit that he received a pro rata share of song royalties during the term. What is not clear is whether he is claiming that he actually co-wrote any songs or merely that he should still receive a portion of the 15% allocated to non-writing members. If the former, why would Tweedy be the one to sue? Did Bennett assign his interest in his songs to Tweedy in exchange for a royalty? Does Tweedy administer his copyrights? Why, if he was a writer, would Bennett not be receiving his performance money from his own PRO and his mechanicals from the labels directly, and why would those not be the parties to pursue?
If, however, Bennett is claiming that he is only a writer insofar as the agreement provides a payment to non-writing members then he is very mistaken. The agreement clearly does not contemplate assigning any copyright interest to non-writing members; they only have a right to participate in the income. Moreover, the agreement is very clear that non-writing members will only be paid for income earned while they are members, which is wholly different from paying out a share for all songs written and recorded during that time (thus giving rise to a continuing obligation to pay).
There are two overarching problems in Bennett's complaint. First, in no circumstance does Tweedy appear to be the proper party. If Bennett was not paid properly according to either the document he signed or the subsequent agreement then it is the corporate body that is responsible. Bennett attaches exhibits to show that he was a shareholder in Wilco World Tours as evidence of his equal interest in Wilco - if that entity owes him money, why not name it as a party? What about the loan-out entity for recording? What about the record labels? Anyone but Tweedy!
The second big problem is the copyright statute of limitations. In fact, Bennett does not even specifically allege copyright infringement, which certainly would be my first approach if I were a co-writer on any of the songs. Of course, he is in the wrong court for that, anyway. Nonetheless, it seems any potential copyright claim would be barred by the statute of limitations. (I'm not familiar with the Illinois statute of limitations on contracts but my guess is that Bennett is really close to that deadline as well.)
All in all, my guess is that Bennett is barking up the wrong tree.