As the battle raged, one voice at the center of the action was largely muted — Judge Carey's.

Many pitched hearings ended with a simple "That's all for today," leaving the combatants puzzling over whose arguments had prevailed. Some argue — anonymously, since they are reluctant to criticize a sitting judge — that this left a leadership vacuum that prolonged the acrimony.

"You gotta make a decision one way or another," one of the main players complained in an interview. "We might think it's a right decision or a wrong decision. But we just need you to make a decision."

As a sitting judge, Carey could not discuss the case. But many experts say his reluctance to aggressively dictate an outcome may have stemmed partly from the fact that the bankruptcy code discourages it. Judges are supposed to guide the case toward a settlement but have few tools at their disposal to corral adversaries.

In 2011, at the end of confirmation hearings that failed to settle the case, Carey noted that he believed Oaktree and Angelo Gordon had every right to protect themselves from what they saw as bottom feeders. JPMorgan was free to push its weight around if that served its ends. And the juniors had the right to step in and pursue what they saw as the best business opportunity.

"But you know," he said, imploring the parties to find their own solution, "at the end there has to be an exit of some kind."

Ironically, one of Carey's most decisive moments — his appointment of a bankruptcy examiner to provide a third-party assessment of the fraudulent-conveyance charges — only produced a heightened level of acrimony in the case.

Once the senior group splintered, Carey recognized that the fraudulent-conveyance charges weren't going to be easily negotiated away. So he appointed a Los Angeles lawyer and bankruptcy scholar named Kenneth Klee to sort through the Zell buyout and determine who might be liable for what. He said he hoped the exercise would make a settlement easier.

Klee's report had the opposite effect.

Klee and his team spent long hours sifting through the Zell deal. When they were through, they produced four thick volumes running thousands of pages that carefully broke down the evidence and assigned probabilities to eight possible outcomes of litigation. Klee's bill: $12 million.

The problem was, the findings were so intricate and inconclusive that everybody felt the report supported their case. As David LeMay, an attorney for the committee representing creditors, put it, "You know, the examiner's statement is like the Bible. There's something there for everybody."

What happened next provided a classic example of how claims trading in bankruptcy court can change the complexion of a Chapter 11 proceeding overnight.

Aurelius had slowly been increasing its position in the junior bonds while accumulating a controlling stake in another esoteric form of junior Tribune Co. debt called the PHONES. A few months after the Klee report landed in late July 2010, Aurelius approached Centerbridge with an offer to buy out its stake, allowing Aronson to go home with what everybody assumed was a handsome profit.

The moves established Aurelius as by far the largest junior creditor with the power to control the fate of two classes of Tribune Co. debt. And that quashed any lingering chance of resuscitating the April 2010 settlement.

Even after the Klee report, Tribune Co. and the senior creditors held out hope they could strike a deal with Centerbridge. But in terms of its demands, Aurelius "was in another universe," Kurtz said.

Aurelius founder Mark Brodsky casts himself as the lonely voice of the oppressed junior creditor. His email signature contains a rolling selection of quotations from the 12-volume "Meditations" of the Roman emperor Marcus Aurelius. A favorite: "Pay no attention to the chatter of your critics. ... If it is good to say or do something, then it is even better to be criticized for having said or done it."

Brodsky, who wouldn't comment, is well-respected for his legal intellect. But his critics abound. He is viewed as a tenacious disrupter of Chapter 11 cases, using all legal remedies at his disposal to boost the value of his stake. In the Tribune Co. case, he publicly accused the original lenders of refusing to negotiate. Instead, he said, they were trying to "extort a cheap settlement as the price for allowing Tribune to emerge from bankruptcy" and suggested that company management had supported them to "cover up and gain releases for their own wrongdoing."

Once he bought out Centerbridge, Brodsky hired Aronson's legal team and began building a set of aggressive legal strategies based on the Klee report. They were, for the most part, untested and risky. But they were plausible enough to extend the case for two more years, including an expensive two-week trial on the fraudulent-conveyance issues.

Aurelius lost that battle. Ultimately, Carey blessed a plan that shared some similarities with the one that had fallen apart in 2010. It gave Aurelius and its allies $431 million for their $1.28 billion in claims — much less than they wanted.

But Brodsky wasn't finished. He also won two other key victories that will allow Aurelius to keep the Tribune Co. case alive in the courts for years to come as the firm seeks to recover the rest of its money.