The story starts in summer 2013, when Rosen was struggling with whether to accept the role of chief judicial mediator in the city of Detroit’s bankruptcy case. A Detroit native, Rosen had served as chief judge for the U.S. District Court for the Eastern District of Michigan since 2009. His colleagues had concerns about judicial hierarchy and status as well as conflicts of interest, because appeals to the case would invariably land on their dockets. His wife, Laurie, said he had more than enough on his plate already with serving as chief judge, adjunct teaching, editing three books, regular speaking engagements and his own judicial docket.

Rosen and his son, Jake, who was 15 at the time, were driving to a golf course on a Saturday morning when Steve Rhodes, the bankruptcy judge on Detroit’s case, called to see if Rosen was ready to make a decision. They talked about some of the challenges before Rosen ended the call to golf with his son, who didn’t comment at the time. On the way home, however, Jake asked if Rosen was truly considering turning down the role.

“I was a (Winston) Churchill guy from my freshman year in college with (K history professor) Ed Moritz,” Rosen said. “He introduced me to Churchill, and Jake had heard all the speeches. He saw those black and white, grainy films of Churchill. He knew of my admiration of Churchill, and he looked at me intently and said, ‘What would Churchill have done, Dad? Do you think Churchill would have refused? Everybody has a time to stand up. This is your time.’ Just like that.”

Jake’s perspective was “a bolt of clarity,” Rosen said, and he accepted the role as chief judicial mediator in the spirit of Churchill’s commitment to courage, determination, loyalty and honor.

‘A true product of the Kalamazoo Plan’

Winston Churchill became a hero of Rosen’s more than 40 years before that conversation— an admiration first sparked in a classroom at Kalamazoo College. Recruited to play tennis at K by Coach George Acker, Rosen threw himself into the team, rigorous academics and experiential opportunities.

He earned a degree in political science under the tutelage of Don Flesche and Elton Ham. Rosen also relished classes with David Scarrow in philosophy, Moritz in history, and Conrad Hilberry and Harold Harris in the English department.

“I had some absolutely wonderful professors, and they introduced me to lifelong passions,” Rosen said. “These were very much broadening experiences for me. I thought the faculty was just terrific.”

The K-Plan fostered Rosen’s natural tendencies toward independence.

“When you’re on campus and off campus as often as I was, you have to learn to live on your own, meet new people, do new things, organize your life, balance a lot of different things,” Rosen said. He spent a term student teaching at an elementary school in Philadelphia. He studied abroad in Stockholm, later returning there on a research grant to complete his Senior Integrated Project. Rosen also spent a term working in the office of Michigan Gov. William Milliken, which primed him for a post-graduation job working for Robert Griffin, who represented Michigan in the U.S. Senate from 1966–79.

“I am one of those students who can trace his career path directly to his career service,” Rosen said. “Had I not worked for Governor Milliken, I’m not sure I would have gotten the job working for Senator Griffin. Had I not worked for Senator Griffin, I’m not sure I would have been a successful lawyer. Had I not been a successful lawyer, I probably wouldn’t have been a federal judge, so the line is pretty straight.”

Learning to think like a lawyer

Rosen worked for Griffin in the Senate for more than five years, simultaneously earning his J.D. through night classes at The George Washington University Law School.

As a legislative assistant, Rosen worked on the Senate floor, visited the White House, and wrote statements and speeches. Building on writing foundations established at K, he learned from Griffin’s “terrific” editing, explored substantive issues involved in legislation, and learned to “think like a lawyer,” Rosen said.

“(Griffin) was a lawyer, and he always would tell me, ‘You’re going to be a lawyer, Jerry, think about this like a lawyer would think about it,’” Rosen said. “He helped me think about things in a logical, clear way. All of that prepared me, and it built my professional confidence.”

When Rosen returned to Michigan, he was hired by Miller Canfield, working in large-scale commercial, constitutional and employment litigation.

After a failed bid for Congress in 1982, Rosen began to reflect on his passion for being in the courtroom as well as his dislike for fundraising, which led him to consider serving as a judge. The following year, he was appointed to chair a committee that selected federal judges, and in 1989, he was nominated to become one himself.

“I think about what I was doing at such a young age, working on the Senate floor, writing speeches, briefing senators. When I went on the bench, I was the second youngest federal judge in the country. I was 38 years old, which now seems ridiculously young. At the time it didn’t.

“When I was up for confirmation, President Joe Biden was a senator and chairing the judiciary committee, and I met with him beforehand. He said, ‘Very impressive file. The only knock against you seems to be that you might be too young, but I was 30 years old when I was elected to the United States Senate, so 38 doesn’t seem too young to me.’”

Integrity on the bench

Rosen served as a federal judge in the Eastern District of Michigan for almost 27 years, including seven years as chief judge, leading with integrity and curiosity.

“It’s the best job in the world,” he said. “Complete independence, no clients, no billable hour requirements, and you can pursue the issues that you think are important to the end, make a decision based on the evidence and law, and not have to worry about politics or clients or advocacy.”

When faced with controversial and challenging cases, Rosen focused on the facts and where the law and evidence led him, whether that was a popular outcome or not.

“I always keep asking questions, and I’m always looking for the answers, and I try to have an open mind,” Rosen said.

For example, he presided over the first post-9-11 terrorism trial, which garnered heavy publicity. After three of the four defendants were convicted, Rosen received notice from the U.S. Attorney’s Office of potential misconduct by the prosecutors.

“I pursued that and ended up overturning the verdicts based on prosecutorial misconduct, which was very difficult and controversial, but I was absolutely persuaded it was the right thing to do. I ended up ordering the attorney general to appoint a special counsel and going out to the CIA to review highly classified documents. Once I finished all of that, it became clear to me that the verdicts had to be overturned.”

In hearing one of the first partial-birth abortion cases, Rosen similarly hired his own expert to help him understand the medical aspects of the case and how that lined up or not with the state statute.

“I wasn’t looking to overturn a state statute as a federal judge,” Rosen said. “I know I disappointed some of my Republican friends who had supported me for appointment to the bench when I overturned Michigan’s partial birth abortion statute, but that’s where the law and the evidence led.”

In his time on the bench, Rosen also handled cases involving physician-assisted suicide, race and other controversial issues.

“People tend to think of me now in regards to the bankruptcy, but those were defining cases,” he said.

Crafting a grand bargain

Detroit’s bankruptcy came more than 20 years into Rosen’s time as a federal judge.

His job, once he agreed to take it, was to deliver a plan of adjustment to restructure the city’s debt obligations that could be agreed to by as many involved parties as possible (which included the city of Detroit, its 170,000 creditors, the state of Michigan, affected counties, vendors, bond holders and bond insurers). And he needed to do it quickly.

“I very much thought—and so did Steve Rhodes—that time was Detroit’s enemy,” Rosen said. “Detroit did not have time to become enmeshed in years and years of litigation trench warfare. There’d be nothing left of Detroit but dust and legal bills.”

Detroit, after all, had filed for the largest municipal bankruptcy in U.S. history, with debt estimated at more than $18 billion. The city couldn’t pay for many basic services or fulfill the pension contributions owed to city retirees. On a long-promised golf vacation in Florida soon after taking up his mediator role, Rosen got up early each morning to work through background reading and talk to lawyers. The deeper he delved, the more he zeroed in on two major bookends.

On one end were the retirees whose futures were in jeopardy. The city had stopped making pension contributions, and the combined pensions and health care for 23,000 retirees were more than $9 billion underfunded, Rosen said.

“These were not flush pensions,” Rosen said. “Civilians were getting about $19,000 on average, and the uniforms were getting about $32,000 on average, but they didn’t get Social Security or Medicare. Kevyn Orr, the emergency manager, was talking about cutting their pensions by 35%, and cuts of that magnitude would have been devastating.”

The other bookend was the city’s lack of assets.

“My job as the mediator was to get deals, and to get deals, you have to either have money or assets that can be monetized to pay creditors,” Rosen said. “Detroit had virtually no assets other than the Detroit Institute of Arts. The city owned the art in the museum, and all of the creditors and the city were focused on liquidating it, which I thought would have been a terrible idea for many reasons.”

With these two pieces—the retirees and the art—circling in his mind, Rosen sat down to brainstorm on another early morning in Florida.

“I had been taking notes, and I had gone through the whole legal pad so that the only thing on the table in front of me was the cardboard backing,” Rosen said. “I doodled this idea I had, and the idea was to get the state to kick-start funding, put the art in a trust, lock it off from all of the other creditors other than the retirees, and flow any money that we raised through the trust to the retirees.”

At the end of the trip, Rosen threw the doodled cardboard in with all his reading, and it landed in a stack of notes behind his desk, where the doodle was forgotten for a time—but the idea persisted.

It took a team

“I realized pretty quickly that I needed some help,” Rosen said. “The case was just sprawling, too many issues, too many groups to deal with. I went through my life Rolodex in my mind. I started calling people, and eventually I had six co-mediators, all very talented people, lawyers and judges, some of the best in the country. We had a dinner at the very beginning, and Jake walked in, and I introduced him around. He was used to meeting judges and lawyers, and he’s usually not very impressed. But when he met this group, he said, ‘So this is like a dream team.’”

With the help of that dream team and many others—Rhodes, Orr, philanthropists, city and state politicians and civic leaders—over 16 months, Rosen oversaw the coming to fruition of the “grand bargain,” as it became known, that he had first doodled on that piece of cardboard. Rosen and his team raised more than $820 million, all of which went into a fund for the retirees to almost fully eliminate pension reductions they were facing.

“The Grand Bargain legislation itself, the state’s part of it, had to be passed by the Legislature,” Rosen said. “Everybody said that would be impossible, because we had a conservative Republican, Tea Party Legislature, both houses and the governor; everybody said they would never pass what was characterized as a bailout for Detroit. For me, one of the most emotional moments in the bankruptcy was when I was up in Lansing for the Senate consideration of the Grand Bargain legislation, and Tom Casperson, who was a conservative senator from the Upper Peninsula, stood up. You could hear a pin drop in the Senate, because he was respected by everybody, and he said, ‘Today, we are all Detroiters.’ The legislation passed both the House and the Senate overwhelmingly.”

By December 2014, Detroit exited bankruptcy by adopting a plan of adjustment that included the $820 million raised through the grand bargain to pay the pensions with more measured cuts than originally loomed.

When Rosen began to clean out the stacks of papers that had accumulated over the course of the case, he came across that original doodle on cardboard, and he left it on his desk to show Gene Gargaro, chair of the DIA.

“He knew exactly what it was right away,” Rosen said. “He said, ‘That’s got to hang in the DIA.’ So there it is, hanging in the DIA.

“Like every kid in Southeast Michigan, I went on field trips to see the DIA, whether through school or the Cub Scouts, but I was not part of that crowd. I was not involved, didn’t contribute. I was just not a DIA guy, but I certainly am now. The DIA has been chosen two years in a row, ’23 and ’24, as the No. 1 art museum in the country (in the USA Today 10 Best Readers’ Choice awards). I’m very proud that we saved the museum. Very proud.”

Ten years later

In 2023, Rosen found himself in demand with journalists wanting to write about the 10th anniversary of Detroit’s declaration of bankruptcy. Inspired, he returned to a draft of his own account, which he had written shortly after the case concluded, despite his initial resistance to the idea.

Around May 2015, Rosen and his wife were having drinks with Jim Nicholson, a civic and business leader in Detroit, when Nicholson asked Rosen if he was going to write a book about the bankruptcy case.

“I said, ‘Jim, I’m not going to write a book. Everybody’s writing a book about the bankruptcy. Nobody needs another book,’” Rosen said. “And he said, ‘Jerry, I’ve known you for a long time. You will never be satisfied with what other people write about the bankruptcy.’ And he was right. I read a lot of what people had written about the bankruptcy, and although there were some very good pieces, very thoughtful pieces, none of them quite captured what happened.”

A few weeks later, on a flight to Washington, D.C., for work, Rosen pulled out a legal pad and started writing—and he couldn’t stop.

“We got to D.C., pulled up at the gate. I just kept writing. The cleaning crew was all around; eventually they kicked me off. I finished writing, and I got in a cab, and I called Steve Rhodes, because I thought he was the only person that could understand. We went through it together. We had different roles, but we were very much partners. I read it to him. He didn’t say a word, and then at the end, he just said, ‘Wow. You have to write this book.’ So I just kept writing. It took me about five months, and then I didn’t do anything with it. It was cathartic to get it all out.”

Revisiting that time in 2023, Rosen sent his draft to several journalists he respected; to David Scarrow, then K professor emeritus of philosophy; and to Michael Hinton, a friend from study abroad in Stockholm, who is now a self-published author. The journalists encouraged him to publish. Scarrow was working on a book about his life, and he and Rosen traded drafts and comments on their respective projects until Scarrow’s death in March 2024. Hinton invited him to visit, and they spent a week reuniting, reminiscing, collaborating, editing and discussing self-publishing.

At the end of that, Rosen took his book and found a publisher. Grand Bargain: The Inside Story of Detroit’s Dramatic Journey from Bankruptcy to Rebirth rolled off the press in 2024. He dodged some of the potential pitfalls involved in writing about real people and events by putting words down on paper while it was still fresh and by intentionally focusing on the positive.

“I made the decision not to write a kiss-and-tell book,” Rosen said. “I decided that there would be no villains. Not everybody lived up to expectations, but I wanted to write a positive story, and in a very real sense, I wanted to honor the heroes and heroines of the bankruptcy. I wanted it to be an inspirational story.

“When I sat down to write the epilogue, I thought I could do it in two or three days, maybe six or eight pages. It’s 26 pages, and it took me six weeks, because there’s so much that’s happened. Detroit is doing amazingly well. It’s a completely different city than it was 10 years ago—not just the statistics of the reduction of the debt and all of that, but the quality of life is so much better now.”

Rosen would know; although he retired from the bench at the beginning of 2017, he still works as a legal mediator in his hometown. In February 2017, he and other retired judges opened the Detroit office of Judicial Arbitration Mediation Services (JAMS), the largest provider of alternative dispute resolution services in the world.

“The years since I’ve left the bench have been incredibly rewarding, fulfilling,” Rosen said. “I go all over the country, mediating and arbitrating cases and working with very smart lawyers and their clients. I just got elected to a second term on the board of JAMS. It’s challenging and rewarding.

“F. Scott Fitzgerald said there are no second chapters in American life; I’m trying to prove him wrong.”