After more than a decade working almost exclusively with employee benefits disputes, I’ve come to appreciate how quickly things can go sideways for plan participants and employers alike. Most people only start researching an ERISA law firm in Chicago, IL after a denial letter arrives or a retirement benefit doesn’t show up as expected. By then, the rules shaping their options are already in motion, whether they realize it or not.
I learned that early in my career while assisting on a disability benefits case for a union employee who assumed the appeal process was informal. He submitted a short letter and a few medical notes, confident the insurer would “do the right thing.” What he didn’t know—and what nearly cost him the claim—was that the plan required objective functional assessments tied directly to its definition of disability. We were able to course-correct, but only because the deadline hadn’t passed yet.
What ERISA Work Actually Involves Day to Day
ERISA practice is quiet, technical, and very document-driven. There’s no room for improvisation. I’ve found that people often expect depositions or live testimony to resolve misunderstandings later. In reality, most ERISA cases are decided on paper, based on the administrative record created before a lawsuit is filed.
I once stepped into a pension dispute where an employee relied on years of benefit statements that conflicted with the underlying plan document. From a fairness standpoint, his frustration made sense. Legally, the analysis hinged on which documents controlled and how courts in this circuit treat those conflicts. That kind of issue doesn’t announce itself unless you’ve seen it before.
Mistakes I’ve Seen Too Often
One recurring problem is treating ERISA appeals as a formality. In my experience, the appeal is often the most critical phase of the entire dispute. Miss a deadline by even a few days, or fail to address the plan’s stated reason for denial, and the claim can be over before it ever reaches a judge.
Another mistake is assuming treating physicians automatically provide the right support. Doctors write for clinical care, not plan administrators. I’ve spent countless hours helping translate medical realities into language that aligns with plan criteria—without overstating or speculating. That bridge between medicine and policy language is where many claims succeed or fail.
Chicago-Specific Realities
Practicing in Chicago means understanding how local federal courts approach ERISA cases. Some judges focus heavily on procedural fairness, while others give wide deference to plan administrators if the process was technically sound. That difference affects how I build a record and which arguments I emphasize.
I’ve also handled cases where employers were surprised by their own plan obligations. In one situation, a company relied on outdated summaries that no longer matched amended plan terms. Fixing that required careful reconstruction of plan history and communications, not dramatic legal maneuvering.
A Grounded Perspective
From where I sit, ERISA law rewards discipline and experience more than aggressive posturing. The strongest cases I’ve worked on were methodical, well-documented, and built with judicial review in mind from the outset. There’s rarely a silver bullet—just careful attention to detail and a clear understanding of how these claims are actually evaluated.
For people facing an ERISA issue, that structure can feel rigid, but it isn’t arbitrary. Once you understand how the process really works, the confusion starts to give way to clarity, even if the path forward remains challenging.