A free resource organized by the questions you’re asking.
Executive Brief
Welcome to Issue #100!
One hundred weeks of contracts, compliance, compensation, and the question that runs through all of it: What does a fiduciary actually owe the people who depend on the plan?
We’ve covered DOL rules and court rulings. PBM compensation structures and contract provisions. Procurement processes and governance frameworks. Specific employers, specific drugs, specific dollar amounts.
But every issue comes back to the same question. And this week, we’re making it easier to find the answers.
The Middleman’s Cut newsletter archive is now a resource library, organized by the questions fiduciaries actually face. One hundred issues, curated into collections you can search, browse, and use.
The Answer
What does a fiduciary actually owe the people who depend on the plan?
Three things:
Loyalty. Act solely in the interest of participants and beneficiaries. Not the employer’s convenience. Not the vendor’s margins. Not the consultant’s relationships. The employees and their families. Full stop.
Prudence. Exercise the care, skill, and diligence that a prudent person would use. That means understanding what you’re buying, how it’s priced, and whether better alternatives exist. It means asking questions when the answers aren’t clear.
Oversight. Monitor vendor performance. Verify that fees are reasonable. Confirm that what was promised is what’s being delivered. Governance isn’t a one-time event. It’s an ongoing discipline.
This isn’t about avoiding lawsuits. It isn’t about checking compliance boxes. It’s about whether the people who depend on this plan are actually getting what they’re owed.
Fiduciary duty isn’t a burden to manage. It’s a responsibility to fulfill. And it’s good business: vendors aligned with your interests deliver higher quality, more cost-effective care.
What 100 Issues Taught Me
Writing this newsletter every week for two years clarified something.
The questions repeat. The contexts change, but the underlying problems are the same:
What does “fiduciary” actually mean for pharmacy benefits?
How do I know if I’m paying too much?
What should my PBM contract actually include?
What does CAA 2026 require of me?
How do other employers handle this?
Where do I start?
These aren’t abstract questions. They’re the ones I hear in every conversation with executives, general counsel, benefits committees, and advisors trying to do right by their plans.
One hundred issues later, there’s an answer to most of them somewhere in the archive. The problem was finding it.
Free Newsletter Resource Library
The New Resource Library
DittoandAssociates.com/newsletter is now organized by question, not just by date.
Contract Terms & Provisions
What belongs in a PBM contract. Audit rights. Exit clauses. Definition provisions. Spread pricing prohibitions. The specific language that protects the plan.
Pricing & Compensation
How PBM economics work. Where the money goes. How to evaluate what you’re paying and benchmark against what’s available in the market.
CAA 2026 & Compliance
What the Consolidated Appropriations Act requires. Disclosure obligations. Documentary requirements. How the regulatory landscape is shifting.
Fiduciary Governance
What “solely in the interest of participants” actually means in practice. How to structure oversight. The difference between compliance and governance.
Case Studies & Examples
Real employers. Real contracts. Real outcomes. The specifics that make abstract principles concrete.
Getting Started
Where to begin if you’re new to this. The sequence that makes sense. First steps that create momentum.
One hundred issues. Curated by the question you’re trying to answer. Free.
Why This Matters Now
The regulatory signals are building.
The Department of Labor has been explicit about fiduciary obligations in the pharmacy benefit context. Courts are letting prohibited transaction claims proceed that would have been dismissed five years ago. The documentary record CAA 2026 creates is becoming the evidentiary record litigators will use.
The question isn’t whether scrutiny is coming. It’s whether your governance structure can withstand it.
The resource library isn’t just an archive. It’s preparation. Every question a regulator or plaintiff’s attorney might ask has probably been addressed somewhere in these hundred issues.
Now you can find it.
What to Do First Thing Monday
Browse the library. Go to DittoandAssociates.com/newsletter. Find the question you’re currently facing. See what’s already been written.
Bookmark one collection. Pick the category most relevant to your current work (contract terms, pricing, governance, etc.) and save it for reference.
Share with your team. Forward this issue to anyone on your benefits committee or advisory team. The library is a shared resource. Make sure they know it exists.
Ask a question. If there’s a topic we haven’t covered, reply to this email. One hundred issues and there’s still more ground to cover.
In Closing
One hundred issues.
I started this newsletter because the questions deserved better answers than they were getting. Fiduciaries were being told to trust their vendors without the tools to verify. Executives were signing contracts they didn’t understand. Plan participants were paying the price.
Two years later, the questions haven’t changed. But the resources have.
A hundred issues of analysis. A book with a framework. Contract scoring tools. Procurement guides. A library organized by the problems you’re actually trying to solve.
To whom much is given, much is expected. A lot of tools and resources have been given. The expectation is that you’ll use it.
Here’s to the next hundred issues. And to clearer thinking, stronger plans, and better outcomes for the people who rely on us.
