The Oakhurst Comma Case: A Lesson in Disastrous Legal Ambiguity
- Marc Roche
- Sep 18
- 5 min read
Table of contents
The $5 million comma mistake – how Oakhurst Dairy learned the hard way
In March 2017, a group of dairy drivers in Maine won a $5 million lawsuit because of a missing Oxford comma. The dispute centered on overtime pay, and the absence of one tiny piece of punctuation created enough ambiguity for the court to rule in the workers’ favor.
For Oakhurst Dairy, what seemed like a harmless omission became a multimillion-dollar mistake.
This case illustrates a hard truth: ambiguity in legal writing is more than a drafting flaw. It is a strategic risk.
For senior leaders, unclear contracts can erode shareholder value, stall negotiations, and damage reputations.
For professionals and learners, ambiguity undermines credibility, creates confusion, and leaves writing open to misinterpretation.
In short, clarity in legal writing is not cosmetic. It is both a safeguard for strategy and a practical discipline that protects intent.
Why ambiguity matters
Executives often see contract clarity as a “legal department issue.” Yet unclear terms can ripple outward into disputes, regulatory challenges, and even corporate collapse. Ambiguity invites competing interpretations, which in turn create opportunities for adversarial behavior.
For learners and early-career professionals, the impact is just as real. A vague phrase in an email or clause in a contract may look harmless, but it can be misunderstood, contested, or ignored. Building credibility means writing in a way that leaves no doubt about meaning.
Where legal ambiguity creeps in and how to quickly fix it
Ambiguity does not usually appear in bold headlines. It hides in the small words, vague phrases, and grammatical shortcuts that slip into everyday documents. Here are five common risk zones and how to correct them.
1. Undefined key terms
Strategic view: Words such as “reasonable,” “promptly,” or “soon” sound flexible, but in reality they invite conflict. What seems “reasonable” to one party may feel excessive to another. In high-stakes contracts, that gap can trigger disputes or litigation.
Practical fix: Define terms explicitly at the start of the agreement.
Ambiguous: “The tenant agrees to repair damages promptly.”Clear: “The tenant agrees to repair damages within five business days of discovery.”
This shift transforms subjectivity into certainty, reducing both operational confusion and legal risk.
2. Passive voice and hidden responsibility
Strategic view: Passive voice blurs accountability. “The report must be submitted by the deadline” does not specify who is responsible, which can delay performance and complicate enforcement.
Practical fix: Use active voice so that every obligation has a clearly identified subject.
Ambiguous: “The report must be submitted by the deadline.”Clear: “The contractor must submit the report by the deadline.”
Active voice accelerates execution and reduces opportunities for avoidance.
3. Vague timeframes
Strategic view: Time is money. Phrases such as “soon,” “as needed,” or “regularly” feel harmless, yet they leave dangerous gaps. A supply chain contract that promises delivery “soon” offers no real protection if goods arrive late.
Practical fix: Anchor deadlines in specifics.
Ambiguous: “Payment is due at the end of the month.”Clear: “Payment is due by 5 PM on the last business day of each month.”
Clear timeframes not only prevent disputes, they also align operational expectations across all parties.
4. Double meanings in legal verbs
Strategic view: Small words can carry disproportionate risk. Modal verbs such as “shall,” “may,” and “will” look interchangeable but carry very different legal weight. Misusing them can transform an obligation into an option — or an option into a binding duty.
Practical fix: Replace ambiguity with precision.
Ambiguous: “The buyer may return the goods.”Clear: “The buyer is permitted to return the goods within 30 days of purchase.”
In governance terms, clarity here means fewer loopholes and stronger enforceability.
5. Catch-all clauses
Strategic view: Catch-all phrases such as “including but not limited to” create flexibility, but if overused they weaken obligations by making them overly broad. The danger is that they may be interpreted in ways that were never intended.
Practical fix: Use them sparingly, and only where flexibility is essential.
Clear example: “The tenant shall maintain the property, including but not limited to plumbing, electrical, and heating systems.”
The key is balance: enough scope to handle unforeseen issues, but not so much that responsibilities lose definition.
The leadership imperative
For executives, ambiguous contracts are not minor drafting issues. They are enterprise risks with measurable consequences. Poorly written agreements can:
Increase the likelihood of disputes and litigation costs
Slow down deal-making and contract execution
Undermine trust between partners, suppliers, and employees
Expose the organization to regulatory and reputational harm
For learners and professionals, the lesson is equally critical. Clear writing builds credibility, strengthens professional authority, and ensures documents withstand scrutiny. Ambiguity, by contrast, signals weakness or inattention to detail.
Safeguarding clarity in practice
The good news is that ambiguity can be managed with discipline and governance. Leaders and learners alike can adopt the following safeguards:
Demand explicit definitions of key terms that affect obligations or timelines.
Insist on active voice in all major responsibilities, so accountability is never hidden.
Specify precise deadlines rather than vague timeframes that leave room for dispute.
Audit high-risk words such as “may,” “shall,” and “will,” treating them as red flags.
Read contracts from the other side’s perspective to spot where ambiguity could be exploited.
These steps reduce risk while creating a culture of precision.
Clarity is strategy, and it is skill
Clarity in legal writing serves two masters.
For executives, it is a strategic safeguard that protects value, reputation, and deal execution.
For learners and professionals, it is a core skill that strengthens credibility and ensures their work is taken seriously.
Even the smallest lapse can have enormous consequences. For leaders and learners alike, the conclusion is clear: words matter more than you think.
The Legal Grammar Advantage
Good legal communication means control — control of tone, of meaning, and of how your reader understands your message. Improving your grammar isn’t being fussy; it’s managing risk.
Clear grammar makes contracts solid. It makes arguments stronger. And it shows authority to clients without you having to say, ‘Trust me.’
Perfect grammar isn’t just about looking professional — it’s the core of a clear, persuasive legal argument, where a misplaced word can weaken your case before it’s even heard.
Write and speak like a lawyer who wins — every time. Download the Lawyer’s Grammar Cheat Sheet and get quick, courtroom-ready rules you can use today.
The Lawyer's Grammar Cheat Sheet by Macson Bell Business & Law.
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