I have an almost genetic aversion to paying for parking. When I can't escape it, the inevitable question arises: pay 75 cents for the minimum time period or take a chance that I can run my errand and be back before anyone notices I haven't paid?* If I misjudge, the ticket might cost me about $30.

75 cents is less than $30. That's basic math. It makes sense to pay the minimum rather than risk being ticketed for the maximum. Right?

Wrong, apparently.

I often encounter litigants who are performing a similar calculation: I could settle now for this amount, or go to trial and be vindicated** Why pay 75 cents when you can pay 0? The risk of losing at trial (a.k.a. getting a $30 ticket) is summarily dismissed.

This is bad litigation math. The choice is not 75 cents or 0 cents. It's usually 75 cents or $30.

In the parking analogy, if I run off without paying, believing that I am faster than the average bear, or more efficient, or that all will go smoothly with my errand, or that there is no parking enforcement officer nearby, that is just a bunch of hope masquerading as knowledge. I have no objective certainty that the chances of getting a ticket are lower for me than for anyone else in this situation. I'm gambling.

Similarly, if a litigant does not have a full appreciation of the relevant risk factors, their assessment of the chances of being vindicated** is likely based more on hope than data.

On the other hand, if I have just seen the parking enforcement officer leave, or I see that the place I am visiting is empty, which means I will be able to complete my errand faster, these are concrete data points that might inform my decision not to pay the 75 cents.* It's a more calculated risk than one built on self-assurance and wishful thinking.

If you are going to trial on facts that are not great, with no assurance that the law is squarely in your favour, and your witnesses are not yet lined up, you simply do not have the data to support your confidence in total vindication**.

If you've thoroughly canvassed all the risk factors, however, that's a different story. I have no problem with parties telling me that the deal on the table is worse than what they might obtain in court, as long as it is a meaningfully-considered conclusion. In my view, vague assertions of confidence, wishful thinking, and inflated expectations are not enough.

Sometimes you have to pay to play.

* the right thing is to pay for parking when required and nothing in this post should be construed as advice to evade parking bylaws

** whatever that means