Staying Aggressive: Maximize The Chance Of Winning, Don't Worry About Looking Good
Don't be afraid to swing and miss; if you win every argument that you make, you may need to make more aggressive arguments.
Matthew W. Schmidt
Ed. note: Matthew W. Schmidt, an attorney at Balestriere Fariello, is filling in for John Balestriere this week.
The famous economist Tyler Cowen wrote that in politics, the goal isn’t to maximize the expected value of your image, but to maximize the likelihood of getting what you want, contingent on victory having been possible in the first place. As he pointed out, this means that you may look ridiculous when you never had a chance of winning, but those are the stakes and you often can’t tell if winning is possible until you play. He also wrote that if you always look good, you’re doing something badly wrong. The same is true in litigation.
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In litigation, there are huge grey areas. Maybe numerically, most legal questions are black or white—if you shoot someone in the face for the premeditated reason of killing them, you’ve committed murder—but like many litigators, most cases that my colleagues and I handle are the type of high-stakes cases that would have settled far earlier if there was a clear answer.
As my colleague John noted in an earlier article, in the end the final determination in a case is made by a judge—usually a single person, possibly followed by several more on appeal—or an even more unpredictable jury of randomly selected citizens. While they’re extremely well qualified and make what they think is the best call, it’s impossible to predict with certainty what way a judge will rule in any case that’s contested enough to get to them. You can deal in probabilities and make an educated guess, but we’ve all had cases that everyone was sure was a winner end up losing, and the other way around.
This means that within your ethical obligations, you shouldn’t be afraid to swing and miss. Just like if you’ve never missed a flight, you’re spending too much time at the airport, if you win every argument that you make, you may need to make more aggressive arguments. Your goal is to maximize the chance of your client winning.
Develop Aggressiveness in New Attorneys
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New litigators—or ones new to private practice—often need time to adjust to the idea of losing. In law school and clerkships, young lawyers commonly have it drilled into them what they can’t do, and are taught to dispassionately analyze claims instead of advocate for clients. Sometimes they’re taught that legal issues are like problems that have a “right” answer.
I once had a junior lawyer working for me who had just finished two years at a very good clerkship, and his first task was to find caselaw and build arguments for a motion that we were very unlikely to win, since we were seeking discretionary relief that was rarely given. I thought that it was a perfect first assignment, as it was a simple argument, had little pressure, and involved the kind of analysis and distinguishing cases that smart young lawyers—like this one—are great at.
Instead, the lawyer came back the next day and told me that, based on his research, he thought that we were going to lose, and that he thought we should tell the client and strongly consider not making the motion. I explained that the client was well aware that it was a long-shot, but thought it was worthwhile to try. The lawyer said that he understood, and went back to work on the research some more.
The next day he came back again, and told me that he’d done some more research, and his conclusion was not only stronger that we going to lose, but he couldn’t find any cases at all that went our way on similar facts. I told him to keep looking, to be creative, and where all else fails to just make the best argument he could.
He ultimately found about a dozen cases that went arguably in our favor—far more than I expected—and with his help the team put together a very strong, persuasive brief. As expected, our adversaries identified how most of those cases were distinguishable, non-controlling, or both, and the court denied our motion six days after the reply brief went in.
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But I like to think that the younger attorney’s takeaway here was that, while we lost, the world didn’t end, and the court’s opinion didn’t even fault us for trying. The judge understood that we were doing our jobs and advocating for our clients, and every time a litigator has an easy argument for his position, there’s someone on the other side who has to make the best of what he has to work with.
Keeping Aggressive in Your Practice
Even if you’ve been practicing for a while, every litigator can use a reminder every so often that while it’s certainly easier to make a winning argument when all the law and facts go in your favor, that’s not what you’re being paid for. Many litigators have a story of some client who made what they thought was an unreasonable demand, something that no court would likely go for. But what these lawyers are forgetting is that the client there was completely right, and not in a generic “the client is always right” sense.
As long as the client is being properly apprised of the odds, you’re being paid to advocate, and most often the reason a client needs to hire someone to advocate for them, as opposed to brokering a quick settlement, is that either the facts or the law don’t all fall neatly in their favor. And even when a client does have something that you think is an easy case, very often there’s an argument that you may not think the court is likely to accept, but it’s worth a try. If you’re not giving it that try—and especially if one of your reasons is that you think you’ll look bad if you lose—you may not be serving your clients as well as you could be.
Matthew W. Schmidt has represented and counseled clients at all stages of litigation and in numerous matters including insider trading, fiduciary duty, antitrust law, and civil RICO. He is of counsel at the trial and investigations law firm Balestriere Fariello in New York, where he and his colleagues represent domestic and international clients in litigation, arbitration, appeals, and investigations. You can reach him by email at matthew.w.schmidt@balestrierefariello.com.
