Win on Contingency: Go Watch Moneyball

The Lawyer as the Underdog General Manager

When Billy Beane became general manager of the Oakland Athletics in the early 2000s, he faced an impossible problem. His small-market baseball team had to compete against the New York Yankees, a franchise with three times the payroll and an endless list of advantages. The A’s had no money, no stars, and no margin for error. Yet, they still had to win.

For any personal-injury lawyer in Ontario working on a contingency-fee basis, that story feels familiar. We represent people who cannot afford to pay up front. We carry the cost of litigation for years, often against insurance companies that have teams of adjusters, endless data, and entire legal departments on retainer. We hear the same doubts Billy Beane did: you can’t compete with that.

And yet, we do.

Our advantage lies in how we define value. Beane changed baseball by replacing instinct with evidence. He used sabermetrics (a data-based way of finding overlooked value) to build a winning team on a limited budget. Contingency lawyers do the same. We use strategy, risk analysis, and disciplined case selection to achieve results that seem impossible on paper.

That is Moneyball lawyering.

The Traditional Game

Before Beane’s revolution, baseball scouts trusted their intuition. They looked for players who “looked right.” They used phrases like, “he’s got a beautiful swing” or “the ball explodes off his bat.” It was a world built on feel, not fact.

Traditional legal practice wasn’t much different. For decades, the measure of success was the billable hour. The more hours you billed, the more valuable you appeared. Lawyers were rewarded for input, not outcome. It was a system that prized time spent over results achieved.

Contingency lawyers don’t have that luxury. We are only paid if our clients succeed. Every hour we spend is an investment, not an invoice. Our metric isn’t hours; it’s outcome. We have to predict success, estimate damages, and calculate whether the expected recovery justifies the effort and cost.

Like Beane, we look for opportunities others miss. Where old-school scouts saw mediocrity, Beane saw potential. Where some lawyers see “low-value” files, contingency lawyers see steady singles that keep the lights on and build trust with clients who might refer the next major case.

Finding Hidden Value

In one of the best scenes in Moneyball, Beane sits in a crowded scout room while a dozen veterans argue about which players “look the part.” He finally interrupts them:

Beane understood that baseball was measuring the wrong things. Teams obsessed over batting averages and home runs…numbers that looked impressive but didn’t always translate into wins. He focused instead on on-base percentage (OBP): the simple act of not getting out.

In contingency law, the equivalent of OBP is liability probability. A case might look like a home run, such as a serious injury, large potential damages, but if liability is weak, the file can collapse. On the other hand, a modest injury with strong liability and cooperative medical support may resolve quickly and fairly.

A good contingency lawyer looks beneath appearances. We don’t chase the flashiest files; we build portfolios of solid, winnable ones.

Every case becomes a data point. Over time, patterns emerge that tell us which files produce fair settlements and which consume time without return. Like baseball, success depends less on spectacle and more on consistency.

Turning Art into Science

Sabermetrics didn’t replace intuition; it refined it. Billy Beane still watched games and cared about chemistry, but he used data to challenge bias.

In contingency practice, intuition still matters. We connect with clients, assess credibility, and read the room in mediation. But “gut feeling” alone is unreliable. Emotion and sympathy can skew judgment, especially when you want to help someone badly injured.

To manage that risk, I’ve learned to track measurable indicators.

• Medical trajectory: objective findings, treatment compliance, and long-term prognosis.
• Credibility metrics: internal consistency between testimony, clinical notes, and prior statements.
• Venue patterns: which regions and judges produce stronger awards for pain and suffering or care costs.
• Economic variables: length of wage loss, future care needs, and realistic discount rates.

Data doesn’t replace advocacy. It makes it sharper. Like Beane’s spreadsheets, these numbers don’t tell the whole story—but they keep you honest about probability.

Building a Balanced Case Portfolio

Beane couldn’t afford a roster of superstars. He built a team of undervalued players who each contributed something small but measurable. Walk specialists. Reliable defenders. Players who did their jobs quietly and well.

A contingency firm works the same way. We can’t build a practice on million-dollar catastrophic cases alone. Those files take years, drain resources, and depend heavily on expert testimony. To survive, we need balance.

We need quick settlements with modest injuries and clear liability. We need mid-range cases that require more litigation but still move predictably. We also need a few “power hitters” – complex, long-term cases that define our reputation.

A firm that relies only on big verdicts risks running out of cash before the payoff. A firm that relies only on small cases may never grow. The key is a steady rhythm of singles, doubles, and the occasional home run.

Beane’s A’s won because he stopped trying to hit the ball out of the park every time. He focused on getting on base. A contingency firm thrives the same way: by stringing together consistent results instead of chasing miracles.

The Industry Laughs…Until It Doesn’t

When Beane introduced sabermetrics, the baseball establishment mocked him. Scouts called his ideas naïve. Commentators said he was ruining the game. Even his players doubted him.

Early contingency lawyers faced the same skepticism. Traditional firms called the model risky or unprofessional. Insurers dismissed plaintiff lawyers as amateurs who couldn’t keep up without retainers or hourly billing.

But results speak louder than tradition. Beane’s A’s went on to win 20 straight games (a record at the time). Across Ontario, small contingency firms now routinely win against major insurers and national defence firms. The model works because it must. Every strategic decision is shaped by necessity, efficiency, and precision.

We don’t have the option to waste time. That pressure creates discipline, and discipline wins.

The Advantage of Constraints

Beane’s greatest weapon wasn’t money; it was constraint. Limited resources forced him to think differently.

Contingency lawyers understand that pressure. We can’t afford unnecessary experts or endless discoveries. Every dollar has to justify itself. That constraint becomes an advantage because it forces creativity.

For example, instead of retaining three separate specialists: a neurologist, psychiatrist, and physiatrist, I might choose one expert with overlapping credentials or rely on treating records to avoid duplication. Each step is strategic.

Budget pressure pushes us to focus on what truly drives outcomes: liability clarity, causation, and credible evidence. Far from being a weakness, that constraint keeps us lean and efficient. It’s our Moneyball edge.

The Power of the “Unknown Associate”

In Moneyball, Beane’s partner Peter Brand, a quiet Yale economics graduate, transformed intuition into numbers. He wasn’t a player or a scout. But he saw inefficiencies others ignored.

Every contingency firm has its own Peter Brand. It might be a clerk who tracks which adjusters make fair offers. It might be an associate who builds a spreadsheet comparing case values by venue. It could even be the firm’s practice-management system revealing settlement trends.

Data doesn’t replace human judgment. It strengthens it. Lawyers who track settlement ranges, cost recovery ratios, and resolution times are already building predictive models of their own performance. Those who don’t are still relying on “the sound of the bat.”

The Psychology of Losing

There’s a moment in Moneyball when Beane says something along the lines of “if we lose the last game of the series, nobody cares what we did.”

Litigation feels the same. A loss can overshadow months or years of effort. But like baseball, law is a game of averages. You won’t win every file. Some “losses” are victories in disguise if they cap exposure or close unproductive files early. Some “wins” cost more to achieve than they return.

A sabermetric mindset helps you detach emotion from evaluation. Every outcome becomes data. When you lose, ask why. Was it liability, quantum, credibility, or venue? The lesson becomes part of your future strategy.

Sustainable contingency practice isn’t about perfect records. It’s about maintaining a consistent, positive average over time.

Metrics That Matter

Baseball evolved beyond on-base percentage into advanced statistics like WAR (Wins Above Replacement). Contingency firms can develop their own equivalents: metrics that track financial health and efficiency.

• Case Value Index (CVI): average net recovery per case, adjusted for time and disbursements.
• Return on File (ROF): profit margin after accounting for time invested.
• Cycle Efficiency Ratio (CER): average time from intake to resolution.
• Adjuster Yield Score (AYS): how far settlements move from initial offers per insurer.
• Litigation Conversion Rate (LCR): percentage of files that proceed to litigation.
• Trial Win Probability (TWP): success rate in specific venues or before certain judges.

Tracking these figures transforms guesswork into insight. Instead of wondering whether a case will “pan out,” you forecast it. Over time, your practice becomes not just reactive, but predictive.

Teamwork and Culture

Sabermetrics wasn’t just about math. It was about building a culture that believed in it. Beane’s hardest job wasn’t running numbers—it was managing ego. Players, scouts, and coaches resisted the change.

Contingency firms face a similar challenge. Everyone on the team—lawyers, clerks, and even clients—needs to understand the “why” behind strategy. Why we turn down some cases. Why we settle others early. Why we invest heavily in certain experts but not others.

Transparency builds trust. When everyone knows the reasoning, the firm functions as a unit. Like Beane’s clubhouse, a healthy legal team values contribution over credit. Every file, big or small, is part of a larger system designed to win fairly and efficiently.

When the League Catches Up

After Moneyball, every team adopted analytics. Beane’s advantage didn’t last forever, but the game was changed permanently.

In Ontario, contingency practice has gone through its own shift. Rules under the Solicitors Act and growing client awareness have made the system more transparent. Insurers now use analytics of their own. The playing field has leveled.

The next advantage will come from integration: combining data literacy with empathy, storytelling, and credibility before judges and juries. Numbers alone don’t win trials. They guide strategy. The lawyers who succeed will be those who can merge evidence-based thinking with human connection.

The future isn’t data or empathy…it’s both.

Lessons from the Streak

In 2002, the Oakland A’s won 20 straight games. But the real story wasn’t the streak. It was the philosophy that made it possible. Beane built a competitive team from players other clubs had given up on. They won because they believed in the system.

Contingency lawyers often represent the same kind of underdogs. Clients who’ve been told their case is worthless, or who’ve been ignored by insurers. Through careful selection, strategic investment, and belief in the data, we give them a chance to win. Every fair settlement and every verdict is another game in that streak.

My Own Moneyball Moment

When I first started handling contingency cases, I felt like Billy Beane in that scout room full of skeptics. Everyone said it was too risky, too uncertain, too exhausting. I didn’t have a deep bench of experts or a corporate backer. But I had metrics.

I tracked everything: insurer behavior, cost recovery, referral sources, turnaround time. Over time, patterns appeared. I could see which cases kept the practice healthy and which ones drained resources. I learned to separate emotional attachment from business judgment. Sometimes the “big case” turned into a strikeout. Sometimes the modest whiplash file became the walk-off win.

When you run a contingency practice like a sabermetric team, you stop chasing glory and start building consistency. And that consistency, not luck, creates sustainability.

The Moneyball Future of Personal Injury Law

Moneyball isn’t really about baseball. It’s about changing how we think about value. It’s about questioning assumptions when the old rules no longer work.

Contingency fee law in Ontario is entering that same phase. As analytics tools, AI summaries, and digital practice management become standard, the firms that understand how to measure success will thrive. Those that rely only on instinct will fall behind.

The real lesson of Billy Beane’s story isn’t about numbers; it’s about belief. Belief that small firms can compete with giants. Belief that discipline beats flash. Belief that data and compassion together can achieve more than either alone.

When I review a new intake, I think of Beane staring at a lineup of overlooked players. I ask not what looks impressive, but what wins.

Because in this practice, as in baseball, the smartest team isn’t the one with the biggest payroll.

It’s the one that learns how to play differently.