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Key Takeaways from LFJs Special Event: How Investors Approach Litigation Finance

Key Takeaways from LFJs Special Event: How Investors Approach Litigation Finance

On Thursday, July 14th, Litigation Finance Journal hosted a digital event, “How Investors Approach Litigation Finance.” The event featured a unique cross-section of investor types, including David Gallagher, Co-Head of Litigation Investing at The D.E. Shaw Group, CJ Wei, Vice President of Private Credit at Northleaf Capital, Benjamin Blum, Managing Director at Flexpoint Ford, LLC, David Demeter, Director of Investment at Davidson College, and Kendra Corbett, Partner at Cloverlay. The event was moderated by Ed Truant, Founder of Slingshot Capital. Below are some key highlights from the discussion: ET: How did you start investing in Litigation Finance? What types of results did you focus on, and how has your strategy changed over time? DG: It takes time to obtain a meaningful number of results from litigation finance investments, and you can learn a lot along the way, even before the results come in. And because you invest in such a small proportion of the opportunities you look at, you try to learn from the investments you don’t make, as well as the investments you do make. And one of the lessons I’ve learned as it relates to deployment strategy, is that good deals are so hard to come by, and are a product of so many variables outside of your control, that it’s better to be responsive to the opportunity set in front of you, than to be wedded to the abstract ideas of portfolio construction or deal structuring. I think adaptiveness is key. KC: We’ve been active in deploying capital in litigation finance for over six years now, and I wouldn’t say our approach has changed dramatically. We’ve been laser-focused on maintaining diversification across cases to avoid binary risks, and finding alignment across all of the involved parties. I think we’ve looked for market specialists, and we haven’t necessarily tried to find litigation finance beta, and instead we’ve looked for partners with a demonstrable value-add and strategic advantage. ET:  For those panelists more interested in credit opportunities in the legal finance space, why did you decide to focus on credit? DG: At the D.E. Shaw Group, the litigation investing team works closely with the Private Credit group, which I like to think broadens the types of deals we do. So, in addition to investing in litigation finance deals with a more typical risk/reward profile, we also invest in less volatile opportunities that are less about litigation risk, and more about timing risk and basic credit risk. BB: There are a few ways to create a credit-like opportunity in litigation finance. In addition, the way David was describing, the other way is to create a credit-like product by lending against a diverse portfolio of individual case fundings. So the asset is a little bit less credit-like, but the investment structure creates a credit-like investment. Both areas are of interest to us, especially when there is strong alignment with the borrower and downside protection through underwriting, to justify accepting a return profile that is either capped or has limited upside. CW: At Northleaf, we have many different funds with many different return hurdles, so we view ourselves as a capital solutions provider to litigation finance businesses. That being said, our thesis around the asset class is akin to a type of Private Credit approach strategy. Principal protection is our priority. We not only have asset coverage of the legal assets, but additional covenants and protections, and bespoke structures where we have guardrails against any downside scenario. ET: From an equity perspective, how is litigation finance the same as, or different from, other equity assets in which you invest? DD: If you suspend disbelief a bit, I would equate it with early venture investing. Liquidity cycles tend to be uncorrelated in the long run, you’re generally creating milestones for capital, outcomes can be pretty skewed, where large winners make up the majority of profit (although it’s certainly more skewed in venture than in litigation finance), and the investment strategy isn’t all that scalable—managers have to be cognizant of all that they’re trying to deploy. DG: I’ll focus on some of the differences. First, a litigation finance investor has no control over the litigation, while an equity investor or investors that own the majority of the company—they do control the company. So the closest analogy is to a class of shares that has no voting rights. Second, LitFin investments are typically illiquid. Equity investments are typically liquid. Another difference is that case outcomes are typically more binary than business outcomes.  And one last difference is that a company you might invest in can pivot and respond as needed to market opportunities, a case you invest in—it pretty much is what it is, and there’s only so much that even the most talented lawyers can do, with the facts and the law involved. ET: One of the common criticisms I hear from fund managers, at least early on in the life cycle, is that investors are not willing to pay management fees to fund their operations. How does the panel respond to this criticism, given that the average litigation finance claim is small—around $3-5MM—and there is a lot of relatively sophisticated operations needed to be conducted by investment managers?   DD: I think there are ways of paying someone a full fee and making sure deployment is there. And that is my primary concern, and I think most LPs primary concern, when it comes to paying a management fee. We’re also concerned about misalignment. At the fund level, people should really be making a large amount of their compensation from performance fees, not salary. KC: It’s definitely a difficult issue. The fee drag that comes with charging investors on committed capital becomes pretty untenable when you’re comparing gross returns to net returns. So from our perspective, at a minimum, fees need to be on an as-committed basis. We’ve also seen scenarios where there is a lower management fee on committed capital that steps up once it’s drawn. It’s just really difficult with some of the commercial litigation strategies to have a full freight fee—2%–committed from investors.

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Which AI Model Is Best for Legal Work? What 2026 Research Says About Accuracy

Law firms, funders and legal departments are being sold AI for contract review, legal research and citation checking, and the models change every few months. So we looked only at independent studies published in 2026 that tested the current generation of models from OpenAI, Anthropic and Google on real legal tasks. The short version: the best models are now genuinely good at reading and extracting from documents you give them, still unreliable at recalling law from memory, and the commercial legal research tools lag behind the best custom systems.

At a Glance

Best overall model for legal document work: Google's Gemini 3.1 Pro. It was at or near the top in every 2026 study that tested it, and it was usually the fastest and cheapest of the leaders. OpenAI's GPT-5.5 found slightly more errors in contract review, and Anthropic's Claude models were the most careful about not flagging problems that weren't there.

Best accuracy recorded on a full legal task: 92%, on a 50-state statutory research test run by Stanford, achieved by a purpose-built research tool. The lesson is that how the AI is set up matters as much as which model sits underneath it.

Range of accuracy: from under 7% (asking a model to recall exact case citations from memory) to 99–100% (catching a citation to the wrong case when the model can read the source). Most real-world document tasks landed between 60% and 85%.

Westlaw and Lexis AI: 58% and 64% accuracy on a Stanford statutory survey test, below a custom-built tool at 83–92%.

Biggest single improvement: giving the model the actual documents instead of asking it from memory cut fabricated citations from roughly 15–40% to about 4–15%, and to under 0.2% with a well-built retrieval system.

Key Takeaways

The model to use. For contract review and extraction, start with Gemini 3.1 Pro. It matched the top performer on catching contract errors (74% vs. 75%) at about one-seventh of the cost and in 90 seconds instead of nine minutes. If catching every possible issue matters more than time or cost, GPT-5.5 with reasoning turned on found the most. For checking citations in a brief, the best 2026 results came from GPT-5 running as an agent and from Claude Code with Claude Opus, which was the most precise.

How to Use It

  • Give it the documents. Never ask a model to supply case law or citations from memory.
  • Turn on the model's "reasoning" or "thinking" mode for review work. It improved error-catching by 9 to 11 points in contract review.
  • Use it as a first pass and a second reviewer, not the final reviewer.
  • For research, use a tool that pulls from a full, current database of the law, because weak retrieval, not the model, causes many of the errors.

What to Expect

  • Contract extraction (pulling out dates, parties, termination and liability terms): about 80–84% accuracy for the best models.
  • Final contract proofreading (defined terms, cross-references, inconsistent language): the best models catch about three-quarters of errors. On a 60-page agreement, expect it to miss some.
  • Citation checking: nearly all citations to the wrong case get caught, but wrong pinpoint pages slip through 20% to 60% of the time.
  • Research answers grounded in the right documents: roughly 6–11% of answers still contain an unsupported statement.

What to Look Out For

  • Citations from memory. When asked to recall exact citations without sources, even the best model scored under 7 out of 100, and 20 of 21 models gave confident, wrong answers more than 94% of the time.
  • Right case, wrong page. Models tend to approve a citation because the case is on the right topic, even when the cited page doesn't support the point.
  • Questions with a false premise. If your question assumes something that isn't true, models often go along with it.
  • Legal research tools' marketing. Westlaw AI and Lexis+ AI trailed a custom-built tool by 19 to 25 points on a Stanford test.
  • Studies funded by vendors. Some of the best-looking results come from companies selling legal AI. Check who ran the test.

Best Practices

  • Ground every task in source documents, and require the model to quote the passage it relied on.
  • Check every citation yourself at the pinpoint page before filing. Automated checkers help but don't replace this.
  • Turn on reasoning mode for review tasks and accept that it's slower.
  • Test a model on a few of your own documents before rolling it out. Rankings change by task.
  • Re-test when a new model version arrives; this field moves in months, not years.
  • Keep a human reviewer accountable for anything that goes to a court, a client or a counterparty.

What the Studies Found

Contract proofreading. In August 2026, researchers had experienced lawyers plant errors in contracts (misused defined terms, wrong cross-references, wrong party names, contradictions) and tested ten current models on catching them. GPT-5.5 caught 75% of errors, Gemini 3.1 Pro 74%, Claude Sonnet 4.6 69% and Claude Opus 4.7 62%. GPT-5.5 cost $1.38 per contract and took about nine minutes; Gemini 3.1 Pro cost $0.19 and took about 90 seconds. Turning on reasoning mode added 9 to 11 points. Every model was far cheaper than a lawyer, and none was close to perfect.

Contract extraction. A May 2026 study tested models on pulling 26 standard fields out of contracts. Among the major models, Gemini 3.1 Pro scored highest (82%), with Claude Opus 4.6 (82%) and Claude Sonnet 4.6 (80%) close behind and GPT-5.4 at 78%. A smaller legal-specific model built by the study's authors scored 84% at far lower cost. The authors work for Onit, which makes that model.

Made-up citations and facts. A January 2026 study had expert reviewers check 2,700 legal answers from 12 models. Asked without source documents, the best models (GPT-5.2 and Gemini 3.0 Pro) cited something false about 15–17% of the time, and the worst over 30%. Giving the models the relevant documents cut that to about 4–15%. A more carefully built retrieval system brought it below 0.2% for every model.

Research with sources. A March 2026 study found that when models answer from retrieved legal texts, Gemini 3.1 Pro produced unsupported statements 5.7% of the time versus 11.3% for GPT-5.2, and that the quality of the search step mattered more than the choice of model. Its authors sell the search component that performed best. An August 2026 study of eight research setups found unsupported answers ranging from under 10% for the best to nearly half for the worst, with the worst results on questions built on a false assumption.

Westlaw and Lexis. In a February 2026 Stanford study, researchers tested legal AI tools against a Department of Labor survey of state unemployment insurance laws. Westlaw AI scored 58% and Lexis+ AI 64%, while a custom statutory research tool scored 83%, rising to 92% after the researchers found that some of its "errors" were gaps in the government's own survey.

Citation checking. A June 2026 study found more than 1,000 court filings containing fabricated citations, a number growing every year, and tested AI checkers on catching them. GPT-5, working as an agent that looks up cases, caught 83% of planted errors; Claude Code running Claude Opus 4.8 was the most precise and scored best overall. No model reliably caught wrong pinpoint cites, partly because page numbers often sit behind Westlaw and Lexis paywalls. A separate August 2026 study found models catch 93–100% of citations to the wrong case but miss many citations to the wrong page, and even GPT-5.4 with full reasoning missed 40% of wrong pinpoints in court opinions.

Citations from memory. A May 2026 study built from 1,000 real U.S. judicial opinions asked 21 models to recall exact case citations without any sources. The best, Claude Sonnet 4.5, scored under 7 out of 100.

The Bottom Line

The 2026 research is consistent: today's best models, led by Gemini 3.1 Pro, GPT-5.5 and Claude, are useful and cheap for first-pass contract review and extraction when they work from the documents in front of them. They still invent law when asked from memory and still miss wrong pinpoint citations, so a lawyer has to verify anything that leaves the building.

Sources (All 2026)

  • Bang et al., "ContractScrub: A benchmark for final review of legal contracts" (Aug. 2026), arXiv:2608.20204
  • Lincoln et al., "A Few Good Clauses: Comparing LLMs vs Domain-Trained Small Language Models on Structured Contract Extraction" (May 2026), arXiv:2605.05532
  • Dantart, "Reliability by design: quantifying and eliminating fabrication risk in LLMs" (Jan. 2026), arXiv:2601.15476
  • Butler and Butler, "Legal RAG Bench: an end-to-end benchmark for legal RAG" (Mar. 2026), arXiv:2603.01710
  • Das et al., "How Much Do Legal RAG Systems Still Hallucinate?" (Aug. 2026), arXiv:2608.14210
  • Afane et al., "Benchmarking Legal RAG: The Promise and Limits of AI Statutory Surveys" (Feb. 2026), arXiv:2603.03300
  • Liu, Stammbach and Henderson, "Who Checks the Citations? Benchmarking Legal Hallucination Detection" (June 2026), arXiv:2606.21155
  • Verma, "Is this Citation on Point?" (Aug. 2026), arXiv:2608.12571
  • Chen et al., "LegalCiteBench: Evaluating Citation Reliability in Legal Language Models" (May 2026), arXiv:2605.10186

Second Circuit Affirms Fee Award That Treated Litigation Funding Costs as Firm Overhead

The Second Circuit has upheld a $4.8 million attorneys' fee award in a sex trafficking case, endorsing a district court's decision to strike time counsel spent communicating with its litigation funder.

In Moore v. Rubin, decided on September 4, a panel of Chief Judge Lohier and Judges Parker and Chin affirmed the award to six plaintiffs who won a $3.85 million jury verdict against former bond trader Howard Rubin under the Trafficking Victims Protection Act. In rejecting the argument that too many timekeepers had been compensated, the panel noted approvingly that the district court had applied a 15% across-the-board reduction and excluded non-compensable tasks, "such as communications with counsel's litigation funder."

The more consequential ruling for funders came below. In February 2025, Judge Brian Cogan of the Eastern District of New York refused to shift roughly $1.84 million in principal and interest owed to a third-party funder, reasoning that how a lawyer finances a practice is irrelevant to the client and the defendant alike. "Whether it is a bank loan, family loan, personal assets, or a litigation funder," he wrote, "it is overhead."

Judge Cogan also declined to follow the English decision in Essar Oilfield Services v. Norscot Rig Management, which allowed recovery of funding costs, observing that neither the statute nor the local rule hints at such recovery.

The funding cost denial was not before the appellate panel, as Rubin appealed only the fee award. The funder, Pravati Investment Fund IV, later sought unsuccessfully to intervene to protect its interest in the fees after the plaintiffs' firm dissolved.

Legalist Asks Manhattan Federal Court to Confirm $108,718 Award Against Funded Claimant

Litigation funder Legalist has asked a federal court in Manhattan to confirm an arbitration award against a claimant it financed, in a rare public dispute between a funder and the plaintiff whose case it paid for.

As reported by Bloomberg Law, Legalist filed its petition on September 8 in the Southern District of New York, seeking to confirm a partial final award of $108,718.45 against Mario Rinaldi. The award, issued on May 18 by JAMS arbitrator the Hon. Elaine Rushing (Ret.), consists of $105,218.45 in attorneys' fees and $3,500 in arbitration costs.

The funding agreement dates to June 2018 and financed Rinaldi's suit against two French champagne producers, which he brought after working to build their brand in New York. A jury returned a $1.5 million verdict in his favor in March 2022, and final judgment with prejudgment interest was entered that December at $2,318,506.85. That judgment has not been collected. Rinaldi told Bloomberg Law he is still pursuing the money with his own resources, having retained French counsel to enforce it abroad.

Legalist alleges in its filing that Rinaldi breached the funding agreement by refusing to cooperate in collection efforts, including by declining to permit communication with his French counsel. According to the memorandum, Rinaldi did not appear in the arbitration at any stage, and has not moved to vacate or modify the award.

The arbitration was held open for Legalist to pursue further relief, indicating the $108,718.45 may not represent the full extent of its claim. No response from Rinaldi appears in the most recent public docket entries.