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The Trial Lawyer's Handbook
The Trial Lawyer's Handbook
Author: Holland & Knight
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The Trial Lawyer's Handbook is a Courtroom Preparation podcast series brought to you by Holland & Knight. This series is hosted by litigation attorney Dan Small and is based on a longstanding article series he co-authored with Judge Dennis Saylor for Massachusetts Lawyers Weekly. Listeners of this series will gain a fresh perspective on how attorneys can address various trial preparation issues and set themselves up for success in and out of the courtroom.
133 Episodes
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What happens when the government treats online "play money" like real securities?In this episode of "The Trial Lawyer's Handbook," litigation attorney Dan Small recounts a civil enforcement action brought by the U.S. Securities and Exchange Commission (SEC) against SG Limited, an early internet stock market game created by programmers overseas that built a large U.S. player base. He explains the SEC's attempt to characterize the game's virtual shares as unregistered securities and resulting allegations that the platform functioned as a Ponzi scheme, leading to a court-ordered freeze of approximately $5.5 million. Mr. Small walks through SG Limited's defense and the strategic choice to keep the case grounded in a clear, common-sense narrative, emphasizing that the platform presented itself as entertainment, not an investment. The episode spotlights the power of storytelling in trial advocacy, illustrated by how the district court responded to SG Limited's arguments in ultimately dismissing the SEC's case.Much like video games have a sequel, however, the story does not end there. In the next episode, Mr. Small continues the narrative at the appellate level.
In this episode of "The Trial Lawyer's Handbook" podcast, litigation attorney Dan Small delves deeper into the naval architect negligence case introduced in the previous episode. During the trial, the two experts disagreed, resulting in a credibility contest. Mr. Small shares the strategy he used to successfully cross-examine the other side's expert witness. In technical cases such as this one, it is your responsibility as the trial lawyer to learn the specifics of the case. By mastering the technical details himself, rather than relying solely on his team and client, Mr. Small was able to go toe-to-toe with the plaintiff's expert during cross-examination, a key factor in ultimately winning the case.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small introduces a new case that illustrates a new strategy for trial. Naval architect Jack Gilbert was accused of selling a boat with stability issues and was sued by the owner of the 93-foot fishing vessel for negligence in federal court in Portland, Maine. Mr. Small provides an overview of the case and the technical details underlying it before describing the central role his "core themes" played at trial as he presented his arguments before the jury.
In this episode of "The Trial Lawyer's Handbook," litigation attorney Dan Small continues the discussion of U.S. v. Rendle and explains why reading the room matters in court. Mr. Small shows how judges, juries and the pace of a trial should guide your choices across all aspects of the proceeding, not just your arguments. He shares a Boston case where a defense lawyer's approach at sentencing hurt the client, and a moment in U.S. v. Rendle when a lengthy cross-examination allowed the government to respond with a strong redirect. This episode offers clear lessons on timing, tone, selecting the right witness, when to object and how courtroom dynamics can lead to plea deals.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small uses the white-collar corruption case of United States v. Rendle and his experience before the famously pro-defense Judge Joseph Tauro to explore the central role of respect in the courtroom. Drawing on stories from his time as a federal prosecutor, Mr. Small explains how rigorous preparation and sound judgment – especially knowing when to push hard and when to "move on" – helped him earn the respect of a judge many colleagues feared. Mr. Small underscores why neither constant combativeness nor habitual capitulation works, how to "pick your battles" in motions and arguments, and why genuine respect must extend beyond the bench to clerks, court staff and everyone in the courthouse.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small underscores the importance of understanding the media as a trial attorney. He recounts lessons learned from a high-profile government corruption case in Boston, where he interacted with reporters from two competing newspapers. As he explains, he inadvertently gave an exclusive quote to one of the journalists, blindsiding and angering the other news outlet. Mr. Small's message: A trial attorney's job is to address the court and inform the press, without favoring one publication over another.
In this episode of "The Trial Lawyer's Handbook," litigation attorney Dan Small recounts attempting to prosecute a New England mob boss and the challenge of filing a complex case before the statute of limitations expired. Mr. Small explains how the case moved between Miami and Providence, how venue and timing decisions shaped strategy and why the trial judge ultimately dismissed the case despite a grand jury indictment. He highlights lessons on venue, audience and the importance of aligning the forum with the story you need to tell.
In this episode of "The Trial Lawyer's Handbook," litigation attorney Dan Small looks back on his experience prosecuting the notorious New England mob boss Raymond Patriarca — or lack thereof. As a 73-year-old man who had spent more than 30 years as the head of a criminal organization, it was not difficult for Patriarca to find a doctor to declare him medically unfit for trial. Mr. Small, needing a doctor of his own to keep the mob boss included in the trial, quickly discovered that Patriarca's reputation preceded him, and shares the difficulties he faced in getting Patriarca into the courtroom.
In this episode of "The Trial Lawyer's Handbook" podcast, litigation attorney Dan Small discusses the opportunities and challenges of "climbing the ladder" in a corruption case. This approach starts with securing a defendant willing to testify against their superiors and then working to uncover what additional crimes or targets they can identify. He illustrates this strategy with the extortion case against Ted Anzalone, in which George Collatos, a Boston city employee, served as a key witness. Collatos was arrested for extorting cash from a building contractor. After he pleaded guilty, Mr. Small and his team brought him before the grand jury to ask about illegal fundraising and other unlawful activities in hopes of obtaining additional information. Eventually, Collatos revealed facts about Anzalone's activities, but it was not smooth sailing. Mr. Small explains why "climbing the ladder" proved to be difficult in this case and how it ultimately ended in Anzalone's acquittal.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small makes the case for "show and tell" in the courtroom. As he contends, jurors do not learn best by listening alone, so powerful demonstratives are essential, especially in complex financial cases. Drawing on the Anzalone money laundering trial, he explains how a simple poster depicting a web tracing $100,000 in cash split into 12 sub‑$10,000 checks clarified the scheme better than words ever could and kept the jury focused on the issues at play. The takeaway: Keep visuals clear, memorable and ever‑present. Ears to listen, eyes to see, hands to hold.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small unpacks the prosecution of Ted Anzalone, a top aide to Boston Mayor Kevin White, through two alleged money laundering schemes: a "birthday gift" check-planting operation that sowed jury confusion and led to acquittal, and a clearer $100,000 cash structuring scheme using sub‑$10,000 cashier's checks to evade bank reporting. Despite a compelling trial win on the structuring count, the U.S. Court of Appeals for the First Circuit reversed, holding that "the law is the law" and Congress hadn't yet criminalized that type of financial activity. Mr. Small reflects on the limits of prosecutorial creativity, a memorable bench rebuke and how the case ultimately spurred lawmakers to close the loophole – too late for Anzalone, whose conviction was vacated, but paving the way for successful prosecutions thereafter.
In this episode of his "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small emphasizes the importance of providing the jury with all relevant facts to help them discern the truth. At times, however, court decisions can hinder a party's ability to tell the whole story. This was true in the United States v. Anzalone case, which Mr. Small prosecuted. Ted Anzalone was charged with extortion and money laundering, but because both charges involved secret cash transactions, it was difficult to present non-circumstantial evidence to the jury. To make matters worse, the defense counsel persuaded the judge to sever the two charges, making it nearly impossible to corroborate the evidence. This episode highlights the importance of always fighting to tell the full narrative.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small delves into the debate on using interpreters for witnesses in the courtroom. In some instances there is no choice: A witness who cannot understand English requires an interpreter. But when it's a gray area, some lawyers argue that an interpreter diminishes the connection between the witness and the jury. Mr. Small disagrees and offers a humorous anecdote from the corruption case United States v. Wallen, which he prosecuted, to support his pro-interpreter stance. He closes by reminding the listeners that misunderstandings often hurt your case and that interpreters help minimize them for both sides.
In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small shares how building genuine trust with a witness can make or break a case, recounting his extraordinary trip to Italy to meet Domenic D'Alessandro in the Frank Wallen corruption investigation. What began as a long-shot effort — navigating approvals from U.S. Department of Justice (DOJ) and and U.S. Department of State, coordinating with the IRS and overcoming internal skepticism — turned into a lesson in human connection. Over a shared meal and conversation, plus more than a few glasses of wine, Mr. Small and Mr. D'Alessandro developed mutual respect and forged a bond that led to Mr. D'Alessandro's voluntary return to the U.S., guilty plea and critical testimony. The story underscores a central tenet in trial preparation: You cannot extract the truth from strangers on a park bench; you must invest the time to create rapport and reliability with witnesses, because trust, not pressure, opens the door to honest testimony.
In this episode of "The Trial Lawyer's Handbook" podcast, litigation attorney Dan Small explores the complexity of federal corruption cases. He highlights a matter he handled as an assistant U.S. attorney in the Boston U.S. Attorney's Office Public Corruption Unit: a case in Brockton, Massachusetts, in which the IRS uncovered corrupt relationships between contractors and Frank Wallen, the city's superintendent of sewers and then-commissioner of public works. Mr. Small shares insights into how the case arose, what work his team focused on and why it was so difficult to prosecute.
In this episode of "The Trial Lawyer's Handbook," litigation attorney Dan Small explains why simplifying a complex case is essential to persuading a jury. Recalling the federal prosecution of U.S. budget director Bert Lance, Mr. Small describes how large investigations can produce lengthy indictments that confuse rather than convince, and emphasizes that focusing on clear, provable charges can strengthen a case. He outlines the risks of overcomplication and the importance of telling a straightforward story that a juror can follow.
In the second part of this special guest episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small is once again joined by Partner Eric Alexander, who leads the firm's Product Liability – Life Sciences Team. This episode's conversation focuses on product liability trials and how they differ from other types of litigation, as well as recent shifts in juror attitudes and the effects on expert witness selection and preparation. Mr. Small shares an anecdote to emphasize that getting the jury to like you isn't just a part of trial, it's the only part of trial. For his part, Mr. Alexander suggests that changes in juror dynamics were likely accelerated by COVID-19 and the associated shutdowns. The attorneys agree that a strong expert nowadays is defined more by the ability to speak "juror's English" than by degrees or professional experience. The dialogue offers a behind-the-scenes look into the world of product liability litigation and the factors that can determine success in the courtroom.
In this episode of "The Trial Lawyer’s Handbook" podcast, litigation attorney Dan Small describes the unnatural environment of the courtroom and the importance of preparing witnesses for the off-putting rhythm of testimony that he summarizes as "question, pause, answer, stop." In the corruption case United States v. Bert Lance, because the defense sought to call numerous character witnesses, the judge limited counsel to four legalistic questions. The most notable witness, Miss Lillian, the elderly mother of then-President Jimmy Carter, had known Lance his whole life and could have played a key role in his defense. However, she was not prepared for the unusual phrasing of the questions and, after an 18-hour flight to get to court, concluded her testimony in about two and a half minutes. Mr. Small reminds the listeners that every witness is Miss Lillian and must be prepared accordingly.
In this episode of "The Trial Lawyer’s Handbook" podcast, litigation attorney Dan Small discusses the value of observing and learning from experienced colleagues, both professionally and socially. He reflects on one of his first significant cases as a federal prosecutor, when the U.S. Department of Justice (DOJ) secured a grand jury indictment in Atlanta against Bert Lance, the former director of the Office of Management and Budget, and three associates on charges that they conspired to violate U.S. banking laws to obtain millions of dollars in loans. Mr. Small joined the DOJ team led by Ed Tomko and Marvin Loewy and learned from watching them and the opposing counsel in action.
In the first part of this special guest episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small is joined by Partner Eric Alexander, who leads the firm's Product Liability – Life Sciences Team. Mr. Small talks with Mr. Alexander about the transition from being in the back row of a trial team to having a stand-up role. After reflecting on the beginning of his legal career, Mr. Alexander offers advice for young litigators on how to prepare for a trial and how to best support the attorneys on your team, plus some important don'ts to avoid in the courtroom. Mr. Alexander also emphasizes that there is no one way to approach a trial. Taking an approach that fits your case and fits who you are is important and will help you to come across as genuine.























