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A Reunion on Location

In a special on-location broadcast at the offices of Gross & Kenny, host Jeffrey Gross, Esq. and co-host Joe Dougherty “bring the band back together” with long-time friend and legal powerhouse JB Dilsheimer, Esq., of Stampone O’Brien Dilsheimer Holloway. This episode marks a return to the trio’s first-ever on-location broadcast format, originally held just before the global pandemic.

The Strategy of the Game: From the Diamond to the Courtroom

The conversation kicks off with a lighthearted look at youth sports, with Dilsheimer sharing his experiences coaching seven-year-old baseball. The trio draws parallels between the patience required on the field and the resilience needed in the legal profession. As Dougherty notes, in a sport like baseball where even Hall of Famers fail 70% of the time, keeping your head on straight is the only way to survive a long season—a sentiment that rings true for high-stakes litigation.

Dealing with the “Difficult” Client

The core of the discussion explores a topic often whispered about but rarely addressed head-on: handling difficult clients. Dilsheimer and Gross argue that clients in personal injury and workers’ compensation are “inherently difficult” not because of their personalities, but because they are “damaged emotionally” by catastrophic life events.

Key insights from the discussion include:

• The Backseat Driver: How a lack of trust can lead clients to try and dictate legal strategy, causing “Herculean amounts of stress” for both parties.

• Aligning Expectations: Jeffrey Gross explains his process of first aligning himself with the client’s frustration before gently bringing them back to the reality of how the law applies to their specific facts.

• The Power of the Cell Phone: Both attorneys swear by giving out their personal cell numbers. It is the ultimate gesture of trust that “cures” mismanagement concerns almost instantly.

Debunking the “Pit Bull” Myth

One of the most profound segments of the episode addresses the public’s perception of what makes a “good” lawyer. Dilsheimer warns against the “Pit Bull” or “Bully” persona often celebrated in pop culture.

“You don’t want a pit bull,” Dilsheimer argues. “You want a lawyer who knows when to be aggressive with a witness and when to hold them or fold them.” He describes the legal process as a high-stakes chess game where intelligence, optics, and compassion are far more effective than brute force.

The Safety Net: Contingency Fees and Firm Resources

The show concludes with a vital reminder about access to justice. Through contingency fee agreements, “Johnny Middle Class” can take on powerful corporations worth hundreds of millions of dollars. Dilsheimer emphasizes that in personal injury cases, the law firm assumes all the risk—often investing six-figure sums into expert witnesses that the firm “eats” if the case is lost. In the workers’ comp world, Gross reminds listeners that fees are capped at 20% by law, ensuring that legal help is always within reach for the injured worker.

Episode Transcript: The Jeffrey Gross Show

Date: June 3, 2025

Host: Jeffrey Gross, Esq.

Co-Host: Joe Dougherty

Guest: JB Dilsheimer, Esq.

Joe Dougherty: All right, ladies and gentlemen around the Delaware Valley, welcome to the Jeff Gross Show here on WWDB Talk 860. We’ve got a fantastic broadcast. I can say we’re bringing the band back together. The first-ever on-location broadcast that I can remember doing was at Stampone, O’Brien, Dilsheimer and Holloway—but not Holloway yet—and it was featuring Jeff Gross. And here we are again. It was right before the pandemic, and we were talking about what was going to happen. I was just on a plane coming back, and I remember that. So, it’s funny, we always like to start off with some fun. First of all, JB, it’s so awesome to have you here.

JB Dilsheimer: Thank you, Joe. Back at you, man.

Joe Dougherty: I do want to say, JB is on our Legends of Justice board. We put together an all-star board: yourself, Bob Zimmerman, Jen Gomez, Sonny Banks, and Frank Soprano. What was amazing about it was it was people that I respect at such a high level. I told you this before, Jeff and Marla, if I have an idea, as much as JB and I have been friends for the last 10 years, if I want somebody to shoot from the hip, he’s going to do it. He’s going to tell me exactly what he feels. When we sat down—we did it online, obviously—the group of nominees was unbelievable. When they put that list together and I told you what an honor it was, man, I saw those people there and I’m like, “Oh my god.” There goes you, there goes Marla Joseph.

Jeffrey Gross: You did call it “Legends.”

Joe Dougherty: That’s right! And it was a beautiful thing. So I just wanted to prove to you, Jeff, it wasn’t just me picking out of a hat. It was an incredible honor.

Jeffrey Gross: I know you know that, but it was incredible. I have to say, I’m very, very impressed with both of you and the board.

Joe Dougherty: And I’ll tell you what, guys like Sonny Banks and Frank Soprano—what I loved was that theoretically everybody’s a competitor, but they went right for it. It was an honor. So I just wanted to get that off the table. The other thing is, we were talking about baseball. You’re coaching your son’s baseball team, JB, and baseball is an interesting sport. You were talking about your son; he may be a lefty or he’s still working that out. He’s seven. You said you brushed them back pretty hard?

JB Dilsheimer: No! If my wife’s listening to this—honey, no!

Joe Dougherty: So I’ll tell you a funny story about my son’s first day ever playing softball or baseball. He’s out in the outfield. Now, I played ball my whole life. I could just play. I could catch when I was young. So I’m thinking—I was 26 or 27 at the time—I’m on three softball teams, a hockey team, blah, blah, blah. Anyway, my kid’s got to be competitive, right? He’s got to be good. He’s out there in left field at Lincoln High School, and he’s on the foul line. I didn’t want my son—I didn’t want it to be like my dad. My dad pushed hard, and that’s how we saw our identity. So I wasn’t going to do that, but that’s why I took the shot here. So my son’s on the line and I’m like, “Yo Joe, move over! Move over!” He’s waving me off. Finally, I look at this guy in front of me and I’m like, “Hey buddy, listen, could you do me a favor and look at my son out there and tell him to move off the left-field line?” So he yells out, “Yo Joe! Can you move over?” Joe says, “Okay, I’ll do it.” He moves. Now he’s lined up perfectly. A ground ball goes to left field. He runs right by it. So I walk out and I’m like, “Yo buddy, you gotta get down on it.” He says, “I got a headache.” I said to my wife, “I don’t think we’re going to need that agent, babe.”

JB Dilsheimer: And then the next game, they had a carnival in center field! It looked like they were all at attention and the national anthem was playing. It’s an adorable game. At that age, you’ve got to get lucky with the coaches. You can’t get unlucky. Through the years, we got lucky and then we got unlucky. I am not a baseball player. I could always hit and catch, but it wasn’t my sport. I played lacrosse in the spring. My baseball knowledge is limited. This will be the end of my coaching career for baseball, because after seven years old, I imagine there’s some more strategy coming up and things I just don’t know. My wife says I said that last year, but I love coaching seven-year-old baseball. It’s hilarious, and they’re getting good too.

Jeffrey Gross: Absolutely. It’s true that you need a good coach who is going to be into it, who is going to encourage and help the kids.

JB Dilsheimer: I’m a cheerleader more than anything. I’m just having fun. At that young age, what you say means a lot. When you are having a bad day and you’re upset with a kid who’s not listening and you treat him a certain way, that could leave a lasting impression.

Joe Dougherty: Great segue to our suggested topic of discussion about handling the “different” client. But before we do that, I’d be remiss since we’re talking about baseball if I didn’t mention my partner, Joe Stampone, who was elected into the LaSalle University Hall of Fame for being the “Sultan of Steal.” In ’67 to ’68, he was undefeated on steals. There’s a dispute about one of them, but I’m on his side, so I’m giving him undefeated. He had more steals that year in LaSalle baseball than ever recorded. And my colleague, Tyler Stampone, played for the Orioles.

Jeffrey Gross: Cool stuff about baseball. It’s an amazing game, especially on the East Coast.

Joe Dougherty: I played American Legion, and we had a kid named Mark Gubicza. He got drafted in the second round and played 16 years in the big leagues. Now he’s the play-by-play announcer for the California Angels. It’s an incredible game. Jim Leyland just got into the Hall of Fame as a manager. He never won 100 games in a season. That means every year he lost 65 or 70 games. The game itself is so interesting because you’ve got to keep your head on straight. If you lost that many times in anything else, you’d lose your mind. A lot of kids who don’t make the major leagues have the hardest time failing. In high school, you’re hitting .500. You get to the minors, you hit .270. It takes time. Are you able to keep your stuff together? Lucky for us, we’ve got a couple of lawyers here who are batting close to 1.000.

Jeffrey Gross: Nice segue! That was good stuff.

Joe Dougherty: Jeff, if you would, remind our listeners about yourself and your practice.

Jeffrey Gross: I handle all workers’ compensation claims on behalf of injured workers—nothing else. That’s my specialty, and I’ve been doing it for 35 years at Gross & Kenny.

JB Dilsheimer: And I’m JB Dilsheimer at Stampone O’Brien Dilsheimer Holloway. We are one of the preeminent personal injury firms in the area. We specialize in catastrophic injury and trial work. We have a doctor on staff and work very closely with Jeff Gross’s firm. He is one of the top, if not the top, workers’ compensation lawyer in the city. You can reach us at stamponelaw.com.

Joe Dougherty: Now, are you related to Dilsheimer? Because there are a lot of Dilsheimers in Center City.

JB Dilsheimer: There are a lot of those. There are a lot of Grosses, too, but they’re not all related.

Jeffrey Gross: JB, you’re going to learn something right now that you won’t believe. When I was introduced to my wife, my friend said, “She’s got the same last name as you, go talk to her.” Her last name was Gross. After talking for five minutes, she said, “You won’t believe this, but my mother’s maiden name was also Gross.” So we hyphenate. We’re Gross-squared.

JB Dilsheimer: I love it! I haven’t married a Dilsheimer. I’ve acquired one, but I haven’t married one.

Joe Dougherty: Guys, today’s conversation is very interesting. We talk about the clients, because they’re the lifeblood of what you do. The client experience is such a big deal. One weak link in the chain from intake to the final call is a major problem. But also when it comes to the clients—handling difficult clients. Major league baseball players have 162 games, and sometimes they have crappy games. Maybe your kid was up all night long or someone hit you in a fender bender. It can be magnified when you have a difficult client situation. JB, I wanted to ask both of you for an example of a nightmare situation—without names, of course—and how you needed empathy in the process.

JB Dilsheimer: Jeff and I look at this business—the clients are inherently difficult because they’ve gone through something difficult. They typically come to Jeff first because they got hurt at work and their life is upside down. The kind of cases Jeff refers to me are where someone is catastrophically injured. Our clients are unusually damaged emotionally from these horrible experiences. We don’t take that for granted. Rather than talk about a specific client, there’s a category of client that can be difficult: the ones that like to control and dictate every facet of the process while they are injured. That creates a Herculean amount of stress. If your car breaks down, you go to a mechanic, not a doctor. If you want to understand everything the mechanic is doing, you’re going to go out of your mind because you have to become a mechanic yourself. We do have clients that aren’t willing to trust us as their lawyer. It’s like a backseat driver on a bus saying, “Are you sure you’re going the right way? I would make a right here because traffic is bad up there.”

Jeffrey Gross: It’s a very good analogy, but it’s so much more profound stress. These people come to us with a whole slew of emotional baggage from their entirety of life experiences. They come to us with an expectation that we have to adjust. That expectation comes from seeing their friends, family, or social media. When they think they’ve got an unbelievably strong case, it’s very difficult to bring them back to reality and say, “This is the law. This is how your case applies. This is why your case is marginal.” The very first thing I do when I meet a client is gauge their expectations and then explain the law. The easiest thing for me to do is first align myself with their expectations. I get why they think this way. I tell them what I can and can’t do. I’m not a miracle worker. I can’t take a case worth $35,000 and turn it into $3 million. On the other hand, I’m not going to let their best facts cloud a set of bad facts and ruin a case that’s otherwise good. I have to align my path with their interests. Usually, it works out 9.9 out of 10 times.

Joe Dougherty: JB, Jeff was alluding to that first meeting. I had a buddy who was in the hospital as a terrible patient. He whispered to me on the phone, “Joe, I’m not a lawyer, but you probably don’t have a case.” Because everybody thinks they’ve got a case! Talk about managing that first meeting so they aren’t their own worst enemy.

JB Dilsheimer: I think COVID got us away from face-to-face initial meetings and made it normal to sign up a client by Zoom. Jeff and I have been doing this a long time, and you get an innate sense of which clients you have to direct and how to do it. What I do in the very first talk is give them my cell number. Not everybody does that, but it creates an immediate air of trust. I tell them, “Call me anytime. I am here to help you.” We understand why you’re difficult. But if you’re going to hire lawyers of the caliber of Jeff Gross or my firm, you have to let us do our job and trust that we care. Our firms have been successful for a long time. We’re at the top of our field. You have to trust that we can fly the plane on autopilot almost. I try to be a regular guy you can talk to.

Joe Dougherty: It is awesome because I look outside these windows here at Gross & Kenny and there are probably 20,000 attorneys outside. If I need a personal injury attorney, I’m coming to JB. Same for Jeff. But you’ve got to let them do their job.

JB Dilsheimer: We earned that honor. We work tirelessly. We have empathy and we’ll communicate, but when I have to coddle a client for four hours about nonsense, I feel like asking, “Why did you not just go to law school and handle this yourself?” My whole premise is so the injured person can worry about getting better. You came to us because we are experts. Why would you get in our way? If we screw it up, you have recourse. We aren’t going to screw it up. I’m no longer in this because I have to get a paycheck; I’m in it because I want to help. Trust your lawyer. Chill out, breathe, and go heal. Also, if you’re a lawyer, don’t take for granted that your client knows the process. Explain it. A large part of my job isn’t teaching clients what to say—they know the facts—it’s teaching them how to say it with honesty and how not to say too much.

Joe Dougherty: You guys operate in a field where you have the “cat with the money bags” on the side of a bus at 3:00 in the morning. I imagine the emotional issues are 10 times worse after clients have dealt with those guys and then land at your doorstep.

JB Dilsheimer: There’s a lot to be said for being a counselor, and I’m happy to do it. It gets really difficult when you have somebody who is inherently distrustful of the system. I have to be careful because some of those TV guys might be sending me cases! But you might have somebody who has been going to a panel doctor and now they’re gun-shy. I had a conversation today with a marketing guy who wants to organize his workplace. I said, “Don’t say a damn word to anybody unless you know everybody wants to do it, because your butt will be in trouble.” If you get injured on the job, the first thing people say is “Go to my boss.” That’s the absolute wrong thing to do. Get educated by attorneys first. If you end up at doctors who don’t remind you of your family doctor, you become gun-shy.

Jeffrey Gross: A common example I see is a client coming to me a month after the accident. I ask, “Why did you wait so long?” The answer is often, “Well, I went to another lawyer, and he said I had a good case but I can’t reach him on the phone.” I ask who it is, and they say, “I don’t want to tell you in case you know him.” They don’t even know the guy’s name because they only talked to the staff. There is a disconnect in some firms where they just don’t communicate. I end up taking a client who has been mismanaged. A cell number cures that pretty quickly. I gain their trust by showing them I’m here for them. If I don’t answer, I call them back. The hardest thing is when a client loses faith and questions our integrity. I’ve known Jeff since we were kids. He trusts me and I trust him because we have integrity.

JB Dilsheimer: Marla and I share the same ethos. Younger lawyers always brag about the cases they just signed up because of naivete. As you get older, that changes. Seasoned lawyers talk about how horrific a case is and how bad they feel for the client. The thing that gets me is when a client accuses us of being underhanded. I have an AV+ ethical rating. I know who I am. When a client refuses to recognize that I am not lining my pockets at their tragedy, it eats me alive. It’s only happened once or twice, and it hurts every time. I stay up until 2:00 in the morning wrestling with how to fix things. Sometimes there’s only one solution: tell the client to go find another lawyer.

Joe Dougherty: I can see the issues as a layman. These cases can last two years. The insurance company gets the opportunity to mess with these clients with video surveillance. It’s a shame when clients become their own worst enemy by allowing the ebbs and flows to eat them alive.

JB Dilsheimer: The misconception is that a successful case will cure the problem. It doesn’t. We reduce a horrible accident to money. Jeff’s side covers medical and salary. Mine covers pain and suffering, lost future income, and medical payments. But it doesn’t bring an arm back. It doesn’t regrow a thumb amputated in a machine. I hand over seven-figure checks and the clients have stars in their eyes, but two days later they wake up and they still don’t have an arm. You couldn’t pay me enough to lose my arm. We are experienced enough to recognize when a client is struggling and still be there compassionately for them.

Joe Dougherty: I got a call on our advocacy line from a woman who was injured. She said she had a lawyer last year. I called that lawyer as a courtesy and he was out of his mind stressed. He said he was getting out of the business because he couldn’t handle the part of it we’re talking about. The resilience you guys have is amazing. You choose to help these people.

Jeffrey Gross: Help is the key word. When we get knocked down, we get back up. A loser stays down; a winner gets back on their feet. I don’t think Jeff and I have many dissatisfied clients. Look at the five-star recommendations. If they are dissatisfied, I am candid enough to explain why I am recommending a certain value. I’ve been practicing for 35 years. I check with my partners. I’m not telling you to take $250,000 or $2.5 million because I want to get out of the case. Someone said to me, “I thought I hired you because you’re a great aggressive trial lawyer.” I said, “I am, and I’m telling you that you don’t have the case to go to trial with.” A good trial lawyer is seasoned enough to tell you when a case is a losing proposition.

Joe Dougherty: One of the great lines of all time—someone said this in the middle of a settlement—”Now you just can’t leave.”

JB Dilsheimer: My partner, Kevin O’Brien, and I love trying cases, but it’s not about us. In negotiations with difficult insurance carriers, where we come down reasonably and they just reject it or stay uninformed, we say, “Fine, we’re not negotiating anymore.” I’ll look at Kevin and say, “Bronx Tale—the ‘Now you can’t leave’ moment.” Kevin just applied that and two weeks after trial, the case settled for $40 million.

Joe Dougherty: That’s a great movie! “It was at that moment they knew they had screwed up.” Let’s talk about that first meeting in a catastrophic situation. I can tell you what it feels like to walk on a beam, but I can’t tell you what it’s like to see a buddy’s family come in after they just lost someone.

JB Dilsheimer: I represent an ironworker right now who fell through two open holes in Pittsburgh because his retractable was allowed to square out too far. When a family comes in on that day, it’s a rough time. You have to align yourself with their interests. The problem with many lawyers is they talk too much and don’t listen. If I don’t hear what they are saying, I’m missing the boat. I empathize with them. Even if what they say seems irrelevant, it’s not—it’s what is on their brain.

Joe Dougherty: How important is that referral relationship between you two?

JB Dilsheimer: Sometimes Jeff calls me and I show up immediately. Jeff is a better listener than I am because I think I’m eloquent by nature. He’s counseled me to calm down sometimes! We had a case with a fatal train accident. I met the family and I told Jeff, “I don’t know if this person has a case, but it was nice meeting them because I feel for them.” I went to all kinds of lengths to investigate that. We like to present a team approach because it maximizes value. If you have two sophisticated attorneys on the plaintiff side, it creates a comfort level for the client. We are at the point where we don’t look “green.” There was a time I faked the funk really well; I’m not faking much anymore.

Joe Dougherty: How is it owning your own firm?

JB Dilsheimer: Best thing I’ve ever done. I love every firm I’ve worked at, but I could never work for anybody else again.

Joe Dougherty: You guys are Philly guys through and through. How much does it help to understand the city and the juries?

JB Dilsheimer: It’s super important. I treat all attorneys with respect. I’ve been surfing my whole life and there’s “localism” in certain breaks. If you go in humble, they see you can surf and you get respect. If I go to Pittsburgh, I’m respectful to show them the ropes. I have defense attorneys sending me cases after they pay me millions because there’s a right way to do it. The problem is people have conceptions of “tough” lawyers being bullies. We are not bullies. A bully is the wrong way to approach a case. I call it the “Pit Bull Myth.” You don’t want a pit bull; you want a lawyer who knows when to be a pit bull with a witness and when to “hold ’em or fold ’em.” You want a lawyer who understands optics.

Jeffrey Gross: It’s a chess game. You must checkmate your opponent with intelligence, not bullying.

Joe Dougherty: We only have a couple of minutes left. The contingency fee agreement—talk about what that means.

JB Dilsheimer: You only pay me if I get a result. If I invest $300,000 and lose a trial, you don’t owe me anything. I eat that money. Typically, my fee is 40% for big cases, but sometimes a third if we settle early. I am funding the case on my dime.

Jeffrey Gross: In workers’ comp, our fee is capped at 20% by law. We don’t charge unless we win, and our costs are reimbursed by the insurance carrier, not the client. You are not on the risk on either side. We are.

Joe Dougherty: This has been the fastest hour in radio. JB, contact information?

JB Dilsheimer: stamponelaw.com or call me on my cell: 215-779-0114. I give it out because I’m a man of my word.

Jeffrey Gross: My cell is 215-512-1500. You call me, I will answer.

Joe Dougherty: Thank you both for being awesome. Thanks for listening, everybody.