The Journal on Sports and Entertainment Law recently sat down with David Friedman, Senior Vice President, Legal & Government Affairs for the Red Sox and Senior Counsel for Fenway Sports Group, to discuss current issues in sports law.

The interview was conducted by Loren Shokes, an Entertainment and Sports Highlight Contributor for the Harvard Journal of Sports and Entertainment Law and a current second year student at Harvard Law School (Class of 2017). The interview is part of JSEL’s interview series with lawyers in the sports and entertainment field that will be featured on JSEL’s website. It has been edited for clarity.

**Please note that, throughout this interview, Mr. Friedman was speaking in his capacity as an individual and a scholar, and not as a representative of the Red Sox, Fenway Sports Group, or any of the Red Sox’s or Fenway Sports Group’s affiliates.*

Loren Shokes, Journal on Sports & Entertainment Law (JSEL): The Red Sox Foundation is the largest team charity in baseball, basketball, football, and hockey and has further enabled the Team to establish and maintain a fantastic rapport with fans in the greater-Boston area. Can you tell us more about what the organization does and some of the legal issues that arise managing a not-for-profit foundation in conjunction with a Team.

David Friedman (DF): Sure, I’d be glad to. Our ownership group and organization are deeply committed to charitable activity and remaining active in the community. What that means specifically is that we spend a lot of time and effort to raise money for the Red Sox Foundation—we’ve devoted more than $82 million to charitable activity since it was created in 2002. That charitable activity is focused on several cornerstone programs, and we also give out grants to charities throughout New England. One of our cornerstones is a scholarship program for poor pubic school students in Boston, another is an inner city youth recreation baseball program so that young kids, boys and girls, can play baseball and softball. We also support the Jimmy Fund, which supports cancer research and treatment at the Dana Farber Cancer Institute. We support a local community center in Roxbury that serves low-income population called the Dimmock Community Health Center. And we’ve supported a new program created at the idea of our Chairman, Tom Werner, called the Home Base Program, in partnership with Massachusetts General Hospital, to treat veterans from Iraq and Afghanistan who have returned from combat or deployment with brain injuries or post- traumatic stress disorder. Those are just some of the things we do and we do a lot more than just that.

And there are all kinds of legal issues that are implicated by the management of a non-profit foundation, including general compliance with charitable laws. Both the IRS and State Attorney General have requirements that we have to be careful we comply with and treat charitable funds and assets pursuant to those laws. When we raise money there are various other legal issues that come up. For instance, we do various types of charitable gaming like raffles and we have to make sure we remain in compliance with whatever state rules there are. Ultimately, those are probably the biggest legal issues but there are other issues involved in the use of intellectual property and as we engage in all kinds of different activities, protecting against risk and making sure that our foundation operates in an efficient way.

**Mr. Friedman recently gave a TEDx talk about some of the challenges faced managing the Red Sox Foundation, especially when trying to measure the human impact of its work, and footage of the talk can be found here:

JSEL: In a panel you conducted in 2014 alongside Larry Lucchino, the former President and CEO of the Red Sox and a graduate of Yale Law, called “The Boss and Counsel,” you discussed your working relationship with Larry and other high level team personnel, partners, and owners. Can you tell our readers about the inner dynamics of working as counsel for a Team and the types of relationships you have cultivated with owners and personnel to make the franchise operate smoothly and efficiently.

DF: Relationships are so critical and clear communication is critical to do any job or human function. Certainly, working for an organization, having those relationships is really, really important and it’s both with the top of the organization, in this case the owners of our team, but also with many of my colleagues in other departments. And part of the reason it’s so critical is that, to really perform your job well as in-house counsel, you have to understand your business. You have to understand your objectives and some of the details of how the business operates and the realities of how you function. You can’t just answer legal questions in a vacuum. So it’s so important to create a relationship of trust. Part of that I think is for in-house lawyers to show our colleagues that we’re problem solvers, not impediments, so that people that we work with want to come to us for help, not avoid the lawyer because they might think, “oh no, I have to go talk to the lawyer who’s just going to say no to me.” So, ultimately our goal for all of us lawyers is to create those relationships and have everyone we advise trust what we say and build our own credibility.

JSEL: I saw in a YouTube video that you talked about the importance of face-to-face contact. In an era with email, Twitter, Facebook, and conversing over the Internet becoming increasingly prominent, can you talk more about the importance of face-to-face contact.

DF: I think that as communications evolve, and we live in the digital age and some people rely on technology more than others for different functions, face-to-face contact is really important because not only can you pick up on nuances, but it’s also easier to listen. I think that there’s a tendency for everyone, especially lawyers, to feel the pressure to respond really quickly. You get an email asking a question and a first instinct might be “I have to rapidly respond and provide an answer.” Well, sometimes you’re better off having a dialogue and not just throwing an answer at someone before you ask them questions or talk it through. As you start to answer, as you’re on the phone, or even better sitting in the room with your client, that person may interrupt and say you’re making an assumption that isn’t true, or you’re not answering my question. So, if you have the luxury and ability to actually sit down with someone, it’s often more effective than shooting off a quick email. And that’s part of the problem with email. People do feel the pressure to do it quickly and some people shoot off emails without even proof reading them. One piece of smart advice is to pause and wait ten seconds before you hit send, because you might have said something you didn’t mean to say.

JSEL: Can you describe the day-to-day tasks your job involves and how much of what you do relies on your expertise as an attorney and how much deals with the business and management of the Red Sox organization as a whole.

DF: My day-to-day job is really fun because it’s so varied and there’s no one typical day. Some days I’ll sit at my computer for a few hours doing research and writing a memo or analysis. Other days I’m in meetings, non-stop, back to back, sometimes inside the office, sometimes outside the office. It really varies so much and it depends on the issues I’m dealing with and how time sensitive they are. I would say that in terms of the substance, a lot of what I do is ultimately legal work and it turns on either expertise I have or expertise that I need to develop, as well as common sense and judgment. Most times having good judgment is more important than “expertise.” You can know a substantive area of the law but there may not be a clear answer. Or, even if there is a clear answer, it’s more important that you’re offering your judgment and trying to steer clients in the right direction.

That being said, there are some issues that I’ll get involved with that are more business or management issues and not purely legal issues. Ultimately, the line can be blurry. And to perform your job as a lawyer well, to provide really sound advice, you need to understand the business, even if you’re not the decision maker on business issues. For instance, if you’re talking about laws governing the re-sale of tickets to sporting events, I don’t set the price of tickets or decide a lot of those polices, but I need to still understand how we do those things from the business perspective.

JSEL: You’re job title was recently changed to include Counsel for Law and Government. Can you explain how your job involves government affairs and issues.

DF: Part of my job is to handle government affairs issues, which vary. They’re mostly city level issues, but sometimes they’re state and could even be federal issues. There’s a wide array of regulatory matters that affect us, involving permitting, licensing, compliance with alcohol regulation, tax issues, sometimes environmental issues. You can think of all kinds of subjects where we might face the potential for either regulation. I think for us at the Red Sox, what makes it especially important and challenging, is that we’re very much in the public profile and under the microscope and that’s great because we want people to watch games and we love the fact that the Red Sox have such a strong brand here in New England. But that also means that we hold ourselves to a very high standard and we know that we will be held to a high standard. So when it comes to regulatory issues, it’s all the more important to understand what the law is, what the issues are, and try to deal with them in an effective way, use good judgment, and provide sound internal advice.

I’ll also add that, for any kind of venue like this to operate, you really have to have a good working relationship with your local municipality, in this case the city. Fenway Park is unique in that we did not renovate the ballpark using public grants or loans or taxpayer dollars. Most stadia receive significant public subsidies. That wasn’t the case when the ownership group decided to renovate Fenway Park and not try and replace it with a huge new stadium. But we’re still under scrutiny and when we deal with the government we want to have a smooth working relationship so that we comply with the law and figure out ways to solve problems. We’re located here in the middle of a neighborhood with lots of residents so we want to have events that have 37,000 people and yet mitigate the potential for traffic, congestion, noise, and other impacts we know would affect the neighborhood and other local businesses.

JSEL: Prior to becoming Senior Vice President and Special Counsel for the Red Sox, you had an extensive legal career, from clerking for Supreme Court Justice Stevens, working at the law firm Hill & Barlow, working in the Massachusetts Senate President’s Office as Counsel and Chief Policy Advisor, and serving as a First Assistant Attorney General in the Massachusetts Attorney General’s Office while managing an office with 490 personnel. Can you elaborate on how your background has best helped you deal with the wide range of issues your job with the Red Sox entails.

DF: I’d like to hope that my background has made me qualified to do my job with the Red Sox and I think it has in various ways. Certainly my litigation background is relevant when I help to work with outside counsel when we have litigation to deal with. I think that my advocacy and litigation background can be helpful when I deal with other issues such as assisting on issues involving Major League Baseball. I think that a lot of the skills I developed as a litigator, skills in terms of understanding how to comb through factual records, how important facts can be, and skills in terms of legal analysis and persuasion, can be relevant and helpful in all kinds of day-to-day activities. There are other parts of my job, particularly the government affairs role, where all of my government service and experience is highly relevant. Sometimes because of the subject matter, there may be a subject that I studied or worked on when I was in government, but even when it isn’t the case, understanding how government agencies work can be quite helpful when you’re on the other side in the private world and intersecting and dealing with government. It’s important to understand how people in government think, and what drives agency decisions and some of the internal dynamics that would explain how the government operates. The other thing I’d emphasize is that in each of these jobs I’ve been very lucky to work with tremendously talented people whom I consider mentors, teachers, and just great lawyers from whom I learned. And here at the Red Sox, I try to take advantage of the experiences and knowledge that my mentors have taught. That includes different types of style, and if you see different lawyers they have different styles of advocacy and of providing advice, and sometimes those different styles can be very helpful to draw upon in a corporate setting like this one. So I have tried to put to use the lessons I learned from these amazing people, from Justice Stevens, Judge Boudin, from a bunch of great lawyers at the law firm I was at, and from the Massachusetts Attorney General, Martha Coakley, all these people are tremendously talented lawyers. One of the best things you can do as a young lawyer is just observe and watch.

JSEL: In a lecture you gave at Boston University, you stated that part of your job requires ensuring that the Red Sox remain apolitical. In light of the recent scandals that have plagued the NFL, including Adrian Peterson, Ray Rice, and Deflategate, how does a team such as the Red Sox, and more generally Major League Baseball as a whole, remain apolitical?

DF: You know, I think when it comes to domestic violence and other disciplinary types of issues, I would say that one of our foremost jobs as lawyers is to ensure really careful compliance with laws, both because you have exposure if you don’t comply, but also because it’s consistent with our values at the Red Sox. So we’re not really apolitical in that sense. Red Sox ownership and our senior leadership emphasize various values: openness, transparency, and certainly treating people with respect and dignity. So when it comes to domestic violence, for example, we’ve really been very proactive to try to figure out how to prevent it, how to have training and robust education of all employees, not just players.

JSEL: Concussions are a growing concern for athletes of all ages across all sport divisions. As a result, baseball’s 2012 CBA incorporated various safety measures to better protect players including the Rawlings S100 batting helmet, prohibiting collisions at home plate, and approving more protective caps for pitchers. However, the rules are not absolute or mandatory. For example, the agreement to ban most home plate collisions was materialized in Rule 7.13 but was only enacted on an experimental basis and didn’t adopt more restrictive measures that required sliding and prohibited blocking in all circumstances. Moreover, pitchers are not currently required to wear the heavier and more cumbersome padded isoBlox cap. My question then is, with the current CBA set to expire on December 1st of this year, do you expect to see any further modifications or amendments to the current guidelines, including increasing or further expanding the safety provisions, in the next CBA?

DF: That’s a great question. Certainly in all the leagues player safety is a really, really important component and if you think about the amount of money that teams and owners pay to players, it’s in everyone’s interest to keep them healthy. I think across sports, it’s fair to say that there’s a greater understanding of a lot of these issues than there was just a couple of decades ago. Concussions are much more of a problem in the NFL than in baseball, but your question’s still a great question.

I think as far as the process goes, naturally the collective bargaining agreement is a product of negotiation between the Players Union and the League, and teams can weigh in and ask the Commissioner, who represents the League and the owners, to take various positions. But ultimately it’s a negotiation between the Commissioner and his office and the Players Association. So it’s very hard to predict on some of these issues what the end result and the rules will be. I don’t personally know exactly what the Players’ positions will be on some of these questions, such as helmet-like caps for pitchers, or some of the rules involving plate blocking, or sliding into bases to break up double plays, which is a hot topic after a pretty serious injury in a playoff game last year. So it’s very hard to predict. I think that those will be very important issues debated in the negotiations, some of the more important issues that are on the table. I know that there have been cases in the past, certainly where the League has pushed for pretty strong protections for players. Sometimes the Player’s Union sees issues differently, or the players may have different views about the risk versus protections on certain things. The baseball players union is a very robust union with very intelligent advocates and lawyers, and whatever the final outcome of the CBA will be a product of truly robust negotiation.

JSEL: From Draft Kings to FanDuel and countless other sites, daily fantasy sport (DFS) leagues have become a billion dollar industry but their legality is becoming a hotly contested issue. Some have even gone so far as to describe it as “legal chaos” as their legality hinges on a favorable yet uncertain interpretation of the 2006 Unlawful Internet Gambling Enforcement Act (UIGEA) that created a carve-out exemption for fantasy sports games that reflect player’s skills and knowledge rather than luck or chance. Commissioner Manfred has stated that he believes DFS is consistent with federal law and NFL Commissioner Roger Goodell publicly expressed his support for season-long fantasy football leagues, while at the same time the New York Attorney General declared that daily fantasy sports constituted illegal gambling in New York. What is your viewpoint on the future of fantasy sports, and fantasy baseball in particular?

DF: The Red Sox haven’t to date taken a public statement on these recent developments. The Commissioner of baseball generally speaks for baseball on this issue. The Red Sox, as well as MLB, in the past had engaged in agreements with Draft Kings in particular. I’m quite sure we wouldn’t have Draft Kings as a sponsor if we thought they were doing something illegal. Our primary operations are here in Massachusetts, and as a Massachusetts-based team, I tend to look first and foremost at what the Massachusetts Attorney General says, and she has been pretty definitive that she doesn’t see a legal prohibition on daily fantasy sports games with respect to federal or state law, that’s her perspective. At the end of the day, daily fantasy games have been very effective at engaging fans. That doesn’t mean people shouldn’t be concerned about consumer protections and the like, but I was actually quite surprised by the New York Attorney General’s position, and especially his rationale and some of the arguments that he’s offered in support of his ultimate conclusion.

JSEL: Can you tell me more about your career path and what drew you to sports law?

DF: It’s funny because in law school my career plan was not to necessarily be a sports lawyer. In fact, if you had told me I was going to end up working for the Red Sox, I would have laughed and said that’s never going to happen. It shows that in law unpredictable opportunities sometimes can pop up and if you work hard and sometimes are lucky, unique possibilities can be there and doors can open.

Prior to this job, I really enjoyed working in government. I had a couple of really great government jobs that were really great, challenging, and fun. When the Red Sox were looking for lawyers here, I saw this organization as such an important part of New England’s fabric. You know, the Red Sox are a private company but it’s so much more than that; it’s Fenway Park, a place where people come and build memories, and as we’ve discussed it’s a company that’s really involved in the community. What drew me to this job was a combination of those factors and that sports law is interesting, challenging, and a lot of fun.  But I hadn’t gone out and pursued a job generally in sports law and in that sense, this was more of an accidental opportunity than anything.

JSEL: Would you please expand on what you mean by this was an accidental opportunity.

DF: I wasn’t actually looking to leave the Attorney General’s office, so this opportunity was accidental, both in the sense that I learned that the Red Sox had a vacancy in the law department and also just that it was an accident that I ended up talking to them in the first place because I wasn’t networking in the sports law industry. From my perspective, I hadn’t planned to go into sports and it wasn’t my original career ambition to work for the Boston Red Sox.

JSEL: What advice would you give law students interested in pursuing careers in sports law and going in-house?

DF: My advice, and many other lawyers in sports offer very similar advice, is first, certainly you should network, and get to know people in the industry, and learn as much as you can about sports law and what those jobs are really like. That includes trying to develop an understanding of what people in these various sports law jobs do. You might really enjoy it, or it might not be what it seems on first blush. It’s one thing to go and watch a few games, but a lot of what we do is focused on business law. Of course, there’s different types of jobs in sports. Some are more transactional, some might be things that litigators might go into. I think just developing an understanding is quite important. Beyond that, above all, it’s important in law school and in the first few years out of law school to develop a set of skills. We often encourage students to go to a law firm for a few years, although that’s not the only route by any means. Many good firms provide terrific training and they’re a great way for young lawyers to work for various clients and start to build those skills. Ultimately, if any team or league or company is hiring a lawyer for an in-house job, they’re going to be looking for someone with a skill set who is able to do things like write effectively, communicate effectively, negotiate, understand contracts and transactions, advocate, and develop position papers. I would say those skills are a lot more important than having specific expertise in specific sports law subjects.

To generalize at a high level, many in-house jobs are transactional in nature where the focus of your work is working on negotiations and agreements between corporate sponsors, companies, vendors, and the like. For a transactional job, if you’ve been a transactional lawyer in the past in another setting, whether it’s at a law firm as a corporate lawyer or even a tax lawyer or someone who’s more transactional, that’s a logical path. But litigators can also end up in sports. Our General Counsel of Fenway Sports Group, Ed Weiss, started out as a litigator. I was a litigator early on. Those skills can be relevant in all kinds of ways. So I think that if you’re drawn toward a trial lawyer-litigation path and you’re still interested in sports law, there’s no reason to be pessimistic or think that can’t work