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This is Scott Becker with the Becker Business and Becker Private Equity Podcast. We're discussing today sports with David Pivnick and we'll also Talk about sports CEOs in sports with David Pivnick. David's a lawyer by background, brilliant, brilliant person. One of the smartest I get to visit with on a regular basis. We'll talk about what makes a great CEO in sports. Why do some teams constantly outperform others? Why do my Chicago sports teams have such poor leadership and CEOs? David, let me turn it to you. I know you're watching basketball right now. You're probably watching hockey right now or that time of year. You've also got giraffes coming up first, let's talk for a second about the Knicks and the spurs and, and sort of leadership in building those teams and why do some teams get built so well and others struggle? Any starting thoughts from you?
C
Yeah, I mean the first thing is talent identification and having a cohesive framework. And those two teams were built in very different ways. Obviously. The Knicks have been incredibly aggressive in making, you know, big, big, big trades. They've acquired multiple all star level players in terms of Carl Anthony Towns, Mikhail Bridges and OG and Anobi in massive trades and they've given up, you know, real talent. The they, they traded, you know, RJ Barrett, you know, Emmanuel quickly, Julius Randall and five first round picks in the trades for those guys. But they put together a team that's got elite defenders at multiple positions, that's got a lot of shooting across the board. And then they brought in a guy in Jalen Brunson when he was a good value frankly, and was a little bit underrated. I can't believe, you know, the Mavericks allowed him to leave, but they took a swing and so they put together really superstars at every position on in the starting lineup. Don't have a lot of bench, but they took those big swings. They used all their assets to have the best five man unit possible and it's been really quite successful for them. The spurs on the other hand, you Know, I don't want to say they've gotten lucky to disparage them, because it's not like they did anything wrong. They made a couple, you know, good moves to steer headlong into a rebuild. They stockpiled lottery balls in drafts that had, you know, massive talents, and then they got incredibly lucky. So getting the first pick in the Wembanyama draft, getting the second pick and being able to get Dylan Harper last year and being in a position to get Stefan Castle a few years ago as well, is really how they built their team. They've made good complimentary trades for a guy like the Aaron Fox, but the spurs are going to be really, really good for a really long time as long as Victor Wembanyama is healthy. And so a lot of their success is based on how lottery balls fell and. And the fact that they ended up with the number one pick in a draft we're having the number one pick was incredibly consequential.
B
Take a second here. When Jalen Brunson came over to the Knicks. So we've been watching this all week. You know, people were. When. When he came over, all the sports commentators were lamenting that move by the Knicks. You know, they said he's the 10th best point guard at that point, the 9th best point guard. You know, the Knicks made it seem like it was be a game changer. It's ended up being a game changer. What did they see that all the sports commentators didn't see? Or is it just that they're taking shots at the plate and smart enough to nurture talent, and when it works out, they keep it? How do. How do you look at that? Because I watch the stuff where Ring lambasted a few years ago for making such a big bet on Jalen Brunson, and he's turned out to be so valuable. How does that happen? And why do my franchises do so poorly at those decisions?
C
Yeah, I mean, I think the first thing is not getting bogged down in measurements and looking at who the actual player is. So I think a large part of it is just Jalen Brunson is an undersized point guard. He plays, you know, in the league where obviously height is incredibly important. And he's not tall. Like, he's tall compared to you and I, but he's not tall compared to the NBA players. And so I think a lot of it was just people were looking and saying he's a complimentary piece. And he was the second best lead guard on the team behind Luka Doncic, which is Not a shot at Jalen Brunson. Luka is just that good. And I think people got stuck in those metrics and weren't able to focus on the actual player and his talent. And Jalen Brunson does a lot of things well. I mean, he was an incredibly successful high school basketball player at a not, you know, dominant program at Stevenson in the Chicago suburbs. He went to Villanova and won national championships with a great team. And he's back with some of his teammates in New York, which I think that, you know, cohesion helps and he's just a winner. I mean, he consistently shows up in big moments, he's consistently a strong leader on the court. He makes the right play, he hits big shots, he's not scared of the moment. And he's tough. Clearly watching him play, he's both physically and mentally tough. And so I think people weren't appreciating some of those intangibles, were getting caught in some of the other metrics. His height, where he was drafted initially, and the fact that there aren't a lot of players, you know, who are undrafted or second round picks, in his case, second round pick, that have that kind of success, but not looking at who the actual player was and what drives him day in and day out. And I mean, I don't mean that just to say he tries harder. It's that he shows up to play, makes the right decisions and makes the team around him better so that he's not limited by just his size or any other metric.
B
No, it's really fascinating to watch. When you look at, besides the NBA, when you look at really well run franchises, who do you think about in sports? What comes to your mind when you think about really well run franchises?
C
I mean, one of them is, you know, if you look at baseball, I think the Dodgers and the Tampa Bay Rays are the two best run franchises in sports. They do it very differently. The Dodgers obviously have a completely unlimited checkbook, unlimited budget. And so when you're able to spend a ton of money and never have to worry about the consequences of those spending decisions, it's a little bit easier, you know, to use your resources well, because even when you have a miss, it doesn't hurt. But, but the balance to that is they've consistently made great talent acquisition, they take big swings, they've built a cohesive roster, and they consistently have a ton of prospects that are rated in the top 10 and top 100 prospects list, which not only allows them to retool on the fly, but also allows Them to have a lot of great trade pieces to make deals with other teams to acquire talent. And those are not just resources. They're stockpiling based on their wealth. And then in Tampa, you know, they've got an organization that doesn't spend a lot of money, doesn't have as strong a fan base, doesn't have the revenues coming in, and they've still built a consistent winner because they identify talent. They do a good job identifying international talent. They do a terrific job in the draft. And then their farm system, their minor leagues, they've clearly put in place a lot of coaches that are good at developing talent so that they're maximizing the assets that they're getting so those two teams in baseball stand out. And then in hockey, I think it's hard not to respect what, what the Las Vegas Golden Knights have accomplished on a lot of levels. I mean, they had a terrific, you know, they came into the league, you know, about a decade ago at this point, and from minute one, they took a sort of unique stance at the expansion draft where they, they recognized salary cap is a real thing and other teams have constraints. And so from day one in the expansion draft, they were looking to make moves and acquire additional draft picks, resources by taking on some teams less desired contracts. And they've, they've just continued with that approach throughout. And I think there's a lot of people who find the Knights distasteful, whether it's people who are upset about the Carter Hart dynamics and him being back in the league, whether it's people who are upset that every year Vegas seems to have one or two or three injuries and players who are on long term injured reserve. And then they had guys to get around the salary cap, but they're not violating the rules of the game. They're, they're sort of leveraging those rules, taking advantage of loopholes that apply. And so I can understand why other people might be frustrated, but you kind of have to respect the fact that they're willing to consistently put themselves in a position to succeed, use their resources to get the best possible players and build around them and, and take a
B
second on this issue of CEOs and Lessons from sports. I mean, obviously sometimes as a law firm and we've got this fantastic law firm, one of the 30, 40 largest in the world, and sometimes we're competing against the top five law firms that feel like the Dodgers with unlimited money to spend. Are there lessons from sports that you could transfer to business? And how do you think about these? Everybody tries to Always say, like, oh, this guy's on leadership. Tom Brady on leadership.
C
And.
B
And how do I translate that to my professional career? And I see the diligence of all these things that Tom Brady does, but I feel very inadequate compared to Tom Brady or Djokovic or one of these guys or Wayne Gretzky. How do you sort of translate some of these lessons from sports to business? And do you ever try to do so, just use sports as entertainment?
C
Yeah, I absolutely do draw the comparisons, and I think some of it goes to some of the things we've just talked about. You have to be able to succeed and thrive within your zone. So if you're, you know, in our case, you know, in the top 40 or 50 law firms in terms of size and revenue, making sure you're comparing yourself to your peers, figuring out, you know, from a pricing standpoint, from a client standpoint, from a marketing standpoint, from a talent standpoint, compensation, how you stock, you know, stack up and where you can leverage, you know, the advantages you have, fixed weaknesses, etc. Enter new markets, bring in new talent. The other part of it, though, is finding opportunities, being opportunistic and deliberate, and seizing those opportunities. So looking internally, we've done a really great job at a couple things over the years. One of them is consistently developing young, strong, talented lawyers into young, talented partners at the firm who are developing business. We've gotten folks involved from an entrepreneurial standpoint in business development, whether it's just marketing or networking, but building those relationships so that we have a lot, consistently a lot of young attorneys who are starting to develop or expand client relationships so that we're continuing to push upwards on that front. The second thing that we've done, and, you know, I don't think it's fair to McGuire woods as a firm to compare us to the Tampa Bay race. But I think we've done a really good job identifying talent. We're very intentional in recruiting and bringing in laterals who we think are going to be accretive to the firm, both from a personality standpoint, but also a business standpoint. And so several of our leaders, you know, I would use examples like Tom Zahn and John Finger as great examples. Jeff Cockrell are folks we've brought in as laterals where they were already very talented attorneys, talented business developers, but folks who frankly hadn't reached their full potential. And we were able to bring them in, support them, and help them do exactly that, such that they've gone from being stars to being superstars, and we've helped develop that. And I think they deserve the credit for that success. But I think the firm, you know, being able to identify that kind of talent and putting people in position to succeed is incredibly important and something that plays, whether it's in sports or business or the business of a law firm.
B
Thank you very much. No, I absolutely love that perspective. Are there any sports owners that you think do a very poor job? Es owners. Is there anybody that you're comfortable talking about that you think is actually sort of deserves to be labeled as they're not doing a very good job as an owner?
C
Yeah, I mean, basically all of the Chicago sports team teams, owners. And I say that slightly tongue in cheek, but. But not really. I mean, where. Where owners tend to have a poor track record tends to be two places. One, they're either, frankly, just too cheap and. And too frugal for what they're trying to accomplish. And when I say trying to accomplish, I just assume owners of sports teams should want to win championships. You can make money owning an NFL team. It's very lucrative. You can make money in the other sports. The teams are all appreciating, but ultimately, for the most part, and like the Bears have historic ownership where the family wasn't independently wealthy, absent the team. Most sports, you know, most professional sports teams are owned by incredibly wealthy people who had significant wealth amassed before acquiring a team. They don't really need the team from a financial standpoint. And so my view is they should be devoting whatever resources are necessary to make it a winner. And so I think, you know, where there's a consistent failure, it's. It's where teams are not spending money appropriately, not leveraging their resources, not taking advantage of opportunities because they're not spending money. And then the second place is rushing rebuilds, doing things halfway. So whether it's rushing a rebuild or not taking advantage of an opportunity, when you're on the precipice of a championship, not making the necessary trade, not doing what is required to put yourself across the finish line. And I think those are things that unfortunately, have all too consistently been problems for most of the Chicago teams. You know, the Blackhawks now are in the midst of an incredibly long rebuild, which I'm hoping they'll get out of soon and start turning the quarter into success. And the other teams have largely been mired in mediocrity for the last, you know, several decades, other than the Cubs finally winning in 2016 for the first time in 100 years and then immediately reverting back.
B
Yeah. Let me ask you for a couple comments on something. I'll give you three things. The Hawks defense, the Cubs pitching, and the Beers defense. These are three things that from all I can tell, all are just absolutely horrendous. Still, the Hawks have six guys out there on defense that all seems still young and evolving, but no serious stop run defense, the Bears defense, thank God we scored a lot of points last year because it seemed like a civ at times. And the Cubs pitching, everybody knows that pitching so important in baseball. Why is their pitching still so challenging? Why is that that these things seem so obvious to a fan and I guess that's why we're not really GMs or presidents. But they seem so strikingly bad. Why is that?
C
I mean, they're very different frankly in terms of the circumstances. So I mean, look, let's start with I'm a big believer in the Blackhawks defense long term, so I, I put them in a different bucket than the other two to start with. I, I have a bias here because I'm a huge Blackhawks fan and I'm fair relatively neutral on the Cubs and, and don't particularly care for the Bears, but I don't think it's my bias. The Blackhawks have poured significant resources into the defense they've used. You know, top number two overall pick on Lev should have a seven pick on Korchinski, a 25 pick on Ridzell. Those three guys are all incredibly young and absolutely looked incredibly young at times next year. But I think all three of those guys are going to be stars in the league. I think they all have a ton of potential. It takes a much longer time for defensemen to develop in the NHL and the team around them hasn't been great. But I think those three all have bright futures still and are developing. Maybe not, you know, on the straight line, you might hope, but are developing and have lots of potential. And then we've got guys like Vlasic and Kaiser who are rock solid defensemen already. Louis Crevier came into his own last year. So I think the Hawks defense is really just a matter of seasoning. Maybe we add a veteran presence this year to help, but I think it's a matter of seasoning and allowing the guys to finish developing. I think the Bears and the Cubs, the biggest problem on both fronts there is they simply haven't focused on the defense. You know, the Bears have had an absolute wealth of high draft picks and frankly, I think, excuse me, they've done a fairly good job with those picks, but it's almost been entirely focused on offense, you know, taking, taking right on the offensive line, who I think is terrific by the way. I think that was a great pick, but they took him when guys like Jalen Carter were available on defense and would have been a complete difference maker on D. The Cubs have spent some money the last couple of years. They've made big moves, but it's been moves for guys like Kyle Tucker last year and Alex Bregman this year. They haven't gone out and got via trade or signing. They haven't used their resources to bring in a stud pitcher. And so I think a lot of it right now the biggest difference is the Hawks have spent the resources and focused on the defense. It just hasn't all developed around and into form, into shape just yet. The Cubs and the Bears really haven't spent the time meant money and effort to work on their defense. So it's it continues to be in their pitching. So it continues to be a problem, but likely will remain that way unless and until they do spend the resources to actually fix the problem.
B
Let me ask you this question. Look, I always think about a business and not or so you've got a great player like a Cody Bellinger letting him go, replacing with Kyle Talker letting him go, replacing with Adam Bregman. This seems to me almost the the worst way to go about things. Instead of conjunctiving, you know, adding great talent to talent, it's constantly sort of one in, one out and that doesn't really help you grow. It's like building a team in business. We need lots of great lawyers, not one great superstar. That leaves, we pick up another great superstar. You need lots of them. And the same with building a pitching staff. But why does this seem to be so sort of stuck in place? I mean it does seem to be sort of remarkable to watch the Cubs, we all know pitching is not where it has to be. They keep on trying gerrymandered ways to do it and it's very frustrating. And the Bears, as you've said, have not spent a lot of money on the offense. The office moved in the right direction. Many of us thought this year they'd start spending some time in the defense. And the defense, it seems like they're. They're not quite. Not quite there or not making the effort. What are your summer thoughts on why this happens or why that thought process is?
C
Yeah, I mean first, I love the way you conjunctive the word conjunctiving into the English language. I think that was a nice addition. So kudos on that. And in terms of the teams, I mean, look, I think there's a difference between the Bears and the Cubs and the approach that they almost necessarily have to take, which is to say, I get where the Bears are coming from, but I don't. On the Cubs, the Bears have a salary cap, and so they've clearly made it their priority. I. After literally decades. I mean, it's been decades since the Bears have successfully developed a franchise quarterback. You could argue they've never successfully developed a franchise quarterback, and they have a guy in Caleb Williams who could very much be a superstar at the position. And so I think the decision, knowing that you've got limited draft picks, knowing that there isn't really a farm system in football to develop folks over the years, and knowing that there's a pretty rigid salary cap, I think the Bears are devoting a lot of assets to positioning Caleb Williams and the offense in the best possible place to succeed in recognition that you need a quarterback who's a superstar to win consistently in the NFL, and they don't want to squander the guy that they. That they could be relying on for the next 15 years. And so I think they are trying to put Caleb Williams in the best position to succeed, hoping he's good enough and the defense can show up just enough to get them wins. Which. Which, by the way, to be clear, I think could work. Like, I think that is a possible solution, and it's rational. I mean, they don't want to blow another quarterback prospect, as they have so many times with guys like Trubisky, who I think had some potential, not Caleb Williams level, but they just didn't support him well. The Cubs, on the other hand, are just being cheap. Like, I don't have a better explanation. They clearly are aware of the fact the pitching is lacking. They raise ticket prices every year at Wrigley. They. They're making an absolute fortune in ticket revenue, and they just haven't done enough to fix the pitching. And the fans, frankly, deserve better. There's no reason that the team didn't go out and trade for or sign pitchers to help. And when you look at, you know, guys like Freddie Peralta getting dealt out of Milwaukee, which is inexcusable by the brewers considering he makes 8 million bucks this year. But where the Cubs aren't getting in, you know, maybe a division rival won't trade with them, but there are other opportunities. You know, Franber Valdez went for far less money to Detroit than everyone anticipated and would have been terrific in Chicago. And So I think the Cubs have simply not spent the money there. They've done sort of the bare minimum to suggest that they're trying and making an effort to win without actually devoting appropriate resources to doing exactly that. And I think they're paying for it in the results on the field because of that.
B
No, I actually love your analysis. Your analysis on the Bears makes tremendous sense and helps me make sense of some of this stuff. Hopefully people could translate some of this to business or other situations that they're watching. I love what the Knicks have done with the spurs have done. I love your perspective on the Cubs. I think they've just let this go knowing that they absolutely and then they don't have depth. And so as soon as they have an injury it's truly a disaster at pitching. And I think your assessment of the Blackhawks, I miss having a couple anchor senior veteran defenseman, you know, in, in, in, in. Like you say, at some point you got to turn that rebuild around and have enough players out there or people do get quite discouraged and then they don't want to stay with the Hawks past their entry level contracts. And so for so we'll see how it goes. David, Fascinating to visit with you. You're one of the brightest people I get to visit with ever. I really enjoy it. Thank you so much for joining us on the Becker Business and the Becker Private Equity Podcast. Thank you very, very much for joining us.
C
Thanks for having me. Scott. Always a good time.
B
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Podcast: Becker Private Equity & Business Podcast
Host: Scott Becker
Guest: David Pivnick, McGuireWoods LLP
Date: June 5, 2026
In this episode, Scott Becker is joined by David Pivnick, a partner at McGuireWoods LLP, to dive deep into leadership, team building, and decision making among sports franchises. Together, they explore why certain teams consistently excel, the characteristics of impactful sports CEOs, and what business leaders can learn from world-class franchises and their management strategies. The discussion centers on examples from the NBA, MLB, and NHL, with a particular focus on the decision processes, risks, and philosophies behind franchise success or stagnation—especially reflecting on Chicago’s sports scene.
Timestamps: 00:30–03:40
"They put together a team that’s got elite defenders at multiple positions ... and then they brought in a guy in Jalen Brunson when he was a good value ... it’s been really quite successful for them."
—David Pivnick [01:46]
"A lot of their success is based on how lottery balls fell ... and ended up with the number one pick in a draft where having the number one pick was incredibly consequential."
—David Pivnick [03:18]
Timestamps: 03:40–06:23
"People were looking and saying he’s a complementary piece ... he’s not tall compared to NBA players ... people weren’t appreciating some of those intangibles, were getting caught in some of the other metrics."
—David Pivnick [04:46]
Timestamps: 06:23–09:35
"They recognized salary cap is a real thing ... from day one in the expansion draft, they were looking to make moves ... they’re sort of leveraging those rules, taking advantage of loopholes that apply."
—David Pivnick [08:29]
Timestamps: 09:35–12:50
"We’ve done a really good job identifying talent. We're very intentional in recruiting ... both from a personality standpoint, but also a business standpoint."
—David Pivnick [11:20]
Timestamps: 12:50–15:21
"Where there’s a consistent failure, it’s ... not spending money appropriately, not leveraging their resources, not taking advantage ... and then the second place is rushing rebuilds, doing things halfway."
—David Pivnick [14:00]
Timestamps: 15:21–18:56
"The Cubs and the Bears really haven’t spent the time, money and effort to work on their defense ... it continues to be a problem, but likely will remain that way unless ... they actually fix the problem."
—David Pivnick [17:53]
Timestamps: 18:56–22:51
"The Cubs have simply not spent the money ... they’ve done sort of the bare minimum to suggest that they're trying ... without actually devoting appropriate resources."
—David Pivnick [21:42]
“You have to be able to succeed and thrive within your zone ... leverage the advantages you have, fix weaknesses, enter new markets, bring in new talent.”
—David Pivnick [10:23]
“Most professional sports teams are owned by incredibly wealthy people who ... don’t really need the team from a financial standpoint ... They should be devoting whatever resources are necessary to make it a winner.”
—David Pivnick [13:34]
"We've helped develop stars into superstars ... putting people in position to succeed is something that plays, whether it’s in sports or business."
—David Pivnick [12:39]
"Instead of conjunctiving ... adding great talent to talent, it’s constantly one in, one out, and that doesn't really help you grow."
—Scott Becker [18:59] “The Cubs ... just haven't done enough to fix the pitching, and the fans, frankly, deserve better.”
—David Pivnick [21:08]
The conversation is analytical, insightful, and occasionally candid—drawing on real frustration with local teams, admiration for successful franchises, and the practical business lessons to be learned from sports.