Jimmy and Dee Haslam bring financial might and ‘burning desire’ to win to Milwaukee Bucks ownership

Damian Lillard took center stage during the official kickoff of the Milwaukee Bucks’ season Oct. 2, with the top 75 all-time player being the first to meet the assembled media. Team governor and co-owner Wes Edens, who opened the day with an individual question and answer session, was followed on stage by general manager Jon Horst and new head coach Adrian Griffin.

Lillard took photos with the trio and then with fellow owners Jamie Dinan and Mike Fascitelli. The group then stood off to the side as Lillard spoke about his trade from Portland to Milwaukee.

Notably absent from the pomp were Dee and Jimmy Haslam, the chief executive officer and chairman of Haslam Sports Group (HSG) and the newest co-owners of the franchise. They would arrive to the Sports Science Center later in the afternoon when the hoopla receded, and quietly spend the next day observing the opening of training camp while visiting with local business and political figures.

Their arrival in Milwaukee – and the NBA – in April has been met with curiosity and some concern, specifically with national basketball pundits wondering if Marc Lasry’s decision to sell to the Haslams portended the imminent departure of Giannis Antetokounmpo.

Jimmy Haslam was courtside late in the regular season and in the playoffs, but the couple and HSG staff have maintained a low public profile despite visiting quite regularly since December. They also have had a hands-on approach in an important offseason full of basketball business.

The Haslams, through HSG, oversee a burgeoning sports empire and told the Journal Sentinel they come to Milwaukee with one simple mission – to provide the resources and mentality necessary to win another NBA championship.

“That desire to win is not just for us, although we’re incredibly competitive, but we also recognize how important it is for these communities to have a winning team,” Dee Haslam said. “That gets us excited to be part of that story.”

Jimmy adjusted himself in his seat next to his wife and picked up on her sentiment.

“Coming from business to achieve success, whatever that is, you’ve got to take chances,” he said. “Wes and I laughed all the time when we agreed to do this with Dame – that does not come without a lot of cost and we’re rolling the dice again.

“The Bucks winning the title here in ’21, you probably couldn’t put a dollar value on it to this community. That’s what we want so badly to do for Cleveland. Not for our family, but for our players, our coaches and people that work for the Browns and our fans who have suffered for so long. That’s why we’re so dedicated to doing what it takes to win.”

The Journal Sentinel spoke to about two dozen people who have worked with and for the Haslams with the Cleveland Browns and Columbus Crew for this story to find out what sort of ownership ethos they are bringing to Milwaukee. And while there have been disagreements and questions over their methods or manner, the majority belief is that the Haslams want to win, and at the highest of levels.

How the Haslams built their wealth

James “Big Jim” Haslam II founded Pilot Oil Corporation and began opening gas stations in 1958, and his son James “Jimmy” Haslam III joined the company in 1976. Over the next three-plus decades, Jimmy’s leadership role in the Knoxville, Tennessee-based company grew as he oversaw its substantial expansion in size and scope.

In 2010, Pilot Oil Corp. merged with the Flying J truck stop chain to form Pilot Flying J, which was one of the largest privately held companies in the United States.

Also based in Knoxville, Dee’s family had operated one of the largest television-production companies in the country through the early 1990s. After the family sold that company, she helped found television-production company RIVR Media in 1998 and remained CEO until 2018.

As their private businesses grew, the Haslams began to get into sports ownership. Jimmy took his first step in 2002, partnering with his brother Bill (later the governor of Tennessee) to purchase the Tennessee Smokies, a Class AA minor-league baseball team, for $7.5 million. They would own the team until 2013.

Jimmy and Dee Haslam bought a 10% minority stake in the Pittsburgh Steelers in 2008 and in August 2012 they purchased the Cleveland Browns for a then-record $1.1 billion. The NFL does not allow ownership in multiple franchises, so the Haslams sold off their shares of the Steelers over the following eight months.

In the spring of 2013, the FBI raided Pilot Flying J’s offices for deceiving customers in a rebate scheme. Despite employee claims otherwise, Jimmy denied any knowledge of the fraud and was never indicted or charged in the years-long investigation.

In July 2014, the Pilot Flying J board of directors admitted it defrauded its customers and agreed to reimburse them ($85 million) and pay a $92 million government fine to end the prosecution. Nineteen employees plead, or were found, to have participated in the crime with several going to prison.

Trials for the that case were still ongoing in 2017 when Warren Buffet’s Berkshire Hathaway holding company bought 36.8% of Pilot Flying J for $2.8 billion.In December 2018, the Haslams partnered with the Edwards family of Columbus, Ohio, to buy the Columbus Crew of Major League Soccer for $150 million. After this purchase, the Haslam family created the Haslam Sports Group and began looking into the NBA as its next step.

After examining buying the Minnesota Timberwolves in 2021, the Haslams zeroed in on purchasing Lasry’s 25% share of the Bucks late in 2022. On Jan. 31, 2023, Berkshire Hathaway bought an additional 43.2% of ownership in Pilot Flying J for $8.2 billion. A few months later, the Haslams had agreed to purchase Lasry’s share of the Bucks for $800 million.

While still controlling 20% of the nation’s fifth-largest company (ranked by revenue) is no small thing, the Haslams can now be considered a sports family – and one with considerable heft.Forbes valued the Browns at $4.6 billion (No. 19 in the NFL) and the Crew at $550 million (No. 15 in MLS). The same publication listed Jimmy Haslam as the 99th wealthiest American with an estimated net worth of $8.7 billion. That places him as the 13th wealthiest sports owner and fourth wealthiest in the NBA.“Having very accomplished (partners) like Jimmy and Dee, because they really are a team, and having the resources that they have as well as my own resources, we think it’s the right combination,” Edens told the Journal Sentinel. “So I’m really, really excited about that.”

Cleveland Browns have yet to find success

The Haslams are best known because of their ownership of the Browns, who they bought from Randy Lerner in August 2012 with league approval coming in late October. They brought in former Philadelphia Eagles president Joe Banner as CEO and shortly thereafter team president (and former Green Bay coach) Mike Holmgren said he would resign after the season.

The Haslams quickly reshaped the organization that had three winning seasons from 1990-2011, as general manager Tom Heckert and head coach Pat Shurmur were fired a day after a 5-11 season was concluded.

The Browns haven’t fared much better since.

They have had just one winning season and have had six head coaches, five general managers and several high-ranking executives, including former Packers execs John Dorsey (GM 2017-19), Alonzo Highsmith (vice president of player personnel, 2018-19) and Eliot Wolf (assistant GM, 2018-19).

The organization reached its nadir in 2016 and 2017 when it went 1-15 and 0-16 under chief strategy officer and former Major League Baseball executive Paul DePodesta, executive vice president of football operations Sashi Brown and head coach Hue Jackson. At the time, the team leaned heavily into analytics, which many in the NFL considered an unorthodox way to run a team.

The early years of the Haslam ownership had two sides. On one, employees loved working for them as people. On the other, the work environment they created was rife with insecurity. Coaches and executives told the Journal Sentinel they often didn’t know who was in charge, or who was trying to curry favor to survive the next wave of changes.

“Organizationally, Cleveland – pardon my French – was a little bit of a (expletive)-show, but it felt like a family there, which I thought was cool,” former Browns fullback Danny Vitale said. “We stuck together during a tough time and I just thought (the Haslams) were super supportive of us the whole time.”

Which created an odd tension.

“A fantastic place,” said a former coach who currently is working for a different NFL team. “The people that worked in that building were some of the best people. When we play Cleveland, it’s like homecoming for me – it’s one of the most fun games I play.

"But when you work there, it’s an absolute den of thieves. You have no idea who’s influencing what, you have no idea when you’re going to get stabbed next. It’s high-stakes poker. It’s just what it is. And whichever way the wind blows and (Jimmy) decides, that’s it.”

For the half-dozen agents who spoke to the Journal Sentinel – only some of whom had direct negotiations with the Haslams – this creates a perception of disloyalty and not knowing what they’re doing. But for those who were part of the day-to-day, it was just a matter of the Haslams being guided by the wrong people.

“I think when you hire people to do a job, maybe they let you down sometimes, you know what I mean?” Highsmith said.

The former coach agreed.

“You get into this trouble and he doesn’t know how he got there because he trusted somebody and someone’s opinion,” the coach said. “Then he trusts somebody else and you go down another road. Then all of a sudden you’re hiring Freddie Kitchens and the whole thing is (expletive) up.”

But there is a consensus that the current regime of GM Andrew Berry and head coach Kevin Stefanski, hired in 2020, were sharp moves and a good pairing with DePodesta. They are the longest-tenured and most successful (30-26, one playoff appearance as of Oct. 22) duo under the Haslam ownership.

“In order for anything to work, you have to have all the parties on the same page,” said Highsmith, who is now the general manager of football operations at the University of Miami. “The only reason why it didn’t work with us, John Dorsey and me, everybody wasn’t on the same page. You had analytics department, you had the football department, you had Mr. Haslam, and each one of those facets were different people. So now I think they’re all similar, working in the same direction.”

There was a cost for such change, too, though salaries for executives and coaches are not widely reported.

“They do a great job of taking care of their people financially, so that will never become an issue," Jackson said. "When you have the money they have, that’s never going to be a problem.”

Regarding player salaries, the Browns have made several the highest paid at their respective position in NFL history, including the 2022 decision to trade for and extend quarterback Deshaun Watson to a record-setting, fully guaranteed $230 million deal.

Watson had not played in 2021 after 22 civil lawsuits were filed against him alleging sexual assault and inappropriate conduct during massage sessions.

“The Haslams are gonna spend money now,” Highsmith said. “I don’t think he has a problem with that part.”

But if front-office members and coaches felt the Haslams were too involved, or too present, the opposite viewpoint was held by players. None the Journal Sentinel spoke to had any issues with the Haslams on a personal level, and even if agents questioned their philosophy or their willingness to sign players with questionable character, none of them said their players bad-mouthed the Haslams personally.

One former player who is still in the league recalls asking Jimmy Haslam for advice on a potential investment while in the Browns weight room, and he appreciated Haslam’s honesty and availability. Vitale fondly recalls Haslam coming to see him in the rehab area to check on an injury.

“What I loved about the Haslams is that they were very visible figures,” Vitale said. “You could tell they were very invested in the team.”

Despite the general likability of the Haslams by their players, the Browns ranked 21st in a 2023 NFL Players Association survey of players and received an overall “C” grade. The organization received D grades for nutrition, the weight room and locker room in Cleveland Browns Stadium.

Opened in 1999, the stadium tied for the 12th-oldest venue in the NFL and Highsmith said there wasn’t much ownership could do with the place. The Haslams recently have been engaged in discussions with the city and county to massively upgrade and renovate the stadium.

The Browns received A or A+ grades for their strength and training staffs and C marks for the treatment of families and travel. One agent cautioned against that rating, though, noting how some players who had not been anywhere else might have rated the team lower than veterans who have more experience.

“He made sure all the food was available – like really good food,” said the former player, who has played for three other teams. “I’ll never forget that. Anything available. I’ve never been to another place like that. They take care of their business to make sure they get the players what they need. They’re really cool.”

On the practice side, the Haslams spent an initial $5 million to renovate the club’s Berea, Ohio, practice facility in 2013 and then partnered with the city to pay for additional $15 million worth of work 2016. They have subsequently purchased land around the facility and work has slowly been done to continue to expand the footprint of the site for future additions and upgrades.

“There’s a burning desire in him to win,” said Jackson, now the head coach at Grambling State University. “He’s not going to cheapen anything. As you see, look at the contract Deshaun Watson has. He’s going to put what he thinks is best to give them the best chance to win.”

Haslams saved the Columbus Crew and won an MLS Cup

In 2017, the owner of the Columbus Crew, a charter franchise in Major League Soccer, made known his intention to move the team to Texas – leading to quick action in the city to prevent that. A central figure was orthopedic surgeon and Crew team physician Pete Edwards, who enlisted the help of his family to put together a plan to keep the team. The Edwards family had been a major real estate developer in the town for five decades but needed more financial backing.

Alex Fischer, a longtime friend of the Haslams, was the CEO of a nonprofit called The Columbus Partnership at the time. He connected the families, and they quickly partnered on a $150 million purchase of the Crew in December 2018.

“When they decided to come down here on the ownership side in Columbus,” Edwards said, “it really was a feeling where they knew what it was like for a city to lose a team and they were willing to step up and create an environment where that didn’t happen again to an Ohio club. That point in and of itself kind of tells you where their heart is.”

Along with buying the team, the Haslams pledged to contribute $155.4 million to a new stadium project. Construction continued through the pandemic and the 20,371-seat venue was completed in July 2021 with a $313.9 million total price tag, the centerpiece of a 33-acre mixed-use district.

“He came into Columbus and built a brand new stadium during (expletive) COVID,” one NFL agent with ties to the area said. “Nobody’s working, somehow he got them to work. He’s got juice, there’s no doubt about that.”

In the last five years under the Edwards-Haslam ownership group, the Crew has experienced relative consistency. They hired experienced and previously successful soccer executive Tim Bezbatchenko as president and GM, and head coach Caleb Porter. Along with some of the finer facilities in MLS, the club also has at its disposal one of the larger “designated player” (or transfer) funds in the league, allowing the Crew to sign some of the better players available.

And though the Crew missed the playoffs in 2019, they won the MLS Cup in 2020. It was the second title in franchise history.

“This ownership group led by the Haslams has led with their pocketbook,” Fischer said. “I mean, the hiring of a world-class president and a coach – the coach is now the second one – but we had a good successful run and they’ve continued to up the game. To making certainly some of the most expensive personnel moves in our club’s history and Major League Soccer. It may not be the absolute top, but it’s the top echelon. To making their investments in the stadium and back-office personnel and to their philanthropy in our community.

“Across every aspect, they put their money where their mouth is. And more important than their money, they put their heart and soul into everything that they do. The combination of the money and the passion is where the magic happens.”

But after missing the playoffs in 2021, Porter was dismissed. The team also missed the postseason in 2022. Off the pitch, Dee Haslam acknowledged they made a “misstep” in 2021 when they tried to rebrand the team as Columbus SC and introduced an entirely new logo. The change infuriated the fan base, and the club quickly pivoted off that decision.

Unlike their more hands-on approach to personnel in Cleveland, however, there is a feeling in Columbus that the Haslams let their soccer staff go about their jobs without much interference. And, there always will be the element of communal goodwill from a fervent fan base and community for not only saving the team, but investing significant resources into the city with the new arena district.

“They came down and kind of were the knight in shining armor to keep this team in Columbus,” Edwards said. “They bring a level of professionalism and experience and desire to win that is what you want in a partner.”

What will the Haslams ownership of the Bucks look like?

Following the NBA’s approval of the HSG ownership bid in April, Jimmy Haslam and Edens briefly met with local reporters to discuss their new partnership. The pair acknowledged they had really only met over the phone, introduced via mutual friends. But they came together quickly as Edens made a clandestine trip to Cleveland and the Haslams visited Milwaukee in late December.

“These opportunities don’t come up a whole lot, so it’s not like you can pick and choose – you have to be opportunistic,” Jimmy Haslam said. “And it’s really through luck.”

After missing out on the Timberwolves, the Haslams said the opportunity to buy into the Bucks appealed to them because of Milwaukee’s proximity – and similarity – to their Ohio communities.

When asked why not buy a controlling share of the Phoenix Suns, they maintained it wasn’t as appealing due to its distance. The Haslams also felt then-Charlotte Hornets owner Michael Jordan already had buyers committed.

As for the Bucks ownership structure, the Haslams insist that having entrenched and experienced partners is a benefit, much like they have in Columbus. They admit – as does Edens – that they will continue to learn about one another, but feel their like-mindedness in terms of how to go about supporting a winning sports organization is an important connection.

In a unique agreement carried over from the Edens-Lasry pairing, the Bucks governorship (who represents the Bucks in league matters) will be held by Edens for the next five seasons with Jimmy Haslam assuming it in 2028-29. But for the day-to-day operations of the club, Edens and the Haslams say the governorship is merely a title.

“We agreed with Wes early on that no matter who the governor was, that in any major decision – so coach, GM, key player, signing over X amount – we both had to agree, and it’s worked,” Jimmy Haslam said. “We’ve already gone through some pretty tough (decisions).

“So you go through those situations and kind of get a feel for how everybody operates and Wes is super easy to get in touch with, good communicator. I’m sure we’ll hit some bumps in the road. He’ll get aggravated with us and we’ll get aggravated with him, but so far it’s gone well.”

Edens cited the Haslams' experience in owning the Browns and Crew as a reason why the initial months of their partnership have gone smoothly, and said there is a commitment to true collaboration that may have waned over the previous years.

Edens also noted that their combined financial resources and shared commitment to chasing a championship over sliding under tax lines has been a good starting point.

“He’s a serious guy, but he’s a very good guy and very focused on what I’m focused about, which is winning,” Edens said. “It’s easy to say that. It’s harder to actually go commit the resources. What’s happened here (with the Lillard trade) is a perfect example of that. We made a very significant commitment with this trade and I think it’s the right decision. Lillard gives us the best chance, we thought, to win.”

Which is why back in April, Haslam and Edens wanted to make it publicly clear there would be continued commitment to spending on player salaries – which would include a “repeater-tax” luxury bill in 2023-24 and potentially beyond.

Those unfamiliar with the Haslams in NBA circles wondered where they fell in terms of spending to that level. When told of these questions, those who worked for the Browns and represented players found it amusing anyone would think that Jimmy and Dee would somehow not spend or approve transactions that gave the Bucks the best chance to win.

“The best thing that could happen to a small- or mid-market franchise in sports is to have a wealthy owner come in and purchase the team, who has deep pockets and wants to spend – it’s not an investment,” said former University of Wisconsin and Browns left tackle Joe Thomas, a Brookfield native who remains an ardent Bucks fan.

“For a mid-market like Milwaukee to have owners whose highest priority is winning and putting together a good entertainment product and making the fans of Milwaukee proud, that’s the best-case scenario for ownership.”

Any lingering financial questions started to be answered in May when the team fired coach Mike Budenholzer with about $16 million left on his contract. In June, the team re-signed center Brook Lopez for $48 million and forward Khris Middleton for up to $102 million in free agency and then acquired Lillard in a late-September trade.

In fact, several NFL agents who spoke to the Journal Sentinel before the summer correctly predicted the Haslams would be involved in a “big splash” in their first full season of ownership.

While sending out guards Jrue Holiday and Grayson Allen in the Lillard deal meant the Bucks didn’t necessarily increase their tax burden for this year, they did inherit the roughly $170 million left on Lillard’s contract through 2026-27. Then Antetokounmpo signed a three-year extension worth up to $186 million through 2027-28.

Since 2020-21, the Bucks have spent like a so-called “big market” franchise, and the Haslams’ investment gave the organization only more financial might. While the newly signed collective bargaining agreement will handcuff Horst by reducing the number of roster-building tools at his disposal, the ability to afford the roster is not in doubt.

“When you’re a team like the Bucks, is your owner prioritizing making money or prioritizing winning?" Thomas said. "Then you see the resources that they provide. I would say without a doubt they will always prioritize winning.”

The same can be said in Cleveland and Columbus, too. And while they do not hide from fact the Browns have not had the success they've envisioned to date, the Haslams and those who used to work for them acknowledged this is a different situation than assuming total control of the Browns.

“We did decide to make a coaching change,” Jimmy Haslam acknowledged. “We changed out a couple of key players, which I think was a surprise to all of us, but the basic, key things – arena, practice facility, really stable ownership group that had been in place for a while and done a nice job, arguably the greatest player in the world – so things were in place here. It wasn’t a total rebuild, reclamation like we encountered in the two places in Ohio. It’s nice to be able to come in, Wes understands the business, Jamie does, we’ll learn the business and not have to Day 1 ‘go to work.’”

Those who tried to establish that culture in Cleveland believe that can make a difference, too.

"Not everybody is able to get that kind of situation where you’re walking in and you’ve got one of the best players in the world on your team, you’ve won a championship, there is a culture there of winning, they’re used to winning, there’s expectation, there’s probably collaboration, alignment," Jackson said. "All those things are in place so you don’t have to scale the wall to figure it out."

An off the court question some Bucks players initially had for Jimmy and Dee Haslam would be if they can form the same strong personal relationships that many had with Lasry and his family, which only helped accentuate the close-knit bond of a small roster.

“I think it’s really important they know we’re there and care and that we care about not just them as a player but as a person,” Dee Haslam said. “That is something that we really try to emphasize is, look, you’re a great player, we really appreciate what you do, but we’re going take care of your mind, your body, your family. Those things are really important because that’s what we do.”

For those who played for the Haslams in Cleveland, that isn’t lip service.

“I think people will definitely gravitate to him in that way,” Jackson said of Jimmy Haslam. “He doesn’t have a problem connecting with people. I’ve never seen him act like he’s so big that people can’t approach him or have a conversation.”

Vitale and Thomas have been particularly impressed with Dee Haslam, and agents and former staff agree the players will love the couple.

“I thought they were really cool people,” the former player said. “They’re around all the time, they’re around all the players. You could talk to them.”

Sitting side-by-side in the office of one of the Bucks’ personnel executives in the Sports Science Center, the last echoes of the team’s first training camp practice provided the soundtrack for Jimmy and Dee Haslam’s first lengthy public comments as Bucks co-owners.

There were no grand declarations, other than to say they’re in it to bring more NBA titles to Milwaukee. They’ve experienced that joy firsthand in Columbus, but more than a decade of struggles in Cleveland has proven pulling it off is very difficult regardless of resources committed. But their ownership philosophy to date meshes seamlessly with that of Edens and the other Bucks principal owners.

“We’ve had a chance to win a championship every year,” Bucks forward Pat Connaughton said. “And it doesn’t happen every year and I think our ownership group is unique in that they understand that. They want us to win as many as we can, but as long as we are contending for championships (that's the goal). And with Jim now, they’re (still) willing to make the financial decisions to put us in positions to do that to the best of our ability.”

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This article originally appeared on Milwaukee Journal Sentinel: Haslams bring financial might, ‘burning desire’ to win to Bucks