When the Los Angeles Dodgers square off against the Chicago Cubs for the Major League Baseball season opener in Japan’s Tokyo Dome this Tuesday, Dodgers co-owner Todd Boehly will watch with mixed emotions.

No doubt he’ll revel in the spectacle. Thanks to a pitching roster that includes three of Japan’s biggest stars—Yoshinobu Yamamoto, Roki Sasaki, and super-slugger Shohei Ohtani—Japanese fans practically think of the Dodgers as their national team. The Dodgers’ World Series victory over the New York Yankees last year drew an average of 12.9 million Japanese viewers; Game Two in that series had more Japanese viewers than Americans. Tickets for Tuesday’s game and a second on Wednesday sold out instantly, with premium seats on the re-sale market changing hands for as much as $20,000. The roar of the crowd inside the 50,000-seat “Big Egg” will be thunderous. Millions more Japanese will tune into the games on television. The Japanese media, which covers the Dodgers obsessively, is sure to whip itself into a frenzy.

But Boehly’s ability to appreciate all that excitement will be tempered by frustration that the Dodgers can’t cash in on it. The Dodgers, he argues, are the “obvious choice” to lead an effort to take MLB global—in a market where America’s national pastime has long been more popular than it is in the country where it was invented. Boehly sees that as a huge opportunity, not just to sell merchandise and broadcast rights, but to create high-tech, interactive experiences, where Japanese fans can virtually step up to the plate against Ohtani, or re-enact Freddie Freeman’s dramatic World Series grand slam. “We are confident we could do something in Tokyo and Osaka that would bring in a couple of million people every year,” Boehly says.

It won’t happen, he laments, because long-standing MLB rules stipulate that revenue collected from markets outside the U.S. must be shared equally among all 30 teams in the league. “If we’re told that we get only 3% of the business, that makes it hard to justify the investment. For us to plant Dodger-branded flags in Tokyo—which we’d love to do—Major League Baseball needs to figure that out.”

Figuring that out, as Boehly sees it, will require the MLB to recognize that it has an archaic governance structure that prevents the league from adapting to change and capitalizing on new opportunities. “When the constitution of baseball was written and all these agreements were made, the idea of global sports in a world where information and news moved around at the speed of light was just unfathomable,” he argues. Under MLB’s legacy rules, many of which were designed to reduce the advantages of better financed, free-spending teams like the Dodgers and Yankees, even minor changes in the way the league operates require the approval of 22 out of the league’s 30 teams. Boehly thinks that is too high a bar.

Boehly, a champion wrestler in high school and college, began his career in finance. But his knack for spotting and exploiting governance failure has helped him build a multi-billion-dollar sports and entertainment empire that includes some of the world’s most lucrative franchises. In addition to his 20% personal stake in the Dodgers, Boehly is co-owner of the Los Angeles Lakers basketball team, and co-controlling owner and chairman of the Chelsea Football Club. Through his holding company, Eldridge Industries, his investments in the entertainment industry include Penske Media (owner of The Hollywood Reporter, Variety, Rolling Stone, and Billboard); Dick Clark Productions (the world’s largest producer and proprietor of live television programming); Fullwell Productions (producer of “The Big Bang Theory”); as well as licensing rights to the songs of Bruce Springsteen. In 2023, Eldridge Industries and Dick Clark Productions acquired the assets of the Golden Globe Awards, prizing them away in contested takeover from the Hollywood Foreign Press Association, the non-profit group that had run the awards for eight decades.

In growing that empire, Boehly has developed a consistent management playbook. He is impatient with outdated rules, willing to make huge and often heavily leveraged bets, and takes an unsentimental, asset managers’ approach to balancing risk.

When the Dodgers came ups for grabs in 2012, Boehly was a senior partner at Guggenheim Partners, a Connecticut-based private equity fund. The Dodgers then-owner, flamboyant billionaire Frank McCourt, had been forced to file for bankruptcy because of a costly divorce settlement and string of bitter legal battles with the MLB. Boehly quickly assembled a coalition of investors that included Mark Walter, Guggenheim’s controlling partner, as well as basketball legend Magic Johnson and Hollywood mogul Peter Guber. The group paid $2.15 billion—the most anyone had ever spent to acquire a sports team at the time—to close the deal.

The purchase was widely lampooned as overpriced and overleveraged. But Boehly had worked out that, because of the size and wealth of the Los Angeles market, broadcast rights for Dodgers games were worth far more than skeptics understood. Within a year Boehly’s consortium had secured a media rights deal with Time Warner Cable worth $8.35 billion over 25 years—revenue the Dodgers then used to sign an army of blue-chip players and turn the Dodgers into the MLB’s second-most valuable franchise with an estimated valuation today of $5.5 billion. In recent years, the Dodgers have consistently led the league in attendance, revenue and playoff appearances. In October the team capped its transformation with a stunning five-game World Series victory over the similarly deep-pocketed Yankees.

One key to the Dodgers’ success has been the team’s willingness to pay top-dollar for star players, many of them from Japan. The MLB doesn’t have a salary cap for players, but since 1997 it has imposed a punishing “luxury tax” on teams spending more than a certain predetermined amount on payroll (last season the threshold was $241 million). Boehly doesn’t balk at paying it. The Dodgers’ payroll, according to Cot’s Baseball Contracts, is about $389 million, the largest in the league. The team pays an estimated $110 million in penalties, bringing its total outlay for player compensation to $500 million.

In December 2023, the Dodgers signed Ohtani to a record-breaking 10-year, $700 million contract, the largest in sports history. A few weeks later, the Dodgers announced that they had also signed right-handed Japanese pitcher Yoshinobu Yamamoto to 12-year contract worth an additional $325 million. Ohtani not only helped to recruit Yamamoto, he made the deal possible by agreeing to receive only $2 million annually from 2024-2033, deferring the remaining $680 million of his payout until after 2034. Under terms of his contract, Ohtani, who is now 30, will get annual payments of $68 million starting at age 40 until he turns 50.

That bet has paid off handsomely. In 2024, Ohtani became the first MLB player to hit over 50 home runs and steal over 50 bases in a single season.

Boehly credits Ohtani for proposing such a large salary deferment. “He was so thoughtful,” says Boehly. “[Dodgers president] Andrew Friedman would have never had the courage to go to him and say, ‘How about we defer, you know, $680 million of your $700 million?’ But Ohtani recognized that the only way for to him to become a true legend would be to win the World Series. And the only way to win the World Series was to build winning a team. So what he really offered us was the financial flexibility to be able to field a team that will make him a legend. That’s just staggeringly wise.”

It’s also hugely controversial. Critics charge the Dodgers’ lucrative broadcast deal and their massive spending on players give them an unfair advantage over other MLB teams that is sucking the soul out of baseball. The Dodgers have fanned the flame of those complaints by using deferred contracts more extensively than any other team, committing more than $1 billion in deferred payments to seven players, including Ohtani, Mookie Betts, Blake Snell, and Freddie Freeman. Other teams have emulated the strategy leading some to complain that MLB is doomed to wind up like European soccer leagues, polarized into permanent classes of haves and have-nots. 

Boehly bristles at the suggestion that the Dodgers are just winning championships simply because they throw more money at stars than other teams. But he’s also skeptical of the idea implicit in Michael Lewis’s 2003 book, Moneyball: The Art of Winning an Unfair Game, that small teams with limited budgets like the old Oakland A’s can hold their own against rich clubs like the Dodgers and the Yankees by using data and statistics to identify undervalued players.

Boehly says Dodgers’ owners are just taking an asset managers’ approach to maximizing their investment. “There are there are two versions of [the moneyball] strategy,” he argues. “The first version is where you’re playing a game where you are picking up pennies and turning them into nickels. In our version, because of our market, we have the ability to pick up gold bars and turn them into diamonds of the same weight. The market allows for us to play what some people call a premium game but we would call a value game. We’re able to play in the luxury market versus the discount market. There is still value to be had in the luxury market but you have got to make a choice. Are you going to buy player X at $300 million, or are you going to buy player Y?”

Boehly is grappling with a different set of challenges at Chelsea Football Club—so far with mixed results. The Chelsea acquisition, like that of the Dodgers, was born of owner distress. In 2022, in the wake of Russia’s invasion of Ukraine, the United Kingdom froze the assets of Russian billionaire Roman Abramovich, who had owned Chelsea for 19 years, because of his perceived ties to Russian president Vladmir Putin. Boehly, Walter, and a third partner, Swiss billionaire Hansjorg Wyss, teamed up with Santa Monica-based private equity giant Clearlake Capital to purchase Chelsea for $5.25 billion—setting a new record for the most expensive team transaction in sports history.

Chelsea has forked out nearly $1 billion in net transfer fees to players since the acquisition, more than any other club in the league. Notably, though, instead of spending astronomical sums to lure individual superstars as have the Dodgers, Chelsea has built a roster of up-and-coming younger players and is trying to hang on to them with longer contracts that spread out amortization expenses. League rules allow for 11 starters per match, with only five substitutions. But Chelsea has built up a roster of nearly 40 players with an average age of under 25, by far the largest and youngest squad in the league.

That squad has yet to find its footing. Chelsea sank to No. 12 in the league table in 2022-2023 recovering to 6^th in 2023-2024. Despite the record transfers Chelsea posted a pre-tax loss in the three years to the end of the 2023-24 season and appears to have managed to remain in compliance with the League’s sustainability and profitability requirements only by selling the women’s football team and two hotels to its parent company. Revenue at the club declined 7% in 2024, according to Deloitte, even as revenue at rivals for four of the league’s other Big Six Clubs—Manchester City, Manchester United, Arsenal, and Liverpool—improved.

Another difference between Boehly’s role at Chelsea versus the Dodgers is that, at the former, Boehly and his allies don’t have majority control. Although Boehly was the public face of Chelsea ownership in the first two years after the acquisition, he and fellow investors Walter and Hansjorg collectively hold only 38.5% of the consortium that owns the club while Clearlake holds 61.5%. It has been widely reported that Boehly has fallen out with Clearlake’s co-founder, Behdad Eghbali. The two men have sparred over, among other things, the decision to mutually part ways with head coach Mauricio Pochettino and plans to build a new stadium whether at the club’s traditional site, Stamford Bridge, or at nearby Earl’s Court. Boehly, Eghbali, and another Clearlake co-founder Jose E. Feliciano, each have veto power over all major Chelsea decisions. The Athletic and Bloomberg have reported that both private equity firms have explored the possibility of bringing in new partners to buy the other out.

Boehly has a firmer hand over the Golden Globes, although obtaining that was controversial and, as Boehly puts it, required a “knock-down, drag-out battle.” The Hollywood Foreign Press Association had long been mired in allegations of mismanagement, corruption, and sexual harassment. In 2021, when a Los Angeles Times investigation revealed that the HFPA had no Black journalists, NBC dropped the show and no other television network would screen it. Boehly stepped in as interim CEO, and worked with HFPA leadership to expand and diversify the voting membership and establish clears standards and processes about how the awards should be run. But he eventually lost patience with the fractious group. In 2023, a for-profit partnership between Eldridge Industries and Dick Clark Productions purchased intellectual property and broadcast rights to the Golden Globes. As part of that deal, the HFPA was dissolved and a non-profit entity was created to manage the HFPA’s philanthropic endeavors.

Several former members of the HFPA are suing Boehly for fraud. Critics have decried the deal for betraying the values cinematic excellence. “Once corrupt, the Golden Globes is now nothing but money in a billionaire’s bank,” fumed Evening Standard editor Alexandra Jones.  

Boehly is unapologetic. And in its new, private incarnation, the Golden Globes appears to be thriving. The awards ceremony was picked up by NBC in 2023, and last year signed a five-year broadcast deal with CBS. Boehly says comedian Nikki Glaser, who won plaudits for her performance as host this year, has agreed to reprise that role for the next three years. Where the old HFPA was a coterie of about 80-90 southern California-based some full-time, some part-time, and some with no clear professional roles at all, the reconstituted Golden Globes voting body is a racially and ethnically diversity group of 334 journalists based in 85 countries. The new Golden Globes has leaned in to diversity and inclusion even as many US political leaders leaned the other way. The awards now highlight a much broader range of international films and shows. As The Wrap’s executive editor Steve Pond put it: “The old body of Globes voters had the word foreign in their title…but their successors are apparently doing more to put the foreign influence into the show itself.”

The fundamental problem, Boehly argues, was that the HFPA leadership failed to recognize how technology had transformed the entertainment industry, enabling stars and studios bypass journalists to communicate directly with fans. It didn’t help that the board had to get 75% agreement from members to make any changes.

“Their inability to adapt was the root of their demise. They weren’t bad people. But there are market forces in every industry and if you don’t have the governance to respond..?”

As his empire expands, Boehly is looking to make bigger, bolder bets. He has many plans in motion. In Japan, he’ll meet with Tokyo governor Yuriko Koike and a mix of media companies and fin-tech investors. Then it’s off to Korea, followed by Hong Kong to attend a conference hosted by friend and mentor Michael Milken. In the U.S., meanwhile, Boehly is looking to build a nationwide network of elite sporting academies modeled on the St. James Performance Academy in Springfield, Virginia in which Eldridge is an investor.

“Now I am thinking about building platforms, not just making investments,” he says. “If I put an investment of $50 million into something and make $100 million on it, that’s great. But now I am getting to the point where $100 million doesn’t move the needle. What I need to be doing is figure out how to build platforms that create multi-billion-dollar value.”

When Yamamoto throws the first pitch for the Dodgers in Tokyo Dome tomorrow, Boehly will be there, looking down from his skybox, and swinging for the fences.

This story was originally featured on Fortune.com