Authors: Jonah Keri
When Wayne Clevinger first met Friedman, he saw the potential for all those qualities. Clevinger’s firm, MidMark Capital, based in Morristown, New Jersey, is a small private equity shop that manages $300 million in funds. MidMark constantly searches for promising young junior associates. The typical path might see the company hire someone in his early to mid-twenties, keep him for a couple years, then wish him well as he heads off to get his MBA. It’s a stepping-stone job for many Wall Street neophytes, though a few young associates will return from business school, then rise through the MidMark ranks. Within a few months, Clevinger realized that
his new hire wasn’t going to grad school to get his MBA, nor did he need to. Instead, MidMark would bump him up to senior associate in just two years, an unprecedented move by the company.
“He was the complete package,” said Clevinger, MidMark’s cofounder and managing director. “He had a winning smile and great personality. He was so damn bright, he actually appeared bored at times—he
was
bored. So we got him doing projects a junior partner would normally handle, and he handled them well. We wanted to make him a partner as quickly as possible.”
Clevinger recalls the moment he knew Friedman was destined for big things. A couple of months into Friedman’s tenure at MidMark, Clevinger and most of the other partners and senior associates had to attend a black-tie affair. It was a delicate time to drop off the grid: MidMark was trying to nail down the purchase of a home health care company, but the two sides remained far apart on price. Clevinger left for the gala, frustrated by the lack of progress. He called Friedman, who was working late as usual. Did he want to take a shot at wrapping up the transaction, Clevinger wanted to know.
“I can wrap it up if you like,” Friedman told his boss, “or do even better if you like.” The young associate believed in his negotiating skills and had a handle on all the numbers. “It’s your baby, full speed ahead,” Clevinger said, eager to see what Friedman could do. Friedman closed the deal as promised. He also materially improved its terms, as promised.
Friedman’s duties expanded rapidly. At any given time, MidMark might have held fifteen companies in its portfolio. Friedman’s job was to do the modeling for all of them—to project revenue and net income streams and break down best- and worst-case scenarios based on the dynamics of their particular industries. Crunching the numbers came easily to him. But taking the numbers and wielding them in negotiations? That, he loved. Friedman helped negotiate company purchase prices, lining up all manner of financing and using stock options and other incentives to convince a company’s
senior management to put their own skin in the game. He advised MidMark when to make a modest investment and when to go all-in on a company with big potential.
Sternberg kept in close contact with Friedman. Already working the kind of breakneck hours typical of a young Wall Street associate, Friedman toiled into the middle of the night on his own time, doing financial analysis to assist Sternberg’s Devil Rays bid. When Sternberg and Silverman closed the deal to purchase the 48% stake in the Devil Rays, they wooed Friedman to join them. Friedman had no experience of any kind in a baseball front office. But it wasn’t hard to see how his combination of analytical and people skills could translate to baseball. If he could forge a compromise with high-powered business execs, he could work out contracts that would benefit a baseball team and its players. If he could persuade a CEO to take a mutually beneficial risk, he could do the same with another team’s general manager. If he could run complex mathematical models to gauge the value of a financing deal, he could weigh the merits of a baseball trade. That was the thinking anyway.
“A really smart, analytical GM is going to be better than one who is not as analytical,” said Matt Finley, another managing director at MidMark. “If you have the ability to get to nuggets of truth, you have the ability to perform better than someone who manages by the seat of his pants. That’s my belief in anything. Any complicated business can benefit from serious analysis, if there are enough data available.”
Sternberg made his pitch: if he came to work for the Devil Rays and learned the ropes for a couple of years, when the ownership transfer was done Friedman could run—or at least co-run—the baseball side of the team. It was an offer that required guts to make, and guts to accept. The Oakland A’s quantitative approach to winning on a budget had been compared to the methods used on Wall Street. But no one had successfully parlayed a career on Wall Street into the role of major league general manager before. Meanwhile, Friedman, like Silverman, would be leaving what could be a hugely lucrative career behind if he accepted Sternberg’s offer. His
decision was in many ways far more difficult than Silverman’s: Friedman was working on multimillion-dollar deals every day, on his way to making partner at a successful private equity firm, while Silverman had willingly stepped away from the rat race to pursue other ventures.
Friedman went home to Houston to mull the decision with his family. His father told him to stay with MidMark. His girlfriend wanted to stay in New York rather than move to Florida. His mother had a different take.
“She told him, ‘Andrew, you have to go with your heart on this,’ ” Clevinger recalled. “I thought, ‘Oh boy, we’re done.’ ”
Friedman took the job with the Devil Rays, with the nominal title of director of baseball development—though he and Silverman would soon gain promotions. When Sternberg seized control in October 2005, Silverman took over as the youngest team president in baseball, while Friedman became executive vice president of baseball operations, joining Jon Daniels of the Texas Rangers, another young gun plucked out of the business world, as the two newest members of “the Twenty-Something General Manager Club.”
Baseball wouldn’t have been ready for Silverman and Friedman five or ten years earlier. But the two men benefited from their own good timing. With the help of Dan Feinstein (a onetime video coordinator with the A’s who was also featured in
Moneyball
), former Houston Astros general manager Gerry Hunsicker, and other baseball veterans, Friedman could assume the role of GM, knowing baseball had started to accept people with younger, nontraditional profiles in that role. With the help of skilled, handpicked sales, marketing, and operations people, Silverman could also settle in. Not only did Silverman and Friedman join the Devil Rays at just the right time, but they left their Wall Street careers behind right on time too. Friedman’s first employer, Bear Stearns, would collapse during the Wall Street meltdown of 2008—the husk of a once-proud company was sold off to JPMorgan Chase. Silverman’s former employer, Goldman Sachs, would remain very much intact, though it would become a symbol for Wall Street greed and impropriety,
absorbing multiple accusations of everything from accounting irregularities to the U.S. subprime mortgage and European debt crises to an excessive coziness with the federal government that allegedly enabled the company to escape serious repercussions.
Silverman and Friedman experienced one of the biggest shifts from their old existence almost immediately. Neither would sign contracts, instead considering themselves, as Friedman said, “employees at will.” Sternberg and his two young hires trusted each other. They sought to build an environment where everyone in the organization could do their job without fear of someone else micromanaging or undermining them—those types of bullying being hallmarks of the Naimoli era. Silverman and Friedman would thoroughly vet every hire, searching for people who not only were business- and baseball-savvy but were also self-starters; they meant to create a culture in which independent thought was rewarded rather than punished.
The organization had its first cathartic moment at Halloween 2005, immediately after operating control passed to Sternberg. Working under Vince Naimoli and his minions had felt like being the protagonist in
Office Space
, who fills out just enough TPS reports to avoid getting dressed down by each of his eight bosses. But under Sternberg, Silverman, and Friedman, a raucous Halloween party broke out instead, with the entire office staging a spirited costume contest. A group of staffers dressed as “the Ghosts of Devil Rays Past,” honoring the unfortunate Tampa Bay legacies of Vinny Castilla, Wilson Alvarez, Paul Sorrento, Lou Piniella, and others. Chaim Bloom, a player development intern who would rise to become assistant director of minor league operations, stole the show, dressing as Greg Vaughn’s regrettable four-year, $34 million contract and having everyone sign it for him.
“People had been beaten down by the Vince regime,” said Phil Wallace, who spent two years as a special projects analyst with the Devil Rays, researching and assisting on multiple projects, including an eventual name, logo, and uniform change. “It was refreshing
to let people do what they needed to do, to incentivize people for good work, and to have everyone actually enjoy coming to work every day. Sometimes it was just the little things. The first week or two [after Sternberg took over], they put up a suggestion box. It was the first time people were really allowed to express their opinions,
ever
.”
Both Silverman on the business side and Friedman on the baseball side began delegating responsibilities, trusting others to perform their appointed tasks while the executives handled their own. They were following the example set by Sternberg, who spent most of his time in New York; he talked to Silverman often but otherwise let his people run the show. How that delegation took shape varied, though, as the differences between Silverman’s and Friedman’s personalities became evident.
Silverman looked the part of the Brooks Brothers–clad Wall Street graduate. He frequently went out into the community, eager to repair the damage done by Naimoli’s combative approach, be it with the local Chamber of Commerce or at Little League field dedications. All the while, Silverman listened first and spoke second, without revealing too much information—typical of the close-to-the-vest style of a Goldman Sachs banker. The only thing missing was the Wall Street attitude. When Silverman joined Keli McGregor, Jeff Cogen, and other MLB presidents for league meetings, he carried himself differently from the rest.
“The egos in those rooms are not real open to suggestions and change,” said Cogen. “But Matt wasn’t like that. With him, it was more, ‘Tell me why you do things this way.’ ”
Friedman could be equally guarded about information, despite his more gregarious personality. When he later went on to make trades, the media wouldn’t find out beforehand because he hid his intentions like Phil Ivey at a final table. But Friedman also showed emotion. As Billy Beane did during A’s games, Friedman often hit the treadmill during Devil Rays games to avoid getting too worked up over his team’s play. He also maintained some of the habits
formed during his youth. Friedman was not only baseball’s first Wall Street–trained GM but the first to describe the concept of arbitrage in baseball while ejecting a stream of tobacco juice from his mouth.
Friedman was also the first GM to make video games a regular part of his stress management regimen. Soon after Sternberg took the reins, the organization spruced up Tropicana Field, adding fun features whenever possible. One section, “the Mountain Dew Extreme Zone,” included a setup for stickball and an adjacent video game area. The most popular of those games was “RBI Baseball,” complete with the old Nintendo console. When the season ended, someone got the idea to bring the game up to the Devil Rays’ offices. It ended up in the baseball ops conference room. Friedman hadn’t played the game since the 1980s, but like many baseball fans and gamers his age, he was still a sucker for its fun-and-easy format. Soon, nearly everyone in the front office was playing. They’d hold NCAA tournament–style brackets, bringing in as many as thirty-two office employees to battle for supremacy. Friedman and baseball operations director Dan Feinstein would usually be the last two standing. Friedman was once again working impossibly long hours (as he had on Wall Street), and “RBI Baseball” made for a great way to blow off steam.
He didn’t like being interrupted, though. Sandy Dengler, Friedman’s assistant and director of baseball administration, walked in one day while he was playing. “Dan O’Dowd is on the phone,” she said. “Damn it!” Friedman yelled, slamming down the controller to take the call from the Colorado Rockies GM.
During the 2007 draft, Friedman’s love for “RBI Baseball” and his supreme trust in his staff collided. The game had to be moved out of the conference room so that scouting director R. J. Harrison and a phalanx of scouts and cross-checkers could form their own war room. The Devil Rays took Vanderbilt pitcher David Price first overall, following Friedman’s recommendation. Knowing Tampa Bay wouldn’t pick again until number 65, Friedman snuck out to play some “RBI,” getting fed frequent updates while reveling in eight-bit glory. He would return for the team’s second pick, then
duck in and out multiple times thereafter. By the middle to late rounds, though, he’d left the drafting to Harrison and the scouts. While teams threw darts at late-round lottery tickets, Friedman and Feinstein scooted down the hall to battle for the “RBI Baseball” championship of the world.
“He doesn’t make you feel that you’d better toe the line and not goof off because he’s the boss,” said Josh Kalk, the team’s baseball operations analyst. “Even when I hadn’t been there very long, it felt like my opinion had some weight to it, that they valued it.”
Outsiders agreed. The Devil Rays’ willingness to divvy up responsibilities wouldn’t just make employees feel more valued. With the role of GM or team president evolving into a job filled with complex analysis and far-flung decisions, farming out tasks was the logical and necessary next step to take.
“We’re transitioning away from the GM as superhero,” said Vince Gennaro, author of
Diamond Dollars: The Economics of Winning in Baseball
. “Today you have to have an infrastructure in place if you want to successfully run an organization.”