Texas Longhorns baseball coach David Pierce was torn. A Houston native, Pierce has always been a diehard Astros fan. He’d suffered through Houston’s many postseason heartbreaks, and he was hoping that 2017 would finally be the the team’s year to win the World Series. He just didn’t like that they would have to beat the Los Angeles Dodgers to do it. He couldn’t root against the Astros, but the thought of rooting against a former player pained him. And one of his former players happened to be Dodgers president Andrew Friedman.

In the early nineties, Pierce was an assistant coach at Houston’s Episcopal High School, and Friedman was his leadoff hitter. They won a Southwest Preparatory Conference championship together in 1995. Pierce still felt a pull toward his old pupil, so he settled on a compromise. He grabbed his phone and tapped out a message to Friedman. Good luck, he wrote. I’m pulling for you. It’s mixed emotions for me, but I want your team to do well.

In the end, of course, the Astros won the most infamous World Series of the modern era (although the recent controversy around Dodgers third baseman Justin Turner violating COVID-19 protocols may qualify the 2020 series for an honorable mention). Pierce learned his lesson. This year, after the Tampa Bay Rays eliminated the Astros in the ALCS, his loyalties were entirely with the Dodgers. But he didn’t dare send Friedman a message. He didn’t want to risk another jinx. Instead, the superstitious coach watched and waited through the roller-coaster six-game series. Finally, after Julio Urías retired the final three Rays batters on Tuesday night, Pierce grabbed his phone again. This time the message was unequivocal: Congratulations!

 “I was thrilled for him,” Pierce says. “He was always so driven to win. That was what stood out about him all those years ago. He wasn’t an exceptional player, but he was an exceptional teammate. He made everybody else better, and that’s what he’s doing now. His success doesn’t surprise me.”

For the 43-year-old Friedman, the World Series win was the culmination not only of an unusual postseason played during a pandemic, but also of an improbable baseball journey. Friedman first swung off a tee in Houston in 1981, and now he was hoisting the Commissioner’s Trophy just four hours up Interstate 45 in Arlington. To make a career in baseball, he’s had to move to nearly every corner of the country. And to reach that pinnacle, the pennant, he had to return home to Texas.

Friedman played shortstop for the West University Cheetahs in 1988.Courtesy of the Friedman Family

Friedman inherited a love of baseball from his father. Kenny Friedman played as an infielder at Episcopal and at Tulane before returning to Houston to become a prominent lawyer. Among Kenny’s clients were the Houston Astros, and the family had season tickets behind home plate. But watching those pro players from some of the best seats in the house wasn’t enough for Andrew. He wanted to get closer to the action.

When Andrew was in elementary school, the Friedmans developed a routine around home games. After school, Kenny or Barbara, Andrew’s mom, would pick their son up and take him to the Galleria—in those days, “the most cosmopolitan space in Texas,” as Texas Monthly’s Richard West wrote of the famed Houston mall. The young Friedman, with a stack of cards in his backpack, would station himself at the visiting team’s hotel and wait for players to appear. The almost outrageous work ethic that has marked Friedman’s career as an executive—working through an appendectomy and the birth of a son—dates back to those afternoons spent collecting autographs.

Friedman once asked Montreal Expos legend Tim Raines to sign fifty cards. Raines took the deck to his hotel room on the first night of the series and returned them all, signed, the next afternoon. As he got older, Friedman learned that he could get more signatures if he provided the players with some sort of service. So he made a mental map of every store in the massive mall, and he’d tell the major leaguers where they could buy a toothbrush or a gift for their wives.

From the Galleria, Friedman would walk himself to the Astrodome. And even though he never had his ticket, he always found his way into the game. “He was out there so much,” Kenny Friedman says, “that the guards thought he was one of the player’s kids.” When Kenny arrived at the stadium, he’d often descend the stairs to discover that his seat was occupied. There would be a stack of signed cards, cleats, and jerseys that his son had spent the afternoon collecting. During the game, the two would discuss stats and strategy. “This has been in his blood since he was a very small child,” Kenny says.

Even away from his home turf in Houston, Friedman would find ways to score autographs. When Kenny Friedman traveled to baseball cities for work, he’d often bring his boys and stay through the weekend. On workdays, Kenny would take care of his business and bribe the bellhop to help make sure Andrew and his brother, Brent, didn’t cause too much trouble. Once, on a trip to Chicago, they wound up at the same hotel as the visiting Expos. When Kenny returned from work, the seven-year-old Andrew told him that he’d talked to Pete Rose.

“What’d Mr. Rose have to say?” Kenny asked.

“He said, ‘Get out of my way, kid!’” Andrew reported.

Then Andrew flashed a signed card in front of his father and smiled.

Autographs weren’t all he took from legends like Raines and Rose. Friedman also studied their games and their styles of play. By the time he was seven, he was so much better than his peers that he moved up to play with eight- and nine-year-olds in the West University Little League system. He didn’t start his first game, but within a few innings he’d wormed his way onto the field at second base. Soon, he was repositioning the infielders. “The other parents were like, ‘Who is this kid?’” Kenny says. “He’d only been on the team for thirty seconds.”

Even when he moved to centerfield, Friedman would still manage his teammates. He preferred the other outfielders to play as far away from him as possible, so he could wind up with more catches. “He had speed,” says Mike Seamen, who coached him in club ball from ages thirteen to eighteen. “He had a great arm. He could hit. The only thing he couldn’t do was pitch. I tried. I tried and tried. He had a very live arm. He just couldn’t get it over the plate very often.”

In a funny bit of foreshadowing, Seaman’s team happened to be named the Dodgers. On fields from Pershing Middle School to Rice University, Friedman developed a feel for the game that still balances the Sabermetrics in his decision-making to this day. He also developed the batting and baserunning ability that made him a standout youth player. Friedman was such a skilled runner that he’d sometimes taunt opposing teams by running halfway between first and second base, then stop to challenge the catcher to choose which bag to try throwing him out at. “I batted him leadoff because he’d normally bat his way onto first,” Seaman says. “Three pitches later, he’d be at third. Then all I needed was a pop fly.”

At Episcopal, Friedman’s high school teammates took to calling him “Pig Pen” because of the dust cloud that accompanied him into every base. He always seemed to slide in head first. “I can’t recall a time his jersey was clean after the first inning,” says Brad Kirklin, who played with Friedman and now works as an attorney at Houston’s Henneman Rau law firm. “If there was a base to be taken, he’d take it. He was always hustling. He was sort of like our little Pete Rose.”

Friedman adopted every trait of the major leaguers he admired—including their penchant for chewing tobacco. The school forbade students to use tobacco products on campus, but that didn’t always stop the baseball players. One day, he and a teammate named Patrick Hall stayed after practice to take a few more swings in the batting cages. They thought they’d gotten away with the big rigs they’d stuffed in their lips, but when a coach caught them, the two were made to run back and forth, from foul pole to foul pole, until they were on the brink of puking.

Many former teammates remember Friedman in that way—as a hardworking but fun-loving teammate who thought of little besides baseball. None of them anticipated he’d grow up to orchestrate two separate franchises’ World Series appearances. “We all sort of had those distant dreams,” Hall says. “But most of us just hoped to play in college and get another four years out of it. Andrew was a hustler. He was a go-getter. But did I think he’d end up in a front office, doing Moneyball stuff? No. I never would have guessed it.”

Another teammate, Temple Brown, says he would have bet anything against Friedman becoming a baseball executive back then. But now, looking back, he can see the signs. Even in high school, Friedman could do complex math equations in his head. In college, Brown went to Southern Methodist and Friedman to Tulane. When Brown visited, Friedman would fund their nights out in New Orleans by playing video poker. He never lost money and often ended up with $100 or more. Friedman introduced Brown to horse racing and had a knack for picking long shot winners. And he could talk his way into any situation. In high school, he seemed to have a permanent hall pass. And once, when Friedman visited SMU, the pair persuaded thirty female classmates to let them borrow their cars. The stunt had no point beyond just being able to look out at a row of BMWs lined up on the curb.

“He was in love with the game,” Brown says. “His family had some great connections in Houston. And I think he had some skills and talents that the casual observer would never have noticed. It’s been fun, over the years, sending him so many congratulatory texts.”

As with almost all high school bonds, many former teammates fell out of touch with Friedman over the years. But once he became MLB front office royalty, old friends reconnected, sending blind emails to his public Dodgers account. Friedman has never failed to respond. He’s reunited with many at ballparks around the country, though he draws the line at giving free tickets to Astros fans when the Dodgers play in Houston.

Some of his other childhood relationships have stayed strong even as Friedman has crisscrossed the country, from New York to Florida to California. Mike Seaman was so taken by the kind of kid Friedman was that he and his wife, Tina, named their son Robert Andrew. He goes by Andrew.

As their careers have progressed in parallel, David Pierce and Friedman have also remained close. When Pierce scouts in Los Angeles, he visits his former leadoff hitter at Dodger Stadium and enjoys an evening at club level. This June, Pierce felt his Longhorns had fallen into a rut. The coronavirus had cast uncertainty around the season, and players couldn’t even show up to campus yet. Pierce decided to host Zoom calls with his squad and a collection of some of the brightest minds in baseball. One of the guests was Friedman. The call was scheduled to last thirty minutes, but Friedman answered questions for more than an hour. The long call left Pierce and Friedman little time to catch up, but the coach made sure to tell Friedman that he’d put together one hell of a team in Los Angeles, and that he hoped the Dodgers would have the chance to compete for a championship.