Goldstein was hired by general manager Jeff Luhnow to oversee the Astros' pro scouting efforts, which includes comprehensive scouting of both Minor League and Major League players across the 30 teams, as well as independent leagues and foreign professional leagues.
"I know Jeff is sticking his neck out when he brought me on, and I totally respect that," Goldstein said. "It's something that drives me to prove him right and try to help this team."
His background might be unusual, but he's certainly no stranger to compiling respected information. He specialized in scouting and player development during his time at Baseball Prospectus and had developed a solid network of working relationships within the industry among scouts and general managers.
Goldstein's efforts nowadays are focused on trying to help restock and reshape an Astros team that's rebuilding through the Draft and player development.
"My job is to do the best to stay ahead of Jeff and the other 29 organizations in baseball," said Goldstein, who lives in DeKalb, Ill. "When something comes up via a trade or Minor League free agency or anything involving players below the Major League level, my job is to come in with recommendations. It's still the same job, talking to scouts and trying to gather information, but now I'm just talking to our scouts."
Goldstein was at the helm when the Astros drafted a pair of players in the Rule 5 Draft earlier this month, including No. 1 pick Josh Fields, a hard-throwing pitcher. He'll be instrumental in Houston's preparations for next year's First-Year Player Draft as well. The Astros have the No. 1 overall pick for the second straight year.
The fact that Goldstein holds such an important job in the Major Leagues is surprising when you consider his background.
He didn't attend college and instead jumped right into the real world, working for an international consulting firm at 19 years old. He grew up in Ohio as a Mets fans because of his New York-based family, which couldn't stand to root for the Yankees after the Dodgers bolted Brooklyn for the West Coast in the 1950s.
Goldstein grew up a classic baseball fan and collected baseball cards. His world changed, however, when he got his hands on a copy of the Bill James Baseball Abstract in the 1980s. James' books were considered a predecessor to publications like Baseball Prospectus.
"That was a watershed moment for me," he said.
It wasn't until Goldstein, who dabbled in the interactive industry and worked in consulting and marketing, started writing for Baseball America and developing his email prospect newsletter did he one day envision working for a Major League club.
"It was something fun that I had a passion for," he said. "I started Prospect Report, and it started growing on a strange level and some teams were interested in the information I was putting out there. One day, [MLB.com's] Peter Gammons mentioned it an article when he was still at ESPN, and that was kind of the explosion."
Suddenly, Goldstein had 10,000 subscribers and a growing reputation as the go-to analytical mind when it came to scouting reports. Teams took notice, including the Astros. When he was hired last December, Luhnow put an emphasis an analytics and was a fan of Goldstein's work. The GM requested a meeting with him while the Astros were in Chicago to play the Cubs.
"You get an invite from a GM and you say, 'Yes!'" Goldstein said. "We talked for about three hours and it was a really good conversation, very direct conversation. I thought it went really, really well, and Jeff did, too. We finished it up with him telling me he'd like me to fly to Houston for more formal discussions."
The Astros hired Goldstein, and a dream was fulfilled. Goldstein is just one in a handful of new-age hires by Luhnow, each of whom will be counted upon to help get the Astros get back to respectability on the field and into contention in the AL West.
"Jeff is an information junkie and he wants everyone's opinion on everything," Goldstein said. "That's fantastic. When we're talking about trades or free-agent signings, he'll look at me and say, 'What do you think?' That's a big role, and I'm completely honored to be part of this."