In 1999, Dobrow traveled to rural Leyden, Mass., on an assignment for now-defunct SPORT magazine. His mission was to chronicle the Draft day experiences of Brad Baker, a promising 18-year-old right-hander ultimately selected by the Boston Red Sox as a supplementary first-round pick.
It was a dramatic day, to be sure. A large contingent of friends and family gathered at the Baker residence, anxiously following the Draft via a sputtering dial-up internet connection while waiting for the phone call that would change everything.
"I was taken with the experience; it was so rich and so colorful," recalled Dobrow of his time spent with the Baker clan. "It really stuck with me, so I visited again in 2005 and reconnected with Baker. I got to know his team of agents, and in talking with [agent] Jim Masteralexis I soon realized that there was a much larger story to be done. From there it became a source of considerable obsession."
Knocking On Heaven's Door is the result of this obsession, a book that painstakingly chronicles the professional careers of Baker and five other clients of DiaMMond Management (a "mom and pop" agency headed by Masteralexis and his wife, Lisa). Also profiled are pitchers Charlie Zink, Manny Delcarmen and Matt Torra and outfielders Doug Clark and Randy Ruiz.
The "Heaven" of the book's title is, of course, the Major Leagues. While four of the six aforementioned players have reached this promised land (however briefly), the journey is epic, and nothing is guaranteed.
"The Minor Leagues are a place of yearning, and what fascinates me is the anguish of almost," said Dobrow. "You're so close to something you want so much and that most won't get, and that dynamic is fascinating. They're all enormously talented people who have survived so much winnowing, and that's a considerable achievement. But no one grows up wanting to be a Minor League Baseball player."
The long odds and grueling nature of Minor League life lead to what Dobrow calls a "contradictory culture."
"On one hand, nothing could be more wholesome [than Minor League Baseball]," said Dobrow. "It's family-friendly, with the mascots dancing on top of the dugout doing the YMCA. And the players are so earnest and unjaded at this point in their careers, which leads to an authenticity you seldom get [in sportswriting]."
"But it's also a savage world, where an injury to a teammate who plays the same position as you is a good thing," he continued. "And the financial discrepancies are remarkable. In the Majors the minimum salary is $400,000 and the average is $3 million. But there are a lot of terrifically talented players out there only making $10 or $15,000 a year. That cut-off is unlike anything I know of in our culture. You can be a near-great doctor and still be well compensated."
This mammoth gap between the baseball haves and have-nots leads to all manner of corner cutting, and one of the (many) dramas that plays out in Knocking On Heaven's Door involves the temptation of performance-enhancing drugs.
"I wanted to show that dilemma from the Minor League perspective. It's a different moral equation than when it involves the Clemenses and Bondses of the world, guys who have made their fortunes many times over," said Dobrow.
This struggle is personified in the stories of Clark and Ruiz, with the former steadfastly staying clean and the latter succumbing to temptation.
"Some questionable choices were made, but I wanted to present everything in context," said Dobrow. "It was important for me to visit these players, meet their families and see them in their own environment."
In doing so, Dobrow ended up traveling from "Portland, Maine, to Portland, Ore., and lots in between."
"I wanted to be there for the richest moments, whether that was Brad Baker's pro debut in Florida, going to the Clark household to watch one of Doug's games on TV, or sitting with Charlie Zink's mom and girlfriend at Fenway when he finally made his debut," he said. "This is a family journey. I'm interested in Brad Baker's grandmother staying up past midnight to listen to game webcasts, or Randy Ruiz's grandmother banging on doors in the Bronx in her nightgown yelling 'Randy made it! Randy made it!'"
But for every such moment of triumph, there are many of despair. The book's protagonists get demoted, traded, released and injured while trying to navigate personal relationships and maintain a sense of normalcy in their day-to-day lives. It's no easy task.
"There's so much failure in the game, but that's part of the journey and something I didn't want to shy away from," said Dobrow. "It's important to provide an honest and authentic picture of these harsh realities."
This leads to an important question when it comes to contextualizing a professional baseball career: How does one define success?
"The Baseball Encyclopedia will show that Doug Clark collected one hit in 11 [Major League] at-bats, and that's likely to be the final entry. He's 34, and while he might resurface, that's highly unlikely," said Dobrow. "But behind that one hit is a marvelous story, one of tremendous success. His long haul in the Minors deeply enriched him as a person, and he's become a great ambassador for the game."
And that helps illuminate the larger point, one that Knocking On Heaven's Door makes so well.
"Baseball transactions are listed in the newspaper in small agate type, just a record of who was released, promoted or traded," said Dobrow. "But beneath every line is a rich human story."