Minor leaguers with major aspirations

‘Knocking’ follows players in their quest

Manny Delcarmen made it to the bigs with the Red Sox before being traded. Manny Delcarmen made it to the bigs with the Red Sox before being traded. (Danny Moloshok/Reuters)
By Bill Littlefield
November 23, 2010

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‘You try to rearrange your life for baseball, and it doesn’t give, ever, in the minor leagues.’’

Thus speaks the soon-to-be-ex-wife of Brad Baker not so long after her husband has been tagged a “can’t miss’’ prospect.

Baker is one of the six ballplayers whose careers Marty Dobrow follows as they try to make their way to the big paychecks and glorious perks enjoyed by the small number of men who manage to create careers in the big leagues.

Despite his notices, Baker never became one of the fortunate. Over the course of almost a decade, he bounced around various minor league cities because, according to Dobrow, “baseball [was] still the fuel of his self-esteem.’’ Eventually Baker quit, sort of. In the last glimpse Dobrow gives us of the pitcher whose promise has faded, he is on a high school mound very close to the ballfield where he had wowed the scouts a decade earlier, but on this evening in 2009, Baker is pitching for Teddy Bear Pools and Spas against the best hitters Manny’s Appliances can send to the plate.

Baker’s story is not the least unusual.

Players — even genuine top prospects — probably have to dream hard to stay focused on making the bigs under trying circumstances. The six players featured in “Knocking on Heaven’s Door’’ need all the encouragement they can get, and it comes from their agents, Jim and Lisa Masteralexis, and their partner, Steve McKelvey, who run their DiaMMond Management as a kind of mom-and-pop on a shoestring budget. Besides their agency, Jim Masteralexis works as a lawyer and his wife and McKelvey are professors.

Like the players they represent, life is less than grand for the three. The company runs at a loss until their clients start earning real money. The problem is that very few of DiaMMond’s players make it to the big leagues, and most of those who do end up dumping their longtime, hard-working agents for more wealthy and powerful representation. By the end of the decade or so covered in this chronicle, McKelvey throws his hands up in exasperation at the lack of loyalty, saying that he’s done with working with “with twenty-year-olds. That’s not what I want to do with the rest of my life.’’

All of which is not to say that ’’Knocking On Heaven’s Door’’ is without bright and happy moments. One of DiaMMond’s clients is Manny Delcarmen, who not only made it to the big leagues, but pitched admirably for the Red Sox for several years and appeared in the 2007 World Series. The fact that Delcarmen grew up in Jamaica Plain rooting for the Sox lends a Hollywood luster to the story of his success, though most scriptwriters would have cued the credits before the Sox traded the hometown kid to Colorado last August for a prospect.

Like the many other books and movies set in the minor leagues, “Knocking on Heaven’s Door’’ mentions long bus rides, sportswriters who are invariably “grizzled,’’ groupies in halter tops, baseball executives who can seem heartless, and proud families following the fortunes of their ballplayers as those fortunes rise or tumble, pitch by pitch. If equating a call up to the big leagues with “Heaven’’ is bound to seem excessive to some readers, it apparently doesn’t to the clients of DiaMMond Management. According to Marty Dobrow, even the dreamers who are 30 and still wintering in their parents’ basements would be surprised to hear that anybody could see the object of their yearning any other way.

Bill Littlefield hosts NPR’s “Only a Game’’ from WBUR and teaches English at Curry College. He can be reached at

KNOCKING ON HEAVEN’S DOOR: Six Minor Leaguers in Search of the Baseball Dream

By Marty Dobrow

University of Massachusetts,

323 pp., illustrated, paperback, $24.95