Jennifer Gonnerman closes Life on the Outside by recounting her subject's recurring dream. In it, Elaine Bartlett returns triumphant, decked out in her finest outfit, to Bedford Hills Correctional Facility, where she was locked up for almost two decades. She's swept through the building like a VIP and taken to a gathering at which she delivers a rousing speech against drug laws. "Remember when you used to look down your nose at me?" she admonishes her mythical audience. "Well, look at me now."

Years after her release; after having successfully navigated high-stakes battles with her parole officers, her employers and her family; and after having developed an activist's fame through news stories like those Gonnerman filed for the Village Voice, Bartlett's highest hopes are still not centered in the free world but, rather, squarely inside Bedford Hills.

It's the perfect coda to Bartlett's biography, crystallizing the book's primary theme: Once you go to prison, you never really leave.

Having spent her life's formative years at Bedford, it is no surprise that Bartlett still views both her successes and failures through its frame. This is perhaps the most demoralizing aspect of the high incarceration rates and absurdly long prison sentences created by the Rockefeller drug laws: The imaginations of too many black New Yorkers are bound by the justice system.

Yet the world people face when they get out of prison is filled with other, more concrete obstacles. Gonnerman illustrates these legal and social landmines by deftly blending Bartlett's personal journey with explanations of the policies that complicate ex-cons' lives. She doesn't divert the narrative into lengthy histories and analyses, but she does pause long enough to point out how and why policymakers carefully laid each of the traps Bartlett stumbles across--from those that landed her in prison in the first place, to those that keep her from leaving it behind.

Gonnerman begins with the chilling tale of Bartlett's 1983 arrest in an Albany sting. Her case is extreme: She was set up by a drug-dealing police informant. Nonetheless, it illustrates the zeal with which cops, prosecutors and judges enforced the Rockefeller laws throughout the 1980s. When she was 25, Bartlett's first offense--transporting coke from Harlem to Albany--got her 20-to-life.

One of the book's most affecting passages juxtaposes Bartlett's fate 17 years later with that of those who destroyed her life. After recounting Bartlett's deliberately humble performance for a parole board in 1999, Gonnerman tells us that, by this point, the lead cop had become deputy superintendent of state police. The informant had been arrested for a later cocaine deal but was a savvy enough defendant to plead to a lesser charge and get a mere six years. (He later died of an overdose.) And the state's annual prison budget had grown from $450 million when the Rockefeller laws passed in 1973 to $1.7 billion.

Bartlett's notoriety as an inmate activist and her song and dance for the parole board got her onto Governor Pataki's clemency list in 2000. But when she got home, she realized that much of her life was still governed by the criminal justice system.

Gonnerman focuses on Bartlett's difficulty navigating parole. She illustrates how, ironically, the primary challenge isn't the rules--curfews, travel restrictions, even bans on what sort of pets you can have--but the way they're enforced. Your future depends largely on which parole officer you draw, and how that person chooses to wield the law.