BOSTON—Everyone deserves a second chance, right? Well… how about six? That’s how many the Massachusetts parole board has given convicted killer Charles Hughes — the man serving life for gunning down an 18-year-old during a 1989 Roxbury robbery.

As reported by the Boston Herald, the state parole board has decided to once again open the gate for Charles Hughes — a man serving life for a 1989 Roxbury murder — to walk free for the sixth time.

The Crime That Started It All

In April 1989, prosecutors say Hughes and partner-in-crime Mac Hudson staged a fake drug buy in Roxbury. The plan: pretend to be customers, pull guns, demand both drugs and money. When the victims bolted, Hughes and Hudson chased them down and opened fire.

Eighteen-year-old Derek Twitty was killed. Another man was shot but survived. Eyewitnesses picked both shooters out of photo arrays, and Hughes was arrested a month later outside his girlfriend’s house — initially for disorderly conduct. The murder charge followed soon after.

Life in Prison — On Layaway

In 1990, a jury convicted Hughes of second-degree murder. The sentence: life in prison with the possibility of parole. And for the past two decades, the “possibility” part has played out like a running gag.

Paroled in 2005, revoked. Paroled in 2009, revoked. Paroled in 2016, revoked. Paroled in 2019, revoked. Paroled in 2022, revoked. Now, in 2025, he’s paroled yet again.

DA Says No, Parole Board Says Yes

The Suffolk DA’s office wanted no part of this sixth try. “We made our opposition to his parole clear at the March hearing and we have no further comment,” a spokesperson said — DA-speak for “when this goes sideways, don’t come knocking.”

The parole board, however, painted a far sunnier picture. In their unanimous decision, they said Hughes has “demonstrated a level of rehabilitation” that makes his release “compatible with the welfare of society.” They noted he’s never committed a new crime or fled while on parole — which in most states is considered the bare minimum, not an accomplishment.

Same Script, New Conditions

Every revocation has been for the same reason: drugs and booze. This time, the board is piling on conditions — a 10 p.m. to 6 a.m. curfew, three AA meetings per week, a long-term residential treatment program, a recovery coach, and weekly counseling for both mental health and substance use.

On paper, it’s a carefully choreographed redemption arc. In reality, it’s the same script as the last five sequels — and everyone remembers how those ended.

Life Doesn’t Mean Life in Massachusetts

Hughes’ revolving-door parole history isn’t just a quirky detail — it’s the system laid bare. A “life” sentence that works like a season pass to the exit. Violent offenders failing their way back into the public’s trust over and over again.

For the family of Derek Twitty, there’s no parole, no conditions, no retries. Their loss is permanent. The system, however, seems committed to giving Hughes unlimited mulligans until one finally sticks.

Countdown to Season Seven

So now the question isn’t whether Hughes can stay sober or follow the rules. It’s how long before the parole board finds itself ordering “Season Seven” of this real-life rerun. And in Massachusetts, that renewal is always just one hearing away.