For the first time in 25 years, Philip Pynn is a fully free man after a sentence of time served for smuggling drugs into Her Majesty’s Penitentiary.

Pynn’s 2014 trial and manslaughter conviction made him the face of celebrity criminality and the so-called St. John’s mob.

But it’s the sheer length of his record, dating back to 1999, that’s earned him the moniker of career criminal.

Now, his longtime lawyer Mark Gruchy believes Pynn is ready to retire, after being sentenced to time served with no conditions attached.

Philip Pynn, 39, is escorted into provincial court this afternoon in St. John’s. He was later sentenced to time served for assault and smuggling drugs into HMP, and is now a free man, with no conditions, for the first time in 25 years. pic.twitter.com/7fSWJBvSCf

— VOCM News (@VOCMNEWS) June 27, 2025

Pynn, 39, actually got almost 4.5 years for breach of probation, assault, and twice smuggling cocaine, fentanyl and the horse tranquilizer Xylazine into the Pen.

And twice he almost died doing it, as drugs hidden in his mouth, down his leg, behind his scrotum and in his rectum seeped into his system and he was rushed to St. Clare’s, where several times he flat-lined and was brought back by staff.

He had inserted the drugs in a rush as police arrived to arrest him for breaching curfew conditions.

But Judge Rolf Pritchard accepted a joint submission from Gruchy and the Crown, Trevor Bridger and Robert Roach, for a 53-month sentence, equaling enhanced credit for the time Pynn has spent on remand at HMP.

Court heard that one of Pynn’s first stops will be the John Howard Society, to help him get clean and stay out of trouble.

Pynn was asked how he felt moments after the decision.

“It feels really good. Really, really good. First time since I’ve been 13 that I’ve been actually free.”

Asked if he thought Pynn would stay that way, Gruchy replied, “Hopefully.”