His arrival in the Holy Land caps an unorthodox journey that began in Flatbush, Brooklyn, where he grew up and was shot at the age of 15, passed through the high-flying hip-hop universe, and landed him in a maximum security state prison before he was eventually deported to Belize - where his father happens to be prime minister.
"Being in Israel is just the exclamation point," he said Thursday. "This is the ultimate place to be who you are."
During a two-hour conversation on a hotel balcony overlooking the walls of the Old City of Jerusalem, Shyne said his connection to Judaism goes back to his childhood - when he was still known as Jamaal Michael Barrow.
His mother claims Ethiopian Jewish ancestry, but the man who now calls himself Moshe Levi Ben-David says his roots go even deeper and that even as a boy in the streets, he was oddly drawn to Judaism and identified with its biblical heroes.
"I grew up in a war, constantly battling and the only person I could relate to was King David. Of course I love Michael Jordan, I love Mike Tyson, I love the typical people that people love, Muhammad Ali, but I had more of a connection with King David," he said.
Shyne, 32, has swapped his hip-hop attire of oversized basketball jerseys and diamond studded teeth with the traditional black suit and white knee-high stockings favored by the Belz Hassidic sect. He wears a black skullcap over his shaven head, but in a reminder of his former life, he still wears stylish black Ray Ban sunglasses.
Where he once rapped about loose women, fancy cars and hollowpoint bullets, he now fires off staccato sentences about Jewish law, peppered with Yiddish, in the same raspy voice once compared to that of the Notorious B.I.G.
"Wherever I go it is going to be the same shtick. This is who I am, you dig," he said.
In his teens, he was discovered by Combs - then known as Puff Daddy - who signed him to his Bad Boy record label. Shyne embraced the lifestyle of women, booze and partying but said he was already turning it around when "the incident" happened.
In late 1999, Shyne was out one night at a Manhattan club along with Combs and his then-girlfriend, Jennifer Lopez, when he was involved in a high profile shooting that left three people injured.
Combs was cleared of gun possession charges but Shyne was sentenced to 10 years for assault, gun possession and reckless endangerment. Shyne says he acted in self-defense after someone else pulled a gun.
It was in prison where he said he became "Baal Tshuva," the Hebrew term for a newly observant Jew. He changed his name, prayed regularly, kept kosher and observed the Sabbath. His faith helped him come to peace with his troubled past and his lengthy incarceration, saying it was God's will and part of his 'Tikkun' - a spiritual voyage to make amends.
"He (God) gives kindness and He gives judgment. I've done some terrible things in my life, I've not always been the best person I can be and I gotta pay for those mistakes," he said. Proclaiming his innocence in the shooting, he said, "my guilt is endless for a lot of other things that I didn't get caught for, so that is how I try to look at it."
He was released a year ago and then deported to his native Belize while appealing his U.S. deportation. He reconnected with his estranged father, Prime Minister Dean Barrow, and he now serves as a goodwill ambassador.
He arrived in Israel several months ago for the Jewish New Year and has since undergone a conversion process and a symbolic circumcision.
Amid his religious studies he is preparing a comeback. His two new albums, "Gangland" and "Messiah," are scheduled to be released in March by Def Jam records.
His goals now include becoming the biggest music star in the world, but also marrying an "Israelite" and building a religious seminary in Jerusalem for Ethiopian children. More than 120,000 Ethiopian Jews now live in Israel.
The journey has influenced his music. He says the themes of helping others by highlighting injustice remain the same, but he has toned down his rhetoric.
"I naturally stopped using the N-word, I naturally stopped being misogynistic," he said. "My connection to God is the water that nourishes who I am and allows me to grow."
But Shyne said he can't forget his past altogether.
"I still drop the F-bomb ... but overall I am not the same person, 10 years of not having a woman, 10 years of not being able to kiss my mother makes me love women on a level that I never loved woman," he said. "I can still blow somebody's head off if they try to hurt my mother. We all have that in us."