A Ride Through Smitty Bop’s New Haven

Smitty Bop boasts he is ​“so New Haven.” And he is telling the world in detail what that means — in song, and on video.

“I love my block,” he proclaims in one of his newer videos.

The rising rapper also has this to say about his hometown:

All I see is drug dealing, gang banging …/
Life’s a gamble, that’s why we carry eights …/
You’re Kermit Carolina and I’m Toni Harp/
Which means I’m winning and you losing …/

Those last lyrics come from one of his first music videos, ​“I’m So New Haven.” He released that one in 2014.

Smitty Bop — aka Smitty, aka Michael Smith, 25-year-old graduate of Wilbur Cross High School, son of Newhallville and the Tre, musical performer and recording artist — had already been shot before he made that track. By the time he unleashed a cascade of new music and videos in 2019, he had already learned what life is like behind bars and then back on the streets.

He lived to tell the tale. And leaped back into the music.

Smitty discussed his musical journey, and how it reflects his lived experience in the city he loves, during a candid interview Thursday on WNHH FM’s ​“Dateline New Haven” program. (You can watch the episode above.)

On the program, for the benefit of people with different lived experiences of New Haven, Smitty also broke down some of the references in three of his videos, including the one with those Carolina-Harp lyrics.

The video, ​“So New Haven,” follows teenaged Smitty from the summit of East Rock to College and Crown streets to the intersection of the Farmington Canal Trail and Thompson Street, by the Newhallville block where Smitty spent his formative years after his family moved from Henry Street. The block shows up not just in this video, but others.

I’m so New Haven/
203/
Shout out my community …

He discovered his love for rap at dance parties during middle school at Wintergreen Magnet. The school gave kids laptops. In sixth grade, Smitty started bringing his computer home after school and recording tracks with his buddies on Thompson Street. They took beats from Youtube and recorded over them.

By the time he was in Wilbur Cross, he upgraded to an iMac. With Garage Band, he and his friends crafted their own more sophisticated beats and backgrounds for original rap videos.

During that time he got a close-up look at how the criminal justice system worked, through his father, also named Michael Smith. His father was among 105 people arrested by federal and state authorities in 2012 during ​“Operation Bloodline,” which targeted alleged drug-gang members. It was believed to be the largest such sweep in New Haven history. Before trial, the defendants were housed not in state, but at a facility in Rhode Island; their lawyers had limited access to them to help prepare their cases. ​“I couldn’t even go see him,” Smitty recalled. (Read here about how a federal judge ordered authorities to stop violating defendants’ rights.)

“On the bright side,” Smitty said of his father in the ​“Dateline” interview, ​“he’ll be home soon.”

Life, Smitty concluded, is a gamble. Thus the stanza in the song quoted at the top of this story. ​“Carrying eights,” he claimed, refers to crazy eights — a card game played for money on the block.

The Toni Harp verse also refers to one of Smitty’s mentors, former Hillhouse High School Principal and basketball coach (and current Board of Ed community-outreach administrator) Kermit Carolina. In the song, Smitty is taking a good-natured teasing dig at Carolina: Carolina ran for mayor months before the video was shot, against Harp. Harp beat Carolina.

As a freshman basketball player at Cross, Smitty competed against Carolina’s Hillhouse team. Smitty played point guard. He scored 37 in one game against Hillhouse on the freshman team, he said. (Hence the rib in the song.) He loved playing basketball.

His game took a hit one Christmas Eve while he was still in high school. Smitty and neighborhood friends found themselves on the Farmington Trail in a stretch of Dixwell, not Newhallville. Not their turf. They were held up at gunpoint, he said. He had nothing to give up. Shots rang out. One hit Smitty in the abdomen. He spent a month in the hospital, got a new small intestine.

“I speak on that without me speaking on that” in the ​“So New Haven” video, Smitty said, meaning the experience informed the message. ​“When I got shot, those guys were gangbanging.”

He recovered from the shooting. His hoop game didn’t. As for his music, he didn’t lose a beat.

Smitty returned with a deeper and updated view of his city and the stakes of the gambles of street life in ​“10K,” one of a slew of music videos, all shot in New Haven, that he has released over the past year.

This video, and some of the others, reference the two years Smitty spent behind bars on an illegal-gun charge. Like his father, he was identified as a Bloods gang member, an accusation he denies. At Corrigan Correctional Center, Smitty recalled, he spent 11 months in 23-hour-a-day isolation with one other inmate. Prison officials put the cellmate, an identified Crip named Buck, in with Smitty, identified by the system as a Blood. They believed the idea was to pit them against each other. Instead of fighting, Smitty said, they became friends.

“Prison taught me a lot. Me doing those two years was a wake-up call: I’m really away. I’m really in jail. I’m not with everybody else.”

On the other hand, ​“in there,” Smitty said of Corrigan, ​“I wasn’t writing raps.”

When he came out, the words and the beats flowed like freedom.

Recorded above Phil Collins’ ​“In The Air Tonight,” the ​“10K” video takes us on a cruise through New Haven after dark. It follows Smitty driving below the dramatic blue lights on the newly rebuilt Q Bridge, then past the 11-story glimmering glass Alexion office tower that went up on College Street around the time Smitty was honing his rap game on Thompson Street.

The video also shows him reuniting with his mother, hanging out by the Smoker’s Stop in Dixwell Plaza, and, of course, with his friends in the Ville. Along with lots of shots of wads of cash and plumes of smoke.

You can make a killing the dope game …
You gotta throw your dukes up, you gotta rumble …
But when you make it back, stay humble …

And, riffing on a trope as old as the blues: ​“People love you when you have the money — when you goin’ broke, it’s like, ​‘Fuck you.’”

The video pays tribute to Sean Reeves, one of two close childhood friends Smitty has already lost to gun violence during his short life. In the ​“Dateline” interview, he spoke of his affection for Sean’s father, who has been working with law enforcement’s ​“Project Longevity” to try to convince gangbangers to stay out of the life.

“Big Sean is making big moves,” Smitty said.

“10K” doesn’t follow Big Sean’s Project Longevity script. It doesn’t tell anyone to stay in, or out, of that life.

“I’m trying to tell people, ​‘Be you. Do you. Don’t let somebody tell you what you could do. People can tell you what to do and minimize your thoughts and make you think you can only do that. Cancel everybody else out. Do what you feel is right.’”

That message stays constant in the evolving musical output of Smitty Bop and the evolving city that defines his world.

Here are some more examples of recent all-New Haven Smitty videos that I find myself returning to, including …

.… a meditation, beginning in front of the Whalley Avenue lock-up, on ​“what’s free” …

… and a joyful romp through his favorite new retail spot in New Haven, downtown’s Sneaker Junkies.

He plans to keep pumping out the music. He spoke of a new set of tracks he’s ready to release in coming months, of upcoming live performances.

Count on Smitty to keep telling ​“So New Haven” stories about a city where it often seems as though we travel in different orbits — yet where our worlds collide more than we may realize.

In the meantime, you can find Smitty Bop’s music here on YouTube and here on SoundCloud; find him here on Instagram.