James ‘Little Howlin’ Wolf’ Pobiega, Chicago street busker played sax, performed on cruises, dead at 73

At Argo High School in Summit, his football teammates called James Pobiega — who was also a theater kid who stood six and a half feet tall and wore size 18 cleats — Beowolf. 

Years later, to passersby who might toss a buck into the case of his saxophone as he played on the Michigan Avenue bridge, he was known as Little Howlin’ Wolf — in homage of the Chicago blues legend Howlin’ Wolf, also known as Chester Burnett.

Thousands of children knew him as Buccaneer Bob, the theatrical pirate — complete with eye patch and parrot — who hosted a Wacky Pirate Cruise on the Chicago River and Lake Michigan that for years was offered by Mercury Cruises.

His sister Patti Pobiega called him Jimmy. Friends knew him simply as Wolf.

Mr. Pobiega, a self-taught saxophonist, began busking at Chicago’s old Maxwell Street Market around the same time he graduated from high school in 1968. He played music on Chicago’s streets for the rest of his life.

Mr. Pobiega was found dead Sept. 12 at his Uptown apartment of heart failure, his family said. He was 73.

He studied acting at the Goodman School of Drama and joined an instructor, Patrick Henry, and several classmates in 1969 to form the Free Street Theater. The group performed around the city and later the Midwest.

“Anybody that ever met him never forgot him,” said Dick Shouer, who lives in downstate Freeport and for years rejoiced in seeing Mr. Pobiega at the annual Willow Folk Festival — a church fundraiser in rural Stockton that began in 1968.

“He could put a flute up each nostril and play them at the same time,” Shouer said. “He looked kind of ferocious, but it was just Wolfy.”

“He was a big adventurer, always on the move,” said Patti Pobiega, a retired nurse who’s his only sibling. “He was very creative and didn’t like to spend a lot of money doing a lot of things, which is from our meager upbringing.”

Mr. Pobiega was born Aug. 23, 1950, in Oak Park to Michael Pobiega, who drove a milk truck, and Alice Pobiega, who held several jobs, including working as a secretary for a roofing company.

“He taught himself many instruments as a kid and was the kind of kid that grabbed the microphone at weddings,” his sister said.

Mr. Pobiega, who had a gruff voice, worked as Santa Claus at Water Tower Place, enjoyed scuba diving as a hobby and instructor, had bit parts in a few productions, including a goofy music video with Tim Kazurinsky and the Chevy Chase movie “Bad Meat.” But music was his passion.

“He marched to his own drummer,” said Bob Spaulding, a diving pal who went to the Cayman Islands in 2019 with Mr. Pobiega and did dives with him at Haigh Quarry in Kankakee.

“He was probably one of the most interesting people I’ve ever met, a free spirit from a different time,” said Bob Agra, whose family owns Mercury Cruises and hired Mr. Pobiega as Buccaneer Bob after he responded to an ad in the Reader in 1990. 

Mr. Pobiega’s music, though never commercially successful, found a wider audience in the early 2000s after Twig Harper, a musician who was working at an antique store in Wicker Park, bought one of his self-released albums at a Chicago thrift shop and circulated it among friends in the underground experimental music scene. One wrote to an address listed on the back of the album, reaching Mr. Pobiega at his parents’ home in Justice.

“His music resonated with me and my crew because it was the true American tradition that we all champion — free jazz, folk and blues but from the street level as a busker — and we did tours with him on the East Coast and recorded with him,” Harper said. “His music is like the music of the twilight — in between worlds, psychedelic, cosmic, disjointed. And that’s kind of how he lived his life, too, in this really beautiful, intense way.” 

Mr. Pobiega self-released dozens of singles and three albums — two in the 1980s, one in 2005.

“I first met him when I picked him up at his parents’ house, and we played a festival in Minneapolis,” said Harper, who later moved to Baltimore.

Mr. Pobiega visited him there, fashioning a living space from an abandoned garage with no utilities behind a home where Harper’s brother lived.

“He had a grill, a workout bench, a wood stove, all super-interesting architecture from stuff he’d salvaged, and he’d just work on his music,” Harper said. 

He said he’ll miss the long, stream-of-consciousness voicemails Mr. Pobiega would leave.

“He was a storyteller,” Harper said. “And you were just on board for the ride.”

Services have been held.