Andrew Bayley’s ward map jigsaw puzzle. This and most photos in this post are by Bayley.

[This piece also runs in Time Out Chicago magazine.]

It was a blast from the past when Andrew “Cooter” Bayley, an old bike messenger colleague of mine, asked me to pedal the torturous boundaries of the newly redistricted First Ward with him. Back in January, just after City Council approved the new ward map, Bayley made headlines by using a computerized laser-cutting program to turn the map into a handsome, 50-piece Baltic Birch plywood jigsaw puzzle.

“I thought the new map was ridiculous, so I turned it into puzzle,” explained Bayley, who currently interns at an architecture firm. “Now I want to explore the interaction between this particular form of gerrymandering and the urban infrastructure that defines it.”

He also invited First Ward Alderman Proco “Joe” Moreno to cruise the perimeter of his Near Northwest district with us, but the bike-friendly young politico couldn’t make it on such short notice. “I would have loved to have joined you,” Moreno later told me on the phone. “This is a very diverse ward and I love living here.”

Moreno at the ribbon cutting for the city’s first on-street bike rack last summer. Photo by Steven.

While the First Ward previously resembled a badly drawn cobra, after the remap its outline became even more arcane. Rotated ninety degrees, the new ward looks like a pixilated schnauzer gazing back at its own tail. “I would have preferred to have a continuous rectangle but that’s almost impossible when we have a voting rights act that requires us not to discriminate against the rights of African Americans or Latinos,” says Moreno.

The alderman adds that while the complex new ward boundaries may be trickier to comprehend, they make amends for the historic use of gerrymandering as a strategy to keep minorities off of City Council. “In a sense we’re paying for the sins of our fathers. I hear the criticism that it’s a new day in Chicago and we don’t need these protections anymore. But I think we should leave that decision up to those populations who have been historically discriminated against.”

Riding the ward boundary through an alley south of the Paseo Boricua business strip, we passed this mural behind Dr. Pedro Albizu Campos Puerto Rican High School reading “Humboldt Park is not for sale!”

Moreno says he voted for the final compromise map because it achieved the Latino Caucus’ goals of creating 13 largely Latino wards, three more than before, which better reflects the city’s current demographics. The final map also includes 19 mostly white wards and 18 majority African-American wards, a loss of one seat for a population that fell by more than 181,000 over the last decade.

But Moreno admits he’s saddened that his friend Second Ward Alderman Robert Fioretti, will face an uphill reelection battle since the boundaries of his ward were flipped from the Near South Side to the Near North Side, excluding Fioretti’s home from the district. “With the original map the Latino Caucus introduced he would have kept his ward but unfortunately a ward had to be adjusted to ensure that African-American aldermen would maintain their numbers,” Moreno says.

On our ride Bayley and I encountered this colorful van outside an auto parts store in Ukrainian Village.

But Andrew and I aren’t thinking of Fioretti’s misfortune as we embark on our ride from Swim Café, 1357 W. Chicago in Noble Square, after lunch on a hot Saturday. He’s riding a battle-scarred fixie and clutching printouts from the 61-page ordinance that uses archaic language to delineate the new wards. The Byzantine boundaries often include alleys and frequently place two sides of the same street in different districts.

He reads me a sample: “Beginning at the intersection of North Hoyne Avenue and West North Avenue; thence east on West North Avenue to the alley just northwest of North Milwaukee Avenue; thence southeast and north along the alley just northwest of Milwaukee Avenue.” My brain grinds to a halt.

We came upon this memorial to Officer Edward Massas at Superior and Racine, near a Kennedy Expressway offramp. According to the Tribune, in 2008 Massas, an off-duty police officer, was thrown from his motorcycle after losing control on the ramp.

With Bayley navigating, we pedal west on Chicago and south on Armour, and then cut east down an alley between Superior and Huron. After tagging the Kennedy we zigzag our way west into Ukrainian Village, passing a bar with live Mariachi music and two guys up to their elbows in grease as they try to fix their van, covered with colorful graffiti. The directions route us to Humboldt Park where peddlers are selling carved gourds and domino tables decorated with photographs of salsa musicians.

Bloomingdale Avenue from Humboldt Boulevard to Lawndale Avenue makes up a stretch of the boundary, so we drag our bikes up onto the Bloomingdale Line and ride west along the elevated railroad tracks. We’re trespassing but we encounter plenty of people walking dogs or strolling hand-in-hand.

Bayley on the Bloomingdale.

After we descend, the route slithers back east so, dripping with sweat, we slake our thirst with Italian ices at Miko’s, 3000 W. Lyndale. From there we follow a ridiculously serpentine route along alleys northeast of Sacramento and Fullerton, At times we get so confused we have to check the position of the sun to orient ourselves.

We passed by the shrine to “Our Lady of the Underpass,” a salt stain on the wall of the Fullerton Avenue viaduct below the Kennedy, said to resemble the Virgin Mary.

After a couple more hours of painstaking navigation we finally return to Swim. I ask Andrew what he thinks we’ve accomplished with our twenty-mile gerrymandered journey. “By circumnavigating the First Ward boundary, we’ve exposed just how arbitrary that line is,” he says. “This shows what happens in physical reality when you create a ward that has more to do with politicians’ self-preservation than common sense.”