On May 28, the day before he died, Bobby Cann said good-bye to his mother, aunt, and uncle at Midway airport. It was the first time they'd visited the 26-year-old since he moved to the city from his native New Hampshire three years earlier. They'd taken the architecture boat tour, snapped photos by the Bean, and met Cann's new girlfriend.

In person, Cann had the limber energy of a Muppet and an astonished, open-mouthed grin. He was shaggy, but not in a grubby way, and often wore large, heavy-framed glasses. After moving to Chicago he'd taken a job at the REI store in Lincoln Park, which played into his passion for cycling. He joked that it was a sympathy hire, since his bike was stolen during the job interview.

Cann, a journalism major, was hired a year later as a copywriter at Groupon. He was quickly promoted to "editorial tools specialist," a wonky, catchall troubleshooting role. (I also worked at Groupon, until last fall.)

After parting ways with him at Midway, his family had dinner in the terminal before boarding their separate flights. They spent most of the meal praising Cann, who was on the cusp of another, significant promotion at Groupon.

The following afternoon, 28-year-old Ryne San Hamel was also celebrating. After watching the Cubs triumph over the Sox at Wrigley, he went for drinks at a nearby bar, after which he, his brother, and two friends loaded into San Hamel's silver Mercedes S500. They headed south toward the Loop.

San Hamel, whose friends call him Ryno, comes from a politically connected suburban family. As a kid, he played on a youth baseball team founded by his father, and batted leadoff for his high school varsity squad. After a few years of college, he worked in a string of bars and held a management position for the bar specials website Allyoucandrink.com.

San Hamel has a youthful face, blue eyes, and curly blond hair. It's not hard to picture him on a rookie baseball card, taking a knee and grinning. When he has appeared in court—on felony charges in Cann's death—he keeps his eyes down and rarely speaks. His attorney, Ron Neville, declined to comment on his case.

"He really is a good kid," says a longtime San Hamel family friend. "This is something that could have happened to any of us."

Ryne San Hamel

Chicago Police Department

San Hamel grew up in Park Ridge, a prosperous northwest suburb. He's the second of four children. His grandfather, Frank San Hamel, was born in Austria before World War I. After immigrating to Chicago, Frank spent four decades working as a staff artist at the Chicago Daily News, the afternoon newspaper known for its aggressive, lurid reporting.

Frank's son William was a political operator in the 70s, managing Thomas Tully's successful campaign for Cook County assessor. He later ran Ted Kennedy's state campaign for the 1980 Democratic presidential nomination.

After he left politics, a private trade-school venture brought William San Hamel under regulatory and media scrutiny. In 1985 he secured a low-interest loan and millions in bond financing from the state government for the Center for Robotic Technology in Edison Park. Two years later, the unaccredited school defaulted on the state loan.

Neville, the attorney representing Ryne San Hamel, also defended his father against a state lawsuit to recover the loan. "There was nothing sinister about it," he told me. "It just wasn't a successful venture." The suit was settled out of court for an undisclosed amount.

Following a Chicago Sun-Times investigation documenting inadequate training resources and skeleton staffing, the school was the first ever to have its operating license revoked by the Illinois Board of Higher Education. It was a fall from grace for the connected political insider, who had been enough of a player in 1984 to get this notice from gossip columnist Michael Sneed, then writing a column with Cheryl Lavin for the Tribune:

"Congrats to baseball fans Bill San Hamel and wife Bonny, who became parents of a son Wednesday and named him Ryne."

Henniker, New Hampshire, where Cann grew up as the oldest of four children, sits at the foot of a ski area, surrounded by lakes and forest preserves. Cann was an avid hiker and camper, but after the move to Chicago, cycling became his focus.

"In the nicest way, because he didn't have a bad bone in his body, he made me feel like an idiot for not wearing a helmet." —Philip Bird, recalling the day he met Bobby Cann

Ironically, Cann ended up in Chicago because of a car. The summer after he graduated from the University of New Hampshire, Cann was taking a cross-country trip when he had to abruptly ditch his 1997 Camry in Chicago to fly back to New Hampshire for his grandmother's funeral.

"He decided that if he had to go back to retrieve the car, he might as well try to find a job," says his mother, Maria.

He quickly got one at REI. In the summer of 2010, he was working at the Lincoln Park store when a new employee showed up, a recent transplant from Philadelphia. The new guy, Philip Bird, had ridden his bike in without a helmet.

"In the nicest way, because he didn't have a bad bone in his body, he made me feel like an idiot for not wearing a helmet," Bird recalls. Cann showed him a few helmets from the store's inventory, and the two became fast friends.

Later, when Cann and I were both working at Groupon, he biked into the office one bitter February morning. While I was hovering over the Keurig machine in the break room, he wandered in with a red face and helmet hair. I confessed that I rarely rode my bike after October.

Cann broke into a broad grin. Through the window, under a whirl of tiny snowflakes, the river was iron gray. "I really love it," he replied.

Bird, who now works at an ad agency, says that when they frequently rode bikes together, Cann made a point not to zip in front of cars or yell at oblivious drivers. "He was adamant about not pissing drivers off, and having them out there taking it out on someone else," says Bird.

On Cann's Facebook page, which was filled with pithy bons mots, he once wrote, "The problem with cars is that sometimes people drive them while they're drunk, and that cabbies drive them at all."

The year San Hamel graduated from high school, he was arrested twice behind the wheel on alcohol-related charges. Those charges were ultimately dismissed, which is the norm in Illinois for DUI defendants who can afford a private attorney.

On a Friday in January 2003, San Hamel was pulled over shortly after midnight, when a state police sergeant spotted his white Pontiac drifting between lanes on I-294. During the stop, the sergeant discovered open containers of Miller Lite in the car, and arrested the Loyola Academy senior for underage drinking.

In Illinois, it's illegal for drivers under 21 to be on the road with any alcohol in their system. But in this case, San Hamel wasn't charged with DUI. Instead, he was charged with underage drinking, a misdemeanor, and got four months of court supervision for that and other traffic charges, including a citation for illegal transportation of alcohol.

Had San Hamel received an outright conviction for illegal transportation, rather than court supervision, he'd have been hit with a mandatory one-year license suspension—which likely would have prevented his next arrest.

In Illinois, fewer than a third of DUI arrests ended in conviction in 2011, the most recent year reported. Most cases end up under court supervision, an option unique to Illinois. If an offender successfully completes the court supervision period, the case is dismissed and the charges dropped.

"People don't realize how broken the system is," says Cathy Stanley, court watch director for the Alliance Against Intoxicated Motorists. "It really needs scrutiny and needs to be tightened up."

In Stanley's mind, the biggest loophole is the routine thwarting of supposedly mandatory license suspensions for those who are charged with DUI or who refuse to take a Breathalyzer.

It seems one key to getting off easy is being arrested in the suburbs. "A lot of times, the village attorneys are just out to make money for the village," Stanley claims. In plea deals, village attorneys can reduce charges or overturn license suspensions in exchange for adding hefty fines, Stanley says. Prosecutors in the state's attorney's office, by contrast, "work much harder getting convictions."

Donald Ramsell, a criminal defense attorney and author of the Illinois DUI Law and Practice Guidebook, notes that villages have the option to use state prosecutors, but typically hire their own. "They know the business of DUI," he says of suburban municipalities. "People are so desperate to get their driver's licenses back that they can hold it hostage for a higher fine."

For defendants, deals like that can erode respect for the DUI enforcement system, says Ramsell. "It's a lesson learned, but it's not the one that people want them to be taught."

At 2:22 AM on December 29, 2003, less than a year after San Hamel's prior arrest, a police officer in Lake County spotted him making an unusual turn. After pulling him over in Riverwoods, the officer noted that San Hamel had "glassy and bloodshot eyes," and "a strong smell of alcoholic beverage" on his breath.

San Hamel, then 19, was charged with misdemeanor DUI. He refused to take a Breathalyzer. That's supposed to draw a mandatory six-month license suspension, but San Hamel's suspension was rescinded in a plea deal before the suspension took effect.

The village attorney dropped the misdemeanor DUI charge, and San Hamel paid a $1,886 fine for making an improper turn. As part of the plea bargain, he also attended DUI school and completed one year of court supervision. The improper-turn citation was dropped too.

Ten years later, after San Hamel was charged in the fatal crash after the Cubs-Sox game, private investigators found nothing on his driving record but a red-light ticket from 2010.

Bobby Cann introduced his girlfriend, Catherine Bullard (top), to his aunt (bottom), uncle, and mother shortly before he died.

Courtesy Catherine Bullard

On the morning of Wednesday, May 29, Cann's coworkers gasped when he walked into the office after his long weekend off.

The night before, after saying good-bye to his family at Midway, he was hanging out with his girlfriend, Catherine Bullard, at his Lakeview apartment. While they were cooking dinner, he turned to her and asked, "Do you wanna shave my head?" Cann normally sported a mountain-man look, including a beard that grew icicles when he biked in the snow. ("Beardsicles," he once called them.)

Cann had a big meeting that day. He'd been offered a shot at a developer job on Groupon's engineering team, and was meeting with some of the engineers to review the programs he'd built for the company's editorial department.

Though Cann had started as a copywriter in 2010, he taught himself coding and was promoted to operations four months later, writing software designed to make routine tasks easier. He once wrote a program that generated titles for Groupon deals from a questionnaire, Mad Libs style.

The engineering team was impressed with Cann's work, and had called the meeting to discuss rolling out his programs on the company's international platform. After the transition, he'd be up for a permanent job on the dev team.

Before the meeting, Cann asked his girlfriend over Gchat about dates for a September camping trip to Glacier National Park in Montana. He wanted to request the time off that afternoon.

Later, taking a lunch break, Cann chatted Bullard:

goat cheese is beautiful

when it absorbs the pink from the beets

It was the perfect day for a ball game. The Cubs' crosstown match against the White Sox started at 1:20 PM under sunny skies, with temps in the low 80s. San Hamel watched from one of the rooftop venues near Wrigley, according to court records.

Around 4:30, the Cubs won walking away, and fans in blue and red poured out of the stadium to celebrate. San Hamel ended up at Moe's Cantina on Clark Street. The cavernous bar was packed.

Much of San Hamel's work history revolved around bars. He was a managing member in Debonair Entertainment, the group behind Amp Rock Lounge. After the Lincoln Park bar folded in 2010, he worked as a VIP manager at Vertigo Sky Lounge, looking after high rollers willing to spend hundreds of dollars on bottle service. More recently, he worked in a similar role at Cuvee, also in River North.

In 2011 San Hamel's childhood friend Jake Muellner founded Allyoucandrink.com. Muellner and San Hamel were the company's two managing members. According to Muellner, San Hamel's involvement in the site "has been very minimal, from start to finish." Muellner would not comment on San Hamel's current interest in the company, which is restructuring.

"We don't condone misuse of alcohol, and we don't condone drinking and driving," says Muellner.

At Moe's, San Hamel closed his tab sometime around 6 PM. He left the bar with his younger brother and two female friends, who both work as bartenders. The foursome piled into San Hamel's Mercedes. He took the wheel.

At 6:15 PM, Cann's girlfriend was in a meeting for the theater company she volunteers with. She saw a call from Cann's phone and immediately became worried—he rarely called her.

But it was good news. Cann, still at the office, wanted to let her know that he'd gotten the time off for the trip to Glacier National Park. He was about to shut down his computer and head home to catch the Blackhawks game.

The call lasted three minutes. Cann signed off with a chipper "See you later!"

Minutes later, he hopped on his bike and headed north on Larrabee. As always, he was wearing his helmet.

The intersection where the collision occurred

Alison Green

Yojimbo's Garage, a bike shop on Clybourn just south of Larrabee, is closed on Wednesdays, but owner Marcus Moore had come in that evening to build a bike for a friend. A little after 6:30 PM, he heard squealing car tires and smashing metal.

Moore hurried outside. Just in front of the shop, a silver Mercedes had come to rest, trailing wreckage behind it. Moore looked north and saw a black Infiniti that had spun perpendicular to traffic, straddling the center line.

The scene was chaotic. It took about a minute for Moore to notice that there was someone lying on the pavement by the opposite curb. Moore rushed over as bystanders dialed 911. Emergency units were dispatched at 6:36 PM.

Seconds after the crash, Julie Dziak, a nurse driving home from her job at Northwestern Memorial's neonatal intensive care unit, pulled over to assist. Rushing to the small crowd that was gathering around the injured man, she saw he was wearing a helmet—a cyclist had been hit. His injuries were horrific.

He lay unconscious and wasn't breathing. Blood poured out of his mouth. His left leg was severed. Dziak detected a weak pulse, improvised a leg tourniquet, and began giving CPR.

Within minutes, paramedics arrived. Dziak, covered in blood, felt for a pulse one last time—still there. An ambulance rushed the cyclist to Northwestern Memorial.

At 7:09 PM, Robert George Cann was pronounced dead.

Crashes killed eight cyclists in Chicago last year, according to the Illinois Department of Transportation. Another 939 suffered serious or incapacitating injuries.

It's part of a rising trend. A city study found a 27 percent increase in bicycle-injury crashes between 2005 and 2010. The number of cyclists surged in the same period, putting more bikes on an infrastructure that's not fully prepared for them.

"The norm in the Chicago area is driving recklessly and speeding," says Ron Burke, executive director of the Active Transportation Alliance. "Too many people are traveling in a reckless, dangerous way, whether it's driving a car or riding a bike. Of course, when you're a person on foot or a bike, you're nowhere near as dangerous as a person in a 3,000- pound car."

Last October, a truck fatally struck Neill Townsend on Wells Street after a car door opened in the cyclist's path. Townsend's death helped galvanize support for an ordinance passed by the City Council in June that doubled fines for dooring cyclists, to $1,000.

After Cann's death, many in the cycling community pointed out that the sections of Larrabee and Clybourn near the crash site lack bike lanes. Writing for Streetsblog, Steve Vance also noted that Clybourn was designated a "crosstown bike route" in the city's Streets for Cycling Plan 2020.

That would make it a likely candidate for protected bike lanes, which run between parked cars and the curb. But, Vance wrote, because Clybourn is a state route, it's under an IDOT moratorium on protected bike lanes until at least 2014.

"Could it have been prevented?" Burke says. "We'll never know for sure."

When the news of Cann's death squawked back to the crash scene over police radios, the mood shifted. Officers sealed off the street. Their attention focused on the driver of the Mercedes, soon identified as Ryne San Hamel.

The police smelled alcohol on his breath, and asked him if he'd been drinking. He replied that he had, according to court records. The officers gave him a field sobriety test, reporting that he failed it. San Hamel allegedly refused to take a Breathalyzer test.

At 9:45 PM, facing a night in the 18th District lockup, he asked for medical attention. Officers drove him to Northwestern Memorial, where Cann had died from his injuries hours earlier.

At the hospital, blood drawn from San Hamel—more than three hours after the crash—showed a blood alcohol level of .15, nearly twice the legal limit, according to assistant state's attorney Maria Augustus. (The blood alcohol level she cites is higher than previously reported.)

The prosecution alleges that San Hamel was speeding by at least 20 miles over the limit, traveling southbound on Clybourn, when he struck Cann, who rolled onto the hood and into the windshield of the Mercedes. San Hamel then veered into oncoming traffic, according to the prosecution, striking the Infiniti and sending Cann flying across the oncoming lane. I spoke to an eyewitness who confirmed this account.

It's unclear where Cann was at the moment of impact. According to the police report, Cann was riding southbound on Clybourn, clear of the intersection with Larrabee (meaning San Hamel would have rear-ended him). The prosecution says that Cann "appeared to be turning southbound" onto Clybourn from Larrabee.

Bullard, Cann's girlfriend, was confused when she heard this. Cann's route home would have taken him north. Was he turning south to stop at Yojimbo's, the bike shop, not realizing it was closed?

A security camera at New Zalka, a Middle Eastern restaurant on Clybourn, captured the crash. The owner of the restaurant says that the video, which police copied, has been automatically erased from his system.

Two people who have seen the video gave me different accounts. One said it showed Cann turning south onto Clybourn from Larrabee, a right-hand turn. The other said it appeared to show him crossing Clybourn on Larrabee. The intersection is controlled by a stoplight.

Across the street from the New Zalka there's a makeshift memorial and white ghost bike. More than five months after the crash, fading police spray paint on the pavement still marks the spot where Cann landed.

On October 25 a ceremony was held at the Clybourn-Larrabee intersection to designate it Honorary Bobby Cann Way. Alderman Walter Burnett Jr. unveiled the new street sign.

Alison Green

San Hamel has pleaded not guilty to the seven felony counts—including reckless homicide and aggravated DUI—for which he faces a sentence of up to 54 years. No trial date has been set, and he remains free on a $100,000 bond. He is prohibited from drinking alcohol or driving as a condition of bond.

San Hamel's attorneys have told Judge William Hook that their client is voluntarily attending an alcohol treatment program, and have filed a motion to release his Mercedes from police impound. Judge Hook is expected to rule on the request at a November 8 hearing.

San Hamel did not respond to repeated phone calls and a letter requesting comment for this story.

Recently I visited Vertigo Sky Lounge, the River North bar where San Hamel once worked. A manager told me that San Hamel hadn't worked there for "about a year," adding cheerfully, "He still comes by to party with us, though."

On October 25, around 100 people gathered at the crash site for a ceremony designating the Clybourn-Larrabee intersection Honorary Bobby Cann Way. Dozens of Cann's former coworkers from Groupon and REI were there. Cann's family flew in from the east coast.

Before unveiling the honorary street sign, Alderman Walter Burnett Jr. announced that Clybourn would be the first IDOT route with protected bike lanes. An IDOT spokeswoman confirmed the plan, but did not provide a timeline for the installation.

"Bobby told me that biking was very safe," Cann's mother, Maria, said to a TV news crew. She was surprised but glad that they had come. "But no infrastructure change can make it safe to share the road with intoxicated drivers."

Bird, who worked with Cann at REI, says Cann's death is constantly on his mind when he rides.

"If it can happen to him," he says, "it can happen to anybody."

For Cann's family, the protected bike lanes on Clybourn will be a step in the right direction. "It's good that there's something positive to come out of this," says Cann's uncle John Santini Jr. "But it's a shame that we're down a man. A good one."

Earlier, Santini told me about the last time he saw Cann, at the airport the night before he died. "I watched him walk away and I thought, 'I am really impressed,'" Santini recalls. "I can still see him walking down the hallway at Midway."

Correction: This article has been amended to reflect that Bobby Cann graduated from the University of New Hampshire.