
Cashman is taking bike lane backlash to a whole new level. He’s pouring his own time and money into an advocacy group he launched called Pedal Safe Boston. He’s convening neighborhood groups and meeting with lawmakers about legislative fixes to create bike lane standards.
He has even spent $100,000 to evaluate whether a statewide ballot measure to regulate bike lanes would be a more effective way to make streets safer.
Last week, the 72-year-old businessman took me on a two-hour, 10-mile ride to show me what he called “the good, the bad, and the ugly” of bike lanes in Boston.
It would be easy to paint Cashman as anti-bike lane. He insists he’s not that guy. He describes himself as a regular cyclist who knows his way around public infrastructure, having made his money as a contractor on massive projects from the Big Dig to dredging harbors.
And when he bikes around Boston, he sees a lot of mistakes and missed opportunities, blaming Wu for prioritizing quantity over quality. Since 2022, the city has added 15 miles of protected bike lanes — doubling the number of dedicated bike lanes. But too many were done on the affordable, he claims, just paint and plastic flex posts instead of concrete barriers and standard lane sizes.
“I’m for bike lanes,” Cashman tells me, “but I’m for bike lanes that basically are safe.”
But groups that have pushed for years for a better bike lane network are wary of Cashman’s motives. Someone even set up a website, pedalsafebostonscam.com, describing Pedal Safe Boston as a “scam.”
A flashpoint has been Cashman’s call for a pause on bike lane construction until a proper master plan is completed. It’s an idea championed by mayoral challenger Josh Kraft and City Councilors Ed Flynn and Erin Murphy, who proposed an ordinance to reexamine the city’s current strategy.

Bike advocates say making biking safer is about creating more lanes, not fewer, and they’re frustrated that Cashman hasn’t been willing to work with them.
“I would just wish that Pedal Safe Boston would engage in the conversations already taking place, as opposed to throwing stones from the outside,” said Galen Mook, executive director of MassBike, a nonprofit that advocates for improving bike infrastructure.
“There’s a little bit of privilege with the Pedal Safe Boston team because they have influence and money,” he added. “They haven’t actually gone through the literal decades’ worth of work of how the city has been putting down bike lanes.”
To better understand Cashman’s beef with Boston’s bike lanes, I went on a bike ride with him. We departed from his home on Dartmouth Street, where he again cursed the bright-green painted, two-way bike lane on a one-way street.
The last time I rode a bike in downtown Boston was September 2022 during the month-long Orange Line shutdown, when Wu encouraged commuters to seek alternate transportation like biking. I made a harrowing 8.5-mile trek from my home in Milton to the Financial District via Dorchester’s Morrissey Boulevard and South Boston’s Dorchester Avenue.
Would biking feel any safer three years later?
To my surprise, it did, but not enough to convince me to bike regularly around the city. I appreciate how the Wu administration has closed gaps in the bike-lane system, but for the uninitiated, the network can still be confusing and hair-raising.
For example, the ride along Commonwealth Avenue to the bike path around the Public Garden was easy, but once you cross over to Boylston Street and head down Essex Street into Chinatown, you have to shift onto one of those red-painted lanes cyclists are supposed to share with buses.
So what happens if a bus comes along? I found out soon enough when a Silver Line bus barreled toward me and honked. I did not need to be told twice to get out of the way.

Cashman and I turned onto Harrison Avenue in Chinatown, where we shared the road with cars for about a block before finding a protected bike lane on Kneeland Street and crossing onto a bus/bike lane on Washington Street in front of Tufts Medical Center. Then we made our way to the parking-protected bike lane on Tremont Street in the South End.
As a driver, I’m always confounded when street parking is moved off the curb for a bike lane. But as a cyclist, these were my favorite paths because I felt sufficiently separated from traffic.
Cashman, too, likes parking-protected lanes but not so much bike lanes lined with flex posts — plastic bollards that act as more of a visual cue than a physical barrier to protect bikers.
The Wu administration, in response to neighborhood outcry over flex posts, began yanking some of them, not long after Kraft tapped into anti-bike lane sentiment. (A Suffolk University/Boston Globe poll in July found that 50.2 percent of likely voters indicated that bike lanes made it slower and less convenient to get around.)
But bike activists aren’t happy about the flip-flop on flex posts, and I can see why. They’re better than nothing, a compromise to make it easier for emergency vehicles to squeeze through congested city streets, said Mandy Wilkens, a spokesperson for the Boston Cyclists Union.

Remarkably, it was only 2008 when then-Mayor Tom Menino christened the city’s first official bike lane on Commonwealth Avenue by Boston University. Mayor Marty Walsh continued to expand bike lanes, but Wu, during her 2021 mayoral race, pledged to take it up a notch.
But what’s good for the cyclist might infuriate drivers, so bike lanes have become a series of trade-offs. Chances are, if a bike lane doesn’t make sense, it was a compromise.
And that’s how one ended up on Dartmouth Street in front of Cashman’s home. The short segment was to appease Back Bay neighborhood groups concerned about congestion, reduced parking, and safety if the Berkeley Street bike lane extended to Storrow Drive.
Neither Wu nor her chief of streets, Jascha Franklin-Hodge, would talk to me about Cashman. Instead I got this statement from a city spokesperson: “The City is making street improvements that address traffic, relieve congestion, and make the roads safer for all users.”
Ironically, I came away from my bike ride with Cashman more hopeful about Boston’s biking future — despite the resentment over bike lanes from Back Bay to Mattapan to West Roxbury. Hopeful because a world-class bike network feels within our reach.
Cashman, despite his grumbling about Wu, says the city should invest in better bike lanes. By his estimates, spending tens of millions of dollars annually over the next decade could produce a safer system that entices more people to ditch their cars.
So if we don’t get there, we can only blame ourselves.

Shirley Leung is a Business columnist. She can be reached at shirley.leung@globe.com.