By John J. Sheehan, Founder, Law Office of John J. Sheehan, LLC · Wakefield and Boston, Massachusetts | Last reviewed: October 2026
I was born and raised in Boston, the son of an Irish immigrant from County Kerry, in a working-class family, and that upbringing gave me a deep appreciation, pride, and respect for the American Dream. It also shaped the kind of law I practice. Since graduating from Suffolk University Law School and joining the Massachusetts bar in December 1993, I have focused on people who were hurt on the job and people injured because of someone else’s negligence. I am also fluent in Spanish and represent many clients from the Latin American community in Greater Boston.
Bicycle crashes sit at an interesting intersection of that work. Some cyclists are commuters or weekend riders. Others are on the clock, delivering food or packages, and a single crash can raise questions under workers’ compensation law, auto insurance rules, and ordinary negligence at the same time.
Where Workers’ Compensation Ends and a Lawsuit Begins
Much of my practice has involved representing injured workers before the Massachusetts Department of Industrial Accidents, the agency that hears workers’ compensation disputes. The compensation system is straightforward in principle. An employee hurt on the job receives medical treatment and a portion of lost wages without having to prove fault, and in exchange the employer is generally protected from a negligence lawsuit. Some injured workers stop there without realizing another claim may exist.
When someone other than the employer or a co-worker causes the injury, Section 15 of Chapter 152 allows a separate third-party claim against that person. A courier knocked off a bicycle by a delivery van, or a construction worker struck by a passing car at a road job, may have both a compensation claim and a negligence claim. The compensation insurer has a lien on any third-party recovery for the benefits it paid, so the two cases have to be managed together from the beginning.
What Compensation Covers
Massachusetts compensation benefits follow a set structure. A worker who cannot work at all generally receives weekly temporary total disability benefits under Section 34 equal to 60 percent of the average weekly wage, subject to a state maximum, and partial disability benefits apply when the worker can return to lighter or part-time duty. Section 36 provides separate payments for permanent loss of function and certain scarring. Many claims eventually resolve through a lump sum settlement approved at the Department of Industrial Accidents, and that settlement should account for any pending third-party case so the two recoveries do not work against each other. Find Attorneys’ checklist for workers’ compensation accident victims covers the first steps after a workplace injury.
Employee or Independent Contractor
Delivery and gig work add a complication. Whether a cyclist counts as an employee for compensation purposes depends on how the work is actually structured, and app-based couriers are often classified as independent contractors by the companies that hire them. That label is not always the final word. And regardless of the label, a negligent driver can still be held responsible through a personal injury claim, which is why the classification question should never stop an injured rider from looking at every source of recovery.
A Work Injury With Two Recoveries
The interaction between the two systems is easier to see in a real case. Among the results listed on my case results page, a construction worker tripped on a wire loop protruding from a demolished concrete floor and suffered a fractured kneecap and a neck injury. The workers’ compensation claim settled for $350,000, and separate claims against the third parties responsible for the site settled for $450,000, for a combined $800,000. The worker also obtained Social Security disability benefits. Coordinating those claims, including the compensation insurer’s lien, was what allowed each recovery to stand.
Past results depend on the specific facts of each case and do not guarantee a similar outcome in any other matter.
Massachusetts Rules That Shape Bicycle Cases
Massachusetts strengthened its protections for cyclists in 2023. Under the vulnerable road user law that took effect in April of that year, drivers must leave at least four feet of space when passing people on bicycles, pedestrians, roadside workers, and others outside a vehicle, as explained by the state. When there is not enough room in the lane, a driver may cross the centerline if it is safe to do so. The same law amended Chapter 85, Section 11B to require cyclists riding at night to use a rear red light as well as a reflector.
Opening a car door into traffic is another common source of injury in Boston’s dense neighborhoods. Chapter 90, Section 14 prohibits opening a vehicle door until it is reasonably safe to do so, and a violation can be strong evidence of negligence in a dooring case.
Fault is still contested in many of these claims. Under Chapter 231, Section 85, Massachusetts follows a modified comparative negligence rule, so an injured cyclist can recover as long as his own negligence is not greater than that of the people he sues, with the award reduced by his share of fault. A missing rear light, a ride through a red signal, or earbuds in both ears can all become part of that argument. Photographs of the bike and the scene, contact details for witnesses, and the police crash report help settle those disputes before they grow.
When a Crash Takes a Life
The Massachusetts wrongful death statute, Chapter 229, Section 2, allows the executor or administrator of the estate to bring a claim on behalf of the family. Damages can include the fair monetary value of the person to the family members entitled to recover, reasonable funeral and burial expenses, and punitive damages of at least $5,000 when the death resulted from gross negligence or willful, wanton, or reckless conduct. The claim generally must be filed within three years of the date of death, subject to limited exceptions. Under Section 6, the estate can also recover for the conscious pain and suffering the person experienced before death, a claim that depends heavily on medical records and on the accounts of first responders and witnesses at the scene.
Families dealing with a fatal crash often need help with the probate step first, since a personal representative must be appointed before the claim can proceed. Speaking with Boston wrongful death attorneys early allows that appointment, the preservation of evidence, and the insurance notices to move forward together. When the person who died was working at the time, the family may also be entitled to dependency benefits under Section 31 of Chapter 152, which makes coordination between the two claims especially important.
Deadlines and Several Paths to Recovery
Most personal injury lawsuits in Massachusetts must be filed within three years under Chapter 260, Section 2A, and workers’ compensation claims carry their own notice and filing requirements. For a rider hurt on the Southwest Corridor or a delivery worker struck in Chelsea, an early review can sort out which of these systems apply and which deadlines are already running.
Many of the clients I represent are working hard to build a life here, much as my own family did. When an injury takes that ability away, the law offers several paths to recovery, and the job is to make sure none of them is missed.
Disclaimer
This article provides general information about Massachusetts workers’ compensation, bicycle injury, and wrongful death law. It is not legal advice, and reading it does not create an attorney-client relationship. Benefit amounts and deadlines depend on the facts of each case. Anyone injured at work or in a crash, or who has lost a family member, should consult a licensed Massachusetts attorney.
