Baltimore Faces $455K in Injury Bills Cop Stopped for a Sandwich. A Tree Rotted for Two Years. Now Baltimore Is Paying $455K

Baltimore’s city government approved more than $230,000 in injury settlements this week after a string of incidents involving a police officer grabbing food, a crumbling sidewalk, a falling tree, and a runaway trash truck. The Board of Estimates approved $230,271 for five different injury claims, though $455,271 in total settlements were recommended by the city’s legal department. None of these were losses in court — the city chose to pay rather than fight.

Case	What Happened	Settlement
Josephine Benjamin	Thrown from MTA bus after BPD cut it off	$40,000
Darrell Fletcher	Dead tree fell in front of his car	$43,271
Theresa Wright	Tripped on broken sidewalk, two bones fractured	$340,000 (shared)
Unnamed plaintiff	Reckless trash truck injury	$47,000
Daryl Bailey	Struck by Fire Department sedan while crossing on green	~$225,000 (pending)

Current Status

• The Board approved $230,271 in claims at its April 2 meeting.
• The Daryl Bailey settlement — the largest item, worth close to a quarter million dollars — was deferred and will appear on the April 15 Board of Estimates agenda.
• If the Bailey payment clears April 15, total city payouts on this batch of cases will exceed $455,000.

The Officer Wasn’t Responding to an Emergency. He Was Getting Lunch.

In 2022, a Baltimore woman named Josephine Benjamin was thrown from her seat on an MTA bus and received possibly permanent injuries after a Baltimore Police Department vehicle cut off the bus while turning into a private parking lot on Edison Highway.

When the city’s law department presented the case to the Board of Estimates, the reason the officer turned into that lot came out. “I think the officer was going to a carry out,” Bradford told the board. “Yeah, there was a sandwich shop.” The officer no longer works for BPD and no longer lives in Maryland. The board approved the $40,000 settlement unanimously.

This wasn’t a split-second emergency. No lights, no siren, no call — a bus passenger paid for it with her body.

Related article: $2B Lawsuit ON Travelers for Refusing to Settle a Wrongful Death Case Travelers Held the Checkbook and Allegedly Wouldn’t Open It.

The City Knew That Tree Was Dead. It Did Nothing for Two Years.

In December 2023, Darrell Fletcher was driving on Druid Park Drive when a dead, mature tree fell in front of his car. He struck the tree while trying to avoid a collision, totaling his vehicle and injuring himself in the process.

This wasn’t a freak weather event. The tree had been dead for at least two years before the accident. Baltimore had two years to notice, flag, and remove it. It didn’t. The Board approved a $43,271 payment to Fletcher, citing the cost of further litigation and evidence of his injuries.

A Sidewalk Crack Fractured Two Bones and Cost Three Government Bodies $340,000

In July 2022, Baltimore resident Theresa Wright stumbled on an uneven sidewalk on East Baltimore Street, fracturing her left ankle and her right elbow. She required multiple surgeries and may need more in the future.

Her case brought in three defendants: the city, the State of Maryland, and BGE. All three agreed to pay Wright a combined $340,000 to settle the case. That number reflects the severity of her injuries and how many parties shared responsibility for that stretch of pavement.

A Fire Department Car Hit a Man Crossing on a Green Light — On Camera

This is the case that isn’t finished yet. In November 2021, Daryl Bailey was crossing Saratoga Street when the pedestrian signal showed green. A Baltimore City Fire Department sedan struck him. A CitiWatch camera captured the whole thing.

Bailey suffered multiple injuries including a torn rotator cuff that may require surgery. Through negotiations, the city’s law department agreed to resolve his claim for close to $225,000. The Board deferred a final vote until April 15 — but the camera footage and the city’s own legal team recommendation make approval the likely outcome.

What This Tells You If You Were Hurt by the City Too

These five cases share a pattern: city property fell apart, city employees drove carelessly, and Baltimore paid out rather than let a jury decide. That’s not unusual. The Baltimore City Board of Estimates consists of five voting members — the Mayor, the President of the City Council, the Comptroller, the City Solicitor, and the Director of Public Works — and approving injury settlements is a standard part of its agenda every two weeks.

What matters for anyone injured by city negligence is understanding how the pipeline works. In Baltimore, you cannot simply file a lawsuit against the city without first running a claim through its Law Department. That process determines whether the city settles quietly or fights in court.

The cases approved this week suggest the city will pay when evidence is strong — a camera recording a government car striking a pedestrian on a green light, a tree sitting dead for two full years, a sidewalk that’s been broken long enough to fracture two bones. Weak documentation or shared fault can complicate any claim significantly.

FAQs: Suing Baltimore City for an Injury

Can a private citizen sue Baltimore City if a city vehicle hits them? 

Yes. Maryland law allows injury claims against municipal governments. In Baltimore, injured residents typically file first with the city’s Law Department. If the city accepts fault and the evidence supports it — like a CitiWatch camera recording — the claim usually reaches the Board of Estimates for settlement approval.

Who actually approves Baltimore City injury settlements? 

The Board of Estimates formulates and executes the fiscal policy of the city, including approving legal settlements. The five-member board meets regularly and publicly, meaning approved settlement amounts become part of the public record.

Does the city admit fault when it settles?

 Not necessarily. Each of these cases was a settlement, meaning the city did not lose a lawsuit but instead chose to pay the plaintiff to end litigation and resolve the disputes out of court. Settling avoids the cost and risk of trial — it is not a formal admission of wrongdoing.

What if the sidewalk involved BGE or the state — not just the city? 

As Theresa Wright’s case shows, responsibility for public infrastructure can be split across multiple parties. Her $340,000 settlement came from the city, the State of Maryland, and BGE jointly. An attorney can identify all potentially liable parties before you file.

Do I need a lawyer to pursue a claim against Baltimore City? 

You are not legally required to hire one. However, city law departments negotiate these settlements regularly and have experienced staff. Having legal representation levels that playing field, particularly when injuries are serious or multiple parties share liability.

When will Daryl Bailey’s settlement be finalized? 

The item has not been approved or denied and will be on the agenda for the Board of Estimates meeting on April 15. The board meeting is public and its agenda is published in advance on the Baltimore City Comptroller’s website.

Could a Baltimore injury claim affect my taxes? 

Potentially. Settlement proceeds for physical injuries are generally excluded from federal taxable income under IRS rules, but amounts tied to emotional distress or punitive damages may not be. A tax professional can clarify what applies to your specific payment.

Sources

• Baltimore Sun: Baltimore could be on the hook for more than $450K in injury settlements (April 1, 2026)
• Baltimore City Comptroller — Board of Estimates: https://comptroller.baltimorecity.gov/boe
• Baltimore City Government: https://www.baltimorecity.gov/comptroller/about/board-of-estimates

Last Updated: April 2, 2026

Disclaimer: This article is for informational purposes only and does not constitute legal advice. Legal claims and outcomes depend on specific facts and applicable law. For advice about a particular situation, consult a qualified attorney.