ATTORNEYS AT LAW · EST. 1992

When the stakes
are high,
experience
matters.

For thirty-four years, Sterling & Associates has tried, settled, and won the cases other firms told clients were unwinnable. Over $150 million recovered in personal injury, medical malpractice, and business litigation across Massachusetts and New England.
$150M+
recovered for clients
98%
success rate
0
fee unless we win
Personal Injury
Med-Mal
Business Litigation
CASE FILE EXCERPT
FILE N° PI-24-0418

Truck Accident
Settlement

VERDICT · APR 2024
$12,500,000
Confidential settlement, Worcester County Superior Court
Client — a 39-year-old mother of two — suffered catastrophic spinal injuries when a commercial truck driver, in violation of FMCSA hours-of-service rules, crossed the median on I-495. We obtained the carrier’s driver-log records, retained two accident-reconstruction experts, and proved the carrier had knowingly waived the driver’s fatigue restrictions. Settlement reached day three of trial.
Practice area
Personal Injury · Trucking
Lead counsel
Michael Sterling · Diana Torres
Court
MA Superior, Worcester
Duration
18 months filing to settlement
Past results do not guarantee future outcomes.
$150M+
Total recovered for clients
2,541
Cases successfully resolved
35+
Years combined experience
98%
Success rate at trial & settlement
Chapter I · Practice Areas

Six disciplines.
One firm that has tried them all.

Sterling & Associates is built around full-service trial practice. Our partners have first-chaired cases in state court, federal court, and the Massachusetts Appeals Court — and we draw on that bench depth in every matter we accept.

§ I

Personal Injury

Catastrophic injury, wrongful death, slip-and-fall, dog bites, premises liability. We have first-chaired more than 400 PI matters since founding.

§ II

Car & Truck Accidents

Commercial trucking, rideshare, distracted-driver collisions. We retain certified accident-reconstruction experts on every serious-injury matter.

§ III

Medical Malpractice

Birth injury, surgical error, missed diagnosis, hospital negligence. Working with a panel of board-certified physician experts in 14 specialties.

§ IV

Business Litigation

Breach of contract, partnership disputes, fraud, non-competes. We represent both plaintiff and defense in matters from $250K to $50M+ in controversy.

§ V

Employment Law

Discrimination, wrongful termination, wage & hour, whistleblower. Filing in MCAD, EEOC, and Superior Court — we have done all three this year.

§ VI

Workers' Compensation

Construction accidents, repetitive-stress injuries, occupational illness. Pursued simultaneously with third-party PI claims where applicable.

Chapter II · Why Sterling

"No fee unless
we win" is a
floor,
not a slogan.

Contingency-fee work means we get paid only when you do. That is the easy promise. The harder promise — the one that defines us — is that every matter, regardless of size, is staffed by a named partner from intake to verdict.

Other firms triage your case to associates and paralegals after the consult. We don’t. The lawyer who tells you we’ll take your case is the lawyer who tries it. That’s why our settlement-to-trial ratio — cases we are willing to take to verdict — is more than triple the regional average.

.01

No fee unless we win.

Contingency on all personal-injury, medical-malpractice, and most employment matters. No retainer, no hourly — ever — on these.

.02

24-hour intake line.

Sterling answers nights, weekends, and holidays. After an accident, the first 72 hours are critical — insurers move fast; we move faster.

.03

Partner on every matter.

The attorney who handles your free case review is the attorney who tries it. We do not bait-and-switch with associates after retainer.

.04

Verdict-ready, not settlement-ready.

Every case is prepared as if it will go to verdict. Insurance carriers know it — which is why our settlements are, on average, 31% larger.

Our Boston library · 14th floor, 112 State Street.
Open to clients for case-prep sessions by appointment.
Chapter III · Our Attorneys

The named partners
who try the cases.

Partner I

Michael Sterling, Esq.

Founding Partner · Trial Litigation

First-chaired the $12.5M Worcester trucking matter and the $8.2M Beth Israel malpractice case. 34 years of jury trial experience across Massachusetts.

Partner II

Diana Torres, Esq.

Senior Litigator · Medical Malpractice

Leads our medical-malpractice practice. Tried 47 jury cases to verdict; secured the $4.7M Mass General birth-injury settlement in 2023.

Partner III

James Whitfield, Esq.

Trial Attorney · Business Litigation

Heads complex-commercial litigation. Recovered $6.1M in a 2024 partnership-dispute jury verdict — the largest in Suffolk County that year.

Chapter IV · Notable Results

The docket,
in the firm's own words.

A selection of representative verdicts and settlements. Past results do not guarantee future outcomes; every matter is fact-specific.

Date
Matter
Jurisdiction
Counsel
Recovery
04 / 2024
Truck Accident · Catastrophic Spinal Injury
Commercial carrier violated FMCSA hours-of-service rules; mid-trial settlement
MA Superior, Worcester
Sterling · Torres
$12,500,000
09 / 2023
Medical Malpractice · Surgical Error
Failure-to-diagnose pulmonary embolism; jury verdict, 9-day trial
MA Superior, Suffolk
Torres · Sterling
$8,200,000
11 / 2024
Business Litigation · Partnership Dispute
Breach of fiduciary duty & fraudulent conveyance; jury verdict
MA Superior, Suffolk
Whitfield
$6,100,000
07 / 2023
Workplace Injury · Construction Fall
Third-party general-contractor liability; pre-trial settlement
MA Superior, Middlesex
Sterling · Whitfield
$4,700,000
02 / 2025
Wrongful Termination · Whistleblower
FCA retaliation claim, financial services employer; confidential settlement
US Dist. Mass.
Whitfield · Torres
$3,400,000
06 / 2024
Premises Liability · Slip-and-Fall TBI
Hotel chain defendant; mediated settlement
RI Superior, Providence
Sterling
$2,150,000

Cases listed are representative; full case list available on request. Settlements include attorney fees and litigation costs per fee agreement. Past results do not guarantee future outcomes.

Chapter V · Free Case Review

Confidential.
No obligation.
No fee unless we win.

Tell us about your matter. A named partner will review your intake within one business day and call you to schedule a complimentary 30-minute consultation — in our State Street office, by Zoom, or at your hospital bedside if needed.

CONFIDENTIAL

Free Confidential Consultation

Intake form · reviewed by named partner within 24 business hours.

By submitting you consent to Sterling & Associates contacting you about this matter. We do not share intake information with third parties. Privacy & disclaimer.

Chapter VI · Client Testimonials

What clients say,
on the record.

"
Rated 5 out of 5
“Diana took our medical-malpractice case after two other firms turned us down. She put the hospital on notice, retained three experts within a month, and got us a settlement that means our daughter has the care she needs for life. We will never have words for what she did for our family.”
Eleanor & Marc P.
MEDICAL MALPRACTICE · CLIENTS SINCE 2022
"
Rated 5 out of 5
“Michael Sterling tried our trucking case himself — not an associate, not a paralegal. He was in the office at 6 AM the morning of opening, and he was the only lawyer in the courtroom who had actually read the FMCSA regs. The carrier settled on day three for an amount we hadn’t dreamed of. He was the same man at the kitchen-table consult as he was at the verdict.”
The Caswell Family
PERSONAL INJURY / TRUCKING · CLIENTS SINCE 2023
"
Rated 5 out of 5
“James Whitfield represented our company in a partnership dispute that two other firms told us was unwinnable on the facts. He went through 14,000 emails, found the smoking gun, and won a $6.1M jury verdict in nine days of trial. The opposing firm settled three similar cases against us within ninety days.”
R. Okafor, CEO, Ironwood Ventures
BUSINESS LITIGATION · CLIENT SINCE 2024
Chapter VII · Office & Hours

112 State Street.
Fourteenth floor.

Sterling & Associates
Attorneys at Law
112 State Street, 14th Floor
Boston, Massachusetts 02109

Mon — Fri
08:30 — 18:30
Saturday
By appointment
Intake line
24 hours · 7 days
Hospital visits
Available statewide