Breach of contract, partnership disputes, business torts, and class-action defense in Illinois state and federal courts. More than sixty of our litigators' matters have gone to verdict — and most of the rest resolve on our clients' terms once the other side reads the trial brief.
Discuss your disputeSterling & Blackwood LLP · Est. 1987
Chicago counsel for defining moments.
Trial lawyers and trusted advisors to the city's families and enterprises since 1987 — in the courtroom, the boardroom, and everywhere the outcome matters.
Article I — The Firm
Thirty-eight years.
One standard.
Sterling & Blackwood was founded in 1987 by two Cook County prosecutors who believed a law firm should prepare every matter as though it will be tried. From a two-desk office on LaSalle Street, the firm has grown into one of Chicago's most trusted litigation and advisory practices — without ever losing the discipline of the courtroom.
Today our attorneys counsel family-owned manufacturers, regional banks, real estate developers, and the executives who lead them. We are deliberately selective: fewer matters, senior attention, and no handoffs to junior staff on the decisions that decide outcomes.
Article II — Practice Areas
Six disciplines.
Singular preparation.
Every practice group is led by a partner who has taken a matter to verdict, to close, or to final decree. Select a discipline to see how we work.
Entity formation, governance, private placements, and acquisitions for Midwest middle-market companies. We have closed more than three hundred transactions — and structured them so carefully that none has produced post-closing litigation between the parties.
Discuss your transactionWage-and-hour audits, non-compete drafting and enforcement, executive agreements, and defense before the EEOC, the IDHR, and the NLRB. We keep employers out of disputes where possible — and prevail in them where not.
Discuss your workforceAcquisitions, dispositions, financing, 1031 exchanges, and zoning before the Chicago Plan Commission and Zoning Board of Appeals. We have represented developers in more than forty entitlement proceedings across the city's wards.
Discuss your propertyMultigenerational planning, business succession, guardianships, and probate litigation. The group has drafted plans governing more than $2.1 billion in family and closely held assets — and defended those plans when challenged.
Discuss your legacyGrand jury subpoenas, internal investigations, and trial defense in securities, healthcare, and public-corruption matters. Led by a former Assistant U.S. Attorney for the Northern District of Illinois, the group has resolved nine of its last ten investigations with no charges filed.
Discuss your exposureArticle III — Verdicts & Results
The record,
in numbers.
Client names are withheld under confidentiality agreements. Representative matters illustrate experience — they are not guarantees of outcome.
$42.7M
Federal jury verdict for a family-owned components manufacturer against a defaulting supplier — full award affirmed on appeal following a three-week trial in the Northern District of Illinois.
Not guilty.
Complete defense verdict for the former CFO of a regional bank on a five-count federal indictment. The jury deliberated four hours.
$310M
Sale of a Chicago logistics group to a national carrier — negotiated, documented, and closed in seventy-four days with no post-closing claims.
Article IV — Counsel
The people behind
the practice.
Fourteen attorneys and counsel, admitted in Illinois, the Seventh Circuit, and the bar of the United States Supreme Court. These are the partners you will meet first.

Margaret A. Sterling
Managing Partner
Commercial trials. Northwestern Pritzker School of Law, J.D. 1984. Admitted in Illinois, the Seventh Circuit, and the U.S. Supreme Court.

James R. Blackwood
Senior Partner
Corporate & M&A. University of Chicago Law School, J.D. 1986. Three hundred transactions closed for Midwest middle-market companies.

Elena V. Okafor
Partner, White-Collar Defense
Harvard Law School, J.D. 2003. Former Assistant U.S. Attorney, Northern District of Illinois. Leads the investigations group.

David T. Nakamura
Partner, Trusts & Estates
Columbia Law School, J.D. 2005. ACTEC Fellow. Counsel to more than two hundred Chicago families across three generations.
Article V — In Their Words
“They tried our case like it was theirs. We settled for three times the opening offer two days before jury selection.”
Article VI — Contact
Bring us the matter that keeps you up at night.
Confidential submissions are reviewed by a partner within one business day. For urgent matters — an arrest, a subpoena, a deadline — call the office directly.
- Office
- Sterling & Blackwood LLP
225 West Wacker Drive, Suite 2100
Chicago, IL 60606 - Telephone
- (312) 555-0148
- intake@sterlingblackwood.law
- Hours
- Monday – Friday, 8:30 AM – 6:00 PM
Saturday by appointment
Thank you — your request has been received.
A partner will review your note and respond within one business day. If your matter is urgent, call (312) 555-0148 and ask for the intake partner.