Sterling & 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.

Office225 W. Wacker Dr., Suite 2100
Telephone(312) 555-0148
HoursMon–Fri, 8:30 AM – 6:00 PM

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.

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.

Breach of contractBusiness tortsPartnership disputesClass actions
Discuss your dispute

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.

Mergers & acquisitionsGovernancePrivate placementsSuccession
Discuss your transaction

Wage-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.

Non-competesEEOC & IDHR defenseWage & hourExecutive agreements
Discuss your workforce

Acquisitions, 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.

AcquisitionsZoning & entitlements1031 exchangesLease disputes
Discuss your property

Multigenerational 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.

Estate planningSuccessionProbate litigationGuardianship
Discuss your legacy

Grand 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.

Grand jury practiceInternal investigationsSecuritiesTrial defense
Discuss your exposure

Article III — Verdicts & Results

The record,
in numbers.

Client names are withheld under confidentiality agreements. Representative matters illustrate experience — they are not guarantees of outcome.

0Years at the bar
$0MRecovered for clients
0Matters resolved
0Trials to verdict

$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 of Sterling & Blackwood LLP

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 of Sterling & Blackwood LLP

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 for white-collar defense and investigations

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 for trusts, estates and private wealth

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.”

Chief Executive · family-owned manufacturer, client eleven years

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
Email
intake@sterlingblackwood.law
Hours
Monday – Friday, 8:30 AM – 6:00 PM
Saturday by appointment
The Chicago River and skyline at dusk, two blocks from the firm's offices on Wacker Drive
Chicago River at dusk, near the firm's offices

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