Michelle Obama’s Brother Craig Robinson Lawsuit, $30K School Kicks Out Two Sons After Racism Complaints—2024 Settlement Ends 3-Year Case
Craig Robinson—Michelle Obama’s brother—and his wife Kelly just settled their explosive racial bias lawsuit against Milwaukee’s University School of Milwaukee on November 5, 2024. Milwaukee County Circuit Judge Thomas McAdams dismissed the case with prejudice after three years of court battles. The couple accused the $30,000-per-year private school of kicking out their straight-A sons, ages 9 and 11, after they complained about racist classroom assignments during COVID-19 virtual learning.
Settlement terms remain confidential, but both sides issued a joint statement calling the Robinson children “model students” and expressing regret the dispute ended their enrollment. The case reveals how a premier prep school responded when powerful parents questioned classroom content—and what happened when parents filed 135 emails and 350 pages of complaints in 170 school days.
What Sparked the Robinson Family Lawsuit?
The Robinson lawsuit centers on events between November 2020 and June 2021 when Craig and Kelly Robinson noticed disturbing patterns in their sons’ virtual classroom assignments at University School of Milwaukee.
Kelly Robinson began attending her older son’s virtual classes during the COVID-19 pandemic to monitor his education. What she observed triggered months of complaints: repeated racial and ethnic stereotypes in assignments, disregard for children not physically present in classrooms, and what the couple called “insensitivity to socioeconomic status.”
The couple specifically flagged assignments containing the word “plantation” in a Thanksgiving word search, though school officials later claimed the Robinsons “badly mischaracterized” the worksheets. Another controversy involved a discontinued teaching practice where fourth-graders performed Underground Railroad simulations, with teachers acting as “slave catchers” trying to catch students wearing thrift store clothes.
Craig Robinson told Good Morning America: “We saw a repeated use of racial and ethnic stereotypes in actual assignments.”
The Explosive Claims: What the Lawsuit Alleged
The 25-page lawsuit filed April 18, 2022, in Milwaukee County Circuit Court accused USM of breach of contract, consumer fraud, deceptive trade practices, violation of the implied covenant of good faith and fair dealing, arbitrary and capricious termination, and outrageous conduct.
Key Allegations:
- USM marketed itself as committed to diversity but failed to provide the “supportive, inclusive” learning environment promised in enrollment contracts
- The school retaliated against two model students to punish their parents for raising valid concerns
- USM treated students of color “with none of the respect, trust, honesty, fairness or even the basic kindness, mandated by the Common Trust”
- The Robinson sons were denied opportunities to test out of math classes while white students took the exam
- School administrators dismissed bias incident reports instead of addressing concerns
- The termination was “targeted directly” at the Robinson children despite their model behavior
The lawsuit claimed USM’s conduct was “particularly egregious and harmful” because it punished innocent children for their parents’ advocacy.
School Fires Back: The 135 Emails That Changed Everything
University School of Milwaukee hit back hard in a May 19, 2022, motion to dismiss, painting a drastically different picture of events.
USM’s lawyers alleged Kelly Robinson sent an “incessant series of lengthy, misguided, and often disrespectful emails and text messages” to teachers. According to school records, during the 2020-2021 school year’s 170 days, Kelly Robinson sent 135 emails and 350 pages of complaints to the school.
Head of School Steven Hancock wrote in termination letters obtained by NBC News that the Robinsons “failed to fulfill the foregoing commitments as partners with USM” and engaged in “disrespectful” conversations about staff and teachers.
The school’s pretrial report claimed Kelly Robinson “decided she did not like the middle school curriculum” and “neither respected nor trusted the middle school teachers and administrators.” School administrators told her she engaged in “disrespectful and deflating” communications.
USM lawyers argued the school spent “hundreds of hours and tens of thousands of dollars” dealing with the Robinson family’s complaints before making the “exceptionally rare decision” to terminate enrollment.
What Happened to the Robinson Children?
The Robinson sons attended University School of Milwaukee for approximately five years starting in 2016. Craig Robinson described them as straight-A students who never got in trouble.
On April 14, 2021, the Robinsons received a shocking letter informing them their 11-year-old son’s re-enrollment contract was terminated. Two months later in June 2021, they received a second letter terminating their 9-year-old son’s enrollment.
Both letters from Hancock accused the parents of violating the school’s “Common Trust” and failing to relate to teachers and administrators “in a respectful, trustworthy, fair, or kind manner.”
“We were caught off guard,” Kelly Robinson told CNN. “There was nothing that indicated that what we were doing and the manner in which we were communicating was unusual.”
The couple found new schools for their sons, who are now reportedly thriving elsewhere.
The Bias Incident Reports That Triggered Retaliation
Central to the Robinson lawsuit were two formal bias incident reports Kelly Robinson filed through USM’s official reporting system.
January 2021: Kelly filed a bias incident report about classwork containing “harmful content toward underrepresented students.”
March 2021: She filed a second report about “similarly concerning language” in a different assignment.
The lawsuit alleged USM acknowledged receiving the reports but took no action to address the concerns. Instead, administrators allegedly used the reports against the family.
“I thought their bias incident reporting system was a way for them to help in changing the culture,” Craig Robinson told TMJ4. “It was actually turned against us in the end, and now I’ve learned that there is no longer a bias incident reporting system at USM.”
Attorney Kimberley Motley told NPR: “One would have hoped that USM would have taken the concerns from the Robinsons, who have been great allies, and try to make corrections that work for the benefit of all the students.”
Judge Denies School’s Motion to Dismiss—Case Heads to Trial
In a significant December 9, 2022, ruling, Milwaukee County Circuit Court Judge Thomas McAdams split his decision on USM’s motion to dismiss.
McAdams dismissed three counts but allowed three to proceed to discovery:
- Deceptive trade practices – Judge found the Robinsons raised viable claims that USM made untrue or misleading statements about its commitment to diversity
- Breach of good faith and fair dealing – Wisconsin law implies this covenant in every contract
- Arbitrary and capricious termination – Judge ruled the Robinsons presented legally viable claims
The ruling allowed the Robinsons to examine documents and seek testimony under oath about how USM handled past student and parent complaints related to race and discrimination.
Craig and Kelly Robinson released a statement: “We are grateful for the Court’s careful consideration of the merits of our lawsuit and its recognition that we have presented viable legal claims for what USM did to our family.”
USM Head of School Hancock responded that the ruling was “very favorable for USM” and expressed confidence the school would “prevail against their allegations” once the Robinsons were required to provide evidence.
The Pattern of Behavior Other Parents Reported
The Robinson lawsuit alleged a “broader pattern, extending over many years, of unfair treatment and insensitivity by USM toward its students of color and underrepresented students.”
Craig Robinson told the Milwaukee Journal Sentinel in 2022: “We heard from a number of people and realized that our situation wasn’t unique, and that this was a pattern of behavior. And once we heard that, then we felt a responsibility to do something more because we would feel awful if we just packed up and left.”
The couple said multiple other families shared similar experiences with USM administrators dismissing concerns about racial insensitivity rather than addressing them.
Breaking: Settlement Reached November 2024
After two and a half years of litigation, Milwaukee County Circuit Court records show Judge Thomas McAdams dismissed the lawsuit with prejudice on November 5, 2024.
“With prejudice” means the case is permanently dismissed and cannot be brought back to court.
Joint Statement from Craig and Kelly Robinson and University School of Milwaukee:
“The lawsuit filed by Craig and Kelly Robinson against USM has been dismissed, and the parties have resolved the matter. The Robinson Children were model students at USM. Both parties regret that the disagreements between the Robinsons and the school resulted in the Robinson children no longer being members of the USM community. The parties will not be commenting further on this matter.”
Settlement terms were not disclosed. The Robinsons had sought unspecified monetary damages and a jury trial. Tuition at USM runs up to $30,000 per child annually.
What This Lawsuit Reveals About Private School Accountability
The Robinson case exposes tensions between wealthy private schools’ diversity commitments and how they respond when families challenge their practices.
Key Takeaways:
USM enrolled 1,135 students for 2024-2025, similar to its 1,100 enrollment in 2022. The school maintained its reputation throughout the litigation despite national media scrutiny.
The case highlights how schools can characterize parent advocacy as “disrespectful” behavior warranting expulsion—even when parents use official reporting systems designed to address bias.
Both sides claimed vindication: the Robinsons forced discovery and settlement, while USM maintained its enrollment decisions were proper and unrelated to bias complaints.
The fact the school eliminated its bias incident reporting system after this case raises questions about whether institutions truly welcome feedback on diversity issues.
Similar Private School Discrimination Cases
The Robinson lawsuit mirrors other high-profile cases where elite private schools faced discrimination allegations:
- Multiple boarding schools settled abuse allegations for millions in 2024
- Several private schools in California faced lawsuits over handling of racial incidents during virtual learning
- East Coast prep schools paid settlements to students of color alleging hostile environments
Unlike most cases, the Robinson lawsuit featured plaintiffs with significant public profiles and resources to sustain years of litigation against a well-funded institution.
What Happened to USM’s Bias Reporting System?
Craig Robinson revealed during the litigation that University School of Milwaukee no longer maintains the bias incident reporting system the school promoted when his family enrolled their children.
The elimination of this reporting mechanism following the Robinson controversy suggests schools may remove accountability tools rather than address underlying issues parents identify through official channels.
This development contradicts USM Head of School Hancock’s assurances to parents that the school “appreciate, value, and rely on all kinds of feedback from our parents, students, faculty and staff.”
Legal Claims That Survived to Settlement
Three causes of action survived USM’s motion to dismiss and likely influenced the settlement negotiations:
Consumer Fraud/Deceptive Trade Practices Judge McAdams ruled the Robinsons could proceed with claims that USM violated Wisconsin’s Deceptive Trade Practices Act by making untrue statements about its commitment to diversity and inclusion. The school argued the Robinsons weren’t “the public” because they had a contract, but the judge found this reasoning insufficient at the dismissal stage.
Implied Covenant of Good Faith and Fair Dealing Wisconsin law implies this covenant in every contract. The Robinsons alleged USM breached this duty by retaliating against their children for protected parental advocacy. USM argued its contract allowed enrollment termination at will, but the judge found fact disputes requiring trial.
Arbitrary and Capricious Termination The judge ruled viable claims existed that USM’s decision was arbitrary, vindictive, or in bad faith—particularly given the children’s model behavior and academic performance.
These surviving claims gave the Robinsons leverage in settlement negotiations.
How This Compares to Other Education Lawsuits
The Robinson case differs from typical education litigation because it involves contract claims and consumer protection violations rather than civil rights statutes.
Most school discrimination cases rely on Title VI of the Civil Rights Act or state anti-discrimination laws. The Robinsons’ breach of contract and consumer fraud theories offered a different legal pathway that survived initial dismissal motions.
Related education cases include John Cooper School lawsuit alleging institutional misconduct and other private school accountability litigation.
Craig Robinson’s Profile and Why This Case Mattered
Craig Robinson is the executive director of the National Association of Basketball Coaches and former head basketball coach at Oregon State University and Brown University. He introduced his sister Michelle before her speech at the 2008 Democratic National Convention and was on stage for Barack Obama’s victory speech after his presidential election.
Robinson famously vetted Barack Obama by playing pickup basketball with him when Obama first dated Michelle, giving his sister the character assessment that led to their marriage.
His public profile brought significant media attention to the case—something USM alleged was intentional. The school’s motion claimed “the Robinsons appeared first on ABC’s Good Morning America to give an interview disparaging USM, and only later got around to filing their Complaint.”
What Parents Should Know About Private School Contracts
The Robinson case offers lessons for families enrolling children in private schools:
Private school enrollment contracts typically include broad termination clauses allowing schools to end relationships without cause. However, consumer protection laws may still apply if schools make false statements about diversity or other commitments.
Bias incident reporting systems may not protect families who use them—schools can characterize persistent advocacy as “disrespectful” behavior warranting expulsion.
Document everything. The Robinsons’ ability to point to specific incidents, worksheets, and the school’s responses strengthened their legal position.
Consider the power imbalance. Schools with significant resources can spend “hundreds of hours and tens of thousands of dollars” defending their decisions, potentially outlasting families without similar means.
For workplace discrimination issues, see related employment lawsuits.
Timeline of the Craig Robinson Lawsuit
2016: Craig and Kelly Robinson enroll their two sons at University School of Milwaukee
March 2020: COVID-19 pandemic begins; students shift to virtual learning
November 2020: Robinsons alert USM faculty about offensive language in worksheets and projects
January 2021: Kelly Robinson files first bias incident report about harmful content toward underrepresented students
March 2021: Kelly files second bias incident report about concerning language in assignments
April 14, 2021: USM terminates 11-year-old son’s enrollment
June 2021: USM terminates 9-year-old son’s enrollment
April 18, 2022: Robinsons file 25-page lawsuit in Milwaukee County Circuit Court
April 25, 2022: Craig and Kelly Robinson appear on Good Morning America
May 19, 2022: USM files motion to dismiss lawsuit, alleging 135 emails and 350 pages of complaints
December 9, 2022: Judge McAdams denies partial dismissal, allows three claims to proceed
November 5, 2024: Judge McAdams dismisses lawsuit with prejudice after settlement reached
FAQs About the Craig Robinson Lawsuit
What is the Craig Robinson lawsuit about?
Craig Robinson (Michelle Obama’s brother) and his wife Kelly sued University School of Milwaukee for kicking out their two sons after they complained about racist classroom assignments during COVID-19 virtual learning. The lawsuit alleged racial retaliation, breach of contract, consumer fraud, and violation of good faith dealing.
What was the outcome of Craig Robinson’s lawsuit?
The lawsuit was settled and dismissed with prejudice on November 5, 2024, after nearly three years of litigation. Settlement terms were not disclosed. Both parties issued a joint statement calling the Robinson children “model students” and expressing regret over the dispute.
Why did University School of Milwaukee expel the Robinson children?
USM claims it terminated enrollment because the parents communicated disrespectfully with teachers and staff, sending 135 emails and 350 pages of complaints during 170 school days. The Robinsons claim the school retaliated against their straight-A sons for filing bias incident reports about racist classroom content.
What racist content did the Robinsons complain about?
The Robinsons identified repeated racial and ethnic stereotypes in assignments, including use of the word “plantation” in a Thanksgiving word search and a discontinued practice where teachers acted as “slave catchers” in Underground Railroad simulations with fourth-graders.
How much did University School of Milwaukee pay to settle?
Settlement terms remain confidential. The Robinsons sought unspecified monetary damages. USM tuition runs up to $30,000 per child annually.
Who is Craig Robinson?
Craig Robinson is Michelle Obama’s brother, former head basketball coach at Oregon State and Brown, and current executive director of the National Association of Basketball Coaches. He famously vetted Barack Obama by playing basketball with him when Obama first dated his sister.
What happened to USM’s bias incident reporting system?
Craig Robinson revealed during litigation that USM eliminated the bias incident reporting system after this controversy—the same system Kelly Robinson used to formally report concerns about racist content in classroom assignments.
Disclaimer: This information is for educational purposes only and does not constitute legal advice. Lawsuit details, case status, and settlement information may change. Consult official court records, review current case filings independently, and contact an attorney for specific questions about this lawsuit or legal rights.
About the Author
Sarah Klein, JD, is a licensed attorney and legal content strategist with over 12 years of experience across civil, criminal, family, and regulatory law. At All About Lawyer, she covers a wide range of legal topics — from high-profile lawsuits and courtroom stories to state traffic laws and everyday legal questions — all with a focus on accuracy, clarity, and public understanding.
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