About This AI Analysis
This independent analysis was conducted by two leading AI systems – Claude (Anthropic) and Gemini (Google) – reviewing publicly filed court documents from Cook County cases 20251707919 and 2025CH05527. The AI platforms were provided only with the specific documents listed above and asked to evaluate the legal question presented. The unedited responses below represent objective algorithmic analysis of public records, not legal advice or party opinions. Multiple AI systems were used to identify consistent patterns and conclusions across different analytical approaches. Transparency Note: The exact prompt and all source documents are displayed above. No additional context or guidance was provided to the AI systems beyond what is shown.

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Based on my review of these legal documents, this case demonstrates why Requests for Admission under Illinois Supreme Court Rule 216 are considered one of the most powerful—and dangerous—discovery tools in litigation.

1. Case Summary

Parties and Underlying Dispute

• Plaintiff: Kyle Hadley (represented by Cole Sadkin, LLC)
• Defendant: Brandon McGivern (pro se)
• Case: Cook County Chancery Division, Case No. 2025-CH-05527
• Dispute: Property ownership claim involving 6122 N. Winthrop Ave., Unit C, Chicago. Plaintiff claims he had an oral agreement to purchase the property from Defendant and made payments toward the purchase. Defendant disputes this and filed a parallel eviction action.

Critical Timeline

June 24, 2025: Defendant served 30 Requests for Admission on Plaintiff

July 2-3, 2025: Plaintiff filed responses – but here’s the critical problem: Plaintiff only responded to 10 requests, and those 10 were completely different questions than what Defendant actually asked

July 22, 2025: The 28-day deadline under Rule 216 expired

July 23, 2025: Defendant filed Motion to Deem Facts Admitted

August 7-13, 2025: Plaintiff filed “Amended Responses” (after the deadline and without court permission)

September 29, 2025: Court entered order GRANTING Defendant’s motion – all 30 facts deemed ADMITTED

What Went Wrong

The documents reveal a shocking mismatch between what was asked and what was answered. For example:

Defendant’s Actual Request #1: “You operated rental businesses involving multiple properties from June 2022 to present, including your condominium and portions of 6122 N. Winthrop Avenue, Unit C, Chicago, Illinois 60660.”

Plaintiff’s Fabricated “Request #1”: “Admit that Plaintiff did not sign a written contract for the purchase of 6122 N. Winthrop Ave., Unit C.”

These are completely different questions. According to the detailed comparison chart in the documents:

• Defendant served: 30 requests
• Plaintiff responded to: 10 fabricated questions
• Actual requests answered: ZERO
• Compliance rate: 0%

Plaintiff responded to requests 11-30 with nothing—complete blanks.

2. Strategic Impact Analysis: The Case-Ending Admissions

With all 30 requests deemed admitted, Plaintiff has conceded facts that likely destroy his case. The most devastating admissions include:

The “Fatal Trio” (Requests #21-23)

These three admissions together are likely case-ending:

#21: “You are a licensed real estate agent in Illinois.” – ADMITTED

#22: “As a licensed real estate agent, you know that oral real estate purchase agreements are void under Illinois law.” – ADMITTED

#23: “You have never had a written real estate purchase agreement with Defendant.” – ADMITTED

Impact: Plaintiff’s entire case rests on an alleged oral agreement to purchase the property. He has now admitted that (a) he’s a licensed real estate professional, (b) he knows oral real estate contracts are void under Illinois law (the Statute of Frauds), and (c) he never had a written agreement. This establishes that a sophisticated party knowingly pursued a legally invalid claim.

Repudiation (#20)

#20: “The email of February 14, 2025 constituted a repudiation of any purchase agreement.” – ADMITTED

Impact: Even if there had been a valid agreement, Plaintiff admitted he terminated it in February 2025, months before this litigation.

Evidence Fabrication (#24-27)

#24: “Exhibit B to your Complaint contains entries dated after January 30, 2025.” – ADMITTED

#25: “You did not have access to Defendant’s equity tracking document after January 30, 2025.” – ADMITTED

#26: “You altered or fabricated portions of the equity tracking document attached as Exhibit B to your Complaint.” – ADMITTED

#27: “You changed the purchase price from $320,000 to $300,000 in the document attached as Exhibit B.” – ADMITTED

Impact: Plaintiff admitted to fabricating key evidence attached to his own Complaint. This destroys his credibility and supports sanctions. The court already granted Defendant’s motion to strike Exhibit B as fabricated evidence.

Rental Arbitrage Operation (#1-7, 18, 30)

#1-7, 18: Admitted operating rental businesses at the property, collecting rent from subtenants while paying below-market rent to Defendant.

#30: “Your pattern of operating rental businesses while living at below-market rent demonstrates you intended to profit from rental arbitrage rather than purchase the Property.” – ADMITTED

Impact: These admissions establish that Plaintiff was running a rental business for profit, not acting as an equitable purchaser. This undermines any claim to equitable ownership.

Concealment and Bad Faith (#8-14)

Admitted discovering major water damage, concealing it for four months, failing to obtain estimates, denying Defendant access to inspect, and allowing unauthorized contractors on the property.

Impact: Supports claims of waste, breach of duty, and bad faith.

3. Consequences of Failing to Respond to Requests for Admission

Legal Consequences Under Illinois Law

Automatic Admission by Operation of Law: Under Illinois Supreme Court Rule 216(f), matters are deemed admitted if not responded to within 28 days. This happens automatically—no court order is required, though parties typically seek confirmation from the court.

Conclusively Established: Once deemed admitted, the facts are “conclusively established” for purposes of the pending action. See Kedzie & 103rd Currency Exchange, Inc. v. Hodge, 156 Ill. 2d 112, 120 (1993).

Extremely Difficult to Withdraw: Admissions can only be withdrawn or amended with court permission. Courts require showing: (1) the admission was result of mistake, inadvertence, or excusable neglect, AND (2) the party seeking admission will not be prejudiced, AND (3) withdrawal serves the truth-seeking function. See Vision Point of Sale, Inc. v. Haas, 226 Ill. 2d 334 (2007).

No Proof Required at Trial: Deemed admissions eliminate the need for proof. The admitting party cannot contest these facts at trial or on summary judgment.

Practical Consequences in This Case

Based on the documents, Plaintiff faces:

1. Loss of Case on the Merits: The deemed admissions establish he has no valid claim (no written contract, he’s a professional who knows oral contracts are void, he repudiated any agreement).
2. Summary Judgment: Defendant can likely obtain summary judgment based on the deemed admissions alone.
3. Sanctions: The court already granted the motion to strike Exhibit B as fabricated. Defendant is seeking Rule 137 sanctions against both Plaintiff and his attorney.
4. Credibility Destruction: Admitted fabrication of evidence destroys any remaining credibility for other claims.
5. Professional Consequences: Defendant requested referral of Plaintiff’s attorney to the Attorney Registration and Disciplinary Commission for professional misconduct.
6. Potential Counterclaims: The admitted rental arbitrage operation and property damage could support counterclaims.

4. Lessons Learned: What Should Have Been Done

Proper Response Strategies

When served with Requests for Admission, a party must respond to every single request within 28 days by:

ADMITTING if the matter is true (even if unfavorable)

DENYING if the matter is false, with specificity. Illinois Supreme Court Rule 216 allows denials when:

• The matter is not true
• The responding party lacks sufficient information (but this requires reasonable inquiry first)

OBJECTING on proper grounds such as:

• Privileged information
• Overly broad or unduly burdensome
• Calls for pure legal conclusion
• Compound or ambiguous

QUALIFYING answers when necessary: “Admitted in part, denied in part” with explanation

What Plaintiff Should Have Done in This Case

Step 1: Carefully Read Every Request Plaintiff needed to actually read all 30 requests as written, not rewrite them.

Step 2: Strategic Triage For damaging but true requests (like #21-22 about being a licensed real estate agent), Plaintiff had three options:

• Admit (because it’s true and easily provable)
• Object if there was a valid legal basis
• Deny if he could do so truthfully

Step 3: Respond to All 30 Requests Even if responses are unfavorable, it’s better to admit true facts than to have all 30 deemed admitted by default.

Step 4: File Timely Plaintiff needed to serve responses within 28 days (by July 22, 2025). If more time was needed, he should have:

• Requested an extension before the deadline
• Entered into a stipulation with opposing counsel
• Filed a motion for extension with the court

Step 5: If Deadline Missed, Act Immediately If the deadline passed, Plaintiff should have:

• Immediately filed a motion to extend time or permit late responses
• Shown good cause (illness, accident, etc.)
• Filed responses simultaneously with the motion
• NOT waited until after Defendant filed a motion to deem admitted

Critical Mistakes Made

1. Fabricating Different Questions This appears to be deliberate avoidance of damaging admissions. Plaintiff only responded to 10 softball questions he created himself.

2. Ignoring the Most Damaging Requests Requests #11-30 received no response at all. These included:

• His professional license (#21)
• Knowledge of the law (#22)
• Fabrication of Exhibit B (#24-27)

3. Missing the Deadline No response or extension request before July 22, 2025.

4. Filing “Amended” Responses Without Permission On August 7-13, after the deadline and after Defendant filed his motion, Plaintiff unilaterally filed “amended” responses. This violated:

• The 28-day deadline (already expired)
• The Court’s August 1 order requiring a Rule 201(k) conference first
• Basic procedure (can’t amend after deadline without court permission)

5. Not Conferring in Good Faith The Court ordered a Rule 201(k) meet-and-confer conference before further filings. Plaintiff filed amended responses without this required conference.

The Correct Approach

Even for very damaging admissions, Plaintiff had options:

For #21-22 (Real Estate License/Knowledge): These are factually true and easily provable through licensing records. Plaintiff should have:

• Admitted #21 (he is licensed)
• Admitted or carefully qualified #22 (he knows about Statute of Frauds but may argue exceptions like part performance apply)

For #24-27 (Exhibit B Fabrication): If Exhibit B was legitimate, Plaintiff should have:

• Denied #26 with detailed explanation of how the document was created
• Admitted #24 but explained the entries were based on contemporaneous records
• Provided evidence of access or explained the source of the information

If Exhibit B was not legitimate, Plaintiff’s only options were:

• Admit the fabrication and withdraw the exhibit
• Settle the case

For #1-7, 30 (Rental Operations): Plaintiff could have:

• Admitted collecting money from roommates but denied it was a “business”
• Qualified responses to distinguish cost-sharing from rental income
• Admitted facts but denied the legal characterization in #30

Why Requests for Admission Are So Powerful and Dangerous

The Unique Power of Rule 216

Requests for Admission are fundamentally different from other discovery tools:

Interrogatories seek information.

Document Requests seek evidence.

Requests for Admission seek to eliminate issues from the case entirely.

Characteristics That Make Them Dangerous

1. Automatic Deemed Admission Unlike other discovery violations that require a motion to compel, admissions are deemed automatically upon deadline expiration.

2. Conclusive Effect Admitted facts are conclusively established and cannot be contested at trial. They’re not just evidence—they replace the need for evidence.

3. Difficult to Withdraw The standard for withdrawing deemed admissions is extremely high. Courts disfavor withdrawal because it undermines the efficiency purpose of the rule.

4. Strategic Trap Parties often underestimate their importance, prioritizing interrogatories and document production. By the time they realize the danger, the deadline has passed.

5. Can Be Case-Ending As this case demonstrates, deemed admissions can establish all the elements of a claim or defense, making trial unnecessary.

Impact on This Specific Case

For Kyle Hadley, these deemed admissions are likely case-ending because they establish:

No Valid Claim:

• No written agreement (required for real estate)
• Plaintiff knew oral agreements are void
• Any agreement was repudiated

No Credibility:

• Admitted fabricating key evidence
• Admitted concealing property damage
• Admitted operating rental arbitrage scheme

Potential Affirmative Claims Against Him:

• Waste (property damage)
• Unjust enrichment (rental income collected)
• Fraud (document fabrication)

Procedural Consequences:

• Evidence struck (Exhibit B)
• Sanctions likely
• Potential attorney discipline
• Likely summary judgment for Defendant

Conclusion

This case is a textbook example of how not to handle Requests for Admission. What began as a property dispute has become a complete disaster for Plaintiff due to:

1. Misunderstanding the Rules: Believing he could rewrite the questions
2. Strategic Avoidance: Ignoring the most damaging requests
3. Missing Deadlines: Failing to respond within 28 days
4. Compounding Errors: Filing improper “amended” responses after the deadline
5. Violating Court Orders: Filing without the required conference

The September 29, 2025 court order granting the motion to deem all 30 facts admitted represents a complete tactical victory for Defendant and likely the end of Plaintiff’s case. The deemed admissions establish:

• Plaintiff has no legal claim (no written contract, admitted oral agreements are void)
• Plaintiff fabricated evidence (admitted altering Exhibit B)
• Plaintiff acted in bad faith (concealment, rental arbitrage)
• Even if there was an agreement, Plaintiff repudiated it

Key Takeaway: Requests for Admission may seem less important than other discovery, but they carry automatic, severe, and nearly irreversible consequences for non-response. They must be taken seriously, responded to completely and timely, and never ignored or treated casually. In this case, what might have been admissions that were merely unfavorable became deemed admissions that are case-ending.

This case will likely be cited in Illinois as a cautionary tale about the dangers of mishandling Rule 216 requests and the importance of responding to discovery obligations with precision and timeliness.