Who breached the alleged oral agreement first?

AI Prompt:

I am providing you with documents containing emails and text log communications between the parties in a property dispute.. Please review these communications and answer: Who breached the alleged oral agreement first? In your analysis, please:

  1. Identify the key terms of any alleged oral agreement referenced by the parties
  2. Determine which party first failed to perform or repudiated their obligations
  3. Provide a chronological timeline of alleged breaches by each party
  4. Note any admissions about inability or unwillingness to perform

Base your analysis solely on the communications provided. There are some images and screenshots included, make sure to analyze those thoroughly as well.

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.


Based on my analysis of these communications, Kyle Hadley breached the alleged oral agreement first. Here’s my analysis:

Key Terms of the Alleged Oral Agreement

According to the documents, the parties entered a verbal agreement in 2022 with these terms:

  • Kyle would purchase the property for $320,000 (discounted price since Kyle would handle the transaction without commission as a licensed real estate agent)
  • The sale would include approximately $40,000 worth of furnishings
  • Purchase would be completed after Kyle’s condo sold
  • Kyle made a $30,000 payment toward the purchase price
  • Monthly payments ($1,200-$2,080) were for occupancy only, not purchase credits

Chronological Timeline of Breaches

October 2023: First Breach by Kyle

Kyle’s condo sold but he failed to complete the purchase as agreed.

October 9, 2024: Kyle’s Explicit Repudiation

The text messages reveal Kyle explicitly repudiated the purchase agreement:

  • 6:44 PM: Kyle texts “Sell the house. I’ll move out” and “I’m over it”
  • 6:46 PM: Kyle states “Let me know when you want me out. Please return all the money I have sent”

This constitutes Kyle’s unilateral abandonment of the purchase agreement. Brandon’s response “I am trying to sell it to you” shows Brandon was still trying to honor the original agreement despite Kyle’s repudiation.

December 2024: Kyle Misses Extended Deadline

Despite his October outburst, Kyle apparently remained in the property but failed to meet the December 2024 deadline Brandon had set in his July 29, 2024 letter.

February 14, 2025: Kyle’s Second Explicit Repudiation

Kyle admits in writing: “obtaining a mortgage would be a long and difficult process… It does not appear I will be able to do that in the next 4 months.”

April 22, 2025: Kyle’s Conditional Threat

Through his attorney, Kyle states: “I will vacate the property by 7/31, only after my money is returned to me” – threatening to unlawfully withhold possession.

Critical Admissions and Actions by Kyle

  1. October 9, 2024: “Sell the house. I’ll move out” – explicit repudiation
  2. February 14, 2025: Admitted inability to secure financing
  3. April 22, 2025: Threatened to condition vacancy on prior payment
  4. Pattern of non-responsiveness: July 2024-February 2025

Brandon’s Actions Were Responsive, Not Breaches

Brandon’s termination of the agreement (February 15, 2025) came only AFTER:

  • Kyle told him to “sell the house” (October 2024)
  • Kyle’s condo had sold without completing purchase (October 2023)
  • Kyle’s extended non-communication
  • Kyle’s admission of inability to perform (February 2025)

Conclusion

Kyle breached first through:

  1. Initial breach: Failing to purchase when his condo sold (October 2023)
  2. First repudiation: Explicitly telling Brandon to “sell the house” and that he’d “move out” (October 9, 2024)
  3. Continuing breach: Non-responsiveness (July 2024-February 2025)
  4. Second repudiation: Stating inability to obtain financing (February 14, 2025)

The October 9, 2024 text messages are particularly damaging to Kyle’s position – he explicitly told Brandon to sell the property to someone else and said he would move out, effectively abandoning the purchase agreement. Brandon’s subsequent actions appear to be lawful responses to Kyle’s repudiation and breaches rather than initial breaches themselves.


Based on a chronological analysis of the communications provided, Kyle Hadley breached the alleged oral agreement first.

The initial breach occurred on October 9, 2024, when Mr. Hadley explicitly repudiated the agreement via text message, stating, “Sell the house. I’ll move out”. This was followed by a failure to perform after the conditions of the agreement were met and a later formal admission of his inability to secure financing.

1. Key Terms of the Alleged Oral Agreement

The communications reference several key terms of a verbal agreement for Kyle Hadley to purchase the property at 6122 N Winthrop Ave Unit C from Brandon McGivern:

  • Triggering Event: Mr. Hadley would purchase the property after the sale of his condo at 6166 N Sheridan. Mr. Hadley’s condo sold in October 2023.
  • Purchase Price: The agreed-upon purchase price was $320,000.
  • Included Items: The sale was to include approximately $40,000 worth of furnishings. A text message from Mr. McGivern on October 9, 2024, references this, stating, “I am giving you almost $50k worth of my furnishings in that house”. Mr. Hadley acknowledges this was a purchase, not a gift, stating, “We made an agreement for me purchasing them”.
  • No Commission: The price reflected a discount because Mr. Hadley, a licensed real estate agent, would handle the transaction without taking a commission.
  • Purchase Deadline: In a letter dated July 29, 2024, Mr. McGivern expressed his need to complete the sale “by the end of this year [2024] at the latest”. He reiterated this deadline in his February 15, 2025 letter.

2. First Breach of the Agreement

The first documented breach was a repudiation by Kyle Hadley. On

October 9, 2024, during a text message argument with Mr. McGivern over a mini-fridge, Mr. Hadley stated unequivocally that he was backing out of the agreement.

  • At 6:44:13 PM, Mr. Hadley texted, “Sell the house. I’ll move out.“.
  • He immediately followed up at 6:44:19 PM with, “I’m over it.“.
  • He then demanded his money back and reimbursement for an AC unit, reinforcing his intent to terminate the purchase agreement: “Let me know when you want me out. Please return all the money I have sent. Also, I’ll send you the bill for the AC (around 8k)”.

Mr. McGivern’s response, “I am trying to sell it to you”, indicates that he still considered the purchase agreement to be active at that moment, and it was Mr. Hadley who was terminating it.

3. Chronological Timeline of Alleged Breaches

Kyle Hadley’s Breaches:

  1. October 9, 2024: Repudiation of the Agreement. As detailed above, Mr. Hadley explicitly told Mr. McGivern to “Sell the house” and that he would move out, constituting a clear repudiation of his intent to purchase.
  2. Post-October 2023: Failure to Perform. The agreement was predicated on Mr. Hadley purchasing the property after his condo sold. His condo sold in October 2023, yet by February 2025—over a year later—the purchase had not been completed.
  3. December 31, 2024: Failure to Meet Deadline. Mr. Hadley failed to complete the purchase by the end of 2024, a deadline Mr. McGivern had formally established in writing on July 29, 2024.
  4. February 14, 2025: Formal Admission of Inability to Perform. Mr. Hadley admitted in an email that he could not secure financing in the near future, stating, “It does not appear I will be able to do that [obtain a new mortgage] in the next 4 months”.
  5. Ongoing: Unauthorized Property Modifications. Mr. McGivern consistently alleged that Mr. Hadley made unauthorized replacements of a functioning AC unit ($8,075) and washer/dryer ($2,142.28). Mr. Hadley confirmed making these replacements and their costs in his own emails .

Brandon McGivern’s Actions (In Response to Hadley’s Breaches):

Mr. McGivern’s actions, as documented, were attempts to enforce the agreement or responses to Mr. Hadley’s non-performance, rather than initial breaches.

  1. July 29, 2024: Setting a Deadline. Mr. McGivern’s letter was not a breach but an effort to enforce the agreement’s timeline, which had become indefinite after Mr. Hadley’s condo sale.
  2. February 15, 2025: Formal Termination of the Agreement. Mr. McGivern sent a formal letter terminating the verbal agreement. This was not an initial breach but a response to Mr. Hadley’s cumulative failures, citing the missed deadline, lack of communication, unauthorized modifications, and Mr. Hadley’s own admission that he could not obtain financing.

4. Admissions of Inability or Unwillingness to Perform

The documents contain direct admissions from Kyle Hadley about his unwillingness and inability to perform his obligations under the agreement.

  • Admission of Unwillingness (October 9, 2024): The text messages “Sell the house. I’ll move out. I’m over it.” are a direct statement of his unwillingness to proceed with the purchase at that time.
  • Admission of Inability (February 14, 2025): Mr. Hadley’s email is a key piece of evidence. He explicitly states: “It does not appear I will be able to do that [obtain a new mortgage] in the next 4 months.“. He then proposes an alternative: “If this does not satisfy you, please return the $30,000 plus cost of air conditioner and washer/dryer, for a total reimbursement of 40,217. I will begin to make other living arrangements”. This confirms he cannot fulfill the purchase agreement and offers to rescind it in exchange for his money back.

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