Amy Duggar’s husband Dillon King ordered to pay $156k in second unpaid rent lawsuit after fighting $236k debt in court

AMY Duggar’s husband, Dillon King, has been ordered to pay over $156,909.96 in a second unpaid rent lawsuit for his restaurant business after fighting a $236,728.08 judgment in a separate case. 

Dillon owns Wellington’s with business partners and opened the first restaurant in 2020 in Springdale, Arkansas before moving the eatery to Rogers, Arkansas. 

The U.S. Sun can exclusively reveal landlord Hillcrest Holdings, LLC sued Winston Holdings, LLC, aka Wellington’s, Dillon and two business partners for unpaid rent for the Springdale, Arkansas location. 

In August 2018, the plaintiff and defendants entered into a lease agreement to rent the property from September 2018 to December 2023. 

In July 2023, Dillon and his business partners allegedly “vacated the premises which constitutes as a default of the lease and a material breach of contract.”

The court papers continued to claim, “Winston Holdings, LLC failed to make the required monthly rent payments to the plaintiff as required by the lease after June 2023, and its failure to make said payments constitutes a default of the lease and a material breach of contract.”

In February 2024, the defendants responded to the lawsuit by denying the allegations and claimed, “Defendants only admit they ceased making payments after Plaintiff refused to communicate after several good faith attempts.”

They request the complaint be dismissed. 

Then in an amended complaint, the Plaintiff claimed, “[Winston Holdings] caused damages to the Premises and failed to maintain the Premises as required by Article 13.1 of the Lease and further failed to remove several alterations it made to the Premises when it vacated same as required by Article 14.3 of the Lease. 

“[Winston Holding’s] acts and omissions constitute a default of the Lease and a material breach of contract. 

“Boyce, Gayer, and King personally guaranteed [Winston Holding’s] performance of all its obligations under the Lease. Boyce, Gayer, and King have, likewise, failed to make any rent payments to the plaintiff after June 2023, repair the damages [Winston Holding’s]  caused to the Premises while it occupied same, or remove any of the alterations [Winston Holding’s] made to the Premises.”

Dillon, who retained new counsel in the lawsuit, responded to the amended complaint separately from his business partners. 

While Dillon denied the new allegations of causing damages and failing to remove alterations of the property, he admitted that “certain payments were not made to the Plaintiff, but failure for such payments to be tendered were after good faith attempts were made to pay, and to communicate with the Plaintiff. 

“It is denied that a material breach occurred.”

A consent judgment, which is a settlement agreement, was filed on January 2, 2025. 

The judgment is in the amount of $156,909.96. 

The U.S. Sun obtained exclusive photos of the restaurant in 2021. 

The restaurant featured a massive bar with shelves of liquor up to the ceiling, big screen TVs, and a dining area. 

There was a cigar lounge called The Reserve, where customers could smoke while relaxing on leather couches.

Upstairs had more seating for dining, along with a private poker room.

There was also dining on the front patio. 

SECOND LAWSUIT

This lawsuit came just months before Dillon, Winston Holdings, LLC and his two business partners were sued for unpaid rent of the Rogers, Arkansas location on April 2, 2024. 

The U.S. Sun previously reported from court papers, “Tenant has failed to pay Minimum Rent in full each month. Tenant has since made rental payments but has not paid all unpaid rent.

“Since the Final Notice of Default, Tenant has paid the following amounts towards its balance: $23,239.92 on January 25, 2024, $10,000 on February 15, 2024, and $10,000 on March 5, 2024. 

“Despite these payments, tenant has yet to pay Landlord the full unpaid balance.”

The lawsuit continues that the business was still occupying the premises at the time of the filing, despite the past rent due. 

The lawsuit claims Defendants currently owe $86,683.30, plus future rent. 

On October 14, 2024, the Plaintiff and Defendant Winston Holdings, LLC filed that they have entered into an agreement. 

The court papers read, “The Parties have agreed that judgment be entered in favor of the Plaintiff, Hachem Investments, INC, against Defendant, Winston Holdings, LLC, for breach of contract as alleged in the Complaint, in the amount of $240,000. 

“The parties further agree that Plaintiff, Hachem Investments, INC, is awarded recoverable costs of $844.60 and reasonable attorneys’ fees of $18,982.50 as part of this Consent Judgment. That the Plaintiff’s judgment shall bear interest at the rate of 10% per annum until paid in full.”

On December 19, 2024, Hachem Investments, INC claimed Dillon “signed the Settlement Agreement on October 14, 2024.”

The court papers allege Dillon was ordered to pay $50,000 in two separate installments, per the settlement agreement.

They claim he paid the first installment, but missed the payment deadline of December 13, 2024 for the remaining $25,000. 

The court papers continued, “King has refused to perform his obligation to pay the remaining $25,000 he owes pursuant to the Settlement Agreement.

“Accordingly, Plaintiff requests that the Court grant this Motion and enter judgment against King consistent with the Settlement Agreement.”

“The Settlement Agreement provides that if Dillon King fails to make timely or full installment payments, he shall be deeded to have confessed to judgment in the lawsuit for $236,728.08, less any installment of the $50,000 that has been timely paid.”

On December 23, an Arkansas judge signed off on the judgment, as the court papers read, “It is therefore ordered and Adjudeged that Plaintiff has final judgment against Separate Defendant Dillon King consistent with the Settlement Agreement for the amount of $236,728.08, less any installment of the $50,000 that has been timely made.”

DILLON FIGHTS BACK

Dillon responded to the judgment on January 1, fighting the court’s decision to order him to pay the full amount of $236,728.08.

The court filing read, “It is admitted that the agreement was signed, and the first payment was made. However, the remaining allegations are denied – and payment has been offered. 

“King denies liability and the damages owed… Pleading alternatively, any liability derived (which is denied) would be required to come from a breach of contract claim and new action, rather than a Motion, for a defaulted judgment, after a settlement agreement is negotiated and executed.

“One cannot confess to a judgment without executing or signing a judgment, without the cloaking powers of a judgeship.”

Dillon argued the Motion for a Judgment was “wrongly entered.”

He also claimed the judgment was entered before he had the opportunity to file a response and contest it.

Dillon continued, “The motion is wrong and false and should be denied.

“King requests this Court to reconsider its ruling, vacate, the judgment, and allow the proper responding pleadings and briefs to be filed, in addition to a hearing on the merits be heard to protect the integrity and arguments of the parties for appeal, or to preserve therein.”

Plaintiff Hachem Investments, INC. responded on January 3, 2025, “Dillon King signed a settlement agreement with Plaintiff in this case. 

“The Agreement required him to make two settlement payments by certain dates. He failed to make the second payment. The Agreement provides that if he fails to make a payment, Plaintiff may seek certain damages, interest, and fees ‘through motion’ to this Court, and that King ‘shall be deemed to have confessed to judgment’ for those damages, interest, and fees. 

“Plaintiff did so on December 19. Now King effectively seeks to rescind the Agreement that he negotiated and signed. But King cannot renege on his Agreement now. The Court should deny both the Set Aside Motion and Reconsideration Motion.”

On January 13, the Plaintiff filed a Writ of Garnishment, which would allow a creditor to take wages from an employer or funds from a bank account, against Dillon for $234,844.587.

The Arkansas judge has not ruled on the request.

Amy, 38, told The U.S. Sun on behalf of her husband, “We will tell our side when the time is right. But it’s not the right time at the moment.”

AMY’S LAWSUIT

Amy and Dillon were previously hit with a lawsuit for unpaid rent in May 2022 for her store 3130 Clothing. 

Amy and Dillon entered into a five-year lease agreement on October 8, 2018, for $3,332.83 a month for her clothing store, 3130 Clothing. 

On June 1, 2019, the couple added a second suite to the lease agreement, as rent increased to $6,665.66 a month until May 31, 2024. 

The complaint read, “3130 occupied the premises until August 2021, at which time it vacated the premises which constitutes a default of the Lease and Amendment and a breach of contract.

“3130 failed to make the required monthly rent payments to the plaintiff as required by the Lease and Amendment after June 2021.”

The landlord requested unpaid rent from June 2021, plus court costs, interest, and attorney’s fees. 

Amy and Dillon responded to the lawsuit by admitting they vacated the premises in August 2021, but insisted the landlord was the one who “committed a prior material breach of the Lease and Agreement.”

Amy and Dillon then filed a counterclaim against the landlord, arguing that according to the lease, they had a Tenant Improvement allowance in the amount of $31,250 for contractors to improve the leased space. 

Any cost over the agreed amount would be paid by Amy and Dillon. 

In late 2018, the landlord hired a general contractor to perform renovations on the two suites. 

The court papers claimed, “Landlord then deducted those charges from 3130, LLC’s Tenant Improvement allowance and charged Counterclaimants for, what was represented to be, all costs in excess of the allowance.”

They were allegedly charged $66,486, including late fees.

The papers continued to claim, “However, Counterclaimants did not receive any supporting invoices at the time of the charges. 

“Upon information and belief, Landlord charged Counterclaimants in excess of the amounts actually charged by [the contractor] or other contractors in violation of the Lease and Amendment. 

“Landlord also charged Counterclaimants for work performed at units other than Suites B or C, or for work that benefitted all units at 7321 West Sunset that were not to be charged as part of the TI allowance agreement.”

The court papers continued that things then took a “disturbing turn.”

The counterclaim alleged, “On or about May 27, 2021, Defendants were shocked to discover that the leased space had been broken into and trash had been thrown away. 

“Even more shocking, upon review of their security camera footage, Counterclaimants discovered that the owner of Hillcrest Holdings, was the person that, without notice or warning, broke into 3130 Clothing.

“On the day in question, [the owner] – in an apparent fit of rage – unlawfully broke into 3130 Clothing and trashed Defendants’ store. [He] can be seen throwing garbage – such as cardboard boxes – and other rubbish throughout the store with little regard for the damage and mess he left in his wake.”

The court documents continued, “As a direct and proximate result of Landlord’s breaches of the parties’ Lease and deprivation of the peace and quiet enjoyment of the premises through the break-in, Counterclaimants were forced to relocate 3130 Clothing to safer, less intrusive pastures.”

They claimed they “lost substantial revenue” during the relocation period and were forced to pay “substantial relocation costs.”

The landlord responded to the counterclaim by denying the allegations, but admitted he “returned several boxes the defendants had previously dumped on the property to the inside of their premises.”

The complaint and counterclaim were dismissed.

Amy exclusively told The U.S. Sun of the outcome, “It’s been a year since the break-in. It’s been a long legal process. I consider the outcome a win. I feel like I can breathe now.”

ABOUT AMY

Amy appeared on the family’s reality show 19 Kids and Counting. 

She was known as the “rebel” family member, as she did not adhere to Jim Bob and Michelle’s strict dress code and lifestyle. 

She has distanced herself from her uncle Jim Bob, aunt Michelle and most of her cousins.

Amy lives in Rogers, Arkansas with her husband and their son, Daxton.