Xpressdocs Partners, L.P. (“ExpressDocs”) filed a breach of contract lawsuit Monday morning against D’Aprile Properties, LLC, Midwest Lending Corporation, and Ryan D’Aprile (“D’Aprile”), individually; in the Northern District of Illinois, alleging breach of contract in the amount of $317,391.57 for alleged marketing services rendered. The Complaint alleges that the Defendants are ultimately one and the same, as D’Aprile, and the entities largely operate in the same fashion, as such, it alleges the Defendants together failed to pay the marketing bills for over six months. 

Xpressdocs provides a wide variety of marketing services, its website lists brand management, automated direct mail, and print and direct mail fulfillment; as the three primary tabs of services provided. Xpressdocs also is geared towards specific industries, with Real Estate being listed as the first option under “By Industry,” on its website. 

Ryan D’Aprile is a real estate agent based in Illiniois, which also offers financing services and is licensed in Illinois, Indiana, Michigan, Wisconsin, and Florida. Its mortgage financing arm appears to be separate from the real estate portion, but D’April is listed under both entities. 

The complaint alleges, and includes exhibits, demonstrating that the parties have had a Marketing Services Agreement on the books since 2016, this agreement purportedly included a variety of services, including digital services, direct mail, and other sorts of similar activities. 

The fact-intensive Complaint goes into some interesting considerations as to corporate structure of D’Aprile’s holdings, which helps to lay the foundation to naming each entity. For example, the Complaint lays out that when payments were remitted, they came from inconsistent sources, sometimes from D’Aprile individually, and sometimes through the different companies. 

The Complaint admits that D’April had attempted on several occasions to setup a payment plan with Xpressdocs, however, Xpressdocs alleges that these efforts were not good faith and were only to “string along” the company, in the hopes that it would continue to provide marketing services. 

The Causes of Action against D’Aprile and his holdings include, Breach of Contract, Quantum Meruit (in the alternative), Suit on Sworn Account, Conspiracy, and Violation of the Theft Liability Act. In total, Xpressdocs is seeking relief in the amount of the entire unpaid amount, reasonable attorney’s fees, and pre-judgment and post-judgment interest. 

KEY TAKEAWAY

In many ways, this case appears to be a traditional breach of contract case. One thing that is interesting to note is how the Complaint looks to largely dismiss the attempts to pay as being not in good faith. What sorts of measures are acceptable to bargain in good faith to resolve this sort of issue? In the end, seems like a dispute that is ripe for mediation.

Jake Leahy

Jake A. Leahy

Attorney

Jake A. Leahy is a tax attorney at Airdo Werwas who counsels nonprofits, local governments, and businesses in tax, regulatory, and commercial matters.

He is a former Assistant Illinois Attorney General in the Revenue Litigation Bureau, where he handled…

Jake A. Leahy

Attorney

Jake A. Leahy is a tax attorney at Airdo Werwas who counsels nonprofits, local governments, and businesses in tax, regulatory, and commercial matters.

He is a former Assistant Illinois Attorney General in the Revenue Litigation Bureau, where he handled estate tax litigation, collections audits, and matters involving various state agencies. He previously served as a Judicial Law Clerk in the Circuit Court of Cook County, Law Division, Tax & Miscellaneous Remedies Section, working on administrative review actions, commercial disputes, and tax-related litigation.

Jake previously served on the Board of Education for Bannockburn School District 106 from 2017 to 2023, including as Vice President from 2020 to 2023. His experience in local government informs his work with public-sector clients, boards, and nonprofit organizations.

Jake is active in professional and bar organizations. He serves as an Assembly Member of the Illinois State Bar Association, Chair of the Chicago Bar Association’s State & Local Tax Committee and Young Lawyers Section Federal Tax Committee, and a member of the Editorial Board of the DuPage County Bar Association. He was recognized by the Illinois State Bar Association with its Law Student Public Service Award during law school, and by the Internal Revenue Service for his work with the Low-Income Tax Clinic at Holy Name Cathedral.

Jake earned his LL.M. in Taxation from Georgetown University Law Center, his J.D. from the University of Illinois Chicago School of Law, and his B.A. from the University of Illinois at Urbana-Champaign. He is admitted to practice in Illinois, the U.S. Tax Court, and the U.S. District Court for the Northern District of Illinois.

Outside of practice, Jake has completed three marathons, is a regular at Wrigley Field, and appreciates Chicago architecture.

Education

    • Georgetown University Law Center, LL.M. in Taxation, 2025

    • University of Illinois Chicago School of Law, J.D., 2023

    • University of Illinois at Urbana-Champaign, B.A. Political Science: Public Policy & Democratic Institutions, 2019

Admitted to Practice

    • Northern District of Illinois, 2025

    • U.S. Tax Court, 2024

    • Illinois, 2023

Associations

    • Illinois State Bar Association

    • Chicago Bar Association

    • American Bar Association, Tax Section

    • DuPage County Bar Association

    • Celtic Law Association