Tuesday morning, the Department of Labor announced new regulations pertaining to how gig workers are classified. The battle has often taken place in the past at the state level, for example, ride share companies recently invested heavily to defeat propositions in California which would have required that drivers for Uber and Lyft be classified as traditional employees, rather than independent contractors. 

The regulation will require a review period and comments will be received. The 184 page proposed regulation includes a new framework, which departs from the Trump-era test, which primarily considered 1.) the nature and degree of control over the work; and 2.) the worker’s opportunity for profit or loss. While the previous test included three other factors, those two were the primary considerations as to whether a worker can be classified as an independent contractor. 

Under this test, the Eleventh Circuit ruled that an employer’s control of actions in certain instances is justified and is considered to be irrelevant under the economic reality analysis, since the primary analytical framework requires a review of the “nature and degree of the employer’s rule,” rather than a review of why said control exists. Scantland v. Jeffry Knight, Inc., 721 F.3d 1308, 1316 (Eleventh Circuit 2013).

The new test purports to establish a “totality of the circumstances” review, which will include several new factors into a balancing test. The regulation states that this sort of review is well-established, as a six pronged test was established in the Supreme Court opinions Rutherford and Silk. 

The new test would review the (a.) economic reality test, based upon multiple factors to form a totality of the circumstances review; and (b.) economic reality factors, such as (i.) opportunity for profit or loss depending on managerial skill, (ii.) investments by the worker and their employer, (iii.) degree of permanence of the work relationship, (iv.) nature and degree of control, (v.) extent to which the work performed is an integral part of the employer’s business, (vi.) skill and initiative, and (viii.) additional factors. 

KEY TAKEAWAY

The Biden Administration’s proposed regulation represents a staunch departure from the Trump Administration era guidance. The distinction between a qualified independent contractor, and one who should be deemed a traditional employee will be all the more important, as the federal agencies are sure to take note of this sort of issue in an audit or other sort of proceeding. If and when it officially kicks in, a thorough review will surely be warranted to ensure proper compliance.

Read the proposed DOL regulation here.  

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