Lawyers

Caleb Chaplain, Esq.

For more than a decade, Caleb served as the career law clerk to the Honorable Rebecca B. Connelly of the U.S. Bankruptcy Court for the Western District of Virginia. He also clerked for the Honorable Paul M. Black, giving him insight into how bankruptcy judges approach cases across the region.

In addition to practice, Caleb teaches Bankruptcy Law as an adjunct professor at Washington and Lee University School of Law. He is a frequent speaker at bankruptcy conferences and was honored by the American Bankruptcy Institute as a “40 Under 40” recipient.

A Rockingham County resident, Caleb is deeply connected to his community. He serves as Board President for the Second Home Learning Center and volunteers with local arts and LGBTQ+ organizations. His mix of legal expertise and service reflects Caleb’s steady belief that all people deserve clarity and compassion when facing financial stress.

Education

Indiana University Maurer School of Law, J.D.
Dartmouth College, B.A.

Memberships

American Bankruptcy Institute
Bankruptcy Law Section of Virginia State Bar, Newsletter Editor
American Bankruptcy Institute Journal, Coordinating Editor
WORKOUT
Harrisonburg-Rockingham Bar Association

Harrisonburg Office

1951 Evelyn Byrd Ave., Ste E, Harrisonburg, VA 22801

Articles

Chapter 4: Property of the Bankruptcy Estate in Bankruptcy Practice in Virginia (5th ed., 2025) (with Hannah W. Hutman).
Yellow Corp. and the Calculation of Withdrawal Liability, Am. Bankr. Inst. L.J. June 2025, at 22 (with Ian Roberts).
A Practical Approach to Using Bankruptcy Rules Effectively: Part 6: Rule 9024 – Relief from a Judgment or Order, NACTT Newsl., Mar. 17, 2025
A Practical Approach to Using Bankruptcy Rules Effectively: Part 5: Rule 9023 – New Trial; Altering or Amending a Judgment, NACTT Newsl., Mar. 10, 2025
Is Finality Always Worth the Wait?, Am. Bankr. Inst. L.J. Dec. 2024, at 36 (with Brittany B. Falabella).
Rules Are Made to Be Broken . . . if in Conflict with the Code, Am. Bankr. Inst. L.J. Nov. 2024, at 22 (with Vincent J. Roldan).
Hear Me Out: The Supreme Court Gives Voice to Parties in Interest, Am. Bankr. Inst. L.J. Aug. 2024, at 28 (with Brittany B. Falabella).
Discharge, Disclosure and Due Process: Bankruptcy’s Bargain, Am. Bankr. Inst. L.J. July 2024, at 30 (with Brandon Poirier).
Must the Sub V Debtor’s Debts Be Linked to Its Current Business?, Am. Bankr. Inst. L.J. Oct. 2023, at 26 (with David Cox).
Editor of The Best of ABI 2022: The Year in Consumer Bankruptcy (2023).
She Works Hard for the Money: The Chapter 13 Debtor’s Plight in Obtaining Credit, NACTT Quarterly, Jan.–Mar. 2023, at 8 (with Hon. Rebecca B. Connelly) (Cover Article).
No Good Deed Goes Unpunished as COVID Forbearances Come Due, Am. Bankr. Inst. L.J. Nov. 2022, at 26 (with M. Christine Maggard).
A “Cringeworthy,” Cautionary Tale: How the NRA Missed Its Shot at Chapter 11, Am. Bankr. Inst. L.J. Aug. 2021, at 12 (with Vincent J. Roldan) (Cover Article).
New Claim in Town: CARES Forbearance Claims under Section 501(f), Bankr. L. News (Va. State Bar, Bankr. L. Section), Spring 2021, at 6.
The Terminator Argument: The Duty of Competence in Using Artificial Intelligence, Am. Bankr. Inst. L.J. Nov. 2019, at 28 (with Nisha R. Patel).
Debtors Against the SSA: Who May Hear the Case?, Am. Bankr. Inst. L.J. Aug. 2019, at 14 (with Hon. Rebecca B. Connelly).
When Acting in Good Faith Isn’t Enough: A Taxing Decision for IRS, Am. Bankr. Inst. L.J. Sept. 2018, at 14 (with Hon. Elizabeth L. Gunn).
Star-Cross’d: The Tragedy of Chapter 13 and the Modern Student Loan Debtor, ABI Consumer Newsl., Nov. 16, 2018
Repaying Your Student Loans, Part 1: Tax Considerations in Repayment, Credit Abuse Resistance Education Blog, Mar. 17, 2017, available at https://care4yourfuture.org/blog/repaying-student-loans-pt1/.
Avoiding [via] the National Form Plan, ABI Consumer Newsl., Feb. 6, 2017
Federal Rule Amendments Effective Dec. 1, 2015, ABI Consumer Newsl., Feb. 4, 2016

Let's Talk About Your Options

Your story matters. We'll listen, explain your options, and help you move toward a fresh start. Schedule a free consultation today. Available evenings, weekends, and online for your convenience.