Representative cases Jackson has litigated include the following:

• In re BankAtlantic Bancorp. Inc., Litigation, 39 A.3d 824 (Del. Ch. Feb. 27, 2012). Served as lead litigation associate representing Wilmington Trust Company as Indenture Trustee under three series of TruPS documents in three-day trial to ensure that an obligor bank holding company complied with the terms of the indenture with respect to a sale transaction.
• Counsel to limited liability company in Virginia dissolution action; second-chaired trial team that litigated multi-issue dispute in a bench trial.
• Representing university in discrimination lawsuit brought by former student.
• For the past four years, served as lead litigation associate representing a major pharmaceutical manufacturer in connection with the nationwide Average Wholesale Price (AWP) litigation (In re: Pharmaceutical Industry Average Wholesale Litigation (MDL No. 1456)).
• Served as lead litigation associate representing international government contractor in False Claims Act litigation, U.S. ex rel. Paul Funk v. Mission Essential Personnel et al.
• Served as lead litigation associate representing leading mortgage company in securities class action litigation involving residential foreclosure procedures.
• Representing various clients, from individuals to corporations, in adversary proceedings involving fraudulent transfer and preference actions.
• Counsel to land owner in Maryland land use and development dispute; second-chaired trial team that litigated multi-issue dispute in a bench trial.
• Served as lead litigation associate in representation of large retail pharmacy chain concerning challenge to its prescription drug labeling and dispensing practices and procedures.
• Represented large real estate development and construction corporation in Virginia mechanic’s lien lawsuit.
• Assisted in representation of large health insurer raising claims related to prescription drug benefits and reimbursement from pharmacy benefit manager (PBM).
• Served as lead litigation counsel representing family in complex probate litigation matters in District of Columbia Probate Court.
• Successfully represented US Navy sailor, who was charged with premeditated murder, at month-long courts-martial in Washington, DC.
• Represented scores of US Navy sailors and marines before Navy Physical (Disability) Evaluation Board (PEB) in Washington, DC.
• Represented individuals before Administrative Law Judge at Office of Disability Adjudication and Review to obtain Social Security disability benefits.
• Represented pro bono US Army veteran in securing full disability benefits and "unemployable" rating with the Veterans Administration.
• Represented pro bono individual in obtaining full custody and support for minor child.
• Represented pro bono clients in a variety of matters in court or administrative hearings, as well as in mediation. 

In 2003, Jackson began his career as a litigator while serving with the United States Navy’s Judge Advocate General’s (JAG) Corps. As a Naval attorney stationed in Washington, DC, he gained extensive litigation experience defending sailors and marines in criminal matters before courts-martial. In addition, Jackson provided civil legal assistance to hundreds of sailors and marines, and represented over a hundred sailors and marines before the Navy’s Physical (Disability) Evaluation Board.

During his active duty tour in the US Navy JAG Corps, Jackson was selected as Officer-of-the-Year for the Naval Legal Service Office North Central, which included six Naval Legal Service Offices on the East Coast covering a 22-state region, and was awarded the Navy Commendation Medal, two Navy and Marine Corps Achievement Medals, the National Defense Service Medal, and the Global War on Terror Service Medal.

Jackson has continued his service as a reserve officer and in 2009 was selected for promotion to Lieutenant Commander in the United States Navy. He is currently assigned to Commander Navy Installations Command (CNIC) as Deputy Force Judge Advocate helping to deliver effective and efficient readiness to the fleet.