For over 40 years, Jonathan has worked at the intersection of law, public policy, and technology in the tech, media, and telecom fields, both in private practice and in positions at the Federal Communications Commission and The White House. He advises industry entities in advancing opportunistic business, legal, and regulatory strategies and in negotiating and closing business transactions (including M&A). He counsels a diverse set of clients that includes Fortune 50 companies, innovative start-ups, investment firms, and non-profit foundations.
Jonathan’s career began as a radio news reporter and producer in New York City, where he covered a range of local, national, and international topics. His early-career pivot to law school drew him to media and telecom law, and most recently to the legal issues involving content regulation, Section 230, and artificial intelligence. During his 5+ year stint at the FCC, Jonathan was Special Assistant to the Chairman and worked in senior bureau staff positions developing of FCC policy for new technology regulation, spectrum auctions, the digital television transition, and wireless telecom competition.
Jonathan currently co-chairs the Emerging Issues in Technology committee of the FCBA-The Tech Bar® and he speaks in educational settings and at industry gatherings frequently. He holds degrees from The Wharton School of the University of Pennsylvania and Georgetown University Law Center and has been named a “Best Lawyer®” and a Washington D.C. SuperLawyer.
Jonathan has been a WBK partner for 27 years and served as the firm’s Finance Partner from 2017 to 2025. He also devotes time to pro bono legal matters, primarily in the areas of criminal justice and responsible tech, and has been named multiple times to the D.C. Bar’s Pro Bono Honor Roll. Jonathan currently splits his time between D.C. and Los Angeles.
Representative Engagements
- Helped a non-profit public television organization separate from a larger entity and build a for-profit streaming business that ultimately merged with another media company.
- Counseled wireless industry players on spectrum policies needed for rollout of commercial mobile broadband services (including 5G services)
- Obtained state and federal regulatory approvals for numerous media and telecom deals, including obtaining Team Telecom clearance when needed
- Assisted both broadcast and wireless industry clients in navigating the intricacies of virtually all of the significant spectrum auctions since 1998, including the FCC’s innovative broadcast spectrum incentive auction, which repurposed low-band spectrum from television broadcast to mobile broadband use
- Represented Amtrak in spectrum acquisitions and regulatory approvals needed for the deployment of the Positive Train Control technology
- Represented Centennial Communications Corp. in its $944 million merger with AT&T Inc., and Atlantic Tele-Network, Inc. (now ATN International, Inc.) in securing approval for its $200 million acquisition of wireless facilities and customers in 26 markets in six states from Verizon Wireless
- On behalf of Cingular Wireless (now AT&T), devised and implemented structures to accomplish the unwind of a complex infrastructure-sharing arrangement with T-Mobile USA, a process that involved dozens of agreements and numerous FCC approvals
- Assisted Cingular Wireless in a broad range of transactions, including its merger with AT&T Wireless Services, a $1.4 billion spectrum acquisition from NextWave Telecom Inc.; and the acquisition of controlling interests in several affiliates that had acquired licenses as “designated entities” under the FCC’s rules
- Devised the template for the first spectrum lease agreements executed under a new FCC policy in 2003. Many elements of these spectrum leases have become the standard in the industry
- While at the FCC, advised two FCC Chairmen, co-authored rules for FCC spectrum auctions and directed the FCC’s first broadband PCS auction, which brought digital technology to the mobile phone industry and generated $7.7 billion for the U.S. Treasury and earned a place in the Guinness Book of World Records as the largest auction to date
- Director of Outreach for now-U.S. Senator Chris Van Hollen’s first Congressional campaign (2002) (while on leave of absence from WBK)
- Frequently a featured speaker at industry conferences and client seminars
- Senior Federal Communications Commission staff positions in the Chairman’s Office, Office of Plans and Policy, and Wireless Telecommunications and Mass Media Bureaus (1993-1998)
- Assistant Counsel to President Clinton in The White House Office of Presidential Personnel (1993)
- Clinton for President Campaign and Presidential Transition, Washington, DC (1992-1993)
- Associate in two Washington, D.C. communications law firms (1982-1991)
- News Reporter, WXLO-FM, New York, NY (1978-1979)
Honors
- Recognized in Best Lawyers for Communications Law (2025)
- Washington, DC SuperLawyer (2013-2024)
- Recommended by Legal 500 US (2017-2019)
- Martindale Hubbell AV® Preeminent Peer Review Rating (ongoing)
- One of 86 Attorneys Nationwide Named to the BTI Transactions All-Star Team (2008)
- Member, Tech, Media and Telecom Policy Group, 2008 Presidential Campaign of Barack Obama
- Private Sector Advisor – U.S. Department of State delegation to the World Telecommunications Development Conference, Istanbul, Turkey (2002)
- Recipient of the “Hammer Award” from Vice President Al Gore’s National Performance Review for Reinventing Government (1995)
- Dealmaker of the Month, The American Lawyer magazine (May 1995)
- Member, FCBA – The Tech Bar
Pro Bono and Volunteer Projects
- Capital Pro Bono Honor Roll High Honors Recipient (2021, 2023)
- WBK Pro Bono Project | Maryland Parole Partnership
- Co-chair, FCBA Ad Hoc Committee on Emerging Issues in Tech
- Organized and hosted multi-session FCBA program in summer 2021 on the regulation of online platforms.
- Spent six years serving on the board of directors of Kol Shalom synagogue in Rockville, MD
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