An Exclusive Dinner Conversation on Recent Immigration Changes with Former Border and Customs Commissioner, R. Gil Kerlikowske

R. Gil Kerlikowske has a distinguished 40-year career as an urban law enforcement executive and leading the nation’s largest law enforcement organization. Appointed by President Obama, Gil has served as the only Senate-confirmed Commissioner of U.S. Customs and Border Protection (CBP) 2014-2017. CBP has 60,000 employees at 338 Ports of Entry and over 800 employees in 40 nations. As Commissioner, Gil guided CBP’s mission to secure the nation’s borders while facilitating lawful international trade and travel. The largest components of the organization are Air and Marine Operations, the U.S. Border Patrol, Customs and Border Protection, and Agriculture Inspection. The Agency has an annual budget of $13 billion.

Prior to his appointment to CBP, Gil served as the Senate-confirmed Director, White House Office of National Drug Control Policy, 2009-2014, a cabinet-level position. In his role, he initiated the first President’s Strategy on Prescription Drugs, authored the President’s National Drug Control Strategy, and co-authored (with John Brennan) the President’s Trans-National Organized Crime Strategy.

Under the Clinton Administration, Gil was the Deputy Director of the U.S. Department of Justice, Office of Community Oriented Policing Services 1998-2000 where he oversaw $6 billion of government assets aimed at reforming law enforcement policy and operations.

Gil served as the Chief of Police in two large, urban organizations where he instituted significant organizational change. In Seattle (WA), between 2000-2009, he oversaw the organization in the aftermath of the World Trade Organization disorder—completely restructuring Seattle’s response to major international incidents and demonstrations. In Buffalo (NY), between 1994- 1998, Gil was the first “outside” (the Buffalo Police Department) Commissioner in 30 years. He transformed the Department to a community policing organization, winning the praise of both local residents and national leaders. He was twice elected President of the Major Cities Chiefs Association, comprised of the largest law enforcement agencies in the U.S. and Canada. He is the recipient of numerous awards and recognition for his leadership and innovation.

Most recently, Gil was a Resident Fellow at Harvard University, John F. Kennedy School of Government, Institute of Politics (Spring 2017).

Currently, Gil’s consulting practice provides strategic advice to U.S. companies. He is also a Distinguished Fellow at the Global Resilience Institute and a Professor of Practice, Northeastern University. He serves as a non-resident Fellow at the Baker Institute, Rice University and a member of the Council on Foreign Relations. He has been and continues to be a frequent speaker at national and international forums.

Gil earned a BA and MA from the University of South Florida which also bestowed an Honorary Doctorate, Humane Letters in 2010. He is also the recipient of the Army’s Presidential Service Badge.

Jen is a thoughtful leader in Chicago’s business community, known for her commitment to mentoring small and middle-market businesses and her ability to drive transformative growth. Raised in West Rogers Park by a Mexican immigrant father and Jewish grandparents, Jen’s upbringing instilled in her a deep appreciation for hard work, community support, and giving back—values that form the foundation of her leadership style.

As Executive Director of Rise Chicago, Jen drives innovative solutions to the city’s most pressing challenges, including public safety, education, economic growth, and fiscal stability. Her leadership centers on fostering civic engagement, building coalitions, and empowering leaders who share the organization’s vision for a thriving, inclusive Chicago.

Jen brings over 20 years of experience in human resources and client relations, where she has guided organizations through periods of rapid growth and transformation. She has successfully scaled teams, implemented strategies to improve employee engagement, and fostered thriving workplace cultures that deliver measurable business outcomes. As the founder of Bestola Consulting, Jen collaborates with organizations to align their purpose with impact, streamline operations, and enhance people experiences to achieve sustainable success.

Jen’s commitment to community is reflected in her leadership roles across Chicago. As HR Committee Chair for the Chicago Community Loan Fund, she helps steward nearly $200 million to support local businesses. At PODER, she played a pivotal role in securing $6 million to establish the city’s first immigrant integration center in Gage Park. She also serves as Vice President of the Board for SUM, advancing initiatives to uplift and empower communities citywide. These efforts earned her the 2023 Outstanding Volunteer Award from the Association of Fundraising Professionals.

A proud Chicagoan, Jen continues to channel her passion and expertise into creating lasting change, ensuring Chicago remains a world-class city for generations to come.