Team

McCray served as a Senior Advisor and managed the fundraising operation of the Trump-Vance presidential campaign, along with the Republican National Committee, whereby he had over 60 professionals reporting to him nationwide. He oversaw a fundraising effort raising $1.1 Billion in 8 months. McCray worked directly with the Campaign Managers and top leadership/senior staff on the presidential campaign. Further, McCray has developed deep connections with the majority of the Republican Chiefs of Staff and U.S. Senators, and he established significant contacts nationally with industries across the board.

McCray is now the Chief Executive Officer of Highwood Capital, LLC, being heavily involved with development for political, business and non-profit entities. Besides the Trump-Vance presidential – McCray has advised significant entities like the PGA Tour & its First Tee & Birdies for the Brave non-profits, the Washington Caps & Wizards, the Bipartisan Policy Center (Majority Leaders Bob Dole & Tom Daschle’s non-profit), the Eisenhower Memorial, the PGA of America, the Battle of the Bulge, Home Builders Institute, the American Tort Reform Association, the National Army Museum, along with hosting an event for Pope Benedict, XVI during his U.S. visit.

Further, McCray actively advises or has advised numerous U.S. Senators, Governors, presidential campaigns, national coalitions, and corporations in the business and political arenas, including Gov. Ron DeSantis, Gov. Scott Walker, Gov. Jon Huntsman, U.S. Senators Thom Tillis (R-NC), Steve Daines (R-MT), Mike Crapo (R-ID), John Hoeven (R-ND), Deb Fischer (R-NE), Eric Schmitt (R-MO), Tim Sheehy (R-MT) and Jim Banks (R-IN), among other statewide politicians/candidates. 

Before working for Senator Burns, McCray practiced corporate law in Minneapolis, Minnesota at the international law firm of Dorsey & Whitney LLP and in Washington, D.C. at the law firm of Dow Lohnes & Albertson, PLLC in the areas of Mergers & Acquisitions and Private Equity/Finance - advising senior corporate executives, management teams and boards of directors on corporate governance, acquisition guidance, and private equity and venture capital financing arrangements.   

Hailing originally from a cattle ranch in Geyser, Montana, McCray attended Montana State University in Bozeman, Montana, where he obtained his Bachelors of Arts in Political Science with a minor in Communications, with Highest Honors.  While at MSU, Jim served as MSU’s Student body President and the President of the Montana Associated Students, representing all public universities in Montana and actively worked with the Montana Board of Regents, the State Legislature and Montana Governor Marc Racicot. 

In addition, McCray founded the MSU Leadership Institute - an institute dedicated to helping students develop leadership, management and communication skills to effectively enable them to succeed in their personal and professional endeavors.  McCray chaired the National Advisory Board from 2000-2005.  The MSU Leadership Institute continues to thrive today, with an active leadership and development program and brings in renowned world leaders such as the former President of Poland and Nobel Peace Prize Laureate, Lech Walesa and Maya Angelou.  After college, McCray attended Vanderbilt University School of Law, in Nashville, Tennessee, graduating with his Doctor of Jurisprudence in May, 2000.  While at Vanderbilt, McCray served as Managing Editor for and was published in the Vanderbilt Law Review.

McCray recently served as the Chairman of St. Vincent Hospital’s Foundation Board, a Trustee of Vanderbilt University Law School’s National Advisory Board and is presently serving on the Board of Directors to Warriors & Quiet Waters and recent Chairman of the Museum of the Rockies Board of Trustees.

Brad Wilson joined Highwood Capital, LLC in June of 2012. Brad brings to Highwood Capital, nearly ten years of political strategy and fundraising experience, as well as an intimate knowledge of Capitol Hill. Prior to joining Highwood Capital, Brad served as the State Director for U.S. Senator Richard Shelby (R-AL) for eight years. In that role, he served as the main liaison between the State Of Alabama and Washington, D.C., along with running Sen. Shelby’s successful 2010 re-election campaign.

Brad has served as the Special Advisor for Congressional Affairs for the Delta Regional Authority, an eight state regional economic development agency comprising of eight states including Illinois, Missouri, Kentucky, Arkansas, Tennessee, Louisiana, Mississippi and Alabama. At DRA, Brad oversaw all federal government relations and greatly expanded the agency’s profile both in the region, as well as on Capitol Hill, by expanding the agency’s budget and involvement with over six federal agencies.

Brad previously served as Political Director for the Alabama Republican Party during the 2004 Election, where he orchestrated an unprecedented sweep of Republican seats on all levels of the ballot. Brad is a 2004 graduate of The University of Alabama, where he served as the President of the Interfraternity Council, as well as the Jason’s Men’s Honorary. Brad was born and raised in Dothan, AL.

Since joining Highwood Capital, LLC, Brad has worked with and consulted on a wide variety of clients, including The Eno Center for Transportation, a neutral, nonpartisan, transportation based think tank, The PGA Tour’s veteran’s outreach project, Birdies for the Brave, Congressman Connie Mack’s campaign for the U.S. Senate and U.S. Sen. John Hoeven from North Dakota.

Jon Goldberg joined Highwood Capital in September 2017. Since joining the firm, Jon has advised on statewide campaigns in Montana, Indiana, West Virginia, Ohio and Florida. Jon played a key role on Senator Steve Daines reelection campaign in 2020 which was the most expensive race per capita in U.S. History.

Jon has also consulted on a wide variety non-profit clients, including The Home Builders Institute, Montana’s Outdoor Legacy Foundation, Citizens For Responsible Energy Solutions and the Dwight D. Eisenhower Memorial Commission.

Prior to joining Highwood, Jon worked in major gift and corporate partnerships for nationally known advocacy organizations and think tanks, including the Bipartisan Policy Center. He also served as Finance Director for a top-tier Congressional Campaign in Michigan.

Jon earned his Bachelor of Arts from Union College in Schenectady, NY.

Preston Kerr joined Highwood Capital, LLC in May of 2014. Preston brings to Highwood Capital, five years of political strategy, legislative relations and fundraising experience, as well as an intimate knowledge of Capitol Hill.

Preston began his career in D.C. by serving as an aide in multiple roles to U.S. Senator John Cornyn (R-TX). He worked on both political and legislative affairs in the Senator’s personal office and the National Republican Senatorial Committee (NRSC). Following the Senate, Preston rounded out his Hill experience by assisting U.S. Congressman Pete Sessions (R-TX) while he chaired the National Republican Congressional Committee (NRCC) and the Rules Committee. He has also held internships in the offices of U.S. Senator Jim DeMint (R-SC), Wiley Rein, LLP and Ernst & Young.

Since joining Highwood Capital, Preston has worked on a diverse variety of clients including the PGA Foundation, Big Game Forever and Monumental Sports & Entertainment (Washington Capitals and Wizards). Further, Preston has advised and played integral parts on consulting teams for statewide U.S. Senate campaigns in Kansas, North Carolina and Montana.

Preston earned his Bachelor of Arts from Furman University, with a degree in Political Science and a minor in Business Administration. During his time at Furman, he was a member of the Kappa Alpha Order. Preston grew up in Dallas, Texas and graduated from Highland Park High School.

Elizabeth Bentler joined Highwood Capital, LLC in December of 2024, after serving as the Montana State Finance Director for Senator Tim Sheehy’s successful campaign.

Prior to joining Highwood, Elizabeth was the Deputy Finance Director for 70th Secretary of State Michael R. Pompeo’s Champion American Values PAC and CAVFUND, his (c)(4).  Previously, she was the Deputy Director of Statewide Programs at the Republican State Leadership Committee, leading fundraising efforts for the Republican Lieutenant Governors Association, and other down-ballot statewide elected officials.  She has also served in different capacities for the Republican National Committee and the California Republican Party.

Elizabeth is a graduate of Cal Poly San Luis Obispo with her Bachelor of Arts in Global Politics and a minor in Spanish.