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Tennessee Tech alumna, staff member recall memories of service to U.S. Presidents
February 19, 2024, 4:10 p.m.

COOKEVILLE, TN - As Tennesseans mark the annual Presidents’ Day holiday on Feb. 19, a bipartisan pair of Tennessee Tech Golden Eagles are recalling their own fond memories of service to our nation’s past commanders in chief.

tennessee tech cheryl montgomery and bill clinton
Tennessee Tech staff member and former Bill Clinton administration aide Cheryl Montgomery; image submitted

Cheryl Montgomery, director of program development and engagement for Tech’s College of Business, spent more than a half-decade as director of scheduling for U.S. Attorney General Janet Reno under President Bill Clinton following earlier roles on the Clinton-Gore 1992 presidential campaign and transition team.

penny grace judd and george w bush
Tennessee Tech alumna Penny Grace Judd as former George W. Bush administration aide; image submitted

Penny Grace Judd, a Tech journalism graduate from the class of 2000 and current Alumni Association Board of Directors member, served in various roles during the administration of President George W. Bush, including at the U.S. Department of Labor, Office of Management & Budget and in the White House Office of Legislative Affairs.

Montgomery and Judd appeared on a special Presidents’ Day episode of Tech’s “College Town Talk” podcast to revisit their years in the nation’s capital and pay tribute to the university’s role in shaping their respective journeys.

Judd, who was also a former Student Government Association (SGA) president at Tech, says her climb up the career ladder can all be traced back to an internship she landed at the Tennessee Department of Transportation while studying at Tech. She leveraged that internship to secure a spot working at the Tennessee Republican Party in 2000 – an opportunity that positioned her in just the right place for a role in the incoming administration.

“This was deemed a battleground state, so a lot of resources flowed through Tennessee,” said Judd. “The staff here were able to have more relationships with the Bush-Cheney team at the national level. So then, thankfully, after the campaign they were gracious enough to reach out to see if we would be interested in roles in the administration.”

Looking back, Judd says her years on campus – including her time as a writer for The Oracle, the university’s student newspaper – prepared her well for the demands of politics.

“I really enjoyed being part of the journalism department and trying to meet those late-night Thursday deadlines for the newspaper,” said Judd. “Also being a part of Alpha Delta Pi, the UCSC [the off-campus University Christian Student Center] and being in the Student Government Association.”

Judd credits university administrators at the time, including the late President Emeritus Angelo Volpe and former Vice President for Student Affairs Marc Burnett, for being particularly supportive during her term as SGA president.

“I have so much gratitude for all the things they taught me along the way, which were really impactful in gaining skillsets to be able to work in the Bush administration,” said Judd.

While Montgomery’s experience at Tech started in earnest after her successful career in Washington, D.C., the Jackson County native says that the university was always a part of her story.

“I owe my very existence to Tennessee Tech,” said Montgomery. “My parents met at Memorial Gym and married two years later.”

Following her years growing up in the Upper Cumberland, Montgomery found herself working as an aide in then-U.S. Senator Al Gore’s office. Intent on moving back to Tennessee after a year in Washington, D.C., Montgomery tried to submit her resignation – almost missing out on a once-in-a-lifetime opportunity to work on a presidential campaign.

“I had written my resignation letter, walked over to my supervisor’s office to hand her the letter, and she looked at the letter, read it and handed it back to me,” recalled Montgomery. “She said ‘I’m not going to take action on this letter today. Bring it back to me tomorrow if you still want to leave this office.’”

Later that same day, Gore was selected by then-Governor Bill Clinton to be his vice presidential running mate in the 1992 election. Less than 48 hours later, Montgomery was en route to Little Rock, Ark. to be part of the campaign’s scheduling team.

In the years to follow, Montgomery would ascend to a key spot on the staff for the nation’s first female U.S. Attorney General, Janet Reno, who Montgomery says had a little-known “wicked sense of humor.”

Among Montgomery’s best memories was the appearance by Attorney General Reno on Saturday Night Live in the Clinton administration’s final days.

“She decided she wanted to appear on Saturday Night Live dancing on stage with Will Ferrell,” said Montgomery. “She just had this great sense of humor and was a lot of fun to be with and work with under extremely stressful times.”

Montgomery, who recently marked 15 years of service to Tech, says that coming to the university after her years in D.C. afforded her an opportunity to raise her children close to relatives and loved ones.

“Cookeville is a great place to raise a family,” said Montgomery. “My parents are here and at the time my grandparents were still living, and they were here. I wanted my boys to grow up feeling the love and the support that an extended family provides.”

While Montgomery and Judd found joy and purpose in their years atop the federal government, each says their service to their communities today brings its own rewards.

Apart from her service on Tech’s Alumni Board and her work running her own consultancy, PennAvenue Strategies, Judd also chairs the board of directors for Habitat for Humanity of Tennessee and even helped coordinate plans for President Jimmy Carter’s 2019 work project with the nonprofit in Nashville.

“Our mission at Habitat is seeking to put God’s love in action by bringing people together for homes, community and hope,” said Judd. “So many kids across our state are positively impacted by that for generations to come.”

Likewise, Montgomery describes the fulfillment she finds by serving the hometown university where her parents first met and helping students in the College of Business reach their fullest potential. She says the college’s focus on experiential learning gives students at the university a competitive edge.

“Over 50 percent of our students in the College of Business will engage in a résumé-building, for-credit experiential learning activity or project during their time in the college,” Montgomery explained, citing recent hands-on learning experiences that students in the college undertook with local businesses such as Jamie’s Eats & Sweets and The Exceptional Bean.

But would Judd or Montgomery have considered other careers besides the ones they pursued in politics? For Judd, the answer is a flat no.

“I started watching President Reagan on television in my beanbag when I was a young child,” said Judd. “So, I can’t imagine anything else.”

College Town Talk is the university’s weekly podcast produced in partnership with the Cookeville-Putnam County Visitors Bureau. Episodes are available on Apple Podcasts, Spotify, Google Podcasts, Pandora, and other platforms. Learn more at

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