Sports enthusiasts often speculate as to how great a particular player would have been had he not gotten injured early on in his career. Such discussions are pointless and resolve nothing, except perhaps when the sport under consideration is politics, and only then when we have definitive measurements at our disposal to make an educated analysis. John Edwards, Gary Hart, and Cal Cunningham all come to mind. All three were on a clear path to higher office, but their careers were derailed by self-inflicted injuries caused by a lapse in judgement. And that brings me to Derwin Montgomery.
At age 21, Derwin became the youngest person ever elected to Winston-Salem City Council where he served for three terms. That catapulted him to the State House of Representatives and a 2020 run for Congress in the newly formed 6th district. He was outmatched and outspent in the Democratic primary losing to Kathy Manning who would go on to win the general election. Nevertheless, Derwin’s political star was still on the rise.
I first met Derwin in February 2020 when he appeared on Triad Today to discuss his candidacy for Congress. He was extremely articulate and informed about the issues, chief among them were healthcare, pre-K education, and the plight of the homeless. The latter was a topic in his wheelhouse because, at the time, he was running the Winston-Salem based Bethesda Center for the Homeless.
“The work I do every day with the homeless really shapes my political understanding, and how I approach policy through the lens of equity and justice,” he told me.
Under Derwin’s leadership, the center provided meals, shelter, and social resources to hundreds of homeless people.
“I once came across a veteran who had been dishonorably discharged from the military for behavioral health issues which were never addressed, so we helped him navigate through the system to get the support he needed.”
I’ve interviewed tens of thousands of people over the past 50 years, and I’ve developed a pretty good bullshit meter. In my opinion, Derwin was the real deal. He was passionate about causes that affect everyday folks, and he displayed honest sincerity in his answers. As it turns out my bullshit meter wasn’t properly calibrated that day because, unbeknownst to anyone, in the two years prior to our interview, Derwin had been taking luxury vacations, visiting gentlemen’s clubs, driving an expensive car, and funneling money to his media company, all at the expense of the homeless people he was supposed to be helping.
In 2023 Montgomery was convicted of 15 counts of program fraud, having charged over $26,000 to Bethesda for his various private outings. He was facing up to 10 years in prison but instead cut a plea deal to avoid jail. The terms of his deal meant that 14 of the 15 counts were dismissed, he was put on 5 years probation, and ordered to make restitution and pay fines totaling $60,000. Late last month he was arrested for violating the terms of his probation by failing to make his most recent monthly payment, leaving him $5,500 in arrears. He is now in federal custody.
I am conflicted about the plight of Derwin Montgomery. On the one hand, he embezzled money from an agency that helps homeless folks, and he deserved to be punished for it. On the other hand, he did a lot to help those folks while he ran Bethesda Center. I also question the logic of the Court imposing hefty fines which made it more difficult for Derwin to make direct restitution. Finally, it is difficult for me to admit that I was entirely wrong about his sincerity and his compassion for those less fortunate. Yes, he abused his position and broke the law, but he did a lot of good for a lot of people, so perhaps he can work his way through this mess and one day manage to regain his status as a valued public servant. Call me crazy, but I still believe in the guy.
The Rise and Fall of Derwin Montgomery
Sports enthusiasts often speculate as to how great a particular player would have been had he not gotten injured early on in his career. Such discussions are pointless and resolve nothing, except perhaps when the sport under consideration is politics, and only then when we have definitive measurements at our disposal to make an educated analysis. John Edwards, Gary Hart, and Cal Cunningham all come to mind. All three were on a clear path to higher office, but their careers were derailed by self-inflicted injuries caused by a lapse in judgement. And that brings me to Derwin Montgomery.
At age 21, Derwin became the youngest person ever elected to Winston-Salem City Council where he served for three terms. That catapulted him to the State House of Representatives and a 2020 run for Congress in the newly formed 6th district. He was outmatched and outspent in the Democratic primary losing to Kathy Manning who would go on to win the general election. Nevertheless, Derwin’s political star was still on the rise.
I first met Derwin in February 2020 when he appeared on Triad Today to discuss his candidacy for Congress. He was extremely articulate and informed about the issues, chief among them were healthcare, pre-K education, and the plight of the homeless. The latter was a topic in his wheelhouse because, at the time, he was running the Winston-Salem based Bethesda Center for the Homeless.
“The work I do every day with the homeless really shapes my political understanding, and how I approach policy through the lens of equity and justice,” he told me.
Under Derwin’s leadership, the center provided meals, shelter, and social resources to hundreds of homeless people.
“I once came across a veteran who had been dishonorably discharged from the military for behavioral health issues which were never addressed, so we helped him navigate through the system to get the support he needed.”
I’ve interviewed tens of thousands of people over the past 50 years, and I’ve developed a pretty good bullshit meter. In my opinion, Derwin was the real deal. He was passionate about causes that affect everyday folks, and he displayed honest sincerity in his answers. As it turns out my bullshit meter wasn’t properly calibrated that day because, unbeknownst to anyone, in the two years prior to our interview, Derwin had been taking luxury vacations, visiting gentlemen’s clubs, driving an expensive car, and funneling money to his media company, all at the expense of the homeless people he was supposed to be helping.
In 2023 Montgomery was convicted of 15 counts of program fraud, having charged over $26,000 to Bethesda for his various private outings. He was facing up to 10 years in prison but instead cut a plea deal to avoid jail. The terms of his deal meant that 14 of the 15 counts were dismissed, he was put on 5 years probation, and ordered to make restitution and pay fines totaling $60,000. Late last month he was arrested for violating the terms of his probation by failing to make his most recent monthly payment, leaving him $5,500 in arrears. He is now in federal custody.
I am conflicted about the plight of Derwin Montgomery. On the one hand, he embezzled money from an agency that helps homeless folks, and he deserved to be punished for it. On the other hand, he did a lot to help those folks while he ran Bethesda Center. I also question the logic of the Court imposing hefty fines which made it more difficult for Derwin to make direct restitution. Finally, it is difficult for me to admit that I was entirely wrong about his sincerity and his compassion for those less fortunate. Yes, he abused his position and broke the law, but he did a lot of good for a lot of people, so perhaps he can work his way through this mess and one day manage to regain his status as a valued public servant. Call me crazy, but I still believe in the guy.