For the first time in nearly five decades, Donald Caldwell’s office is empty.
Roanoke’s chief prosecutor, who was first appointed in 1979 and who will retire Dec. 31, has occupied a room at the northeast corner of the third floor of the Oliver W. Hill Justice Center since not long after the building opened in early 1983.
His expansive wooden desk, which once belonged to Virginia Circuit Court Judge Jack Coulter? That’s been given away, hauled off by a furniture restorer, and all the stacks of folders, pads and papers its surface once supported have now been filed away or discarded.
Caldwell’s menagerie of hunting trophies has migrated on as well. The taxidermized heads and skins of deer and elk and other felled quarry, mounted around the room for years, were taken down recently before a crew was brought in to give the walls some fresh paint. That upgrade was in anticipation of Roanoke’s incoming prosecutor, longtime chief assistant John McNeil, who won the office in the last election and whose term begins Thursday.
Anyone who holds a position of public power for as long as Caldwell did (particularly someone fond of offering colleagues such consolations as “I’m yelling to you, not at you”) is going to collect a wide array of other people’s impressions, and he is no exception. Various interview subjects called him a demanding taskmaster but also a committed educator. Fiery-tempered. Shrewd. Stubborn. Micromanaging. Dedicated. Controlling. A brilliant legal mind. Formidable, but fair.
Whatever one’s opinion, Roanoke’s longtime top prosecutor ran unopposed for all but his last two races and, after his initial appointment to the job, scored 11 consecutive four-year terms before opting to sit out the 2025 race.
According to the Virginia Association of Commonwealth’s Attorneys, his retirement after 46 years leaves Caldwell the second-longest serving chief prosecutor in the state’s history, just behind Prince William County’s Paul Ebert, who closed out 52 years in 2019, and it puts him just ahead of E.M. Wright of Buckingham County and Suffolk’s Phil Ferguson, who notched 45 and 44 years respectively.
For both Caldwell and the city, his decision to conclude his run marks a milestone that’s daunting to comprehend.
To put it in a broader context: Every defendant in a Roanoke criminal prosecution, from the back half of President Jimmy Carter’s administration on into the second term of Donald Trump, has had their case overseen in one form or another by Caldwell.
“It’s huge,” Roanoke Circuit Judge Chris Clemens recently said of his departure, invoking another sage Virginia fixture: “It’s [akin to] Frank Beamer retiring.
“When Don Caldwell tried a case in a courtroom, you knew that it was going to be a very serious hearing that we were about to have.”
Defense attorney Tony Anderson reflected that he and Caldwell have faced each other across Roanoke courtrooms for the better part of 40 years.
“We’ve had cases … in the hundreds … ranging from minor traffic violations to capital murder and everywhere in between. In my opinion, Don is one of the most adept prosecutors at his craft that I’ve had the pleasure to lawyer with,” Anderson noted.
Salem-based lawyer Aaron Houchens cited a more recent impression: “I tried a jury last Thursday with [Roanoke assistant prosecutor] Jack Patterson, and the jury came back late, like 7 o’clock at night. And, you know, Don’s sitting in the lobby waiting for the jury to come back, with Jack, because … he’s not going to leave. I’ve never had a jury in Roanoke city where Don didn’t wait around to get the verdict with his assistant. I mean, no one else does that.
“He’s there because, one: He’s interested in it because the law excites him, I think, still. But two: He wants to make sure his people are OK,” Houchens said.
“To all the elected commonwealth’s attorneys, Don has been such an incredible mentor and friend,” Virginia Beach’s chief prosecutor Colin Stolle said last week. “I’m on the other side of the state and if I had a problem that came up — with a case or a personnel issue — I’d call him on the phone and seek his advice and guidance on it.
“His departure leaves such a void in our association.”
Today at age 75, Caldwell — who’s also a colonel 21 years retired from the U.S. Army Reserves, and the father of three adult children — remains tall and straight-backed. An avid hunter who has stalked prey in North America and as far away as Africa, he also still competes monthly in cowboy shooting competitions — contests that involve a pair of holstered revolvers, an 1873 Winchester-style lever-action rifle and a double-barrel shotgun, and which hinge on speed, agility and marksmanship.
“It is very much a congenial sport which tends to attract older men and women who like to shoot, want to stay active, have some discretionary income and like friendly competition,” Caldwell recently explained.
Tellingly, he’s also a fan of Western movies, of cowboy epics, and, as his nearly half-century tenure draws to a close, it’s not hard to imagine his exit in terms of the climax of one of his favorite films, “The Searchers” — that famous final shot in which John Wayne, his yearslong quest completed, heads back out into the vast frontier just as a homestead door swings shut behind him, consigning the frame to darkness.
But not so fast on that cut to black.
In a November interview about his life and career, the famously detail-oriented and hands-on Caldwell confirmed that while he may no longer be heading Roanoke’s prosecutor’s office, he does not feel his work there is completely done. Not just yet.
‘The qualities of a leader’
Caldwell was not even 30 when he was appointed to lead the city prosecutor’s office. A native of Botetourt County, an Army reserve veteran and a graduate of the Virginia Military Institute and what is now the University of Richmond School of Law, he spent the prologue of his legal career as a Roanoke public defender. Within a year and a half, however, he’d been recruited to the other side of the courtroom by Robert Rider, the city’s commonwealth’s attorney at that time.
“He was smart. He had the experience. He had a military background. He obviously had the qualities of a leader that you would like to see,” Rider said in mid-December. “I always thought it was a good decision. And the years have proved me right.”
When Rider stepped down in 1979, Caldwell was tapped to serve the remainder of Rider’s term. At that time, he’d been prosecuting cases for only about a year and was just 28.
To his recollection, however, he never had any doubt that someone so young could take on such responsibility.
“I have always been somebody that just was confident in my own judgment,” Caldwell said. “And when I look back, the only thing I’d say [to my younger self] is, you know, stay the course. Trust your instincts. And I would say especially when it comes to your service to the public, [observe] that overarching principle of try to do the right thing for the right reason.
“I might also go back and say Donald, now, computers are not a fad, right? I might pay a little bit more attention to that. But you know, in terms of how I approach life, I don’t really think there’s much I would say different.”
That sense of self-reliance, he believes, came from growing up in a small community, Mill Creek. Feeding cattle and working in his family’s garden. Kitchen-table conversations with his mother, whom he described as firmly religious. And a foundational upbringing with his five siblings: “We grew up in a household where moral principles were taught and you were expected to abide by those principles. I had a lot of opportunity to be exposed to people who were basically doing the right thing for the right reasons.”
Even in elementary school, he said, he found himself entrusted with tasks or supervisory positions occasionally above his modest standing.
“As a patrol boy, in the fifth and sixth grade, I’m armed with my sash and badge … to stalk right out in the middle of Route 11 as it passed through Troutville, raise my hand and stop traffic,” Caldwell recalled.
“I always thought maybe that’s where my authoritarian nature came in, even though I didn’t appreciate that the tractor-trailer bearing down on me might not stop. But it did. And little girls and boys would come across.”
Prosecutorial advances
Today, the office Caldwell has long overseen operates on a $2 million annual budget and includes a slate of 18 attorney positions, a few of which are in the process of being filled, with a four-person administrative staff and a five-member victim-witness program.
Over the past decade, it has seen an average of 2,314 cases per year assigned through Roanoke Circuit Court. The general district court contributes another 24,300 — about 70% of which are traffic offenses — and the juvenile and domestic relations court adds nearly 2,400.
The prosecutor’s office essentially acts as a filter through which the city’s violence, corruption and malfeasance of all sizes flows. Caldwell’s command has spanned generations and has reckoned with the kinds of ripples that come with such longevity: The emergence of such volatile, deeply addictive drugs as crack cocaine and later fentanyl, and the increased presence of methamphetamine, heroin and prescription opiates. The “tough on crime” stance of the 1990s. The advent of the internet and the concepts of online crime and social media. The activities of gangs with expanding networks. The wall of silence Roanoke’s investigators and prosecutors alike have long said they often face when dealing with suspects and victims. Not to mention the global pandemic that scrambled most aspects of life across the first half of this decade, and beyond.
There have also been such high-profile homicides as the case of Timothy Glen Workman, a federal agent for Drug Enforcement Administration who, while off-duty, shot and killed a man during a parking lot confrontation near Valley View Mall and who was first convicted of voluntary manslaughter and then later found not guilty on retrial.
Or the shootings at a Salem Avenue nightspot, Backstreet Cafe, which left one person dead and six injured and prompted a 2002 episode of ABC’s “Nightline,” focusing on gay issues and broadcast live from downtown Roanoke.
When asked about the most resonant incidents, Caldwell’s immediate response was a case from the early 2010s involving 2-year-old victim Aveion Lewis. Aveion’s tiny body was discarded by his stepfather, Brandon Lockett, and later, after an exhaustive wintertime search, recovered from a local landfill; the child’s remains bore a scar from a cigarette, burns on his legs, an untreated fracture and emaciation. While a cause of death remained undetermined, the evidence painted a damning portrait, and two of Caldwell’s assistant prosecutors, Sandra Workman and Sheri Mason, won convictions against both Avenion’s mother and stepfather for second-degree murder and felony child abuse.
“That would probably be the single biggest case that I remember,” Caldwell said. “We were so incredibly lucky. The police found a needle in a haystack and … it worked out, and that pair was held accountable.”
Caldwell’s tenure has seen prosecutorial advances as well, boons in the forms of DNA evidence, of widespread satellite navigation systems like GPS, of higher-definition cameras for home security, businesses and uniformed officers.
“Technology has advanced to such a degree, but you’ve got to understand how it works, what it will tell you and what it won’t,” Caldwell said. “We’ve got Ring cam videos, but the legal system still requires that somebody come in and authenticate the thing and prove that it was reliable and it has not been altered. But all that takes training and it takes exposure.”
Demand for that training has expanded as well. Across its roughly 120 jurisdictions, the state now has between 1,000 and 1,200 assistant commonwealth’s attorneys. Up until about the mid-2010s, localities and individual prosecutors’ offices were responsible for the cost of training, much of which was grant-driven, and larger offices tended to fare better than the smaller ones.
“We started to explore the avenue of using asset forfeiture money as a way to fund that training,” Caldwell recalled. “The idea was: Everybody pitches in … to put [funds] in a pool, very much like an endowment.”
He and several other commonwealth’s attorneys took up that cause and, in January 2014, after a two-year effort, they secured $18 million drawn from the settlement of United States v. Abbott Laboratories to create the Commonwealth’s Attorneys Training Fund. Under state legislation, that sum is now managed and invested by the Virginia Retirement System, and a percentage of it is used to provide training, free of cost, to every prosecutor in the state.
As of Nov. 30, according to Elliott Casey, director of the Commonwealth’s Attorneys’ Service Council, the fund has risen to about $29.6 million.
“Nothing significant gets accomplished without a lot of people being involved, especially when you’re in the political arena of the General Assembly,” Caldwell said. “You have to have commonwealth’s attorneys from both sides of the aisle, so to speak, to lobby for you through the General Assembly to try to get things done.”
Virginia Beach prosecutor Colin Stolle was also part of that push, and recently said of Caldwell’s role: “He’ll be the first one to say that it was a team effort, that lots of people contributed to making it happen. But the bottom line is, he was the driving force.
“It was Don and his vision that pushed it through.”
Was it the political process behind that effort that prompted Caldwell, the following year, to split with the Democratic party and make an independent run for state Senate, in which he finished a distant third against John Edwards and Republican Nancy Dye?
“No, not really, not really,” he maintained. “I guess like John Prine said, ‘Sometimes you just get bored.’ I just felt like — and I still feel like — I could have done a better job. And … not to say anything about either John or Nancy, right? But sometimes a little bit of independent thinking helps.”
On the fence
Periodically over the past decade, Caldwell suggested he might retire from the prosecutor’s office, and in 2017 it appeared he would.
Then, just one day before the deadline, he abruptly jumped into the race when it looked as though the Democratic nominee, Roanoke attorney Melvin Hill, was running unopposed. Caldwell’s campaign against Hill — who had himself once served as an assistant prosecutor in Caldwell’s office, and who’d also been appointed a substitute judge — concentrated heavily on outstanding debts Hill owed to the Internal Revenue Service. Caldwell prevailed, then ran once more in 2021, and won again using some of the same ammunition after Hill again took the Democratic nomination.
More recently, last spring, when McNeil filed to run for commonwealth’s attorney as a Democrat, Caldwell endorsed him. In his interview, however, Caldwell acknowledged he had also gathered the required signatures and was prepared to join the 2025 race independently, a move he said had hinged upon the prospect of additional candidates entering the field.
“I was kind of waiting around to see whether or not anybody that actually had some true qualifications would step forward” to challenge McNeil, he said.
When the campaign commenced, McNeil ran unopposed and ascended to the top spot.
That win caps McNeil’s 25 years of service to the office, a tenure that, early on, included his prosecution of Ronald Edward Gay, the shooter in the Backstreet Cafe attack who was convicted, given four life sentences and died in prison. McNeil was also deployed to Baghdad in 2005 as an Army judge advocate general, returning about a year later with a Bronze Star.
“I think it’s fortunate for the city of Roanoke that it ultimately worked out… that there’s going to be somebody in the commonwealth attorney’s position who has a lot of experience, who does know how a budget works. … And he’s familiar with the system,” Caldwell said.
That said, Caldwell confirmed he does plan to resume working in the office, sometime in the new year, on a part-time basis.
Under the rules of the Virginia Retirement System, he can return to the office as an employee just one full calendar month after his departure.
He would not be going to court, he said, but would work behind the scenes. He pointed to the heavy docket the office is currently carrying, with 20 pending homicides gearing up for trial, and said that he felt he could be most beneficial during the spring when “a lot of these cases will be ripe.”
Caldwell this week also resolved his penultimate case as a special prosecutor. In October, he was tapped to evaluate the resolution of Virginia Attorney General-elect Jay Jones’ 2022 conviction for reckless driving; on Monday, Caldwell determined that Jones had been properly penalized and the matter was concluded. That leaves just one more special prosecution pending, an Albemarle County criminal case, which would fall to McNeil in Caldwell’s absence.
“Make one point clear: This will be John’s office,” Caldwell said.
“If I’ve got some talents, it’s an appreciation of what needs to be done to prepare a case. So I’d work with younger attorneys on that and help them get ready for trial, but they’ll be going to court to try the case,” he said. “If I can help, and, yeah, we’re talking about that, it’ll just be to come back to coach, not to direct.”
The tree
Caldwell’s ethos and his instructions are virtually woven into each case his office handles. Every manilla criminal file folder in the Roanoke prosecutor’s office is bespoke, with inside covers that uniformly contain printed lists of Caldwell’s four “Truisms of Prosecution” in all caps (such as “ACT IN HASTE, REPENT IN LEISURE” and “REMEMBER THAT AS A PROSECUTOR, YOU’RE ONLY AS GOOD AS YOUR LAST HOME RUN”) as well as his 16-point trial preparation checklist, covering imperatives that include “Have you PERSONALLY visited the scene of the crime to familiarize yourself with it?” and “Have you personally reviewed the indictment and is it proper?”
But his intensive approach extends well beyond the printed word.
It’s probably not surprising to those who know him that Caldwell plans to continue working in a coaching capacity, as a large part of his legend revolves around his role as a mentor and trainer — and occasional drill instructor.
“I think that’s part of his legacy,” Tony Anderson observed. “That he developed that style and skill for his office, that it wasn’t easy. I think we’ve all heard stories, and to some extent, probably witnessed some of Don’s aggressive toughness and how he demanded productivity from his staff and kind of gave them a roadmap to achieve it.”
Anderson pointed to Caldwell’s “coaching tree” — the sheer number of attorneys who made their bones at least in part working under him then went on to achieve significant success within the field. Such figures as current Botetourt County Circuit Judge Joel Branscom and commonwealth’s attorneys Eric Branscom of Floyd County, Ann Gardner of Alleghany County and the city of Covington and Wes Nance of Bedford County; Tom Bowers, Salem’s former top prosecutor; and seasoned local attorneys like Hill, Neil Horn and Patrick Kenney.
“I very much analogize him as being like an old sports coach. … He just had that feel,” said Kenney, who spent nearly two years as one of Caldwell’s assistant prosecutors in the mid-2000s before moving into private practice.
“There was a bit of tough love with that. He could be very demanding, but one of the things that I appreciated most about Don … he gave you a chance. Almost right away. He would assign you difficult cases, high-profile cases. Let you start to earn your chops, if you will, by trying cases right away. And that is unique in my experience and I really appreciated that … you know, giving you that chance and sort of helping you with that process.”
To mix arboreal metaphors, there are also apples that don’t fall far. For a staff of its size, Roanoke’s turnover rate remains relatively stable, and some of the faithful become fixtures. Caldwell’s longtime deputy, Betty Jo Anthony, started at the office one year after he did and remained full-time for 38 years, retiring in 2018 but occasionally returning to handle cases involving her fields of expertise. Another deputy, Alice Ekirch, joined the team in 1988 and works there still.
“I think John McNeil is another branch on that tree,” Anderson added. “John is his own man. He’ll make his own decisions, but certainly I think he’d be the first to admit that he’s been influenced on many levels by the years he spent with Don and watching Don’s managerial skills. I think John will be great.”
McNeil acknowledged the challenges his predecessor has often laid down, but also pointed to the motives of his methods.
“When you first start working with Don … it can be a tough experience,” he said. “Don’s not gentle with new attorneys, and nor should he be, because prosecuting crimes in Roanoke city is a very challenging process. There’s a lot of violent crime, a lot of serious crime, and there’s a lot of really good lawyers that you have to fight with in court, so you can’t be shy and you have to be prepared. He is absolutely a strong taskmaster.
“But then once you earn his trust, that you can handle yourself, can handle the cases that are being assigned to you, then he gives you a lot of leeway,” McNeil concluded.
Climbing the tree, and hanging on, however, often involves navigating precarious heights, high winds and patches of abrasive bark.
Botetourt County Assistant Commonwealth’s Attorney Chad Simmons worked in the Roanoke prosecutor’s office from 2012 to 2018, a job he took because he said Joel Branscom told him he’d get a wealth of experience through the city’s caseload and exposure to the kinds of criminal cases the office handles.
That proved roughly accurate, Simmons said, and he also got what he said was Caldwell’s standard trial by fire for newcomers. Over periods leading up to more serious trials, lawyers would be called in to discuss their preparation.
“It’d be an hour or two every evening with him almost berating you, asking questions about the case and you’d better be prepared to answer,” Simmons said. “And if you couldn’t, it was ‘Come back tomorrow.'”
Caldwell often asked trial lawyers to make their opening statements in front of him alone.
“It was a little awkward, giving your opening to just one person sitting at a desk, staring at you,” Simmons said. “Sometimes you wouldn’t get five words out and he would stop you.”
As Caldwell explains it, that method hones both the lawyer’s grasp of the facts and the actor’s motivation that fuels what is essentially their performance. If a lawyer can’t present to an audience of one, he reckons, then they likely can’t manage it before a judge, a jury, and all other parties in question.
“I want to hear them say it like they’ll say it in court … there in the confines of the office,” he said. “Everybody has their own style. It might be very quiet and dry for one attorney. Might be more theatrical and emotional for another. But you should be able to turn that on and off wherever you are … and that just doesn’t miraculously happen just because you walk into a courtroom.”
Said Simmons: “He enjoyed putting young attorneys through the wringer in developing trial attorneys, and he was very good at it. I think he probably used methods that confused people, or that some may not agree with, but for certain attorneys it was very effective. Myself included.
“To my experience, he was never angry if you lost a case. Winning was not what was emphasized. What was emphasized was being prepared to your fullest and doing your job with integrity.”
“There’s only a couple reasons I can think of why people stay in a job as long as Don did,” Simmons concluded. “Because he loved what he did and he loved the people he worked with.”
For all the talk about Caldwell’s tests, however, there remains a crucial question: What determines when one of his staff finally passed their final exam?
“You can begin to see it in their answers, right when you talk to someone,” Caldwell said. “You start seeing the expression in their eyes. You can read their face when they start getting sure of themselves. Then you know they’re graduating.”
With his last day at the helm approaching, he may still be reckoning with the history behind him and the work he hopes to continue, but he professes a military perspective on how he might balance those two poles.
“I spent 31 years in the Army Reserves, and once you’re over, you’re over,” Caldwell said. “I mean, you can come back and attend parades and stuff like that, but you know … you’re given the baton for a certain amount of the race, and once your leg is finished, you pass that baton. Hopefully successfully.”