For longer than the Roanoke City Courthouse has stood at Church Avenue and Third Street, longer than the tenure of its most senior judge, longer than the time spent in prison by many a criminal who passed through the building, one thing has remained constant:
Donald Caldwell has run the prosecution.
And he has run unopposed for re-election every time – most recently last Tuesday, when he secured another four-year term that will make him the longest-serving commonwealth’s attorney in Roanoke history.
The job of putting people in prison, deciding not to, or trying to and failing can be a lightning rod for criticism. Yet Caldwell has done it since 1979 in a way that draws glowing praise from his admirers and grudging respect from his adversaries.
In recent interviews with 40 lawyers, judges, police officers, public defenders, crime victims, hunting companions, co-workers and others, Caldwell emerged as a man who defies simple descriptions:
He is down-to-earth and personable, but has a stubborn streak and a way of speaking his mind that can be brutally blunt.
He is a skilled and respected trial lawyer, but oversees an office that some courthouse critics say could be better organized.
He devotes long hours to his job, but also serves as a lieutenant colonel in the Army Reserves and finds time to teach criminal law at Hollins College, officiate high school football, and take piano lessons.
He has tried and won his share of high-profile cases, but on any given day can be found doing the grunt work in traffic court.
He is not prone to gratuitous dramatics, but has been known to lie down in front of a jury or toss a gun across the courtroom to make his point.
He is honest and fair, everyone interviewed for this story agreed – no buts about it.
“In spite of the fact that he is perceived as a zealous, vigorous prosecutor, you won’t find a lot of criminal defendants and their families who think that Don Caldwell treated them unfairly,” said Clifford Weckstein, the city’s chief Circuit Court judge. “And you won’t find a lot of lawyers telling their clients that Don Caldwell treated them unfairly.
“That, I think, is one reason why … he doesn’t make enemies who come back to haunt him at the polls.”
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Donald Stevens Caldwell grew up on a small farm in Botetourt County, the third of six children in a middle-class family. His father was the Fincastle postmaster; his mother was and still is “the greatest single influence” in his life.
He attended Lord Botetourt High School, where he was elected class president and lettered in football and track.
In 1969 – a time when many young men were growing their hair long, doing drugs and protesting the Vietnam War – Caldwell enrolled at Virginia Military Institute on a football scholarship.
Caldwell was again voted class president by his peers, who remember him as level-headed, self-confident to the point that he didn’t feel compelled to constantly prove himself, and strong-willed.
“You could actually see his jaw set sometimes, and that’s when you could say to yourself, `Well, this argument is over,”’ W.F. Flood said.
Caldwell’s headstrong way sometimes clashed with the VMI way. He was kicked off the football team when he showed up for practice with collar-length hair after a summer in Europe left him feeling a bit resistant to his coach’s authoritarian ways.
In what became Caldwell’s first taste of the judicial system, the coach tried to have him charged with disrespect. “That was the first time I learned about taking matters under advisement,” he said, referring to the outcome of his case.
After considering careers in both law and medicine, Caldwell went to the T.C. Williams School of Law at the University of Richmond. Fresh out of law school, he landed his first job, with the newly created public defender’s office in Roanoke. He stayed for 18 months.
“I think defending always sort of chafed at Don,” said Jonathan Apgar, who worked with Caldwell at the time and is now a Circuit Court judge. “He had such strong feelings about doing the right thing, and so he was never really fond of defending serious criminals.”
The way Caldwell tells it, he got his job as a prosecutor when Robert Rider, then the city commonwealth’s attorney, stopped him one day in a courthouse hallway.
“He said, `Don, I`ve been watching you, and you’ve done such a good job putting people in jail as a public defender that I want you on my side,”’ Caldwell said, using a line he often makes in his public talks.
“I may have said that in jest,” Rider recalled recently, “but I was always impressed with his abilities.”
In 1979, Rider resigned and Caldwell was appointed by Circuit Court judges to fill his expired term. He was 28, the youngest commonwealth’s attorney in Virginia at the time. Caldwell is now in line to surpass Buck Cuddy, who took office in 1940 and stayed for 20 years, as the longest-serving prosecutor since Roanoke was incorporated in 1884.
On the way to becoming a career prosecutor, Caldwell remembered a lesson he learned as a rookie.
“The public defender experience gave me some sympathy and empathy for a lot of people that go through the court system,” he said.
“As a society, we’re extremely fortunate that only a small, small percentage of the people we deal with are truly evil. Most people we see in court are making bad judgments because they are not intellectually sophisticated, they don’t have the emotional skills to deal with life, and their problems are compounded by drug and alcohol use.
“So you have to look at each person individually.”
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Caldwell prosecutes criminals the same way he hunts deer and elk, say those who have spent time with him in both the courtroom and the woods.
“Many times I’ve seen Don in a situation where he could have shot but didn’t,” said David Damico, a Roanoke lawyer who has hunted with Caldwell. The biggest thrill of hunting for Caldwell is not the kill, Damico said, but the tactical challenge that leads up to it.
Likewise in the courtroom, “Don is not driven by the impulse that makes some prosecutors try to put hides on their walls,” Weckstein said.
“Donald has compassion and he understands that his job is to do justice, not just convict,” said Ray Ferris, who has worked with Caldwell as an assistant prosecutor and against him as defense counsel.
Evidence of that can be found on the inside cover of every case file in the commonwealth attorney’s office. Each file carries a list of Caldwell’s “truisms of prosecution.” The No.1 truism: “Don’t confuse moral outrage with proof.”
Sometimes that means never bringing charges.
Like the time Caldwell decided against charging a mother who accidentally – and uncharacteristically – left her 2-year-old daughter in a locked van to die of heat stroke. “I truly believe that … if by some miracle a case could be made against her, I don’t think that society could punish her any more than she’s already punished herself,” he said at the time.
Other times, it means not throwing the book at someone just to get a conviction on one chapter.
Like the time a Roanoke police officer was killed by a woman who said her gun went off accidentally when a screen door jarred her hand. Other prosecutors might have brought a murder charge; Caldwell evaluated the case and charged her with manslaughter.
But that doesn’t mean he’s not aggressive, said Gary Lumsden, who defended the women on the manslaughter charge.
“Once the charge was filed, he was on a mission,” Lumsden said.
In a dramatic closing argument, Caldwell tried to discredit the woman’s contention that the gun had a hair trigger. He cocked the unloaded weapon and dropped it to the floor. When the hammer did not fall, Caldwell tossed it several feet across the courtroom, where it landed at Lumsden’s feet. And clicked.
Instead of allowing his demonstration to backfire, Caldwell told the jury it proved his point. “You’ve got to have tremendous force to have this thing go off,” he said, tossing it twice more toward his assistant.
The hammer didn’t budge, and the jury convicted.
One of Caldwell’s most theatrical closing arguments was in the case of Frances Truesdale, who was charging in 1992 with killing her husband as they drove through Roanoke. Truesdale blamed the shooting on two mysterious robbers, but Caldwell used an entirely circumstantial case to convict her of second-degree murder.
Acting out his theory of what happened in the Truesdales’ van that night, Caldwell jumped on the witness chair and made it the driver’s seat, stomping on an imaginary gas pedal as his voice rose to a near-shout.
Then, to show how Jerry Truesdale could have been shot as he lay sleeping in the back of his van, Caldwell lay down on the floor in front of the jury.
“He was going crazy,” said defense lawyer Tony Anderson, who had minutes earlier delivered an eloquent closing argument on Frances Truesdale’s behalf. “Whatever crack in the door I may have opened, he slammed it shut right in Mrs. Truesdale’s face.”
Over the years, Caldwell’s track record has led other localities to call on him as a special prosecutor in difficult cases.
He won convictions against John David Lafon, who murdered a Virginia Tech student and dumped her body in a Giles County well, and Dennis West, a Salem businessman who killed his wife.
“We can’t say enough good things about Don,” said Betty Elam, the mother of West’s slain wife. “He spent hours and hours and hours on that case. He would call us at midnight from his office; he would still be working on the case.”
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When he isn’t working on a big case, you can find Caldwell prosecuting traffic offenses and misdemeanors in General District Court.
“He was a wonderful boss, and the thing I admired the most about him was that he tried the dog cases along with the rest of us,” said Deborah Caldwell-Bono, who once worked as an assistant commonwealth’s attorney.
Assistants tell stories of nights spent preparing for big trials, when Caldwell would summon them to the office for after-hours strategy sessions. “He would always come in wearing his camouflage pants and his army boots, like he was preparing you for battle,” said Tom Roe, a Fincastle lawyer and former assistant prosecutor.
Caldwell usually brought a bag full of junk food for the assistants and a pack of cigars for himself, Roe said. Puffing on a cigar, Caldwell would coach his lawyers as they ran through opening arguments and plotted ways to undermine the defense theory.
As much as Caldwell is admired by his subordinates, he is also notorious for the rigorous training he puts rookie prosecutors through – a throwback to his VMI days that earned him the office nickname “The Ayatollah.”
“I would say that for my first 18 months, I was in boot camp,” said Joel Branscom, who worked for Caldwell before being elected Botetourt County commonwealth’s attorney. “He fussed at me; he yelled at me. No matter what I did, he said there was a better way to do it.”
As bad as the experience was, Branscom said, “about halfway through I realized it was for my own betterment.” Roe agrees: “He reminds me of [Indiana University basketball coach] Bobby Knight. He would yell and scream, but it was to get you fired up to get in the game.”
Caldwell, who enjoys molding raw talent from law school into a staff of 10 assistants, said his goal is to test his lawyers in the office so they don’t fail him in the courtroom.
Although Caldwell has been elected four times as a Democrat, he makes no claims to the party’s political power structure.
“I think he’s kind of a political anomaly,” Anderson said. “Probably the politician that packs the biggest bag of influence in our area is [House majority leader] Dick Cranwell, but I’ve never seen Don go in and kowtow for Dick Cranwell or roll over for him.”
In fact, when a Northern Virginia judge dismissed a drunken-driving charge against Cranwell’s son in 1993, Caldwell criticized the judge’s decision publicly, saying it created the perception that “preferential treatment” was being given to prominent citizens.
“I have tried to run this office apolitically,” Caldwell said, “What we would do or not do for a Democrat, we would do or not do for a Republican.”
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When the case of Commonwealth vs. Sue Payne was called on the afternoon of June 12 in Roanoke Circuit Court, there was no one there to represent the commonwealth.
The judge had a clerk call the commonwealth attorney’s office, and a bailiff was sent down to get a prosecutor. No one ever showed up.
“They couldn’t find a warm body with a law degree,” said Steve Milani, an assistant public defender who represented Payne. In an unusual move, the judge held the hearing without a prosecutor present, taking under advisement the office’s motion to revoke the suspended sentence of Payne, a convicted embezzler, for not making restitution.
The hearing illustrated a complaint sometimes made of Caldwell’s office: “We frequently have occasion to wish that every assistant commonwealth’s attorney was on time for every case,” Weckstein said, “and that everybody in that office did what he or she was supposed to do on time and was appropriately prepared for every case.”
But overall, Weckstein added, the office “does the more important things well most of the time.”
Caldwell’s staff covers as many as 11 courtrooms a day, and handles more than 55,000 cases a year – the heaviest caseload this side of Richmond. Salem attorney Greg Phillips said that when he prosecuted in the city, assistants would routinely handle 80 cases a day in General District Court while juggling other matters in Circuit Court. “You can’t know everything about 80 cases,” Phillips said.
Critics say the problem is mostly limited to misdemeanor and juvenile court matters, and they acknowledge that no major cases have been lost as a result of it.
Said Caldwell: “There’s no prosecutor’s office in the world that can adequately prepare for all their cases, if preparation means one-on-one contact with the complainant, interviews with all the witnesses, a visit to the crime scene and all the things a prosecutor does for the major cases.
“But if that’s a criticism, I accept the criticism. And I’ll wait for the funding by the General Assembly to give me the 100-plus prosecutors we need to do that.”
It was a measured, composed response delivered during a recent interview that Caldwell squeezed in at 8 a.m., before starting a jury trial. But in other settings, the city’s chief prosecutor can express himself much more forcefully.
“He plays the folksy game,” Milani said. “But when when you cross him, boy, he lets you know that he’s prepared to play hardball” – even if his opponent happens to be wearing a black robe. “He does not assume that because a judge is a judge, and he’s the prosecutor that has to live with the judges, that he’s got to do things their way,” Weckstein said.
While some find Caldwell’s style overbearing, others applaud it.
“I think his stubbornness is a virtue, in that he doesn’t hold his finger up to the political winds before he makes a decision,” defense lawyer Randy Cargill said. “He doesn’t make his decisions based on what he thinks the newspaper or the public might find acceptable. He’s guided by principle and what he thinks is right.”
After 18 years in office, Caldwell seems far from burned out. Friends attribute that partly to his varied life away from work, whether he’s hunting, fishing, teaching, refereeing or being a weekend warrior for the Reserves.
“He’s like a little boy in some ways,” Branscom said. “He’s constantly looking for ways to have fun.”
One way – perhaps the best way – is to work.
“I like the human drama,” Caldwell said when asked what is the best thing about his job. “The old adage about truth being stranger than fiction is absolutely true. You see it so often in the courtroom that it’s unbelievable.”
So when gavels bang court to session this morning, chances are that Caldwell will be in one of the city’s courtrooms; doing his job, watching the show, and having some fun along the way.