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Will Darryl Glenn rise to glory or fizzle out in his first stab at a national office?

Shooting star

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  • Courtesy Darryl Glenn

When Darryl Glenn thumped six candidates off the U.S. Senate primary ballot at the State Republican Assembly in April, many among Colorado's political class were stunned. He stunned them again on June 28, primary election night, by defeating four other hopefuls who had petitioned onto the ballot.

One person who didn't share that surprise was Glenn himself. A virtual unknown in statewide politics, the 50-year-old has experienced a meteoric rise to become the GOP nominee for the Senate seat, culminating years of plotting his course through a political gauntlet that began in 2003 with neighborhood town hall meetings as a local elected official on the Colorado Springs City Council.

But wait. His plan actually might have been formulated as early as junior high and high school when he joined student government groups, abandoning a promising course at Doherty High School as a football running back after an ankle injury. After graduating from the Air Force Academy in 1988, another notch in his resumé, he launched a 21-year military career in active duty and reserve assignments during which he earned a law degree. Stints on the City Council (2003-2010) and the Board of County Commissioners (2011-present) solidified his staunchly conservative cred in what appears to be a deliberate long game up the political ladder. He says in an interview that a Senate seat has "always been on my goal sheet."

Now Glenn aspires to capture that office in Colorado, a purple state that trends toward blue, by unseating Democrat incumbent Sen. Michael Bennet.

That he hails from Colorado Springs is reason enough to look deeper at Glenn's background. But the fact he never faced meaningful political opponents on his way to the Senate race — a process that naturally elicits details from a candidate's life — is all the more reason to delve further into what makes Darryl Glenn tick.

On the surface, Glenn has shaped himself into the darling of the tea party crowd, espousing right-wing views on gun rights, immigration reform, bipartisan politics, "rights of the unborn" and curtailing government spending. (It's worth noting that Glenn has spent a good part of his life collecting government benefits in some form.) And there's no evidence those values don't lie at Glenn's core. But in an increasingly progressive era — i.e., legalization of marijuana, judicial endorsement of gay marriage and re-emergence of civil rights and race issues, as well as the fight against income inequality — one might wonder if Glenn's trajectory could end in the November election.

Still, as long-time political observer and two-time congressional candidate Jeff Crank says, "A lot of people laughed at him and said he couldn't win [the primary]. Yet he won. The question is whether he can catch on with average voters with his message."

Born to parents who served in the Air Force, Glenn moved to Colorado Springs as a young child and attended Will Rogers Elementary, 110 S. Circle Drive, from kindergarten through second grade, he said in a 2008 interview with the Indy. His family later moved to the Village Seven area where he attended Penrose Elementary and Sabin Middle School before advancing to Doherty in 1981.

There, he was one of a handful of black students. Only four were members of the 51-man varsity football team during his senior year, for example, and none played men's golf, cross country or basketball or competed in wrestling, swimming or hockey.

The 1984 yearbook pictured only nine black seniors. Glenn's picture was not included.

Yet despite being part of a tiny minority, Glenn says he didn't feel uncomfortable, and his records don't indicate that he felt a specific need to carve out a place among his fellow black students. For example, he wasn't listed as a member of the black cultural club, Mahogane.

Instead, he joined the student council and was elected junior class president and then senior class president.

Asked about growing up in predominantly white schools in a predominantly white part of the city, he said in 2008, "So it was one of those things to where, just by way of where I was living, I had to learn how [to] function in that environment and I think it helped because you learn how to [succeed], and people judge you on your accomplishments..."

Throughout that interview and others, he didn't name a black role model, but rather called himself a product of the Ronald Reagan era. The only child of two registered Democrats, he developed an affinity for Alex P. Keaton, the Michael J. Fox character on the Family Ties TV show in which Keaton develops conservative views despite his parents being shaped by the liberalism of the hippie era.

"I can't give people a better analogy than that," he said. "I was always out there, wasn't concerned with what color I was, wasn't shy about my opinion, and at that point in time he really moved me. I totally embraced supply-side economics, I'm one of those and I followed everything that he did. At that point in time, he was my role model and that kind of helped shape who I am today."

After what the Doherty yearbook called the junior varsity football team's "stunning season" in 1981, with Glenn as a running back, he suited up for another season as a junior. That year, on Sept. 15, varsity teammate Scott Reitz died five days after suffering a head injury in a Friday night game, never regaining consciousness. A news photo shows Glenn, wearing his No. 33 jersey, with other players surrounding the casket.

Glenn's senior year, he was sidelined from the team with an injured ankle, he says.

Yearbook photos picture Glenn with a wide grin as a member of student government, whose chief goal was to work "toward a very good relationship between the faculty and the student body."

Delia Armstrong-Busby, who later became the only black woman elected to the School District 11 board of education, served on Doherty's staff during Glenn's high school years and saw him as a leader.

Glenn at a 2014 picnic on the anniversary of the Black Forest Fire. - COURTESY EL PASO COUNTY
  • Courtesy El Paso County
  • Glenn at a 2014 picnic on the anniversary of the Black Forest Fire.

"How I could tell when a student was a leader is, if there's a group, who's in the center?" she says. "He was always in the center. If I had to come up with a word, he seemed affable. The success quotient for life is established early on. It's exemplified early in life. He left Doherty and went to the Air Force Academy, which is an exception rather than the rule. For him to be competitive at that level, that's exceptional. He was very well-liked. For him to have found acceptance to the degree I saw, to be at the center of the group, speaks well to his adaptability and acceptability."

Other than student council and football, Glenn doesn't appear in other activities featured in Doherty's yearbook. He wasn't pictured or listed with the National Honor Society, which included 15 percent of his graduating class of roughly 550 students and required a GPA of 3.5 on a 4.0 scale, along with participation in a community organization.

Glenn says he thinks he carried a 3.6 GPA in high school, which, along with what he calls his "extracurricular type stuff," led to the Academy appointment.

Given his grades and status as a student leader, it doesn't track that he would be arrested for third-degree assault on Nov. 22, 1983, six weeks after his 18th birthday, with a charge reflected in court records and on a police rap sheet. Details of the incident aren't available, because both police and court records have been destroyed in the normal course of business.

Asked about the case in early June, Glenn said via email, "Not aware of that and was definitely not charged." Asked again last week, he says, "We're still trying to figure out what that was."

Glenn suggested that the case might have involved Glenn's half-brother, Cedric, who was five or six years older and had several run-ins with the law before killing himself. "We don't know if something happened with him or what," Glenn says. "But the thing is, I was never even interviewed or anything. I've never even had a conversation with a police officer in that light."

As Glenn notes, it doesn't wash that he'd have a criminal record and be admitted to the Air Force Academy a few months later.

While at the Air Force Academy, Glenn says he won several National Power Lifting Championship titles. He also earned the respect of the members of his squadron.

Ron Swanson describes Glenn as "pretty low key" but trustworthy. "He was somebody who kept to himself, didn't cause trouble," says Swanson, who now lives in Colorado Springs and works in the computer industry. "He was somebody you could rely on, depend on and trust. And there were kids back then that I wouldn't trust, and that is a huge, huge aspect of leadership, regardless of whether you're a general, CEO of a company or politician. You have to trust your leaders."

It is not clear, specifically, how Glenn fared in academics, athletics and military training at the Academy, because Glenn didn't authorize release of his Academy records by the Indy's press deadline. Academy records of graduation rates show that nearly one in three cadets who entered with Glenn didn't make it to graduation in 1988.

Now, nearly 30 years later, records show that Glenn isn't among the 58.5 percent of living Academy grads who belong to the Association of Graduates, which supports cadets and the academy, notably in character development.

Immediately after graduation, on June 4, 1988, Glenn married Erin MacLeod of Danvers, Massachusetts.

What's known about Glenn's post-Academy performance and activities in the Air Force comes from Glenn himself, because he also didn't release his service record by the Indy's deadline.

According to his bio on the county's website, he earned a master's degree in business administration from Western New England College and a law degree from New England School of Law. (He was admitted to the Colorado Bar Association in October 1999.) It also states he led a $19 million Iceland Command and Control Enhancement Program implementing performance standards that saved $400,000. He also served as program manager for a $5 billion office responsible for implementing a base realignment and closure plan and supervised 35 communication system programs valued at $1 billion developing war-fighting capability.

Glenn says he retired from the Air Force as a lieutenant colonel after 21 years of active duty and reserve service. It's unclear when he achieved that rank.

Glenn during a Board of County Commissioners meeting in March 2011. - PAM ZUBECK
  • Pam Zubeck
  • Glenn during a Board of County Commissioners meeting in March 2011.

In 2008, Glenn told the Indy he left active duty to avoid deployments away from home, which might have disrupted his family's stability. He has two daughters, now 24 and 26.

"Because of how I grew up," he said then, referring to his father's deployments elsewhere, "I did not want to do that to my kids, and especially because of the option the Air Force gave me, I would have had to be deployed without my family and that was just something I wasn't going to do."

Glenn's wife also retired from the Air Force as a lieutenant colonel. Together they formed the Glenn Law Firm, which specialized in family law, public policy and campaign management consulting, his commissioner bio says.

The couple separated last November and divorced in March, court records show. Erin Glenn has since left the law firm and opened a donut shop in Colorado Springs with plans for expansion in the area.

Asked about her ex-husband, she says, "I'm not going to say anything bad about Darryl. He's a great guy. He's a really great guy. I hope he wins the Senate [seat] and goes on to be president, if that's what he wants." She also noted Glenn "was always interested in politics, from the time I met him."

Besides his law practice, Glenn has worked as a personal trainer, and he redoubled his commitment to good health after his father died in 2006 from lung cancer.

Over the past decade, Glenn, a member of New Life Church, has paid his dues by working the Republican party structure. He served as county party vice chair and as a precinct committee leader. In 2003, he was appointed to the Colorado Springs City Council after losing the election a few months before.

Glenn has been almost religious in attending meetings and casting votes that represent his conservative constituencies in the north and northeast sectors of the city and county, former colleagues say, but he rarely instigated new initiatives.

After he was appointed to replace Charles Wingate, who resigned amid allegations he pawned a city laptop and misused a city credit card, Glenn was elected to two terms without competition. He left amid that second term, in 2011, to assume his county commissioner seat after winning in 2010.

His greatest accomplishment, some former councilors say, was his ability to articulate his right-wing beliefs.

Jerry Heimlicher served with Glenn for five years and says he can't recall a significant contribution by Glenn. "I didn't have the kind of relationship with him that I had with Bernie [Herpin], Larry [Small] and Scott [Hente], because [Glenn] was working all the time and not at City Hall," Heimlicher says, reached by phone at his Germantown, Tennessee, home. "I was retired and was around a lot."

Glenn, he says, "arrived at Council meetings just before the meeting and left right after the meeting. He voted and he left." He described Glenn as a "dyed-in-the-wool" Republican "in every way, shape and form."

"That guides everything he says and votes on," Heimlicher says. "If it is not a conservative Republican strong point, he's going to vote against it every time."

For example, Glenn voted in 2004 with a 5-4 majority to deny benefits to domestic partners of city employees. (That decision has since been reversed.) He also opposed placing limits on campaign contributions, saying, "I think people should be able to contribute as much or as little as they want. I think it's a free-expression, First Amendment right."

His position against a ban of open-carry of firearms in city buildings, though, was overridden, and weapons were banned.

Not afraid to stand alone, he cast the sole dissenting vote on the city's $53 million package to retain the U.S. Olympic Committee's headquarters, a vote that Heimlicher said at the time "let his constituents down."

Another "no" vote by Glenn turned out to be prescient. In 2005 and 2007, he opposed setting up and charging fees for a city stormwater enterprise, arguing the matter should have been submitted to voters for approval. In 2009, voters rebelled, approving Issue 300 and forcing the enterprise's shutdown.

Asked to name his biggest accomplishments, Glenn points to his stormwater vote. "That is something I showed leadership on," he says, "and I think when people go back and they look at that, they will say, 'You know, what if we could revisit that? He was right.' Because that led to so many other issues. ... And that's something that's squarely with me."

The county fair is a signature event for commissioners, including Glenn. - COURTESY EL PASO COUNTY
  • Courtesy El Paso County
  • The county fair is a signature event for commissioners, including Glenn.

Glenn opposed other measures, including traffic camera citations and funding for a homeless housing program, but he didn't always dissent. In 2010, he supported designating raw, undeveloped land north of the city as an urban renewal site, then known as Copper Ridge and now called Polaris Pointe, from which tax money will be funneled to extend Powers Boulevard. (He later maneuvered as a commissioner to keep that project alive.)

Jan Martin, who served with Glenn from 2007 to 2011, called him "easy to get along with" but not very engaged. "I actually always use Darryl as an example when people ask what does a Council member do," Martin says. "You have some who show up just before a meeting begins and leave right after, and you never see them again. That was Darryl. He was rarely in City Hall and wasn't particularly engaged in any of the issues that were happening at the city. I honestly cannot think of a single initiative that was brought forward by Darryl when I worked with him."

Martin says it's possible he spent time within his district, "but working with other Council members, he just wasn't engaged at all. Most of his votes were based on ideology rather than community."

As for his Senate bid, she notes, "I wish I'd seen that much energy and effort put into his service on City Council."

Glenn reacts to that in an interview, saying, that the assessment is incorrect and that the accusation "sounds like somebody that's probably a little disgruntled." He goes on to say, "Nobody hosted more meetings than I did." Indeed, Glenn held quarterly town hall meetings with constituents outside City Hall.

He also takes credit for improving the city-county relationship by encouraging a "regional focus." And he claims responsibility for helping the city switch from a Council-city manager form of government to a Council-mayor form in 2011.

"You know, as the city was going through its governance change, you actually had someone on the county side that was able to kind of help walk the city and county through that transition phase," he says.

It's worth noting, however, that no one interviewed by the Independent for this story mentioned that when asked about Glenn's service. Rather, his conservatism was a common theme.

"He represented the northeast portion of the city at that time, which is a very conservative part of Colorado Springs," former Councilor Randy Purvis says, "and he reflected the district that he served." In fact, Purvis describes Glenn as the most conservative of all Council members at the time, and one who always passed the litmus test. "He opposed any tax increases," Purvis says, noting Glenn seemed aware that "everything one does in public office gets recorded and can be looked up after that."

Bernie Herpin, another former Council colleague, also mentioned Glenn's political philosophy. "He was very frugal — less government," Herpin says, "so he opposed some of the things I voted for with a price tag, like things for parks. He was well prepared and always well spoken. You could tell he was concerned about our city."

Perhaps the biggest accolade comes from former Vice Mayor Larry Small. "I think he's been a hard worker for the city and county, and he certainly pushed his political career forward," says Small, who adds that he lobbied for Glenn's appointment in 2003. "I think it would be a good idea to have Darryl as our senator."

After becoming a county commissioner, Glenn continued his pattern of systematically attending meetings but seldom making waves, with one exception. Term limits.

In 2010, the same year Glenn won his commission seat, voters approved an extension of term limits to three four-year terms, rather than two. However, the ballot question's wording was deceptive, some voters thought, because it asked if commissioners and other county officials should be "limited" to three terms, rather than asking for the limit to be expanded from two terms.

Riding a tide of outrage from voters and editorial writers, Glenn pushed to resubmit the term-limits question to voters in 2012, which was approved. That same year, commissioners Sallie Clark and Dennis Hisey won their third terms.

Asked about Glenn's record as commissioner, Clark credits him with being "pretty easy to get along with," though she noted the two are not close. Hard-pressed to identify an initiative Glenn proposed and fought for, Clark acknowledged his involvement after the Black Forest Fire destroyed some 500 homes in 2013. Glenn cites his role in that recovery effort as a major accomplishment. He hosted regular community meetings following the fire.

Amy Bach with United Policy Holders, an organization that helps insured property owners obtain money they're due following disasters, says Glenn was "open enough" to allow the group to lend aid to fire victims.

"He was open to getting to know our organization, vetting us and welcoming us into his community," Bach says. "He often would come and give an opening remark to kick off the workshop. But most of all he was helpful to Sallie. Sallie was really our point of contact."

Aside from that, Clark says, "I don't recall anything that he was directly involved in. He did ask for a committee with the military to be put together, but I don't know that they ever met. I'm not sure anything came of it."

Glenn rarely misses commissioners' meetings. - COURTESY EL PASO COUNTY
  • Courtesy El Paso County
  • Glenn rarely misses commissioners' meetings.

During his first five years as a commissioner, Glenn didn't hold a leadership position — chair or vice chair, elected by fellow members — until he was chosen vice chair on May 31.

Though political observers say fellow commissioners shunned him because of his stance on term limits, Clark says Glenn didn't seek a leadership role.

"I had approached him a couple years ago and asked him if he was interested in moving up in leadership. He said he was busy with things he was working on, whether personal life or commissioner, I don't know, but he didn't want to step up in that role. It wasn't because we were overlooking him."

Clark, known for her busy meeting schedule and her almost obsessive focus on dissecting issues in detail from the dais, said Glenn's record on paper doesn't amount to much. "He doesn't make motions a lot," she says. "I don't know that you'll find him in the minutes a whole lot."

The Indy's review of meeting minutes over the past 18 months — since he announced his Senate bid — shows he missed only two meetings in 2015 (Aug. 18 and Sept. 3) and three meetings so far this year (March 17, and April 12 and 19, just after the state Republican assembly).

The minutes show he rarely makes motions except to recognize retiring employees, to reconvene after an executive session or for proclamations (such as Veterans Day and government purchasing month).

But one motion is worth mentioning. On Nov. 24, 2015, he introduced a resolution "declaring opposition to the relocation of refugees from the United States Refugee Resettlement Program to El Paso County and rejection of federal and state funds to assist in the program unless the refugees are certified by existing federal processes and procedures to not pose a threat to our community."

The measure was adopted unanimously. While it didn't cause a public stir, a duplicate city measure proposed soon thereafter by Councilor Andy Pico triggered criticism from the community and the measure was dropped.

Also, in October 2015, Glenn moved approval for taxpayers to pay $120,000 in settlements to Wendy Habert and Cliff Porter, a former contract worker and sheriff's employee, respectively, who alleged they were discriminated against by former Sheriff Terry Maketa. Those were among several claims against Maketa that arose in May 2014, including allegations he had affairs with subordinates, which Glenn at that time called "the worst kept secret" in county government. He's never said why, if he knew of the liaisons, he didn't act.

But Glenn's record in elective office may not matter, because he isn't running on his voting record. He's running on his belief system. As he's said again and again, most notably during his State Assembly speech: "I am an unapologetic Christian constitutional conservative pro-life Second Amendment-loving American that will beat Michael Bennet."

He brought the house down.

That high-water mark wasn't reached overnight. Political insiders say Glenn crisscrossed the state tirelessly and reached out via email lists.

"He's worked his butt off since January 2015," says Purvis, who received those emails that listed various appearances and meetings. "He's been working all over the state, meet-and-greets with people to get his name out there and get known."

Crank notes Glenn attended countless GOP Lincoln Day dinners and met with counties' party leaders. "He had clearly worked on the grassroots," Crank says. "I think he put a lot of miles on his car, and he had been doing it for a year and a half."

That grassroots campaign supplanted a media blitz that he could ill afford, considering his paltry fundraising results. He raised $157,000 from Jan. 1, 2015, to June 8, 2016, and ran a campaign with few, if any, paid staff. (Two primary competitors raised more than $1 million each, which included hefty personal loans.)

So it was a needed shot in the arm when, in the final weeks, the Senate Conservative Fund endorsed Glenn and pumped hundreds of thousands of dollars into broadcast ads.

Since the primary, Glenn has hired paid staffers, including a scheduler, a media relations person and Jordan Gerhke, a political operative who worked on the John McCain 2008 presidential bid and formerly was with Robert Blaha's Senate campaign.

Glenn says his top three issues are national security (including an immigration component), veterans benefits and energy independence, which largely focuses on oil and gas drilling opportunities and regulations. While Glenn says others paint him as divisive, he argues that the issues he's championing are bipartisan.

"There's a disconnect," he says. "People are very focused in on things like the defense of this country, energy independence and our debt. They spend more time talking about those issues than some of the wedge issues ... and that's really where our focus is. It's focusing in on those core issues that families are having to address each and every day, and the policies that are impacting their lives."

But Glenn's path to victory must also include filling his campaign till and playing the role of government critic, says Crank, who lost congressional races to Doug Lamborn in 2006 and 2008 and now runs a campaign consultancy.

"He's going to have to raise some money," Crank says. "He's going to have to show himself as an outsider. I think that does play well. He'll have to run a disciplined campaign, stay on message. I think Darryl's message of being an outsider and fighting [commissioners] on the term limits thing, I'd play that up. He went up against people in his own party. He paid some political price for that. If it was me, I would contrast that with the fact that Bennet has voted with the president 98 percent of the time. He doesn't want to challenge anyone in Washington or his party. Darryl's going to challenge people."

Crucial to Glenn's campaign is attracting moderate voters, Purvis notes, because unaffiliateds comprise 35 percent of Colorado's registered voters. "He's going to get the Republican vote, but he's got to grab the majority of that [unaffiliated] in the middle that's up for grabs," Crank says.

That might be tricky, because, as state Democratic Party spokesman Chris Meagher tells the Indy, Glenn "rode the momentum of endorsements of very extreme politicians" including Sarah Palin and Ted Cruz.

"He's a guy who's called [Donald] Trump a patriot and wants to appoint Cruz as a Supreme Court judge," Meagher says. "He thinks the problem is there's too much bipartisanship there. We think those views are too extreme for Colorado."

Immediately after Glenn won the nomination, political heavyweights in Washington, D.C., said the party had forfeited the race by electing Glenn and that Senate Republicans had written off Colorado as a battleground state.

But on July 8, party officials announced a "unity tour" that included U.S. Sen. Cory Gardner, Colorado GOP Chairman Steve House, U.S. Rep. Ken Buck, Secretary of State Wayne Williams and Attorney General Cynthia Coffman.

And Glenn himself seemed to moderate his take-no-prisoners vow to not reach across the aisle in his June 28 victory speech.

"When we work together as Republicans and Democrats, then we will have economic prosperity for everyone. That's how Colorado can lead," he said that night.

"We are too polarized right now. We have lost the art to respectfully disagree, ladies and gentlemen. I'm a proud Republican, but I want you to understand the first thing I recognize is that I'm an American."

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