Robert McDermott never was afraid to journey down an uncharted path.

Whether influencing the way the U.S. Air Force Academy taught cadets as its first dean of faculty or rebuilding USAA as the head of the financial services giant, McDermott often defied conventional wisdom while tackling challenges.

That certainly was true 21 years ago when the retired Air Force brigadier general, charismatic San Antonio powerbroker and then-Spurs chairman hired Gregg Popovich, a former Air Force player, to be the club’s general manager and executive vice president of basketball operations.

It was regarded as a shocking move.

At the time, Popovich’s only head coaching experience had come at Division III Pomona-Pitzer, and he had logged just six seasons as an NBA assistant coach.

In the military terms McDermott understood — he was a decorated fighter pilot in Europe during World War II — it was like the chairman of the Joint Chiefs of Staff selecting a junior officer to head a major operation.

But it paid off big time for the Spurs and McDermott, who died in 2006 at age 86.

More Information NBA career coaching wins (Regular season) Name Wins 1. Don Nelson 1,335 2. Lenny Wilkens 1,332 3. Jerry Sloan 1,221 4. Pat Riley 1,210 5. Phil Jackson 1,155 6. George Karl 1,131 7. Larry Brown 1,098 8. Rick Adelman 1,042 9. Gregg Popovich 997* 10. Bill Fitch 944

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With Popovich now within grasp of his 1,000th NBA regular-season coaching win, many connected with the Spurs are reflecting on that decision by McDermott, who was more impressed with Popovich’s character, military record and leadership qualities than the X’s-and-O’s knowledge he had acquired as an assistant under two Hall of Fame coaches — Larry Brown with the Spurs and Don Nelson with the Golden State Warriors.

“Daddy knew that because Gregg had been at Golden State under 'Nellie,’ who was both GM and head coach, he had gotten a lot of experience,” said McDermott’s daughter, Betsy Gwin. “But really, it was his background as an academy grad and just his commitment to discipline and excellence” that got him hired.

“McD’s” decision to bring Popovich back to the franchise from Golden State in 1994 to head its basketball operations set the 1970 Air Force graduate on the path to becoming the coaching superstar he is today. He has led the Spurs to five NBA titles and molded the franchise into one of the most respected in professional sports.

Popovich became coach of the Spurs after he fired Bob Hill following a 3-15 start during the 1996-97 season. Three years later, Popovich guided the club to its first NBA title.

“Gen. McDermott,” said Paul Ringenbach, a retired Air Force colonel and USAA executive who wrote a biography of his boss, “fought traditional ways of doing things and thinking about things and opened doors to something different. He made significant changes wherever he went, and the Spurs thing fits right in with it.”

While some fans, members of the media and even team investors had misgivings about giving the job of GM to an assistant coach with a thin resume, McDermott was sold on Popovich after conducting his own background check.

“He went with his heart and his gut, and the rest is history,” Gwin said.

Of course, it didn’t hurt that Gwin’s childhood best friend growing up in Colorado Springs, Colorado, was Popovich’s wife, Erin. Because of that relationship, Gwin encouraged her father to make the hire.

Erin Popovich is the daughter of Jim Conboy, who spent 43 years as the Air Force Academy’s athletic trainer before his death in 1998.

But Gwin said she also stressed to her father that Popovich’s tutelage under NBA coaching greats Brown and Nelson had prepared him well to run a team.

“Daddy and I talked about it a lot because he really didn’t know that much about basketball,” Gwin said. “But he knew with Gregg he was going to get someone who would work hard and be ethical and be above board and wasn’t out for glory for himself.”

Ultimately, McDermott made up his mind after calling several of his Air Force Academy contacts for their thoughts on Popovich.

“McD’s decision-making had nothing to do with the NBA,” said Robert Marbut, a former Spurs executive and behind-the-scenes advocate for Popovich. “It had all to do with the Air Force Academy, and he made that real clear. McD did not trust NBA types. But he trusted Air Force Academy types.”

One of the people McDermott called was Lt. Col. Floyd G. “Schott” Davis, former director of athletics and military training at the Air Force Academy Prep School and coach of the 1972 Armed Forces team that Popovich helped lead to an Amateur Athletic Union national title.

“I told him I don’t know where you would find someone sharper in every aspect,” said Davis, 83.

Above all else, McDermott valued reports of Popovich’s impeccable character, said Ringenbach, whose biography of McDermott is titled, “Battling Tradition: Robert F. McDermott and Shaping the U.S. Air Force Academy.”

“He was a very moral man,” Ringenbach said of McDermott. “He believed in the importance of the individual and honor, the West Point (values): duty, honor and country, that sort of thing. That automatically gave Pop a leg up.”

But it didn’t completely seal the deal. McDermott wanted to find out if Popovich’s character was above reproach.

Had there been any red flags in Popovich’s past, Ringenbach believes McDermott might have looked elsewhere.

“If he had found out (Popovich) was perfect (as a cadet and as a coach), but a philanderer, it could have killed the deal,” Ringenbach said. “He had no patience with people who lacked morality.

“Popovich had a leg up because he had gone to the Air Force Academy, was captain of the basketball team. … But him being a solid guy with a good family” was even more important.

Family connection

McDermott had plenty of experience making decisions that rankled traditionalists. While dean of faculty at the Air Force Academy from 1959 to ’68, he changed its curriculum, adding about 30 academic majors to an institution that had copied rival service academies’ rigid approach to science and engineering course requirements.

Although Popovich and McDermott were at the academy at the same time, Popovich didn’t earn a basketball letter until 1969-70, after McDermott had left.

“My dad knew him a little bit,” Gwin said. “But he knew the Conboys well. We kids all grew up together. We were all Catholic. We all went to church and saw each other. Daddy knew of Gregg through Erin. I met Erin in second grade.”

In their post-academy careers, the paths of the McDermotts and the Popoviches didn’t cross until 1988 when then-Spurs chairman B.J. “Red” McCombs gave Brown the luxury of hiring Popovich as his fourth assistant.

“Erin and I had lost touch,” Gwin said. “That was before e-mail and all that stuff, and she didn’t know my last name. We were at a Blockbuster (video store) on I-10 and I saw her and went, 'Erin? Erin Conboy?’ And she saw my blue eyes, and went, 'Oh, my God, Betsy.’ Then we got together as families. It was really nice. Our daughters were the same age.”

Popovich arrived in San Antonio after six seasons as an assistant coach at Air Force and eight as head coach at Pomona-Pitzer in the Los Angeles area.

While Popovich was at Pomona-Pitzer, Marbut was a student-athlete at Claremont McKenna College. The schools are part of a consortium of five undergraduate and two graduate schools with adjoining campuses within walking distance of one another.

“I looked up to Pop,” said Marbut, president of the Spurs-related sports marketing group SAOne in the mid-1990s. “I always saw him around. He was real good friends with my water polo coach and swim coach. He oozed professionalism and confidence.”

Marbut eventually made a name for himself in San Antonio, first as a top aide to then-Mayor Henry Cisneros and then later as president and CEO of the 1989 Junior Olympic Games and the 1993 U.S. Olympic Festival, where he worked closely with business leader Bob Coleman.

While with Cisneros and McCombs on a flight aboard McCombs’ private jet to an NFL function in 1988, Marbut put in a good word for Popovich when he heard of Brown’s plans to hire him as his fourth assistant. McCombs eventually hired Popovich, who spent four seasons with the Spurs before moving to Golden State for two seasons.

“I’ve been around for a long time, and he was the best assistant I ever had,” said Nelson, the NBA record-holder for career regular-season wins with a 1,335. “Because of his work ethic and intellect, he would have been successful in any industry.”

Ownership changes

When a group of 22 investors headed by Coleman and McDermott bought the Spurs from McCombs for $75 million in March 1993, Coleman became president and CEO of the Spurs. But even before the sale was completed, Marbut and others in the organization suggested to Coleman that he consider hiring Popovich as an assistant GM under Bob Bass, with the understanding that Popovich would become GM when Bass retired.

Coleman died in July 2014, but his widow recalls her husband heaping praise on Popovich after they met for lunch late in 1992 before the sale of the Spurs had been completed.

“Bob came home and said, 'Oh, my, we need him,’” Ann Coleman said. “He liked him so much and was so impressed with him. He said, 'We really need to get him before someone else grabs him. We need to find a place for him.’ He thought Pop was such a savvy person. He thought Pop was the future.”

Citing philosophical differences with the ownership group, Coleman resigned as Spurs president and CEO in May 1994. Bass also resigned, opening the door for the new president and CEO, McDermott, to hire Popovich either as an assistant GM or GM.

“When the other investors asked him to become chairman,” Ringenbach said, McDermott “told them he had three conditions: one, they would allow him to trade Dennis Rodman out of town; two, they would allow him to bring Sean Elliott back from Detroit; and, three, hire Popovich.”

But some investors had misgivings about giving the reins of the basketball operation to someone whose only head coaching experience was at a Division III college. At the time, there were plenty of more experienced potential candidates.

“Bob Coleman told me some investors were very uncomfortable,” Marbut said. “McD expressed the same concerns, but he was very inclined to like Pop because of the Air Force contacts. You also had to consider Pop got a graduate degree working under Brown and Nellie.”

McDermott began doing his homework on Popovich and decided to target him as GM, Marbut said.

“He was getting great feedback,” Marbut said. “He liked Coleman’s idea of bringing him back to the organization as an assistant GM, but he wanted to double-down on it.”

Sealing the deal

Another big proponent of Popovich’s within the organization was then-Spurs radio voice Jay Howard. When Coleman and later McDermott asked him about Popovich, Howard said he told them Popovich would be a “great choice” as GM.

“When they talked about him being an assistant GM, I said, 'Why?’” Howard said. “They assumed before you become president of the company, you have to be vice president to learn the ropes. But Pop already had all the elements.”

On May 19, 1994, Nelson granted the Spurs permission to speak with Popovich. One day later, McDermott called Popovich at his home in California’s Bay Area.

“Any leadership position in an NBA franchise is of interest, if you appreciate a challenge and have interest in that challenge,” Popovich told the San Antonio Express-News at the time. “And that is a definite interest (for me). And if it’s in a place and situation you know well, it makes for an interesting proposition.”

To seal the deal, McDermott and two investors, James Leininger and Clayton Bennett, met Popovich for an interview May 26, 1994, in Nashville, Tennessee. The meeting marked the first time McDermott and Popovich had talked extensively.

Afterward, McDermott told the Express-News he was impressed with Popovich’s plan to “build for the future.”

Popovich declined to be interviewed for this article, but he told Express-News sports columnist Buck Harvey shortly after McDermott’s death that he spoke during the interview as if he had nothing to lose.

“I didn’t think it would happen for me then,” Popovich said. “I figured it would be a good experience just to interview. So I held nothing back.”

But Leininger said last week the interview was a mere formality. Indeed, the Spurs conducted no other interviews.

“McD had already made up his mind,” Leininger said. “There were the Air Force Academy ties. McD wanted him.”

Another Spurs investor agreed with Leininger.

“No question, he had his mind made up,” Stephen Lang said. “They were both military. Both thought the same way. Both were indefatigable workers. No foolishness. Classic military. … You had all that, and then look at the guys Pop was an assistant under — very knowledgeable basketball people.”

Of course, McDermott also trusted his daughter’s input.

“Daddy knew (Popovich) had been at Golden State under 'Nellie,’ who was both GM and head coach, and that he had gotten a lot of experience there,” Gwin said. “But, really, it was his background as an academy grad and just the commitment to discipline and excellence (that sold him).”

'Can I have $50,000 more?’

McDermott announced Popovich’s hiring May 31, 1994. Before taking the job, Nelson said Popovich asked for and received an additional $50,000.

“He chatted with me and said, 'I think I’ve got this job,’” Nelson said. “I told him, 'You go back and tell them to increase your salary by $50,000.’ He was reluctant, but I said, 'You get on the phone and do it, damn it.’

“So he gets on the phone, and says (meekly), 'Do you think I can have $50,000 more?’ And the guy, said, 'No problem.’”

Popovich hasn’t forgotten how McDermott’s decision changed his life. In his 2006 interview with Harvey, Popovich said he was always in awe of his former dean and boss. Ringenbach said Popovich wrote McDermott a letter of gratitude after the Spurs won their first NBA championship in 1999.

“He lived every minute, and he lived in service of his community,” Popovich said of McDermott, who was replaced as Spurs chairman by Peter Holt in 1996.

The McDermotts are grateful Popovich made their patriarch look good.

“We’re all just so proud of Gregg because it was just a toenail in the door that daddy gave him,” Gwin said. “Completely, he’s just probably the most brilliant basketball mind there is out there. He’s been successful through all his hard work and dedication. It’s just wonderful.”

torsborn@express-news.net