Remembering longtime Phillies leader David Montgomery | Perspective

In the long history of Philadelphia sports, few people have been as admired and as highly regarded as David Montgomery. The Phillies executive was a person who not only accomplished great things but who gained the utmost respect for his most honorable conduct.

His passing Wednesday has left a gigantic hole in not just the Phillies organization but in the entire Philadelphia area, where he was a humanitarian of the first degree, serving as an extremely active participant in numerous charitable projects.

Montgomery, who was also active in many areas of Major League Baseball, spent his entire 48-year working career with the Phillies, starting as a ticket salesman and eventually becoming a part-owner, president, and chief executive officer. During his career with the Phillies, he not only headed up the development of Citizens Bank Park and the team’s training grounds and ballpark in Clearwater, Fla., but he also presided over the greatest era in team history.

During that period, which ran from 2007 through 2011, the Phillies won one World Series, two National League pennants, and five division titles. Their 2008 Series win was only the second in team history and their 102 wins in 2011 were the most ever for a Phillies team.

Montgomery was more than a successful baseball executive. He was a person with a nearly flawless personality. He was kind, he was modest, he was compassionate, and he was loyal. He cared about other people, and he treated virtually everyone, including fans, as part of his family. He was smart, dedicated, friendly, and a true gentleman who always put others ahead of himself.

“I admired everything about him,” said Charlie Manuel, who managed the Phils during their winningest era. At the same news conference held the day of Montgomery’s death, former shortstop and manager Larry Bowa added: “He was the greatest person I ever met in my life.”

Personally, I had the extreme pleasure of knowing Montgomery for many, many years. We had a lot in common. He and I both grew up in Roxborough. Both of us attended the William Penn Charter School. And the field that last fall was named the David P. Montgomery Field was in the same area where I played baseball as a kid and from which I lived just a short distance away.

During my more than 35 years of writing about the Phillies, including 14 years as editor and publisher of a newspaper called Phillies Report and as the author of eight books about the team, I was in regular contact with Montgomery. For me, he was the voice of reason, always helpful, and the person who would provide an accurate explanation and from whom I could get a straightforward answer.

Sometimes, we would step away from a discussion about the Phillies and talk about our old days of growing up in the same town, attending the same school, playing on the same fields, and knowing some of the same people. He always seemed to enjoy these moments. For me, these were always tremendously enjoyable conversations that often seemed not to last long enough.

In all my years of dealing with Montgomery, I never heard him insult anybody. Sure, he could briefly get a little cantankerous. Who doesn’t? But I don’t recall him ever being negative about anything. Indeed, he was almost always strictly positive, even if the subject deserved some uncomplimentary thoughts.

It was always clear that Montgomery regarded his uniformed people as well as his front-office colleagues with the utmost respect. And he cared about every one of them and would willingly come to the aid of whoever needed help. In part for these reasons, I know of people who have left the Phillies to take better jobs elsewhere but who still relish their days with the team and regret having to move on.

Now, with great sorrow, we know that Montgomery has moved on, too. To say he will be missed is an enormous understatement. He has been a vital part of many of our lives, and such a connection with that kind of person is irreplaceable.

Rich Westcott is a baseball writer and Philadelphia sports historian. The author of 26 books, including eight on the Phillies, he has been a journalist for more than 40 years and is a former president of the Philadelphia Sports Writers Association.