The year was 1971.
David Montgomery had just finished up his MBA at Wharton. Looking for a job to start right away, Montgomery interviewed with various companies like Scott Paper Company and Quaker Oats. He even met with the Philadelphia 76ers.
Montgomery, though, had finished school in December and all of these potential employers did not want him to start until May. Undeterred, he reached out to the father of a high schooler he coached in football at Germantown Academy. Luckily for Montgomery, that father happened to be former Philadelphia Phillies pitcher and future hall of famer Robin Roberts.
Roberts proved to be a great connection. After joining Roberts and a Phillies staffer named Bill Giles at a clinic, Montgomery was offered a job working in the Phillies’ sales department. It was everything Montgomery was looking for. The job offered Montgomery the opportunity to follow his passion for baseball and he was able to start working right away.
“I met Bill [Giles] on a Saturday and started working the following Monday,” Montgomery recalled.
The only catch was the pay. Despite selling season tickets by day and operating the scoreboard by night, Montgomery was still only able to make $150 a week. That was enough for Montgomery to live on in the early 1970’s, but it was definitely less than what he could’ve been making with his MBA in many other jobs.
As low as he started, Montgomery did not take very long to prove his worth. Within a few years, Montgomery was promoted to director of sales and marketing, and by 1980, he was the head of the entire business department.
“I was just blessed with opportunities,” Montgomery said. “And because it was the focus of what I was doing, it never felt like a job to me. I was just pursuing my passion in sports.”
In the 1980’s, Montgomery continued to rise up the ranks. In 1981, Montgomery was part of a group that purchased the team and he started working as the team’s executive vice president.
Finally in 1997, Montgomery reached the pinnacle of his career with the Phillies. After Giles — the same person who hired Montgomery all those years earlier — stepped down to focus on finding the team a new stadium, Montgomery was hired to serve as the team’s president.
In that role, Montgomery found great success. He was key in building a roster that won the 2008 World Series and also helped the Phillies build a new stadium. On top of all that, he established himself as a major force within the MLB. Former MLB commissioner Bud Selig even credited Montgomery for helping to create the revenue-sharing and wild card system.
“I have the utmost respect for him as a person, and he is very, very smart,” Selig told the New York Times. “He always does what he believes is best for the game.”
And despite baseball’s general downward trend in popularity, Montgomery is still optimistic about the future of the game. He acknowledges that the growth of other sports like lacrosse presents challenges for increasing baseball participation amongst youth, but he also points out that baseball has several advantages.
“I believe that the one advantage we have from a spectator standpoint is that we’re played outdoors in the summer,” Montgomery said. “We are still the game that I think has the most appeal in terms of grandparents taking their grandchildren. My mom went to loads of Phillies games and never played the game at all.”
In many ways, Montgomery owes his own career to the many experiences he had with sports as a young child. Growing up in the Roxborough neighborhood of Philadelphia, Montgomery played all of the “big three” sports in baseball, basketball, and football, but the Phillies always reserved a special place in his heart.
As an undergrad at Penn studying history, Montgomery continued to attend Phillies games. Joined by the future governor of Pennsylvania Ed Rendell, Montgomery would sit in the bleachers and try to eat as much food as $5 could buy.
All of these years later, Montgomery still remembers his experience at Penn very fondly. As someone who was “blessed with interest in sports, but not with tremendous athletic ability”, Montgomery had a deep appreciation for Penn’s intramural sports program.
And for Montgomery, his relationship with Penn did not end when he got his diploma. Instead, he has remained very involved. Naturally, a lot of that involvement has been through sports as he is a frequent attendant at Penn basketball games, but he also served as a trustee on Penn’s board.
Of course, all of these commitments have kept Montgomery very busy, but that doesn’t bother him.
“The hours in sports are a little crazy because you work a regular business week and then when the games are on, that’s when your product is shown,” Montgomery said. “That’s not for everyone, but for me, it never felt like work.”
Montgomery’s commitment to the Phillies was seriously tested in 2014 when, at the age of 68, he had to undergo surgery for cancer in his jaw. Some thought Montgomery would just retire, but not even cancer would slow him down. After recovering for a few months on a medical leave of absence, Montgomery returned to the Phillies as team chairman.
Now in 2017, Montgomery is still working as chairman. It’s been 46 years since Montgomery first started as a season-ticket salesman and scoreboard operator, but Montgomery has showed no signs of slowing down.
When Montgomery eventually does choose to retire, he will go down as a great in Philadelphia sports. He was a part of both of the Phillies’ World Series and helped the team capture the imagination of millions in the process.
Calculating the full impact he has made is impossible, but then again, who’s keeping score?