AD 360 – Top 5 Craziest Moments as an Athletic Director

Host: PlayOn Sports
Guests: Greg Vandermade & Scott Rosenberg
Date: February 5, 2025

Episode Overview

In this special, story-driven episode of AD 360, former athletic directors Greg Vandermade and Scott Rosenberg set aside their usual deep dives and industry analysis to share their wildest, most unforgettable moments from their time leading high school athletic programs. With a mix of humor, vulnerability, and candid lessons, they recount the unpredictable challenges and hilarious scenarios that come with the territory. This collection of real-world anecdotes is both a crash course in school administration chaos and a tribute to the resilience of ADs everywhere.

Key Discussion Points & Insights

1. The Surprise Basketball Coach Exit

Speaker: Scott Rosenberg
Time: [02:20 – 07:46]

• Situation: In Scott's first year, the long-tenured basketball coach (and predecessor as AD) suddenly quit three days before the season.
• Administrative Drama: The district struggled with how to allow the coach’s exit meeting with the team. Higher-ups insisted three administrators (including Scott) attend, disrupting the meeting.
• Student Reaction: Players, extremely loyal to their coach, verbally lashed out at the administrators for cutting the meeting short.
• Personal Takeaway: Feeling deeply out of place and questioning his suitability for the role, Scott learned the complexity of leadership and conflicting authority.
• Quote:

  “What the hell do you do as a brand new administrator when your bosses are telling you to approach it this way? You think it's completely wrong.” – Scott [06:30]

2. When Everything Goes Wrong – Soccer Playoff Pandemonium

Speaker: Greg Vandermade
Time: [07:59 – 12:55]

• Setup: Greg’s first big playoff game as AD: National anthem singer is late, the microphone doesn't work, the scoreboard fails, and security is tested.
• Escalation: The underdog home team wins, but a controversial call leads to irate fans attempting to confront officials—security must intervene.
• Personal Reflection: The pressure of being observed by his school president added to the sense of crisis, but post-game, the president congratulates him for managing the chaos.
• Lessons Learned: Importance of backup plans, security protocols, and the reality that “there is no playbook” for some moments.
• Quote:

  “There is no playbook to tell you kind of how to deal with that type of scenario. But… it was trial by fire, if you will.” – Greg [12:36]

3. Budget Trouble—Timing Is Everything

Speaker: Scott Rosenberg
Time: [14:37 – 17:58]

• Background: In Scott’s New Jersey district, school budgets are decided by community vote—and had failed repeatedly.
• Media Snafu: On the very day of a crucial vote, a newspaper publishes Scott’s cheerful interview about a new golf team—infuriating town officials who are preparing budget cuts.
• Fallout: Scott’s superintendent berates him; he’s blamed for possibly triggering even deeper cuts due to bad optics.
• Quote:

  “I just remember my superintendent walking into my office and throwing the newspaper on my desk and going, ‘How are you going to feel about being responsible for an extra million or two getting cut out of our budget tonight?’” – Scott [16:12]

4. The Budget Black Hole

Speaker: Greg Vandermade
Time: [18:39 – 22:29]

• Context: Greg, now newly responsible for all sports’ financials, discovers “Sport X” severely in the red with no clear accountability.
• Difficult Conversations: Must level with the board and the beloved coach, working out a plan for the program to repay its deficit through camps and fundraising.
• Transformation: The experience makes Greg a stricter, more vigilant AD—even earning a “no fun” reputation for budget enforcement.
• Insight: Administrators also have teachable moments, and this was his.
• Quote:

  “I was basically the no fun AD because, hey, I need this PO sign. Okay, let’s check your budget… I then, moving forward, certainly had kind of the guardrails in place.” – Greg [21:31]

5. Getting Served—Leadership and Liability

Speaker: Scott Rosenberg
Time: [23:04 – 26:14]

• Incident: As president of the county ADs’ association, Scott is named in a lawsuit after a player is injured in a county soccer game.
• Panic and Lessons: He frantically confirms insurance coverage for himself and the association, realizing the heavy responsibilities of leadership roles. Admits he should have kept quiet and let lawyers handle it.
• Broader Advice: Leadership brings legal and personal risk; always ensure you’re covered.
• Quote:

  “Sometimes you get leadership roles in organizations, but you don’t necessarily think about the larger overarching responsibilities… Like, you know, if something goes wrong, the president’s the one that’s going to get arrested.” – Scott [24:24]

6. The NBA Family Showcase: Scottie Pippen’s Bargain

Speaker: Greg Vandermade
Time: [26:18 – 31:02]

• Backdrop: Hosting a high-profile basketball showcase involving teams with NBA legends’ sons.
• The Cameos: Derek Fisher and Kenyon Martin purchase expensive floor seats to watch their nephews and sons, respectively. When Scottie Pippen arrives, he opts for general admission—“I ain’t paying that.”
• Staff Dilemma: Security worries about mobbing in the GA section and ends up seating Pippen with the other NBA dads—at the lower price.
• Comic Relief: Shows the humorous, unexpected moments, as well as logistical curveballs, that come with big events.
• Quote:

  “He paid general admission prices. The other ones paid like the top dollar for them… The biggest name of them all is like, ‘no man, put me up in the GA’s.’” – Greg [29:23]

Notable Quotes & Memorable Moments

• On the job’s unpredictability:

  “It's about preparation. We've talked about that so much on this… in the end, it's the relationships that could help you.” – Scott Rosenberg [12:55]

• On teachable moments:

  “We always talk about kids having teachable moments. They're teachable moments for administrators too. You don't know it until you've experienced it, and you don't know how you're going to react to it until you've actually had to live through it.” – Greg Vandermade [17:58]

• On legal exposure as an AD:

  “You in leadership roles, it's smart to make sure that you understand what your responsibilities are, and then make sure that you're covered for whatever could potentially happen in the end.” – Scott Rosenberg [24:57]

Episode Structure & Section Timestamps

• [00:02] – Introduction and episode premise
• [02:20] – Scott’s first year: Basketball coach exit fiasco
• [07:59] – Greg's trial by fire: Soccer playoff pandemonium
• [14:37] – Scott’s budget blunder and media timing nightmare
• [18:39] – Greg’s financial oversight headache
• [23:04] – Scott gets served: Lawsuit scare and president’s burden
• [26:18] – Greg’s NBA family showcase story
• [31:02] – Closing thoughts, gratitude, and encouragement to share stories

Final Thoughts

• Both Greg and Scott highlight how the role of athletic director is often unpredictable, occasionally hazardous, and always subject to surprises, both large and small.
• The episode balances cautionary tales (about legal exposure and budget crises) with lighter, comedic stories about working closely with sports legends and the bizarre moments that crop up in the high-stakes world of high school athletics.
• Listeners are encouraged to connect at conferences and share their own “after hours” stories in person—hinting there are even wilder moments not fit for air.

This episode is a must-listen for aspiring ADs, sports administrators, and anyone who wants an authentic taste of the rollercoaster behind the scenes.