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Manchester High School
437 West Nimisila Road
Akron, OH 44319
(330) 882-3291

  Gregg Olson - MHS Class of 1978
  Chief Financial Officer of the NBA's Portland Trail Blazers

Gregg has been married to Karen (Czworkowski) for 21 years ("I hope there's another 21 left for us," he notes), and they have two children. Sitting in Mr. Csipke's accounting class over a quarter-century ago, Gregg had no idea the skills being fine-tuned would soon be his ticket to success in the front offices of several major league sports franchises. We asked Gregg to fill us in on the details.

Family: Kids highlights

Nicholas is finishing his junior year at University of Oregon, majoring in business and thinking about sports marketing. He's a resident assistant in a campus dorm where his leadership skills have helped him to be nominated for several awards. His travel hockey team was the California State Champion of the Midget B division in 2003.

Alyssa will graduate from Sunset High School in Beaverton, OR in June '06. She plans to attend junior college in the Fall to begin work toward a degree in early child development, preparing her for a career in pre-school education. She was captain of the winter guard [flag corps] that went undefeated in all five performances in 2006. She also marched in the color guard with the marching band all four years of high school.

Location history (where you live, previous cities)

We're currently in Portland, Oregon, where we've been since August 2003. After college we lived in Cleveland, Ohio, until 1995 when we moved to San Jose, CA. We stayed there until our taking up residence in the Northwest.

Education after MHS:

I attended Baldwin-Wallace College in Berea, earning my BA in business administration with a concentration in accounting, and graduating Magna Cum Laude. I received my CPA license in Ohio in 1984.

Your occupation history:

I thought I had landed the best job ever when I got hired at Ernst & Whinney, one of the "Big Eight" accounting firms [for those of you keeping score at home, we're down to the "Big Four" now!], and the only one with its national headquarters in Cleveland. It was a big deal, and I was proud to be there. My first client was the Cleveland Indians, and then it was a REALLY big deal. During the course of my time at E & W I had clients that were public utilities, manufacturers, banking and financial institutions, oil and gas industry suppliers, trade associations, educational institutions and large not-for-profit charities like United Way. I figured I was a "lifer," destined to be a partner in the firm one day. But then, "it" happened: while I was at the Indians doing the annual audit, they hired a new president who decided to make a change in the person running the finance department. I threw my hat in the ring, and at 25 years old became the Chief Financial Officer [ok, so my title was Director of Finance..but there wasn't anyone higher in finance there than me] of a major league franchise.

During the course of ten years with the Indians, my greatest accomplishment - and the thing I still have the greatest pride in - was my involvement in the development of Jacobs Field. I helped pioneer the use of technology for things like real-time cash registers in the ballpark and the bar-code scanning ticket turnstiles that are now used in virtually every public assembly stadium and arena in the country. I had a great run there, and had turned down the headhunter who called me every six months or so with temptations of jobs elsewhere, until...the strike of 1994.

In January 1995 I started my new job as CFO of the NHL's San Jose Sharks. They were a third-year expansion team at the time. It was a chance to help shape something new, and an opportunity to get into entertainment as well as sports. Moving away from family and friends was the most difficult part. But the work was rewarding, and the firm was very entrepreneurial. We ran the team and the building, had a stake in the indoor soccer team and an indoor tennis tournament. By the time I left the company, we owned the tennis tournament outright, had managed a Sr. PGA golf tournament, taken the Major League Soccer Earthquakes to the MLS championship [yes, I have the hardware to prove that one!] and purchased an AHL hockey franchise and moved it to Cleveland. There was a lot going on. But in 2002 the company was sold to a bunch of Silicon Valley investors. After having completed all the work on the sale, it was time to move on to a new challenge.

The Portland Trail Blazers, a franchise in transition [then and now] was calling. They needed a CFO with experience "turning a franchise around," and that was my reputation. The company had lost more money in the one year before I arrived than all the teams in all the years before combined. The most difficult part of this move was dropping our son off to school in California on Saturday and loading the moving van for Oregon on Monday. But he survived his freshman year, and our then sophomore daughter took to her new school like a duck to water..once she got in with the marching band. We're still working with the Trail Blazers, who are currently going through some difficult times. But we see them as opportunities.

Spouse's occupation:

Karen works for the Trail Blazers in the Season Ticket Services department. She worked in customer service in the convention business before the kids came along, but took a break to be a great mom. She had her own cake business in Ohio for years, too.

Interesting things you've done since high school:

I spent several years as DJ in college doing specialty rock & roll shows, plus station format shows. It was a total kick, and lots of fun.

Thanks to my work I've been to All Star games for MLB, the NHL and the NBA. I've been to over 35 stadiums and arenas throughout the country, and met people like Billy Joel, Hank Aaron and Wayne Gretzky. I even got yelled at by the President of the United States once [of course, he wasn't the President then, but George W owned the Texas Rangers baseball team, and we had a little tussle.]

Travel highlights:

Among the greatest trips I've taken are two cruises to Alaska - it's a "must see!" We also enjoy periodic vacations to Hawaii, and I've traveled to Bermuda for work on several occasions.

Current Hobbies / Activities:

I play golf some, but that's been limited at times over the years due to knee surgeries, of which I've had 13 - the latest being a full replacement. I also enjoy reading lawyer and detective novels by the likes of John Grisham and James Patterson.

Favorite Manchester teacher, and why:

Mr. Armenti stands out as a favorite of mine, though I struggled to get good grades in his physics class. I can still hear him preaching during geometry, "As long as your conventions are consistent," and I know he made an impression when I use that line on one of my staff when discussing some problem we're solving.

Favorite subject at MHS:

Accounting was a favorite of mine, maybe because it came so naturally to me. And maybe because it became the basis for the career I chose.

Least favorite subject at MHS:

Maybe chemistry with Mrs. Bartels. Man, she was tough..and I felt hard on me. But she gave me one of the greatest stories about high school when she yelled at Mike Norman to sit up in his chair, even though he was leaning against the back of the seat attached to the desk. She ultimately slipped a yardstick down the back of his shirt to force him upright, upon which he promptly pulled from inside his shirt and leaned back against the chair to hold it in place. The class just couldn't keep it in. It was a classic.

Favorite memories from school:

Generally, I remember feeling like I had such a great corps of friends, many of whom I kept in contact with for years and years, some to this day.

What sports, if any, did you play at MHS?

I played freshman football which I LOVED, but at which I was terrible. After that, I managed the basketball team and was trainer on the football team where I earned varsity letters. I guess my career in sports management really started at MHS.

Other H.S. activities / clubs you enjoyed:

I worked for most of my years in school, so I didn't spend much time in other activities. I was part of class government one year.

Which H.S. reunions have you attended? Any favorite memory?

I went to the 5 and 10 year bashes and had a blast. I missed the last one because I had just started my new job in Portland. I hope to make any future ones, though.

Did you have any favorite high school "hangouts?"

Since I worked at Rolling Acres, you could say I hung out there some.

Favorite music from your H.S. era, and current favorite:

Back then, Journey, Foreigner, Electric Light Orchestra, Billy Joel, Boston, Carole King, Pat Benetar.

Current favorites include Rod Stewart's American Songbook collections, Frank Sinatra's Duets collection, Norah Jones and Nat King Cole [funny how the stuff our folks listened to that we didn't like someone crept into our own library...]

Favorite TV shows:

Law & Order in all its flavors; According to Jim

Biggest Pet Peeve since your graduation:

People who don't know how to drive. I must have picked that one up when I was a school bus driver in college.

Do you still have family living in Manchester? How often do you return?

I have two sisters and a brother who live in Akron, but none in Manchester. My folks both passed away, dad in 1986 and mom in 2000. At most I get back to Ohio twice a year right now.

Gregg appreciates the Alumni Association's efforts to help Panther grads re-connect with each other. "The website is great, and has great content!" He says there's nothing he'd like better than to hear from old friends at: or

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