From caddie to head of golf operations

2021 Ryder Cup / Whistling Straits

Whistling Straits – Mike O’Reilly

Whitling Straits - Mike O’Reilly
A view from the 11th hole (Gary Kellner/PGA of America).

Estimated reading time: 7 minutes

This week’s Ryder Cup matches mark a return to the famed Straits Course at Whistling Straits. The renowned 18-hole layout is one of several designs brought to life by owner Herb Kohler via his hiring of architect Pete Dye.

Working his way up the ranks — the 43-year-old Mike O’Reilly has had a front row seat to watch the growing impact that the multiple course complex has brought to fruition and how it has elevated the overall stature and profile of Wisconsin golf.

In a very short time — Whistling Straits has hosted multiple key major golf events and now the Ryder Cup. O’Reilly shares his detailed thoughts on what makes Destination Kohler a place like no other.

Whistling Straits – Mike O’Reilly


O’Reilly is the Director of Golf Operations for Destination Kohler and has been in that position since 2018. The Darien, IL native began his career as a caddie at age 12 and is now preparing to oversee operations for his fifth major championship at Kohler — the 2021 Ryder Cup at Whistling Straits.

Whitling Straits - Mike O’Reilly

Whistling Straits – Mike O’Reilly

The O’Reilly Story

When people ask me how I like my job, I say, “I have the greatest job in the world. Literally. I get to work at beautiful facilities with a group of people that have become my second family. Come on, does it get any better?” I began my career as a caddie at age 12 at Ruth Lake CC in Hinsdale, IL. Now I am gearing up to oversee operations for my fifth major championship at Kohler, the 2021 Ryder Cup at Whistling Straits.

I can still to this day recall the following advice from my father, Tom O’Reilly — “Figure out what you want to do for a living, then find the company that is the best at it. Once you find them, get a job as a janitor and work your way up.” And that’s pretty close to what I did; I got a job as a caddie at Blackwolf Run in 1996, and began working my way up to the position I am in now. It’s been an amazing journey and I try to remain humble and grateful each and every day.

I was also named the Wisconsin PGA’s 2017 Golf Professional of the Year, which recognizes a golf pro’s accomplishments on and off the course. I also do more than just one role here, I help run the business operations, teach golf lessons, compete on golf courses throughout the state and manage my team through major industry events. I try to work hard, and I’m hopeful that what I do at work, at home and in the community will have a positive impact on the people around me and on the game of golf.

Whistling Straits – Mike O’Reilly

How are things progressing in preparing all facets of Whistling Straits with the Ryder Cup matches coming up next week?

We are currently tying the bow on construction at Whistling Straits in preparation for the event. You would see a full-scale build going on. It is the largest construction build Whistling Straits has seen in its history with the extensive nature of chalet structures, the bleachers and all the additional facilities needed for spectators.

What’s been the most time-consuming aspect in such preparation?

The time consuming and challenging part for me and our team is balancing preparations for the event while also providing a gracious experience to our guests. The golf course remained open into early September so there were a few months with construction and resort play going on at the same time.

Whitling Straits - Mike O’Reilly

Whistling Straits – Mike O’Reilly

Given the myriad of details — when does your day generally start and when are you able to return home for some much-needed sleep?

Well, the short answer is, it depends. Each day can look a little different depending on what is going on with the build, what is happening at the resort, and what the O’Reilly family has going on at home. Some days are “normal”, many days are “long” and some days are “really long”… I am an early riser though so most days start pretty early.  

Whistling Straits is no stranger to golf’s major events — most notably hosting three PGA Championships. How does the Ryder Cup compare? 

The Ryder Cup is one of the preeminent events in all of sports, and there are many operational differences when comparing it to a PGA Championship. Mainly, the sheer size and scope of the Ryder Cup is greater, which ultimately amplifies the number of volunteers, attendance, hospitality offerings, food and beverage, security, media credentials and much more. When it’s all said and done, the Ryder Cup will be considered one of the highest profile global sporting events ever held in Wisconsin.

What impact does the pandemic play in your planning efforts?

First off, I should say that the pandemic has impacted all of us and how it impacted the Ryder Cup pales in comparison to how it affected many other people around the world. And for planning, yes, we did have to modify some operations to ensure we can execute the Ryder Cup safely. Masks will be required inside all structures on property and encouraged outside.   

Whitling Straits - Mike O’Reilly
A view from the 18th hole (Gary Kellner/PGA of America).

Whistling Straits – Mike O’Reilly

When do you plan to close the course to public play? When do you expect it to reopen following the matches?

The Straits Course closed for play on 9/11 and will reopen on 9/29.

Given the various protocols — what’s the expected number of people you’re planning for the matches?

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I don’t want to speculate on exact numbers, but we are planning for everyone that currently has Ryder Cup tickets to be able to attend. Obviously, the PGA of America and Kohler Company, we’re going to adhere to state and local guidelines and recommendations.

The timing of the matches comes in late September — what are the expected temperatures at that time of year?

Late September is one of the best times of year to play golf at Whistling Straits. We typically have some wind, sun and temperatures in the mid-60s. We are hoping the weather is perfect!

Whitling Straits - Mike O’Reilly
A scenic view of Whistling Straits (Gary Kellner/PGA of America).

Whistling Straits – Mike O’Reilly

How will you know if the event has been a success — are there any clear benchmarks?

A win for team USA would be a nice outcome but even if we don’t win, my hope is that everyone that was involved with the 2021 Ryder Cup, the players, fans, vendors, staff, everyone, leaves thinking it was one of the greatest experiences of their life. Is that a measurable benchmark? Maybe, maybe not, but that is my hope.

Best advice you ever received — what was it and who from?

“I’m not okay, you’re not okay, but that’s okay” – Tom O’Reilly. We always strive to be perfect and beat ourselves up when we are not. I learned a lot from my father and there are many other “one-liners” 

I draw on all that he shared with me but this one tells me it’s okay to not be perfect. It also tells me that you are not perfect either and I should not expect that from you. Because of this, I find it’s much better to be curious versus judgmental.