Come Join Us: Bourbon, Churchill & Jeff Ruby’s

Part of a Short Series by Bob White

Over the past decade of showing folks the best of Kentucky, I’ve been asked on occasion to join the group for dinner, drinks, or both.

Usually after a 10 or 12-hour day, I pass on such offers, blaming obligations or plans I rarely had.

There were some exceptions.
The following is one such occasion when joining in for a post-tour night seemed like a good idea.

Come Join US: The Story of Dave, Driller and Ruby's
It was the spring of 2013 when tour planner, Shannon, pulled me into her office for a rare pre-tour briefing on an upcoming two-day assignment.

Discussions with the contact had been ongoing for weeks, she explained - warned that I might just have my hands full with this group of a dozen professionals.

Not one to get easily overwhelmed, Shannon seemed a bit exhausted with the amount of work she'd put into that weekend's itinerary. That caught my attention.

The point-man, a dentist she'd been negotiating with, had allegedly been ultra specific with each detail.

He wanted things to be perfect for the guys' Kentucky trip, and this wouldn't be the first time I'd catered to some stuffy, upper-crust group, if that's what they turned out to be.

“It'll be fine,”  I assured her, “… but thanks for the heads up.” 

I had a driver manning the helm both days, leaving me face-to-face with the group all day, both days.

My hope was the group wouldn't be as demanding and needy as Shannon forewarned.
Luckily for me, they were far from that.

When we picked up the group I was greeted by Dave, a 40-something sporting a candy-striped jacket and Panama hat. This wasn't the point-man, but introductions were quick and Dave was certainly a big personality in the group.

“Meet Driller,” Dave said, pulling in for a handshake a small man of Asian descent wearing khaki shorts and a crisp, white polo. No better nickname for a dentist than Driller, I suppose.

It was all smiles at this point, and Driller seemed far from needy.

Dave, in his flamboyant candy-striped jacket, also seemed like he wasn't one to worry too much about details. Everything seemed fine to me.

Our first stop on Day 1, the former Bulleit Experience at historic Stitzel-Weller, was just a short drive from the Galt House Hotel where we met, so there wasn't much time to feel the group out.

A relatively new addition to the Kentucky Bourbon Trail in 2013, the Bulleit staff were extra kind to Driller's group. Meeting the founder, Tom Bulleit, shortly thereafter was a cherry on top.

From there, the bus drove for an hour to Buffalo Trace. During that time, the group had time for some moderate drinking and my friendly discussion about Kentucky Straight Bourbon Whiskey.

The group was treated to a private tour at Buffalo, so the driver and I had time to chat, relax and roam.

I was headed to say hi to Keith at the guard shack, when I saw that the group's tour was done.

There was Driller, riding the bronze bison statue in front of the gift shop. Dave was there too, with the camera, as the rest of the group egged Driller on.  Oh my…

Now, this isn't encouraged, not permitted, but it was good to see the guys were having fun.

The rest of Day 1 was a success and Driller stayed smiling in the back of the bus, not once questioning any stop or detail or plan we made on the fly. Dave, who I realized was the Alpha Dog in the group, was equally easy-going. The rest of the guys seemed happy just to be there.

All was good.
 

Day 2 started off with Bardstown distilleries and enthusiastic drinking.

My new driver that day, Bill, was a beer drinker from Pennsylvania who meshed nicely with the group.

I learned more about the group and their trips that day, once the guys loosened up.

These guys don't mess around.

Their annual Mardi Gras outing, for example, doesn't just consist of the group mixing with the crowd.

Instead, the guys have their own float parading through the French Quarter with beads and flair.

These guys won't simply attend a party. They bring the party.

Returning to Louisville after Bardstown, we headed toward Churchill Downs for live racing before the main event of watching the Preakness Stakes on the enormous video screen recently added at the track.

Orb had just won the Kentucky Derby a few weeks before, so the crowd would be big and festive.

Less than a mile from the track, Dave alerted me to the cooler being emptied of cold beer.

Oh No!

At the same time, the bus was coming to an unexpected stop in the middle of Crittenden Drive, as scores of buzzing minibikes overtook the street near the railroad tracks.

Traffic stopped in both lanes for the swarm. By the time the “bikers” were clearing, a train was coming down the tracks, so railroad crossing gates started coming down, planting us in park with no beer a mile from the Downs.

“Let’s try here, Dave,” I mentioned, pointing to Derby City Pizza just outside the door.
Without hesitation, Dave and a few others poured off the bus and into the pizza place.

The train was long and slow as it made its way into their downtown railroad yard. Thank goodness.

The bus would be fine. Bill, the driver, didn't get upset about much.

The Derby City Pizza team kindly loaded us up with a few metal buckets of iced-down bottles and the porters took no breaks in boarding the bus as the crossing gates raised.

Everyone was happy and we had enough cold beer to make it that final mile into Churchill Downs to find a parking spot, or drop-off point.

A couple hours were spent at the track, drinking and placing bets. I usually just make a donation, but we had a couple of winners in the group.

The entire crowd of 15,000 cheered, but Orb ended up losing the Preakness to Oxbow, that day.

What a great day. I assumed that'd be the end of our journey, since the group had dinner reservations at Jeff Ruby's, Louisville's premier steakhouse adjacent to the Galt House, where they were staying.

The guys asked me to join them, but I declined.
We said our goodbyes. The guys presented Bill and I with a generous tip and the bus drove off.

All was good. Another successful tour was done.
As Bill was driving back to the garage, I looked over the bus to see a guest had left his phone.

Not one to need instruction, nor one to waste time, Bill pulled off the first and only U-turn I've ever witnessed on Market Street and headed back to the Galt House.

Like riding the bronze buffalo at Buffalo Trace, this is not allowed.

Pulling up to the east tower, I could see a few of the guys hovering at the front desk.
“Ya know what, Bill?” I had decided. “You can just leave me here. I'll be fine.”

I went inside to be greeted by smiles of gratitude. The guys renewed their offer to join them for dinner and this time, I changed my answer to a “yes.”

Most of the group was seated when the few stragglers and I walked into Ruby's. The appetizers were coming, and it appeared the group ordered two of everything.

An oyster, a whiskey and some good conversation passed time before our great steaks made their way to the table.

Mouthwatering slabs of dry-aged beef were placed before each man in the smiling group.

Then, I looked over to Dave, beside me.  He wasn't responding. Was he dead?
His head was nodding. His eyes were closed. I looked at Driller for help.

“Oh, he's fine,” Driller explained. “He'll go out for 10 minutes, then come right back.”
Dave had been drinking for most of the past 48 hours... 
“Go ahead and enjoy your steak, Bob,” Driller affirmed.

Now, I felt out of place. The group, however, went on with their conversations, smiles and laughs.

Sure enough, 10-minutes later, Dave returned as though things were nothing but normal.

Oh man, was that steak good! And the mac & cheese, my word! What's in that stuff?
When time for the check came, Driller instructed the server to put everything on a single tab. 

An emptied bread basket was then passed around like an offering basket at a Catholic Mass. Each of the fellas pitched in a credit card. The server picked the winner of the $2,000.00 tab.

Gratuity, of course, was cash from the group.
That was all a first for me, but it was a first I'm glad not to have missed.

I ended up taking a cab home that night, and again the next morning, to retrieve my car from the bus garage, so that night cost me a bit.
But, aside from the meal and drink, it was well worth cab fare to join a great group of guys at one of Louisville's best restaurants after a fabulous weekend in Kentucky.

I'll never forget it.