Ten Playboys
10/23/23
By Tom S. and Vinny Liska
John Bearce, the owner of Northwestern Ford, was about to make Tom an offer he could not
refuse. An all expense paid trip to the newly opened Playboy Resort and use of a brand-new
Shelby GT convertible for the weekend! Tom, a student was just twenty years old in 1968.
He shares his fantastic story with photographs from the weekend he became one of ten Northwestern “Playboys”.
In the latter half of the 1960’s the economy was booming, the stock market was soaring, and Hugh Hefner’s Playboy
empire was firing on all cylinders. His successful magazine had a target market of young professionals and businessmen
and focused on a trendy nightlife, food & drink, travel, music, good jazz, sportscars and pretty girls with scant clothing.
In 1967 ad revenue topped $20 million and the magazine circulation exceeded twenty million copies per month.
Part of this ad revenue came from Ford’s Shelby operation which catered to this same demographic population.
By this time Mr. Hefner had built a network of eighteen exclusive clubs located in major U.S. cities as well as London,
Toronto, Montreal and Jamaica. He was now ready for something big, really big, the first ever Playboy Resort nestled
on 1,000 acres in the rolling hills of southern Wisconsin, just east of the resort town of Lake Geneva.
The property was conveniently located seventy-five miles northwest of the Playboy Mansion headquarters in
Chicago and forty-five miles southwest of Milwaukee. The $10 million resort would feature the traditional
Playboy Club amenities plus a three hundred room hotel, twenty-acre ski hill, two championship 18 hole golf
courses, a private lake for boating & fishing, riding stables, a skeet range, convention and banquet facilities
along with a private airstrip for his jet setting clientele.
The grand opening event was scheduled for May 4-5, 1968, by personal invitation from Mr. Hefner for the benefit
of the American Cancer Society. Carroll Shelby along with his namesake cars were going to be an integral part
of this gala event. A joint marketing plan was arranged to provide ten brand new Shelby convertibles
to the Playboy Resort for the exclusive purpose of chauffeuring VIP’s and guests around the vast facilities.
John Bearce’s Northwestern Ford dealership in Milwaukee was selected to be the launch point for this outing.
Northwestern Ford was a leading Shelby dealership in the greater Metro Milwaukee area which sponsored a Mustang
club known as the Northwestern Thoroughbreds. The club met monthly at the dealership and organized several road
rallies and other automotive events throughout southern Wisconsin. The club was open to all auto enthusiasts
and despite owning a Plymouth Barracuda, I was one of the active members. As May approached, I was selected to
be one of the drivers for this event. There were five GT 500s and five GT 350s. All had automatic transmissions
except for one red, GT 350, which had the four speed stick shift. [The car has been identified as # 2888 and would
later receive warranty service for the clutch]. Tom was assigned an Acapulco blue, GT 500 with a black interior.
We were told to arrive at Northwestern Ford early on the morning of May 3rd and that the dress code for the weekend
would be dark dress slacks, a dark blazer and a long white sleeve turtleneck shirt. Our job would be to drive VIP’s
and guests around the facilities, into town or wherever they wished to go. We left Northwestern Ford Friday morning
in a caravan, all ten Shelby convertibles with tops down for a sunny one hour drive to the resort.
When we arrived,
we stopped at the entrance security gate and someone in the lead car explained to the security team what our propose
was and that we would be coming and going from the facility at various times over the next three days so it would not
be necessary to present credentials while driving these unique automobiles. This accommodation most likely saved me
from an embarrassing moment and my windshield, which I will explain later.
The white car in the center is # 2476. Car # 2057 is on the right.
Once cleared by security we drove up to
the main entrance and were greeted by Hugh Hefner, the Playboy bunnies, the manager of the club and the key members
of his staff. I remember him telling them that we were going to be providing a service to the guests that weekend
on an on-demand basis so to keep us fully accessible we were to be provided with anything we needed when requested
without delay. Although this excluded services from the staff wearing cotton tails and rabbit ears, it did enable
us to skip to the head of the line to be immediately seated and served at any of the various restaurants. Rightly
or wrongly, we assumed that this generous accommodation entitled us to collect a few souvenirs along the way as we
helped ourselves to Playboy ashtrays, match books and any other trinkets that would fit into our pockets before
heading back to our duties.
Friday afternoon was mostly spent familiarizing ourselves with the facilities. We drove out to the stables, around
the golf courses, lake and the ski area which was still under construction. We then headed out to the airstrip which
we repurposed into a drag strip and put the cars through a number of competitive performance runs. If these cars had
an initial break-in procedure, they were slightly overlooked. Our accommodations for the weekend would be at a motel
midway between town and the club resort which was just east of Lake Geneva off state Highway 50. Because the bunny
dormitories were not completed at the time of the opening, they stayed at a motel across the street from where we were
staying. Although there were a few rumors of one or two of the drivers transporting a bunny from her motel to the
resort, it was probably more of a case of wishful thinking than fact.
# 2057 at the Playboy Resort and now in Australia
As guests began to arrive late Friday and early Saturday, we performed our duties driving these folks to wherever they
requested to go. One of the celebrities I had the honor to transport was Hugh O’Brian who starred in a popular TV western
series titled ‘The Life and Legend of Wyatt Earp.’ Hugh asked to go to the riding stables where I was sure he would hop
onto a horse and gallop off into the sunset. WRONG….the guy could barely sit on a horse much less ride it. His complete
lack of any equestrian skills were confirmed by a Hollywood riding instructor who was quoted as saying “That boy can’t
ride nothin wilder’n a wheelchair”. Long live Hollywood stand-ins and stuntmen.
The actual car Tom drove in 1968. It has been identified as # 2775.
Late Saturday morning, I was traveling back to the club after making a trip into town. I was east bound on highway 50
which was a four-lane divided highway with a grassy center median doing about eighty-five mph. As I prepared to make
a ninety-degree left turn to cross the highway and enter the resort, I applied the brake which slowed me to about sixty
mph as I started to make my turn. At that point the brake pedal continued straight to the floor while the nose-heavy
Shelby began to severely understeer towards the median. Being young, invincible and strapped into a car with a roll bar
I did not fear for my life but recall thinking that I would have to tell John Bearce that I broke his car and it was in
the ditch. My next thought was how to save this from happening and the only option I could think of was to floor the
gas pedal hoping that there was enough power to break the rear end loose and get me pointed in the direction I needed
to go rather than the grassy median strip. That’s what I did and fortunately the 428 did not let me down and with no
oncoming traffic on highway 50 I was on my way into the resort. As I approached the security guard doing about
thirty-five mph, he raised the gate and jumped out of the guard house waving an imaginary green flag as if he was
flagging the rolling start of a one car road race. To this day I am thankful for him raising that gate as surely
it would have taken out the top of the windshield of my beautiful Shelby. The road to the resort was a long uphill
drive which allowed me to scrub off enough speed so that I was able to bring the car to a stop by applying the parking
brake near where many of the other Shelbys were parked. I immediately popped the hood only to find that the brake
fluid reservoir was almost empty. We then checked the fluids on all the other cars and discovered that many of them
also had various fluids that needed to be added. We caravanned back into town to have all these fluids brought back
up to proper levels.
# 2888 was the only 4 speed car sent to the Playboy Resort
Later Saturday afternoon while the opening events were beginning to take place, we had little to do so we headed back
to the airstrip for some more performance runs. I was the passenger in the red 350, the only car with a four speed.
Dale was the driver, and he was going to demonstrate his speed shifting skills, or lack thereof. About midway down
the airstrip, I detected the strong odor of burning clutch, but despite my yelling to slow down, Dale kept his foot
in it and soon the tach needle was revving higher while the speedometer needle was heading south. That was the end
of the 350 as the clutch was toast. The car limped back to the club where it sat for the remainder of the weekend.
Dale was now in retirement.
I have read elsewhere that there was a parade through town during the weekend with the Shelbys and Carroll himself
driving one of his Cobras. Although I don’t doubt that report, I did not participate in the parade, nor do I recall
any of the other drivers talking about it.
Sunday morning was busy once again, but the activity suddenly dropped off shortly after lunch. The plan was for us to
return eight of the cars to Northwestern Ford early Sunday evening. Two of the cars were going to remain at the club
for an extended period for their use. One of the eight scheduled to return was the red 350 which would now go back
sometime later, on a flatbed hauler.
With little to do, four of us, including myself decided to head back to Milwaukee early to spend some time cruising the
strip before we had to turn the cars in. Back then the cruising “strip” in Milwaukee was Wisconsin Avenue east to the
lakefront and then north on Lake Shore drive to Kenwood Boulevard and then back again. There were four of us driving
two abreast in two rows cruising together doing crossovers and having the time of our life out on our home turf.
At the designated time we returned to Northwestern Ford waiting for John Bearce to open the dealership so he could
secure the cars inside and we could retrieve our automobiles. The specified time came and went without John making
his appearance. The thought then crossed our minds that if he failed to appear within a reasonable period, we would
have the cars for our personal use for another day. As the minutes passed this possibility became overpowering and
we concluded that twenty minutes was a sufficiently reasonable time to wait for John to appear so when that time expired,
we were out of there! And so it was, we split, refueled, headed off for a bite to eat and back again to the “strip” to
continue our cruising adventure. I don’t know what ever happened to the other three drivers, but it was the four of us
putting on a show that evening much to our delight.
The next morning, I returned to college and had class on one of the upper floors of the classroom building. One of my
classmates came up to me and asked if I was on the strip last night to which I answered “yes.” Excitedly he asked if I
saw “them” and asked what he was referring to. He said there were four of “them”, all convertibles with roll bars two
by two doing crossovers while cruising. I replied with a huge smirk on my face that I was driving one of “them”.
At first, he did not believe me until I took him to the window and pointed to the blue Shelby parked below on the
street and asked if that was one of “them”. He said “yes”, and I pulled the car key out of my pocket and told him
that after class we were going for a ride. When class ended, we headed to the car, and I drove to the closest onramp
to interstate highway I-94. As I accelerated off the 360 degree ramp I took the car up to the century mark before
braking back to legal speeds. That was the last of my adventurous runs with the Shelby. The rest of the afternoon
was uneventful as I returned the car to the dealership, ending three and a half days of a truly amazing weekend.
Car # 3086
I was happy to return the car because I knew that if I had it any longer, I probably would have lost my driver’s
license and if not, I certainly could not have afforded the gas bills since my fuel consumption that weekend
averaged about five miles per gallon.
A short time later I returned to the dealership for the next Mustang club meeting and remembered seeing one of
the Shelbys on the showroom floor. I glanced inside and noticed that the odometer showed mileage only in the
double digits range which I still find to be somewhat mysterious.
If you are the owner of an Acapulco blue, Shelby GT500 with black interior, I hope you are enjoying the car
as much as I did and enjoyed learning about its legendary beginnings.
A special “Thank You” to Tom (and his brother) for sharing these experiences. They
put some context to the ten, Shelby convertibles sent to Lake Geneva.
Car # 3093
Vinny found this invoice from Playboy to Shelby and the envelope.
Here are the serial numbers of the 1968 Shelby "Playboy" convertibles:
| 8T03S173639-01989 |
8T03S173659-02057 |
8T03S177988-02476 |
8T03S179578-02755 |
8T03S179596-02775 |
8T03J180321-02888 |
8T03J180347-02991 |
8T03J183075-03086 |
8T03J183076-03088 |
8T03J183081-03093 |
If you have on information on this event or information on the other cars not mentioned, please drop me an email
at Coralsnake68@hotmail.com