Spidermonkey of the Week – Jack Cahillane

Riding in the Pyrenees

As a newer Spidermonkey, a few items about this SOTW:
From:          Massachusetts.
Status:        Married. One dog (Poncho). No kids.
Sports:        Former college and open ocean distance swimmer.
Sporty:        Lifelong Patriots & Celtics fan.
Hobbies:     Great food, wine and travel.
Fun Facts:   Have worn the B-52’s wigs. Seen pro soccer games in
                  several countries. Cycled in the Pyrenees. Got kicked
                  out of the Vatican.

Cycling; where to start?
The bike that started it all for me was when I inherited the renowned ‘banana’ cruiser, with leopard skin seat. Also, being the youngest boy in a neighborhood full of young boys that were hell bent on mischief, we were incredibly inventive in the ways we went about it. Continually challenging each other to do wilder and more dangerous stunts, seeing who could get away with the most without punishment from our parents, or broken bones and stitches (though I got my fair share of all of the above). I had the cool bike and embraced the freedom of the 2 wheels. Exploring new neighborhoods and doing lots of wicked jumps and crashes, and trashed the hell out of that cruiser, thinking my parents would quickly provide a newer, even hipper bike. No dice.

Lucky for me, I had a grandma who always came through for me.  She surprised me with a shiny red Columbia 3 speed, won in a drawing at the local Sears. In my hands, it quickly was stripped of the metal fenders and accessories, to try to match with my friends who were embracing the BMX craze that was just starting. Racing up and down the streets, jumping off ever larger ramps and riding the BMX trails we were building in the local woods. Looking back now, it was a self made precursor to the cross bike – full size steel frame with thin wheels that could withstand a high level of abuse..

Chicago, early 90’s. Buying my first real mountain bike. 28 lbs of indestructible steel. City riding, discovering Palos, rides with Scott Bowens to Highland Park (being laughed at by the roadies flying by), trips to Kettle Moraine and to Boulder and Durango, riding in the epicenter of the mountain biking rage… This is where the ‘continuous upgrade’ montage would be played. Spending lots of my bartending tips on bike parts and higher grade components. To top it off, I built piece by piece what would end up as a $4000 mountain bike. It was top of its class in 1995, and can be viewed hanging in my basement at any time.

I thought Spidermonkeys was a swimming club??  Swimming in the Mediterranean .

I bought a road bike in 2000, mostly for around town transport, but also because I needed to get back into some sort of shape after years in the bar / restaurant business, quitting smoking and putting on some pounds. Scott showed me the north branch trail and I pretty much rode that to death as I again found the freedom and enjoyment of the two wheels. As my riding fitness and ability improved, I cautiously entered the “Sheridan zone”. It may not mean much to some riders, but being a solo rider up and down Sheridan can be: a) intimidating, and b) humiliating. As teams and better riders consistently blow by you, it either sends you back to the north branch trail, or you dig in and train harder to keep pace.

It was on one of these rides 2 years ago that I was quickly passed by the Spidermonkeys. I jumped on the back, and rode with the group the rest of the way to HP. Each week, it seemed that I rode nearly the same time as the team. I would usually get caught somewhere north of Evanston, and do my best to hang on the back as long as I could. Last spring, I ended up with the team on a few more rides, and got to chatting with some riders. I was really wowed by the amount of fun people had on the rides, and how they looked out for fellow riders and even gave pointers on how to ride as a group. I got to know Vanessa, John Castro and Dean, and several others.

Scott and Roxanne are my old friends and current neighbors. They were starting to cycle more, and joined the team after doing the MS ride, so they motivated me to get in on the weekend team rides and to join Spidermonkey as well. Vanessa and Dean asked me to join the team for the Harmon 100. I had
done a few centuries, but not with a team. I have to say, it was just about the most fun I could hope to have on a bike while riding 100 miles! Everyone was really having a good time, tons of encouragement going on, the group was riding really well together and challenging each other to make it up the seemingly endless number of hills. I swear that I smiled the whole way, and still keep that as a motivator when I’m having a crappy ride, or it’s too cold… Makes it easier to tell myself, I can’t stop now, or I’ll be off the back of the next team century!

Harmon 100!

On every ride, I see and appreciate the little things that remind me what I think Spidermonkey Cycling is about; Really great people, having fun while they do what they love, in a group who lift each other up, continually motivating and helping everyone improve and achieve their individual goals as we look forward to the team goal; the cold towel out of Dean’s cooler – and a beer to celebrate. Thanks to all who have welcomed me and I look forward to the upcoming season, the MS Ride, and many more.


Poncho, the dog.


  1. Jack, Sorry to hear about your Patriots. Oh wait, no I'm not. coughBrady. Sorry again. haha Cheers to bikes!

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