How does one find the words to eulogize a true hero: a dear friend, a tireless mentor, a great benefactor, and a true inspiration?

When I did my first Pan-Mass Challenge charity ride back in 2001, my coworker Jeremy—who was doing the AIDS Ride—told me about a group training ride starting at Quad Cycles in Arlington. “It’s run by this guy named Bobby Mac… You have to meet him!”

So one weekend I went out and rode with them. Bobby was a charismatic older guy who was the obvious center of the group. He’d bark out endless advice about how to ride, always interjecting a characteristic bit of self-deprecating humor or belting out snippets of songs from the 60s and 70s. He’d shamelessly (but harmlessly) flirt with the ladies, who all adored him. On the road, he always stayed with the slower riders, mentoring them and offering helpful advice for how to both survive and enjoy whatever charity rides they were training for.

Bobby Mac made riding fun.

Bobby Mac
Bobby Mac with Johnny H
Bobby Mac at Ferns during the Tour de Mac
Bobby Mac
Ornoth with Bobby Mac
Bobby Mac

Like so many other neophyte riders, I started out wearing canvas cargo shorts and a tee shirt, riding a heavy, flat-handlebar “hybrid” bike. Over the course of thirteen years with him, Bobby sculpted me into a spandex-clad veteran roadie who rides 10,000 kilometers a year on his carbon-fiber road bike and has raised over $100,000 for cancer research.

But I am just one person out of hundreds and hundreds of riders whom Bobby has encouraged over the years. Himself an inveterate charity rider, he and his team of “Quaddies” were often top fundraisers and volunteer crewmembers for several of the largest charity rides in the area. If you added up all the good works performed by Bobby Mac and the legions of riders he has encouraged, the sum total would be staggering.

As you can imagine, Bobby Mac was a huge part of the local community. He recorded several PSAs on behalf of charity rides and local cycling advocacy. No matter where we went, we’d always run into people who knew him. Whether you were a cyclist or not, it seemed everyone was friends with Bobby Mac. No matter who you were, he made it very easy to feel like you were his best friend.

We also loved Bobby for his idiosyncrasies. It was a mark of seniority if you could say that you’d seen him ingest anything other than Cytomax sports drink. Back when the ride stopped at Kimball Farm, Bobby proved that his popularity extended even to barnyard animals, as “Buff the Powerbar-Eating Goat” would run up to the fence to greet him and receive a treat.

As he aged, Bobby suffered from macular degeneration which gradually eroded his eyesight. I once watched him nearly ride straight into a sawhorse barrier that a road crew had put up when one of our regular roads was temporarily closed. It was a mark of real trust if Bobby let you lead him through a charity ride on unfamiliar roads he hadn’t already memorized.

Due to his worsening eyesight, we all feared that Bobby would eventually be unable to ride. Knowing that his time was limited, in 2006 we organized the first Tour de Mac, a special ride in his honor, complete with tee shirts, rubber wristbands, and an award presentation for the guest of honor. In 2009 we held another ride to celebrate his 60th birthday, which I recorded with an emotional writeup and video. Everyone loved Bobby, but despite repeated operations to maintain his vision, we all harbored silent fears about how much longer he would be able to ride.

However, Bobby wasn’t destined to live long enough for his eyesight to fail him. Three weeks ago, Bobby went into the hospital, suffering from pancreatic cancer that had metastasized. It was terminal, and last night he passed away in his sleep at home.

When his diagnosis first became public knowledge, the hospital’s staff very quickly learned how special Bobby Mac was. They weren't prepared for the hundreds of his friends who came to visit his bedside. The nurses put up signs, limited the duration of visits, and still more people kept coming, sometimes queueing up in shifts of ten at a time outside his hospital room.

The first time I visited him in the hospital, I had something special I wanted to share with him. When a rider surpasses $100,000 in fundraising, the Pan-Mass Challenge gives them a silver pin with the PMC logo as a lifetime achievement award. I had received mine six weeks before Bobby went into the hospital, after 13 years of riding and raising money for the Dana-Farber Cancer Institute.

I wanted Bobby to know about that accomplishment, and how it was due in large part to his inspiration. And that if I was only one of hundreds of riders he’d encouraged, then he’d achieved a whole lot of good in this world. His characteristically self-effacing response was to shrug off his role and emphasize mine, saying that I had long been the most dedicated of his charity riders.

It’s bitter irony to me that the man who was my hero and inspired me to ride the Pan-Mass Challenge was taken from us by the very disease I’ve raised so much money to combat. It goes without saying that this year—my final PMC ride—will be dedicated to the memory of my hero: Bobby Mac. It will be a very emotional ending when I reach the Provincetown finish line for the final time and lift my bike over my head, consciously copying Bobby’s signature victory salute.

With his innate charisma and his natural role as the center of a circle of people, Bobby reminded me a lot of my father, or what he might have been, if my father had been motivated by kindness and generosity. In that way, Bobby has been a role model for me, an inspiring example of what a fatherly male figure could be—and could accomplish—in this jaded, selfish world.

There’s one particular exercise in Buddhist meditation called “Brahmavihara practice”, wherein we use visualization to cultivate our capacity for friendliness, compassion, and joy in others’ happiness. Typically, we start by directing compassion toward someone whom it’s easy to feel affection for, then slowly work our way to people we feel ambivalent about, and then challenge ourselves to work with people we find difficult or hateful. But we start with someone who is often referred to as our “benefactor”.

Years ago, when I started that practice and was asked to identify someone whom I felt unalloyed affection for—someone whom I considered my benefactor—one person’s name immediately jumped to mind: Bobby Mac. Bobby was my exemplar of friendliness, affection, compassion, and generosity. In my opinion, Bobby was the absolute embodiment of the concept of a “benefactor”.

Bobby’s presence and personality made everyone’s world feel much more friendly, much more optimistic. He put a whole lot of love and goodness into the world.

And he took a whole lot of love and goodness with him when he left: both the love of his many friends which was directed toward him in his final years, and also the love and goodness that have gone out of this world with his passing. For everyone who knew Bobby Mac, the world feels a little colder and more lonely without his energetic encouragement and his incorrigible smile.

Here’s to you, my friend, my mentor, my benefactor, my inspiration, and my hero. As you enjoined us at the start of every ride, we will do our best to “ride with love in our hearts and smiles on our faces”, thanks to you, Bobby Mac.

I won’t belabor the ask, but if you wish to make a donation to fight cancer in Bobby’s memory and sponsor my PMC ride, you can do so here.

So my buddy [livejournal.com profile] somervillian, who hosted a few of the Hold ’Em tournaments that I’ve attended, aspires to become a “serious” poker player. A couple days ago he pinged me and asked if I wanted to make a trip down to Foxwoods with him. (For the out-of-towners, Foxwoods is an Indian casino in Connecticut, and presumably the largest casino in the world).

I’ve only been in a casino once before. That was also at Foxwoods, but seven years ago, and I lost a couple hundred bucks on blackjack during that visit. On the other hand, I feel I have a pretty solid grasp of casino blackjack, and I had some extra Xmas cash lying around, so why not go down and give it a shot?

So yesterday we drove down, and I tagged along with my buddy as he signed up for a seat in the poker room.

At a casino, one element of success is in knowing what you don’t know. I clearly don’t know the wacky table games like craps and roulette, nor am I inclined to make the effort to learn them and gain proficiency at them.

But having taken second and third in two of the three friendly Hold ’Em tournaments I’ve been to, I think I could probably succeed at poker, but the casino game—and particularly casino players—are very different from friendly games, so I figured discretion was the better part of valor. I left [livejournal.com profile] somervillian to his own devices and I went to scout out the familiar blackjack tables.

Despite the fact that I lost money back in 1999, I feel I have a very solid blackjack strategy (even back then I started the day up and lost my winnings later). There are “strategy” cards you can download that tell you mathematically what you should do on any possible combination of cards, which makes things pretty easy. I don’t always play by the suggested strategy, but I limit my deviation from the strategy to certain specific card combinations where I feel that taking an additional risk is justified.

Of course, that takes care of a strategy for playing your hand. However, knowing how to win a hand is only half the equation.

You see, if you go by the printed strategy card, over the long run you’ll win about 40 percent of the time. That means that over the long term you’re guaranteed to lose money if you always bet the same amount. So in order to make money at blackjack you need not only a strategy for playing out your hands, but you also need a betting strategy.

My betting strategy is fairly straightforward. It’s based on the premise that the more hands I lose, the more likely it is that I’ll win the next hand, or that the more I win, the less likely it is that I’ll continue to win. In the short term, there’s no real correlation between one hand and the next, but over the long run, the player’s going to win 40 percent of the time, and if I wager and win enough money on my winning hands to cover the hands I lose, then I’ll wind up winning money overall. No?

So the key is if you lose on a $15 hand, you increase your bet to $25, hoping you’ll win the next hand. If you lose again, you increase your bet that much more, to $35, then to $50, $75, $100. Keep increasing until you win (just make sure you’ve got the bankroll to be able to double three or four times). Then, after you’ve won a big money hand, you back down to the minimum bet until you’ve had another losing run, when you can jump in again.

Of course, it’s not quite that simple, and predicting how much to bet and when to jump is an exercise in experience and intuition. I’m not saying the strategy is perfect or that it would work for anyone else; I’m just saying that’s how I play.

So I found myself a blackjack table with a friendly dealer and a $15 minimum bet and put all this into effect. I got raped. As the French would say, I met the man with the hammer. I was getting shit cards and couldn’t win a single hand. I think I blew through my $200 initial buy-in in less than ten minutes, and plopped another $150 onto the table. Then I lost probably all but $50 of that.

I was hemorrhaging. At the abyssal nadir of my losing streak I coined a brand new phrase to keep my spirits up. Likening my losing streak to a airplane crash, I thought: Any table you can walk away from is a good one.

But you have to trust the math. I kept putting money out there, and finally the cards turned against the dealer. By then the minimum bet had increased to $25, which helped my recuperation (recoup-eration?). I trusted the betting strategy: lose, jump, win. Lose, jump, lose, double, win more. Lose, jump, lose, redouble, lose, quintuple, win big.

It took several hours, but I knew I was at least even when I looked down and saw about $400 in chips in front of me. The stack yoyoed a bit with each hand, but the overall trend stayed positive. When my buddy called me to say he was done for the day, I didn’t know precisely where I stood, but I knew I was pretty good. I was in fact pretty surprised when I went to cash out and took $875 in chips with me to the window. Wow. I had a $500 poker chip of my very own! I was flabbergasted.

Yeah. I didn’t actually do the math until I was in the car. Superstitious or something. And that waiting was very hard, because we had dinner before we left the casino (I paid, of course). Finally sitting in the car, I did the day’s tally: not only did I make up the $350 I’d lost initially, but I came away with $525 of the house’s money. Wow!

During the long drive back, we talked about strategy and what we’d both learned about our respective games. I’m afraid I must have been a pretty poor conversationalist, because I was so shocked that I could just play blackjack for a couple hours and walk away with a fistful of Bens. Sure, it was pretty nerve-wracking at first, and there were a couple hands where I had $100 riding on a single play, but I got away with the casino’s money!

The casinos project that you have the opportunity to win big, but ultimately they are in the business of taking money away from you in exchange for a little high drama and entertainment. There’s this theoretical chance that you might win, but it’s a pretty slim chance. Sure, my $525 is nothing to the casino, but it still shocks and awes me that I got away with what— to me—is a tidy chunk o’ change.

Despite the fact that Hold ’Em is absolutely nothing like Hurt Me and the Bates Motel, the variants we always used to play, my adolescent days of hard-core poker seem to have served me well.

It’s been a long, long time since my last pokage, but last night I attended one of my buddy Jer’s friendly Hold ’Em tournaments for the first time. And it was the first time I’ve ever shot Hold ’Em with live ammo.

The result was eminently satisfactory. Early in the game Dita raped me, but I got her back in Spades after going all in to her. That kicked off a lengthy streak of righteous cards and enlightened betting. Our host, a previous tournament winner and everyone’s obvious biggest rival, was the first to go down after the cards viciously misled him down the path of self-destruction.

As the evening wore on, my big stack of chips from my early winnings slowly evaporated, but the field of eight thinned as the old and infirm were weeded out by predators. Thanks to my earlier gorge-fest, I was one of the last three standing, guaranteeing me at least a 20% cut of the pile of green. From there we disposed of Liz, our first-timer who had come to believe that each time she ate a cookie, she won a hand!

That left me to fight it out sumo-style with Jared for first. We dicked around for several hands, obviously playing merit of the cards. The One True Hand finally came to me, but apparently it had come to him, too, because *he* raised *me* before I had the chance to put the boots to him!

So I was all in; this hand would determine who walked away with 30 percent of the till, and who walked away with both 50 percent of the cash as well as bragging rights.

Since I was all in, there could be no more betting, so we revealed our hole cards and just played the rest of the hand out publicly. I had a Queen and a Ten; he showed a Queen and a Jack. So unless I pulled into something, he had the high card, my damned Queen was a cheap hoe.

Next came the flop: Nine, Ten, Four. Jared’s face dropped. Suddenly, I had two dimes and a stranglehold on the baister. Rocknacious! Now it was *his* turn to pray for a card to save him!

The turn: King. Doesn’t help either of us. But wait… that gave Jared an outside straight. Not bluddy likely, but if the final card was an Ace or an Eight, he’d win. Otherwise, the night was all mine. Figger the odds, right?

Goddamn if the river didn’t produce an Ace. Sad, but true. I was relegated to second place, and a $45 take-home. I was just one card away from walking away Optimus Prime! Schade! My butt still hurts, but it still was a fine performance for my first live Hold ’Em game. No guilt, no shame.

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