My grandfather, Nathan Goldstein, would be very ashamed of me right now. Were he alive, that is. Lucky for me, Grandpa Nat died more than 20 years ago.

Let me explain.

Irene and I got together last night with Karen and Charlie Newton, Sharon and Frank Patry, and Risa and Sandy Stewart at Charles Town Races and Slots for dinner and, well, what did you expect—racing!

Before heading to the track, I asked the person who knows more about racing than anyone I know—Barry Malzberg—for advice, and whether he wanted me to place any bets for him. The only thing he told me was—bet Jackson Bend to Show in the Preakness. Which I did.

I’ve never seen the local track as packed as it was last night. It’s as if every gambler within driving distance decided to turn up and wager. Once the Preakness started, and the crowd began screaming, all I could think was, “Where’s Grandpa Nat?”

My grandfather was a bookie, you see (I’ll tell you the whole story someday), and as I looked around at the shouting, the cursing, the veins popping on foreheads, I almost expected to see him there.

Jackson Bend ran third for most of the race, dropped back going into the final turn, and didn’t regain any ground by the time the broadcast cut off reporting on the standings. So I thought, “oh, well,” tucked the ticket into my pocket, and went off with my friends to have dinner before the local racing began. (Those of you who paid attention to who finished where in the Preakness already can tell where this is going.)

After a wonderful dinner, we returned to the track, where I actually won three of my bets on the local races. Here I am after I put $2.00 on Little Runner to Show in the third race. My $2.00 turned into a whopping $5.60.

I won twice more, once in a race that paid out $4.60, and another that paid out $3.00. Since I’d only bet $2.00 per race, my total profits for the night were … $7.20.

That’s the first reason Grandpa Nat would have been ashamed of me. Only betting $2.00 per race? What a piker! But wait, there’s more.

So I go home. I spend today first shopping and then working in the garden. And then tonight I hear from Barry Malzberg that he won his Preakness bet. But—how could that be? I thought Jackson Bend didn’t show?

Ah … but it did, pulling ahead again into third position during the final moments of the race.

Which means that there are two additional reasons my grandfather would have been ashamed of me.

Number two is, of course, that I’d won a bet, but didn’t realize it for 24 hours.

And number three is—I was so flustered while trying to place my bet in the final minutes before Preakness post time that I didn’t even make the bet I’d originally intended. I’d planned to put $2.00 on Jackson Bend to Show. But what I did, in the rush as the clock ticked down, was put $20.00 on Jackson Bend to show! Which paid $6.60—or in my case, $66.00!

Sorry, Grandpa Nat!

And apologies to Barry Malzberg, too, since once I thought I’d lost my Preakness bet, I blamed his bad advice! Which turned out to be good advice after all. I’m sorry I ever doubted you, Barry!

It just goes to show I’m just not cracked up for the gambling life. Just call me the Bizarro Sky Masterson …