If Boston Celtics sharpshooter Ray Allen walked into a carnival, could he win a teddy bear at the basketball booth? Could gold medal-winning Olympic softball pitcher Jenny Finch toss a change-up into a barrel? Could Jeanette Lee, a.k.a. “The Black Widow,” shoot a cue ball powerfully and accurately enough to knock a small tee out of a small circle? If so, how much money would they have to spend to do it?

These important questions have been on my mind since I attended a local carnival recently and saw these games in action.

Let’s start with the basketball game. It seems simple: five bucks will get you three shots at a basket. The distance is about the same as a foul shot, but the hoop is higher than 10 feet, the ball is inflated more than usual so as to be extra bouncy, and the rim’s diameter is not regulation size.

My girlfriend and I, both capable shooters, attempted a total of about 20 shots and made a total of zero. I didn’t see anyone else make one either. So, what gives? It was hard to get a good look at the rim from the side (or, obviously, from above) but I’m pretty sure it was wide enough to fit a basketball.

So was I just having a poor shooting day? Would Ray Allen have fared better? I didn’t randomly choose Allen as my example, by the way. He is regarded as one of the best pure shooters in the NBA (fifth best free throw percentage of all time), has performed well in pressure situations (hit seven three-pointers in Game 7 of 2008 Finals), and as Jesus Shuttlesworth in He Got Game, lived in Coney Island and likely had a lot of practice with this particular boardwalk game.

Even so, I’d love to see how much of his $170 million in career salary earnings Allen would have to spend before winning a prize.

Carnies are better at cheating than they are at grammar.

The softball toss involves a barrel tilted at a 45-degree angle. The goal is to get the ball to stay in the barrel. This is a tricky game because I have seen many people toss it in—you need a soft, high arc that lands just past the bottom lip—but when a contestant is one conversion away from a throwback jersey you can guarantee that ball is popping out.

Jenny Finch is accustomed to throwing underhand, which is the technique required in this game. However she is known for her exceptional fastball, so maybe she’s not the best choice. Perhaps a Gold Glove second baseman like Ryne Sandberg, who has made that soft toss to start a double play thousands of times, is a better option. Does it matter? No, because the game operator will do something—I’m still not sure what—to prevent the meaningful toss from staying in that barrel.

The billiards game was new to me. Three pool balls are set up in a triangle surrounding a small tee. There is a narrow strip of felt about chest high and the object is to shoot the cue ball into the other balls with enough force to knock the tee outside of a small circle drawn on the felt. After taking a couple of free shots and watching others do the same, I learned that a good shot would do the trick. In other words, it wasn’t that difficult.

The prizes for this game were the best of any at the carnival: knocking the tee out of the circle 10 times would get you an NFL jersey, an iPod Touch, and a Nintendo Wii. AND you would get any money back that you spent on the game. The only way you would not get free stuff is if you quit before you made it to 10!

The quality of prizes (at potentially no cost) of course made me even more skeptical, so I Googled this particular game. I came across a post on carnival cheats on the Professionals Against Confidence Crime website that mentioned the game, and I found my answer. Apparently, if the tee is placed in the small space between the three balls or against the back of the front ball, it is not too difficult to win. But if the tee is touching the back balls, they will absorb the hit from the cue ball and the tee won’t move. I didn’t do too well in physics but it makes some sense to me.

How would The Black Widow do? Like most contestants, she’d succeed until the tee was moved. Then she’d probably figure out a way to hit it past the balls and spin it back, thus negating the carnival operator’s ploy.

As for the rest of us? Stick to Whack-a-Mole.

They met during a veterinary school exam at a horse stable in California many years ago — my aunt unsure of exactly what to do, the trainer working in the stable offering words of advice.

My aunt introduced this trainer to her brother (my uncle) and they’ve spotted her at various tracks for years. The most recent encounter was surely going to be the most profitable.

“I trust her,” my uncle said of this trainer after bumping into her at Saratoga Race Course in upstate New York. “She told me to stay away from a horse and it came in ninth.”

OK, so she can pick losers. Big deal. I can do that, and prove it every time I go to the track. In fact, I’d estimate I pick loser at a 95 percent clip.

After warning my uncle about one horse, she gave him a tip on another — a surefire winner for a race on Thursday. None of the horses in this race had ever raced before, so there were not prior results to study. But she had told my uncle that this horse was a “monster in the morning,” meaning he had impressed in his morning workouts.

My aunt was less enthusiastic when she heard about this tip, saying, “She’s never given me a winner.” When my uncle hears this he is not discouraged. “She’s due,” he says. As if to validate her status, he also tells me she can “sit in a box whenever she wants because she knows people.”

So she knows people. But does she know horses? We’re about to find out. Or are we? The rain has forced my younger brother, uncle, and I to abandon our trip to the track and instead go to OTB (off-track betting; a place I used to associate with degenerate gambling addicts, but now view in a much better light). Will the rain affect the race, too?

During the second race, I’m not thinking about the rain. Scrolling across the bottom of one of the televisions mounted on the wall are the scratches for the upcoming races. “Fourth race…Scratched: 1A China…6 Moon Ala Mode…Gelding: 7 Gentlemansapproval.” The phrasing makes me think our horse, Gentlemansapproval, is being scratched. It turns out it is much worse.

When I bring the sad news to my brother and uncle — the “retirement horse,” as my uncle calls him, won’t be racing — I am quickly informed that “gelding” means our horse will simply be without something in the upcoming race. Apparently he was a bit too amped for the race, so his trainers — perhaps my aunt’s friend — decided to castrate him. “This is a good thing,” my uncle assures me.

However, we are worried about the rain moving the race off the grass and onto the dirt. Races are often “taken off the turf” if it gets so wet as to be dangerous. We ask one of the OTB employees and he is confident the race will remain on grass. “It’s only light,” he says, referring to the rain. “It’s clearing up anyway.” My uncle thinks this guy knows what he’s talking about. He doesn’t.

Not as bad as you might think.

Fifteen minutes to post, the race is moved to the mud. My brother has already bet (our horse is 16:1), but asks the employee if he can be refunded. His bet is relatively small, so a refund shouldn’t be a problem. “But you’d be pretty mad if you took back your bet and that horse won,” he reminds my brother. “That’s true,” my brother says, and decides to keep his bet.

My uncle and I haven’t bet yet. I decide I’m going to follow him. I don’t know the difference between grass and dirt as it pertains to horseracing, but I trust my uncle’s judgment. He seems skeptical — the trainer’s tip was given with the assumption that the race would take place on grass. This horse — and the rest of the field — has never raced competitively on dirt; they might hate it.

I could sense my uncle’s doubt, but perhaps using the same logic as my brother, he pulled the trigger. I followed suit. After all, this horse was a lock. He was a monster: grass, dirt, concrete — it didn’t matter.

Except that it did matter. The gentleman got out of the gate OK, but after the horses started kicking up mud, he fell back farther and farther. My uncle noticed it right away. “He doesn’t like the mud,” he said before any of the horses had even separated from the pack. “He doesn’t like it at all.”

As the first two horses finished, the TV switched to the finish line camera. After all the horses had crossed — coming into view for a second before disappearing off the screen to the right — the camera held steady. Why? Because all the horses had not finished. Our horse still hadn’t crossed. It seemed like a full minute before it finally did, though it was probably about 10 seconds after the winner. One horse even finished after it did. So it was 7/8.

The post-race write-up says our horse “broke a bit awkwardly, was urged along near the back, raced off the rail on the turn and faltered then was not urged in the final furlong.” That makes it sound better than it was. As I noted, his start wasn’t terrible. He wasn’t “urged” down the stretch because he was already out of contention.

When I told my dad about how the horse didn’t like the mud on his face, he made a good point. “If it were in first, it wouldn’t have gotten any mud on his face.”

Well at least Gentlemansapproval wasn’t alone. All the bettors who backed him had plenty of mud on their faces as well.