In a revival of last year’s segment of the same name, I asked nearly every woman who has ever appeared on Paddy’s Picks to provide a pick for the Kentucky Oaks. The primary motivation for originally making this article was the opportunity to use the phrase, “Fillies, No Fellas,” the origin of which I’ve forgotten, but it actually turned out well enough to try again.
Unlike last year’s piece, this article is being published after the Kentucky Oaks, giving me the opportunity to provide grades for every single pick. Yes, letter grades. There are two ways that readers can interpret this editorial choice. Assigning grades could allow me to write less while hopefully still providing a fun environment for contributors. It could also allow me to pass harsh judgment on people who don’t know what they’re doing. I refuse to elaborate further.
This year’s Oaks field was not nearly as strong as last year’s but still provided plenty of talented, well-named fillies for some of my most loyal guest handicappers to choose between. Let’s take a look at the field, race replay and full order of finish before getting into our first guest’s analysis.
Churchill Downs, Race 11 (May 5, 2023)
Kentucky Oaks (G1) for Three-Year-Old Fillies, 1 ⅛ Miles on the Dirt
Field:
1- Mimi Kakushi
2- The Alys Look
3- Gambling Girl
4- Southlawn
5- Wonder Wheel
6- Botanical
7- Wet Paint
8- Promiseher America
9- And Tell Me Nolies
10- Flying Connection
11- Defining Purpose
12- Dorth Vader
13- Affirmative Lady
14- Pretty Mischievous
Race:
Order of Finish:
1- Pretty Mischievous (10-1)
2- Gambling Girl (13-1)
3- The Alys Look (30-1)
4- Wet Paint (8-5)
5- Dorth Vader (29-1)
6- Flying Connection (17-1)
7- Defining Purpose (10-1)
8- Mimi Kakushi (33-1)
9- Wonder Wheel (10-1)
10- Southlawn (5-1)
11- Affirmative Lady (22-1)
12- And Tell Me Nolies (45-1)
13- Botanical (6-1)
14- Promiseher America (34-1)
Emma Moquin
As I write this, Emma is on a bus from Penn State to New York. I hope she’s listening to the corresponding Billy Joel song. I don’t know if any of you are interested in hearing about her plans to kick off summer, but a lot of them center around moving as little as possible for several days. As the workaholic in the family, I wish I had her ability to just sit back and relax every once in a while.
Emma’s Pick: 11- Defining Purpose
Emma didn’t provide any reasoning for her pick, so I’ll just use this space to talk about her a little more. Or maybe I should use her platform to promote messages she might support. Everyone should go watch the film, “Almost Famous.” Pulling your goalie in hockey is a dumb strategy and never works. That workaholic joke from earlier was blatantly untrue — I don’t do anything. Taylor Swift’s latest album was lyrically sound but production issues prevented some from enjoying it as it was intended.
Grade: C
Seventh place in a 14-horse field is the definition of a passing performance.
Rebecca Patterson
I haven’t seen Rebecca since her victory in the Paddy’s Picks February Invitational, which she earned despite competing against more experienced handicappers. Whether or not she’s done any work to improve her understanding of horse racing remains unclear. And by unclear, I mean that she hasn’t looked at a horse since February.
Rebecca’s Pick: 3- Gambling Girl
“I’m gonna pick Gambling Girl. I’ll explain a little more later.”
Grade: A
One bob away from cashing. Excellent pick for the invitational champ.
Kristina Stevanovic
Hey, it’s Keeks! Hey Keeks.
Kristina’s Pick: 6- Botanical
“I’m feeling really rusty getting back into this but I think my pick for the Oaks is Botanical. I don’t see stretching out to 1 1/8 miles being a problem. I like that she’s improved in the past few races too. If I had to choose another horse I would go with Defining Purpose. But can purpose really be defined…”
Grade: D-
The rust is real. 99% of the world gets an F after Botanical’s performance. Keeks is a fan favorite though.
Niko Konstantellis
Does everyone remember that little boy in “A League of Their Own” that just kind of hangs out in the dugout and makes annoying comments while his mom and her teammates play baseball? That’s the best justification I can come up with for Niko being in this article.
Niko’s Pick: 5- Wonder Wheel
“If the big opening speed forms a cluster behind, I want a horse that has a good balance of opening and closing speed. And I think Wonder Wheel gives the best mix to be adaptable to whatever the scenario is.”
Grade: C-
Wonder Wheel started dead last, completely blowing up Niko’s entire idea. Who let this guy in?
Maddie Sandholm
What’s Maddie been up to? Well, she won a chess game on her second try last week and wants to try chess boxing next. I’m scared and will continue to dodge the topic. She came down with an undetermined illness earlier this week, but it wasn’t severe enough to try to sabotage me with, so she did the responsible thing and rested until she started to feel better. Oh, and she recently finished her tenure as managing editor of The Fordham Observer, the school newspaper to which she gave part of her soul for the better part of four years. Should I have started with that? As her colleague and friend, I’d be happy to tell you all about about her wonderful contributions to the newspaper, but I already used so much space on chess and sniffles.
Linnie’s Pick: 14- Pretty Mischievous
“I don’t have much of a reasoning here, other than I saw two horses with mischief in their names and I love me some shenanigans.”
Grade: A+
Flawless reasoning. Maddie is the only winning guest for the Kentucky Oaks this year, demonstrating an advanced understanding of shenanigans and mischief.
Shaily Jani
Let’s get back to that chess I was talking about earlier. Sorry, dear reader, for jumping around, but I can’t possibly give you a better update on Shaily’s goings on without mentioning “chessons.” On Thursday nights, six or seven people crowd around a table and watch me teach Shaily how to play chess. Shaily and Maddie offer their apartment and get dinner for everyone, and I bring a chessboard, a contribution that is somehow equal in terms of value. Either my instruction is actually helpful to the larger group of beginners or Shaily is just an entertaining host. But it’s not both, because that would be impossible.
Shaily’s Pick: 7- Wet Paint
“You know those ‘Watch Out, Wet Paint’ signs? That’s the vibe for this pick. The competition better watch out for Wet Paint because she’s a WINNER.”
Grade: B
I want to deduct points because Wet Paint was a vanquished heavy favorite, but in Shaily’s defense, she probably didn’t know Wet Paint was a heavy favorite. So fourth place, woohoo!
Emily Ellis
Emily lives with Shaily and Maddie but does not take part in chessons. I think our friendship has suffered as a result. We were going to read a book together about an illiterate baseball player but she still hasn’t bought it because she doesn’t like me anymore.
Emily’s Pick: 3- Gambling Girl
“Gambling Girl because right now I am also a gambling girl.”
Grade: A
The gambling girl gambled on Gambling Girl. Good gamble, girl. I’m gonna go take a cold shower now.
Jill Rice
At 1:00 in the morning a few weeks ago, I ran into Jill on the corner of 60th St. and Columbus Ave. It was a nice interaction but I learned very little about her day-to-day as of late. I apologize to readers for not prying more. She seemed happy, if that’s any consolation to you all.
Jill’s Pick: 10- And Tell Me Nolies
“I think her name is fun, the lack of space between ‘no’ and ‘lies’ sounds more like ‘noli’ which means ‘don’t’ in Latin, but it’s pluralized in English. Fun, quirky, etc. ‘Don’t’ do well, other horses (she says). Let’s put Wet Paint up there too. She seems cool, and everyone will try to stay away from her. In cycling, the main group of riders is called the peloton. The peloton of horses will stay back from Wet Paint because they don’t want to get dirty! I would not gamble on Gambling Girl, and I truly hate the name Dorth Vader.”
Grade: C-
Bonus points for taking a long shot, but this long shot really ran like one. Talking down Gambling Girl also turned out to be a major reverse jinx.
Gil Russo
Several days after I was published in the Paulick Report, Gil Russo began an interesting social media campaign. In the weeks since, she has posted stories of her interviewing every major film and television star on the face of the Earth. Our rivalry intensifies.
Gil’s Pick: 11- Defining Purpose
“Forte (in the Derby) & Defining Purpose (in the Oaks). There’s a common thread between those names: one’s strength. What they’re born to do. And hopefully, for these horses, that’s winning.”
Grade: C+
I was originally going to deduct points because Gil beat me to an interview with D’Arcy Carden. But then I noticed she links Paddy’s Picks on her professional website, leading to bonus points.
Esme Bleecker-Adams
Esme has grown indecisive in her old age, as you’re about to see. As far as I know, she continues to mold young minds for a living while working as a teacher on the side.
Esme’s Pick: 5- Wonder Wheel
“Wonder Wheel sounds exciting, as does Gambling Girl (I can’t help it I love alliteration), but we shouldn’t sleep on Wet Paint (literally). As a tired person I also appreciate Taxed, but I think Wonder Wheel is my favorite ultimately.”
Grade: A-
I never said I didn’t play favorites, and results are irrelevant in this case. There’s no world where Esme isn’t on the honor roll.
Grace Getman
Grace seems rather preoccupied with law school finals as of late, but if you ask me, I say that she’s exaggerating for attention. All she has to do is open up to Exodus (or Deuteronomy if she’s feeling spicy), write down all 10 things a few times and buy one of those powdered wigs.
Grace’s Pick: 5- Wonder Wheel
“Affirmative Lady feels a bit too ‘Lean In’ for me, Pretty Mischievous is too ‘Aren’t I a rascal’ while being utterly a normie, so I’m forced to pin my hopes on Wonder Wheel, who unlike the two above manages to balance joie de vivre and self-promotion gracefully.”
Grade: C
Aren’t I a rascal?
Kreena Vora
Kreena delivered her thesis presentation at Fordham University Friday morning and spontaneously combusted seconds after it ended. Luckily, she managed to get her picks in for this weekend beforehand.
Kreena’s Pick: 7- Wet Paint
“I want to say Gambling Girl because I’d like to take a gamble on her. But realistically Botanical or Wet Paint. I’d say wet paint because wet paint dries fast.”
Grade: B
Wet Paint was disappointing, but she could have picked Botanical. Avoiding disaster is key in racing.
Ava Peabody
Ava makes her debut on Paddy’s Picks after at least 20 years of not knowing who I was. Besides her recently acquired horse racing quest, I’m aware that she writes and also moonlights as a radio host. I can’t help but worry that my pony hijinks are harshing that very cool vibe.
Ava’s Pick: 5- Wonder Wheel
“For the Kentucky Oaks I’m going with Wonder Wheel because that’s a very evocative name so I have faith in the whole enterprise behind that one.”
Grade: C+
Bonus points for “the whole enterprise,” which is just a funny way to phrase that. Wonder Wheel was a disappointment, but as Ava may or may not know, the key to gambling is to continue betting — the big score is always right around the corner.
Mia Agostinelli
On Friday evening, Mia managed to arrange furniture in her apartment so poorly that her couch was facing a wall. I don’t know if that’s how I would’ve done it, but she does live in Brooklyn now and I wouldn’t do that either. Maybe she’s on to something in that tipsy topsy borough she now calls home.
Mia’s Pick: 3- Gambling Girl
“Out of everything my brain needs to do today, putting thought into that was not on the list.”
Grade: A
Who needs thoughts when you can gamble? Excellent pick under a time constraint.
Clara Gerlach
Alright everyone, gather around for one hell of a story. On May 13 this year, I’ve invited a few friends to Belmont Park to celebrate my birthday. Clara was invited with the understanding that she may be in New York at that time. She had unfortunately planned her trip for another weekend, however, and would be in Florida instead. To fix this issue, she bought a same-day, round-trip ticket to New York to spend the day with me and the rest of her friends. I’m still stunned and amazed.
Clara’s Pick: 7- Wet Paint
“With Matt’s (unhelpful) input, I’m going to say Wet Paint, no one’s going to want to touch them, hence, a clear winner… or not so clear? Depends on the paint.”
Grade: B+
Bonus points because plane tickets are expensive.
Allie Stofer
Fire up “One Last Time.” Allie just stepped down after one year as editor-in-chief of The Fordham Observer. She didn’t step down amid controversy, which would’ve been much funnier, but instead passes the torch after gracefully leading the publication through another year of top-notch local student journalism. I’ll find a follow-up joke later.
Allie’s Pick: 1- The Alys Look
“I’m nothing if not a narcissist and Aly is close to Ali which is basically my name and I always root for myself. Go me!”
Grade: A
Narcissistic word association is a tried and true method to pick a winning race horse. Allie didn’t quite cash in here, but it was frankly harder to pick The Alys Look than nearly any other horse in the race.
Emma Regovich
I’m sure Emma’s doing exciting things in her life, things so incredible that she doesn’t even have the time to tell me about them. All I know is that she, like me, incorrectly picked the University of Houston to win the NCAA Tournament this year. Oh, and I also recently learned she’s from New Jersey and has a December birthday.
Emma’s Pick: 12- Dorth Vader
“I’ll go with Dorth Vader cause its Star Wars day today.”
Grade: B-
Needed more midichlorians.
Courtney Brogle
Courtney continues to thrive at NBC as a member of the crooked leftist media, spreading lies and disinformation proven untrue time and again by this nation’s most vigilent Facebook pages. I can’t imagine what she and her cronies would be capable of if they weren’t held in check.
Courtney’s Pick: 7- Wet Paint
“I think my top pick for the Kentucky Oaks is Wet Paint. She is much more fun to watch than her namesake is to dry, with three consecutive wins at Oaklawn under her saddle. And perhaps in an homage to part of her name, she runs well in rainy/wet conditions, a key factor for the race given the recent forecast of seemingly never-ending spring showers. Her trainer Brad Cox has also won the Oaks twice, so while a tougher field for Wet Paint than her race on April 1, she is certainly one to keep an eye out for.”
Grade: B
As the beaten favorite in the race, Wet Paint was obviously a disappointment for Courtney and many others. Things could have been much worse, but I imagine that the reigning Invitational champion would have wanted more in her return to Paddy’s Picks.
Katrina Lambert
Katrina and I used to take a class about primates when we were at Fordham University. I want to clarify that it was a very interesting class and I enjoyed it, so much that I privately called it “monkey business.” That being said, it was very funny that the two of us were in the same class, were fairly friendly outside of it, and yet still sat on opposite sides of the classroom. I’ll never like someone enough to sit at the front of the room.
Katrina’s Pick: 12- Dorth Vader
Grade: B-
Katrina did provide analysis for Dorth Vader, but it was so confusing that I literally can’t provide enough context to include it in this article. It will likely feature in my review of the Derby when it comes out.
Megan DiDominica
I believe that Megan is in Boston this week to visit Nicole Kraemer, her childhood friend from Oceanside. They hold the honorable distinction of being the second and third smartest students in the Class of 2012 at Florence A. Smith Elementary School. I think I can speak for both of them when I say that they accept these rankings and take a lot of pride in them.
Megan’s Pick: 7- Wet Paint
“First I was going to say Gambling Girl, then Affirmative Lady but I have to go with Wet Paint. I’m ignoring the numbers on the side.”
Grade: B
When have Megan’s instincts ever led her astray? Going with her gut and taking Gambling Girl might’ve resulted in a more heartbreaking loss, but it also would have resulted in a higher Paddy’s Picks grade. Priorities.
Nicole Kraemer
For those of you who haven’t had a two-minute conversation with her lately, Nicole is going to London after graduating from Northeastern.
Nicole’s Pick: 7- Wet Paint
“Wet Paint just seems set up for failure because of his name but I think she’s probably really awesome and would look cool in sunglasses.”
Grade: B
It’s nice to see Nicole’s studying is finally paying off. A solid passing grade in the Oaks.
Marissa Gootee
As an assistant to a fashion designer, Marissa described the fashion world’s treatment of her recently as “mediocre.” This would be so sad and pitiable if she weren’t leading a “Devil Wears Prada”-esque existence. Everyone wants to be like her.
Marissa’s Pick: 7- Wet Paint
“Wet paint bc no one can touch it. No one comes CLOSE.”
Grade: B
Everyone got pretty close to Wet Paint. They got all up in her business and she finished fourth.
Brianna Doucette
Watching Brianna root for the Boston Bruins recently was the slowest death by a thousand cuts I’ve ever seen. What once started as a fun and lighthearted first-round matchup gradually became a waking nightmare as the Florida Panthers came back to eliminate the heavily favored Boston team. At least Brianna has all those Super Bowls to talk about forever.
Brianna’s Pick: 7- Wet Paint
“For the Oaks I’ll go with Wet Paint, usually that’s a slow process but I think this horse might reverse that.”
Grade: B
Wet Paint did not, in fact, reverse the process through which paint dries. I feel like that was an unrealistic expectation.
Isa Piazza
Isa is the first person I have ever heard unabashedly refer to themselves as a “horse girl,” and has been lobbying for some time to gain entry into Paddy’s Picks. I’ve been surprisingly and unfairly elusive in doing that, but have finally managed to get her into an article, opening the door for her to take over the website in a matter of months.
Isa’s Pick: 7- Wet Paint
“I had to google how to figure out betting odds. My brain does not do maths.”
Grade: B
If 14 horses move in the same direction at approximately the same speed and three horses are ahead of your horse, your horse is fourth. Maths.
Gabby Bermudez
Gabby’s Instagram stories have been a little sparse since Paddy’s Picks took a break these past few months. That’s a hilarious joke, of course, as she posts multiple things everyday seemingly without reason or context at times. But it’s true that she hasn’t been able to post any Paddy’s Picks content, a key part of her… enthusiastic posting strategy.
Gabby’s Pick: 13- Affirmative Lady
“I’m choosing horses based on adjectives that describe me. Divinity has failed me one too many times.”
Grade: C-
Go back to the divinity! It’s your brand!
Juliana Burke
Jul has been surprisingly enthusiastic throughout Derby weekend, voraciously cheering on her horses from some indeterminate setting in the United States. It’s not indeterminate to her, but I haven’t asked and have mainly focused on her horse racing endeavors. I’m a good friend.
Jul’s Pick: 1- Mimi Kakushi
“The name caught my eye because of how ridiculous it sounds, but I feel like this horse has some underlying superpower that could take the others down.”
Grade: C+
An eighth-place finish isn’t what I would call a superpower, but maybe it was so well-hidden that it didn’t have any bearing on Mimi’s performance.
Audrey O’Brien
After doing a little research for her picks earlier this year, Audrey has reverted to her chaotic, gunslinging strategy of finding horses that speak to her. Though her deliberate approach was also appreciated, her reckless abandon of yesteryear did have its charm.
Audrey’s Pick: 3- Gambling Girl
“No reason. Just instinct.”
Grade: A
A few guests in this article picked Gambling Girl as a reference to themselves. But I don’t think anyone earned the moniker quite like Audrey, who has made a living on this website through senseless, unhinged success. High marks once again for superb reasoning.