Why Won't El Presidente Accept Smokin' Jay's Match Race Challenge?

This is the actual video of one of the most famous match races in horse racing history, War Admiral and Seabiscuit at Pimlico in 1938. Many of yous have probably seen the movie Seabiscuit with Toby Maguire that detailed this race and the life of Seabiscuit. If you haven't, it's a fantastic movie that you should def check out. 

Let's turn back the clocks though - I grew up around horse racing. My dad would sneak off to the OTB in North Aurora "here and there" (read: all the time) and often times, I'd be with him. Didn't really matter how old I was. Some of my earliest memories revolved around being at Maywood, Hawthorne, and various OTB's in the Chicagoland area. Fast forward to me being 16 - this meant I could now DD my dad to all of these fine establishments. The first trifecta I hit was when I was 16 years old at the Lake Delevan dog tracks in WI. I split $2100 with 2 of my uncles that night (they spotted me extra $$$ to pay for the ticket because I was out of cash) and as a 16 year old, I thought I was fucking loaded because I had $700 cash on me. 

I blew those winnings on Chipotle and put subwoofers in my 1992 Buick Century. True story. 

Now I never got into horse racing myself TOO too much personally, I was more of a fake fan. I know what I know about it because it's rubbed off on me for 32 years. That didn't ever really sit well with my dad. "How can you win money gambling on horses if you don't even bet them you fucking idiot?" is a question oft-asked to this day when I'm drinking with him. But then Coronavirus became a thing, and Chief and I decided to get into the ownership game because why the fuck not? We needed something to pass the time.

Insert Crown's Way Racing. We linked up in an ownership share program and now I'm hooked and have a blast with it. We own parts of 5 horses, two of which are excellent runners: Judy's Way, a 3 year old filly and Smokin' Jay, our prized 2 year old, who we won at an auction in Florida this past June. We named him after the greatest QB in NFL history, needless to say. 

Jay's got nuts the size of cantaloups. Legit his only issue is is that his balls are so big that it kinda/sorta affects him running. We are weighing whether or not to geld him now, but don't want to because we think he could turn into a really fucking good horse and don't want to be out of millions upon millions when we put him out to stud. 

We're talking horse testicles, people.  

Anyways, smokin' Jay broke his maiden at Arlington about 4 weeks back in his 1st career start. I was legit nervous for the race - he was the favorite and I had wagered a hefty sum on him.

Here's Jay CRUISING down the stretch of the 6 1/2 furlong race:

The post race notes said the following: SMOKIN' JAY led the field up the backstretch, raced in the two path around the turn, kicked clear entering the stretch and extended his lead down the lane, winning handily

Give him another 1/8th or two and Jay wins by 10 lengths easily. He was fucking dominant; dominant enough to not only enter him into today's $75,000 stakes race at Presque Isle Downs, but dominant enough to start throwing around the words "Kentucky Derby" (lol) and dominant enough to challenge Portnoy and Portnoy's horse Cross Border to a match race Seabiscuit style. 

I brought it up to Dave on the live stream we were on in Philly last week and he wanted NOTHING to do with Jay:

Put some fucking pants on, Carl

Just IMMEDIATELY shot down the idea. Why? No clue. Cross Border is a monster. He's top 65 in money made of all horses on the planet this year and has won a grade 2 race. 

Here's a snap shot of Cross Border's money profile: 

But guess what? We don't give a shit how good Cross Border is. We want a piece of him vs. Jay. Mano y mano…. I mean caballo y caballo. 

Not that it matters all that much… like, at all… but here's another snap shot of Jay's workout times:

Compared to Cross Border's workout times:

Pretty comparable. When Jay did his first timed workout after we bought him, one of the other jockey's looked at our jockey and asked, "his time was WHAT?!?" in an incredulous tone because it was so good.

So tonight - assuming Jay wins at Presque Isle (fingers crossed/knock on wood) we'll be badgering Portnoy to accept our challenge between our 2 year old pup and his 6 year old champion. I mean, the Barstool Sportsbook app will be live in Illinois hopefully come spring time, so what would be a better way to promote it than a match race between Smokin' Jay and Cross Border? And no, I don't care that Cross Border is a turf horse and Jay isn't trained to go more than 1 1/8 or so. Yet. We'll figure that out later ha ha 

Not saying, just saying…

PS - I have no idea if this is logistically possible or possible in any other way whatsoever, but I choose to believe it is until told otherwise. If Seabiscuit and War Admiral could do it, Smokin' Jay and Cross Border could too. I think. No idea.