Two-time Eclipse Award-winning trainer Brad Cox has enjoyed strong success in the $300,000 Smarty Jones Stakes, a 1 1/16-mile Road to the Kentucky Derby prep race taking place on New Year’s Day at Oaklawn Park.

Two of the last three editions of the Smarty Jones have been won by Cox trainees: Caddo River (2021) and Victory Formation (2023). Cox has three chances to pick up his third Smarty Jones win in four years when he sends out #2 Catching Freedom, #6 Gettysburg Address, and #9 Fidget in Monday’s renewal of the race.

Of the three, Catching Freedom is arguably the most likely winner. The well-bred son of Constitution was entered in the Dec. 23 Gun Runner Stakes at Fair Grounds, but scratched and has turned up in this spot instead.

Catching Freedom debuted in a one-mile maiden special weight on Oct. 1 at Churchill Downs, where he settled in sixth place behind a decent pace before rallying strongly to dominate by 3 3/4 lengths. The runner-up, Cash Only, returned to win his next start, flattering Catching Freedom’s performance.

This flashy debut stamped Catching Freedom as the favorite to win a 1 1/16-mile $100,000 allowance optional claimer on Nov. 9 at Churchill Downs, but nothing went his way that day. After settling off the pace in seventh place, Catching Freedom ran into traffic trouble and had nowhere to run down the homestretch. He didn’t get a clear path until it was much too late to mount a challenge, but even still he was beaten only 2 1/4 lengths while earning a solid 90 Brisnet Speed rating.

None of Catching Freedom’s rivals have earned a higher Brisnet Speed rating in a route race, so if the bay colt can work out a clean trip in the Smarty Jones, he’ll be a formidable win threat. We plan on playing the race accordingly, betting Catching Freedom to win and using him on top of exacta and trifecta tickets.

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Who should we use underneath? Certainly we have to respect Gettysburg Address and Fidget. Gettysburg Address has yet to run particularly fast on the Brisnet Speed rating scale, but he has tactical speed and set the pace when finishing fourth in the Grade 3 Street Sense Stakes at Churchill Downs. That Road to the Kentucky Derby qualifier was contested over a sloppy track, and it’s possible Gettysburg Address prefers fast footing; after all, he won his debut sprinting over a fast track at Ellis Park.

As for Fidget, he broke his maiden racing one mile over the Horseshoe Indianapolis turf course, but handled dirt just fine when switching surfaces for a one-mile allowance at Horseshoe Indianapolis, pressing the pace before taking over to win by one length. Like Gettysburg Address, Fidget needs improvement from a Brisnet Speed rating perspective, but that’s not out of the question for this improving colt.

#1 Informed Patriot can’t be underestimated either, not after finishing 3 1/2 lengths clear of Gettysburg Address when third in the Street Sense. And #3 Lagynos finished half a length ahead of Catching Freedom when third in the Nov. 9 allowance optional claimer at Churchill Downs, though of course Lagynos enjoyed a better trip.

In contrast, we’ll lean against #4 Mystik Dan and #7 Just Steel. Both have shown talent in sprints, and Just Steel posted a sharp 96 Brisnet Speed rating when winning the Ed Brown Stakes at Churchill Downs by 2 1/2 lengths. But their racing records so far suggest that tackling 1 1/16 miles in the Smarty Jones might be less than ideal.

            Depending on your budget, here’s how we recommend betting the Smarty Jones:

            Wagering Strategy on a $15 Budget

            $11 to win on #2 Catching Freedom

            What to say at the betting window: Oaklawn Park, 9th race, $10 to win on 2

            $2 exacta: 2 with 3,9 ($4)

            What to say at the betting window: Oaklawn Park, 9th race, $2 exacta 2 with 3,9

            Wagering Strategy on a $30 Budget

            $16 to win on #2 Catching Freedom

            What to say at the betting window: Oaklawn Park, 9th race, $16 to win on 2

            $4 exacta: 2 with 3,9 ($8)

            What to say at the betting window: Oaklawn Park, 9th race, $4 exacta 2 with 3,9

            $1 trifecta: 2 with 3,9 with 1,3,6,9 ($6)

            What to say at the betting window: Oaklawn Park, 9th race, $1 trifecta 2 with 3,9 with 1,3,6,9

            Good luck, and enjoy the race!