Kentucky Derby multi-race strategy: All in on Journalism

Liking Journalism in Kentucky Derby 2025 as much as I do, I have no problem with the "get-live" to him approach, knowing that I'm not looking to use many favorites, if any, along with him.

The last favorite to win the Kentucky Derby was Justify in 2018, and he concluded a Pick 5 that paid $620,827 for 50 cents. A longer-priced favorite Always Dreaming won in 2017, keying a $50,063 Pick 5. The year before that was Nyquist, and he ended a $24,152 Pick 5. All that is to say, you still need to find the right prices to go with the logical ending, but there definitely is precedence.

We're not betting on precedence, though, we're attempting prescience with a long-shot prognostication in one of the multi-race bets that ends in the Derby. The two that most catch my fancy are the $3 all-3-year-old Pick 3 with the Pat Day Mile (G2) and American Turf (G1) and the all-Grade 1 Pick 5 that begins with the Churchill Downs and continues with the American Turf, Derby City Distaff and Turf Classic.

Things could get spicy right off the rip with no. 3 Book'em Danno, no. 5 Tejano Twist and no. 6 Extra Anejo all figuring among these at between 8-1 and 12-1 on the morning line.

The one-two finishers in the Transylvania Stakes, no. 5 Test Score and no. 2 Scipio, respectively, both look live in the American Turf. If you think the Transylvania is a key race, then 10-1 and 12-1 morning line is a good play.

I'm Willing to be a little chalky in the Derby City Distaff, as No. 2 Kopion looks extremely tough against these, and nobody expects her 8-1 morning-line price.

In the Turf Classic, I'm comfortable being narrow on the Chad Brown-trained duo of no. 4 Redistricting and no. 10 Spirit of St Louis. They're 10-1 and 9-2, respectively, which is about 5-2 as a joint venture. Not huge, but we're beating the morning-line favorite and others in the process.