Preakness 2021: Brad Free's picks and analysis

MIDNIGHT BOURBON can upset the Preakness, assuming he gets a different trip than his better-than-looked sixth in the Kentucky Derby. Midnight Bourbon runs best when he is forwardly placed, but he was unable to establish a forward position in the Derby. He raced in the back half of the field, lost ground most of the race, and missed by slightly more than eight lengths. Under compromising circumstances, he actually ran very well.

Midnight Bourbon will be ridden for the first time by Irad Ortiz Jr., who is expected to utilize the colt’s speed. Midnight Bourbon previously employed a front-running/pace-pressing strategy finishing in the money in five straight graded races prior to the Derby, including a Grade 3 win.

With a pace-pressing trip outside the favorite, Midnight Bourbon can post a minor upset in the odds range of 5-1. Of course, Midnight Bourbon can only win the Preakness if he can catch the Kentucky Derby winner, drawn two stalls to his inside.

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A cloud hangs over Preakness favorite MEDINA SPIRIT, the wire-to-wire Derby winner who subsequently tested positive for a medication that is banned on race day. From post 3, Medina Spirit is expected to employ a front-running strategy again in a field with only two other speeds – Midnight Bourbon and Concert Tour, Medina Spirit’s stablemate.

It is not likely the stablemates will duel. Medina Spirit is a tough customer to pass in the lane. If he clears his pace rivals, Medina Spirit could be gone again.

ROMBAUER skipped the Derby, enters the Preakness fresh, and could hit the board at a big price. Each of the last five Preakness Stakes run in May included a longshot who finished in the money after skipping the Derby (Tale of Verve, Cherry Wine, Senior Investment, Tenfold, Everfast). Rombauer has improved with each start. He runs well rallying from behind a fast pace and also chasing a slow pace, such as when he was third in the Grade 2 Blue Grass. Rombauer, first-time Flavien Prat, is a bomber to hit the board.

FRANCE GO DE INA is a longshot from Japan whose sixth in the UAE Derby was better than it looks. He broke slowly, trailed early, and finished okay. Interesting that Joel Rosario committed to the longshot import rather than wait for Concert Tour, whom he rode in his first four starts. France Go de Ina faces modest U.S. 3-year-olds and could surprise.

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Concert Tour skipped the Derby, has trained well since, and has speed. His ability beyond 1 1/16 miles is uncertain, but he could influence the pace. From his outside post, he could produce speed and compromise Midnight Bourbon.

The Chad Brown-trained Crowded Trade enters with the same three-race pattern as 2017 Preakness upset winner Cloud Computing, also trained by Brown – maiden win, Gotham runner-up, Wood Memorial third.

The others would be a surprise.