Betting the Jackpot Hi 5 with Handicapper Ed DeRosa
At 0h04, on December 13, 2025 • By Ed DeRosa, Woodbine
‘Boots’ was made for betting in six-figure Jackpot Hi-5 pool
When it comes to playing Jackpot Hi-5 wagers, I look for two things: 1. A longshot I can key, and 2. A carryover that can pay out.
Race 10 on Saturday at Woodbine checks both of those boxes with 12-to-1 morning line No. 7 Give Me the Boots harnessing my attention for the $269,656.92 carryover with mandatory payout on the super high five.
Race 10 is the last of 10 on the penultimate card of the year at Woodbine. Post time for the six-furlong entry-level allowance race with optional $32,000 claiming price is 5:40 p.m. ET.
Ten horses entered the race, meaning there are 30,240 combos to the Jackpot Hi-5. This would be like playing a trifecta in a 32-horse field. Having a key opinion for these types of wagers is essential.
Give Me the Boots is definitely a longshot to win, but given her run style I could see her hanging around for a piece of this. She is in for the $32,000 claiming tag versus the allowance condition, which makes her experience an asset against these. She is 8-for-25 on synthetic at Woodbine, including five-for-ten at this distance.
My strategy is to key her with both No. 6 Sinclarity and No. 8 Home for a Rest. I like Sinclarity reuniting with jockey Pietro Moran and the five-pound weight allowance, and Home for a Rest has six consecutive efforts of being first or second and just looks rock solid to run to form and finish in the top half of this field.
The horse I like least among the logical contenders is No. 5 Just Follow me, who at 4-to-1 morning line is one who will have to beat me. She has not run to her stakes-level class from last year and is just too short a price to gamble on her returning to top form given the spotty record this year.
