How to bet the Woodbine Mohawk mandatory payout super high 5

Now that we have all that Kentucky Derby funny business out of the way, we can move on to the actual highlight of the horse racing calendar each and every year: the mandatory payout on the Jackpot Hi-5 at Woodbine Mohawk Park.

This is one of the time-honored traditions, gathering family around the fire at midnight to await daddy's lucky numbers crossing the finish line in correct order. Eventually, great-grandpa's birthday will amount to something.

Until then, I'm here to break down the race and possible strategies for tackling this pool, which often draws sizable handle. We're looking at a carryover of C$183,666.04 (about US$133,000) on a bet with 15% takeout. That's free money if the new money is less than C$1.2 million, and any time we can find pools where the house rake is essentially zero, we have to take a look.

Recent payouts give us useful bookends for what to expect. The last Jackpot Hi-5 paid out on March 28 with a combo of 3-1 second choice, 6-5 favorite, 12-1 fifth choice, 89-1 12th choice and 9-1 fourth choice, returning $2,380.80 on a 20-cent ticket. The month prior produced a monster $45,921.27 from a 10-1 co-sixth choice, 2-1 favorite, 53-1 10th choice, 10-1 co-sixth choice and 82-1 11th choice. Call it a working range of low four figures on a pedestrian sequence to mid-five figures when the bombs land.

This mandatory payout is race 12 on Saturday with a post time of 10:56 p.m. ET.

The main players

From a talent angle, the horse that pops off the page is No. 12 Chain Gang. He has always had ability and ample speed, but as evidenced from his page, he has had several obstacles to overcome. Trainer Nick Gallucci has been on record about the gelding's breathing problems, and maybe those issues arose in his 2026 debut, where he finished up the track in the Open. He came back nine days later and qualified sharply behind a stakes horse named Lite Up The World for Tony Beaton. Beaton actually is entered in the eliminations for the Charles Juravinski Memorial this weekend, while Chain Gang finds himself several rungs down the class ladder, dropping from the Open into this non-winners of $9,000 race. The second tier is a problem given the closest speed off the wings of the gate is No. 3 Jack Panic, so it's tough to tell whether Chain Gang will land in a functional spot.

Chain Gang is a coin-flip proposition. If he hits the track without an issue, he is supposed to smoke this field. The gamble is whether he'll show up, and there is honestly more intrigue and money to be made betting on him putting in another clunker. That is perhaps the path of least resistance — recognizing he may be much the best but could still have wrinkles to iron at a short number, providing no value for our tickets at all.

My main players beyond him are mostly huge prices on the morning line. I'll start with the shortest at 8-1, No. 1 Soaring Now. He has always had talent and speed. He's a consistent type now that he's an overnight horse and no longer a Grand Circuit contender, and he continues to tout a strong late kick that could prove potent if the race goes around the 1:50-and-change speed par that seems likely. The inside draw should place him close enough to the lead where his kick could land him in front, but as a closing type, he'll remain at risk of having too much ground to recoup depending on the pace.

The next two who pop out to me seem like they will try to press some pace into the race. One admittedly is not an exciting price at 7-2 on the morning line — No. 7 Lous World — but he's showing sneaky glimpses that signal a potential blastoff by driver Mark MacDonald. His last two efforts from the pylon post logically placed him toward the middle of the race. But three starts ago out of post 9, MacDonald had a clear grip of restraint and found prompt acceleration when the possibility of a mid-pack seat materialized. That spurt of speed is evidence enough that he can send off the wings, and his sharp off-the-speed efforts against better also signal that this could be a spot to just send and try to roll. He seemingly has the speed to carry against this field.

The other possible speed is somewhat more far-fetched but an interesting use at 15-1 on the morning line: No. 6 JMR Speak Away. This seemingly was Louis Roy's choice over No. 5 Livinthebeachlife, a horse who usually prefers lower classes but enters off an all-right race. JMR Speak Away uncorked a solid mile off a ground-saving trip to just miss an upset win. He admittedly hit his best speed when others were plateauing late in the stretch, but he still kicked home in :26.1, and finding that type of speed has to be a confidence booster for Roy in his second time at the controls. He also showed plenty of gate speed when one level down the class ladder with noted speed driver Billy Davis Jr. at the reins. Pushing forward from here could perch him in a solid striking spot as opposed to cutting the mile, which maybe helps him stay focused and put together that quick turn of foot late.

Lastly, No. 4 Waterloo is a cheeky contender at another solid number of 15-1. He raced all right against claimers at Dover Downs before coming into the Carmen Auciello barn, where he has put together a noteworthy progression. In his first start at long odds, he got a typical sit-back trip to see what he could make happen and managed to sprint home in :26. Auciello then made a debatably lateral move into a claiming handicap, where he got a much more aggressive drive and vaulted off a second-over trip for second. He's a long-shot key for me inside the underneath spots because he seems to possess the ability and fitness to get at least a minor prize, and if this does turn out to be a somewhat quicker race, he's probably not good enough to beat some of the others.

Some ideas of approach

As dumb as it could possibly look in retrospect, trying to beat Chain Gang out of the number — or at least some top slots of the number — is probably the best approach if we want a shot at a solid four- or five-figure return. This race presents potential conditions where betting against the chalk like this may not prove to be a fool's errand. The trickier piece is figuring out how to properly layer these contenders alongside fringe players not mentioned: No. 2 Hungry Man, No. 3 Jack Panic and No. 8 Major Perry N — the last of which probably has the best shot of being involved in a prominent number. There's also the puzzle piece of No. 10 Whatchulookin At, who figures to take money and has the class to do well here, but I have no idea what type of trip lands him higher than fourth. He could be the horse along with Chain Gang to make me look dumb, but we're trying to cash big on the opportunities present in this race. Succumbing to chalks won't get us there.

I'm likely using No. 1 Soaring Now, No. 6 JMR Speak Away and No. 7 Lous World as win contenders. Since Lous World figures to be a short price, we're better off mapping some key wheels instead of just putting all three on top, the better to maximize our bankroll and potential cashing opportunities. I also have the feeling of No. 4 Waterloo hitting some bottom side of the number — at highest third, at lowest fifth — so that can also help us not expend too greatly and buy some leverage on the combinations.

Below is one approach. The first three tickets place Lous World on top. The next five hedge in case he lands in the second or third spot instead (all tickets are for the 20-cent base):

Lous World on top:

• 7 / 1,6,8 / 4 / 1,3,6,8 / 1,2,3,6,8,11 = $7.20
• 7 / 1,6,8 / 1,3,6,8 / 4 / 1,2,3,6,8,11 = $7.20
• 7 / 1,6,8 / 1,3,6,8 / 1,2,3,6,8,11 / 4 = $7.20

Lous World second or third:

• 1,6 / 7 / 4 / 1,3,6,8 / 1,2,3,6,8,11 = $4.80
• 1,6 / 7 / 1,3,6,8 / 4 / 1,2,3,6,8,11 = $4.80
• 1,6 / 7 / 1,3,6,8 / 1,2,3,6,8,11 / 4 = $4.80
• 1,6 / 1,3,6,8 / 7 / 4 / 1,2,3,6,8,11 = $4.80
• 1,6 / 1,3,6,8 / 7 / 1,2,3,6,8,11 / 4 = $4.80

These combos cost $45.60 in total and, in my view, provide good coverage for how the race might play while putting solid prices in the mix to make the payout worthwhile. A combo that knocks Chain Gang out and lands two midprices should clear well into four figures even on a pedestrian sequence. The total investment is a reasonable hedge given the core stance relies on No. 12 Chain Gang again encountering problems and not just wiping this field away. Once the dust settles on the finish line, this whole approach could be torn to shreds, but can you blame me for wanting to take a shot?

Best of luck however you approach playing the Jackpot Hi-5 mandatory, and whether these thoughts helped you in your strategies or not, you're welcome.

Horse Racing Nation coverage of Woodbine Mohawk is made possible through a sponsorship by Woodbine Entertainment Group.