There is no atmosphere in sports quite like Churchill Downs on the first Saturday in May. Between the mint juleps, the towering hats, and the spine-tingling rendition of “My Old Kentucky Home,” the Kentucky Derby remains the undisputed crown jewel of American horse racing. For the horses, the 152nd “Run for the Roses” is a quest for immortality. For bettors, it is a quest for a perfect ticket.
This year, the stakes are getting a unique twist. While every trainer and jockey is focused on crossing that finish line first, BetOnline is asking you to look at both ends of the spectrum. Their $10,000 First and Last Contest adds a layer of strategy that goes beyond just picking the fastest horse—it rewards you for identifying the one that simply couldn’t keep up.
Breaking Down the $10,000 First and Last Contest
Most Derby contests are straightforward: pick the winner and walk away. BetOnline has decided to spice things up by challenging your knowledge of the entire field. To win the lion’s share of this prize pool, you need to correctly identify the first and last-place finishers.
It sounds simple, but predicting which horse will struggle in a crowded 20-horse field is an art form in itself. Here is everything you need to know to get your skin in the game.
How to Qualify
Before you start dreaming about that $10,000, you need to ensure your account is eligible. The barrier to entry is remarkably low, making this accessible for both “whales” and casual fans.
- The “Buy-In”: To qualify for any prize, you must place at least $5 in real-money wagers on the Kentucky Derby.
- The Deadline: You must register and submit your selections by Saturday, May 2nd, at 6:45 pm ET.
- Flexibility: If news breaks about a late scratch or a track condition change, don’t panic. You can change your selections any time up until the entry deadline.
The Prize Structure: Three Ways to Win
The $10,000 prize pool is divided into three distinct tiers. This is great news for bettors because it means you don’t necessarily have to be perfect to see a return. If there is a tie, the prize pool will be split evenly among the winners.
| Prediction Success | Prize Pool Share |
| First Place AND Last Place | $5,000 (Cash) |
| First Place Only | $3,000 (Cash) |
| Last Place Only | $2,000 (Cash) |
One standout feature of this promotion is the absence of a rollover requirement. In the world of online betting, “cash” often comes with strings attached (meaning you have to bet the winnings several times before withdrawing). Not here. The winnings are pure cash and will arrive no later than Monday, May 4th, 2026, at 6:00 pm ET.
Strategy: Picking the Top and the Tail
Winning the $3,000 share is a traditional handicapping challenge. You’re looking at speed figures, post positions, and how well a horse handled the distance in the prep races. But how do you pick the horse that finishes last?
Predicting the “Dead Last Finisher” (DLF) requires a different mindset. You aren’t necessarily looking for the worst horse, but rather the one most likely to “bounce” or give up if the pace doesn’t go their way.
Often, the horse that finishes last is a “speed” horse that tries to lead the pack early, gets exhausted by the blistering Derby pace, and eventually fades to the back of the pack to save energy once they realize the win is out of reach.
Final Thoughts for the 152nd Derby
Whether you’re a seasoned handicapper or someone who picks horses based on how “punny” their names are, the BetOnline First and Last Contest offers a low-risk way to potentially snag a high-value payout. For the price of a $5 wager—which you were likely going to place anyway—you get a seat at the table for a $10,000 pool.
As the horses head to the gates this Saturday, remember: in this contest, the horse trailing the pack is just as important as the one wearing the roses.
Bookmark our SportsBetting.Legal guide to gambling on the 2026 Triple Crown to maintain an edge this season.
Sources: Official Website | Fox News
