The 2020 Triple Crown was so strange we rolled out something new, a Bankroll Challenge that we promised might be like a University of Kentucky men’s basketball freshman and one-and-done. But here we are again, our second Kentucky Derby Day Bankroll Challenge and right on the heels of a somewhat successful Kentucky Oaks Day Bankroll Challenge Friday.

We upped the ante for Derby Day with a $200 bankroll for The Saratoga Special handicappers to use any way they see fit on the 14-race card topped by the 147th running of the $3 million Kentucky Derby presented by Woodford Reserve.

Followers of Rob Whitlock enjoyed a good day at the betting windows – or perhaps through your ADW account – after he scored on two win wagers Friday. Rob placed a mythical $20 win wager on Shedaresthedevil in the Grade 1 La Troienne and after last year’s Kentucky Oaks winner went gate-to-wire that produced a $54 payout.

Rob’s bankroll got significantly larger in the next race, the Grade 2 Eight Belles, when his $20 win bet on Obligatory resulted in a $350 payoff. Those two scores gave Rob a profit of $304 from his mythical $100 bankroll.

Tom Law was the only other handicapper to cash a winning mythical wager, winning on his five-horse $1 exacta box in the Eight Belles. The exacta of Obligatory and Dayoutoftheoffice returned $93.70. That brought Tom’s losses on the day to just $6.40.

Here are the bankroll bets for Kentucky Derby Day. Good luck.

John Shapazian

Race 6: $50 Win 2-Zofelle.
Race 9: $50 Win 5-Du Jour.
Race 12: $100 Win 14-Essential Quality.

Tom Law

Race 1: $2 Win/Place 2-Santos Dumont.
Race 3: $5 Win/Place 4-Cash Rocket.
Race 5: $2 Exacta Box 9-Regular Guy, 10-Scales Of Justice, 11-Masqueparade.
Race 8: $2 Exacta Box 5-Prevalance, 6-Starrinmydreams, 7-Whiskey Double, 8-Dream Shake.
Race 9: $20 Win/Place 4-Annex.
Race 10: $1 Pick 3 4-Flagstaff, 5-Tap It To Win, 9-Whitmore, 11-Hog Creek Hustle with 3-Colonel Liam, 5-Domestic Spending with 1-Known Agenda, 9-Hot Rod Charlie, 11-Dynamic One, 14-Essential Quality, 15-Rock Your World.
Race 11: $20 Exacta Box 3-Colonel Liam, 5-Domestic Spending.
Race 12: $1 Exacta Box 1-Known Agenda, 9-Hot Rod Charlie, 11-Dynamic One, 14-Essential Quality, 15-Rock Your World, 17-Highly Motivated.

Charles Bedard

Race 7: $2 Pick 3. 2,3,4/3,5,6/2,4,13.
Race 7:   $1 Pick 3   4/3,5,6/2,4,13.  
Race 8:   $1 Pick 3   3,6,5/2,4,13/1,4,9.
Race 9:   $2 Pick 3   2,4,13/1,4,9/ 2,3,9.
Race 10:  $2 Pick 3   1,4,9/2,3,9/9,14,17.
Race 10:  $2 Exacta 9/14.

Rob Whitlock

Race 10: $50 Win/Place 8-Get The Prize.
Race 12: $100 Win 1-Known Agenda.