The Kentucky Derby future wager question before a big prep race: Now or later?

Shanghai Bobby is the third consecutive undefeated two-year-old male champion to cap his Eclipse Award-winning season with a win in the Breeders' Cup Juvenile, but will the champ's three-year-old debut in the Holy Bull Stakes on Saturday at Gulfstream Park be met with the same zest as Uncle in 2011 and Hansen in 2012?

There's zero chance that Shanghai Bobby will be the 1-to-20 Uncle Mo was when winning the Timely Writer Stakes, but he might be around the 9-to-10 Hansen was when second to Algorithms in last year's Holy Bull (at a one-turn mile; this year's race is 1 1/16 miles).

I'd be beyond shocked if Shanghai Bobby weren't favored, but a deep field featuring Bern Identity, Clearly Now, Dewey Square, Frac Daddy, Itsmyluckyday, Sr. Quisqueyano, and Tulira Castle should keep the price in that even money range--especially since the Breeders' Cup Juvenile (his first race around two turns) was so slow based on metrics used by people who can move an odds board.

I'll have (what I hope is) the pleasure of being in Las Vegas this week both before and after the Holy Bull, and all of the probables above are listed for wagering on the Wynn's Kentucky Derby future wager pool (link goes to free Brisnet.com Ultimate PPs of all horses offered).

Derek Simon and I have talked about our approaches to future wagers on the TwinSpires.com podcast, and listeners know that Shanghai Bobby (15-to-1), Frac Daddy (22-to-1), and Dewey Square (35-to-1) wouldn't appeal to me at those prices, but Bern Identity (50-to-1), Itsmyluckyday (65-to-1), Tulira Castle (100-to-1) Sr. Quisqueyano (225-to-1), and Clearly Now (250-to-1) have more appealing prices.

The question is, do I bet now or later? My thinking right now is that Shanghai Bobby is definitely the most likely winner of the Holy Bull but not of the Kentucky Derby. The way I plan to bet that opinion is to "let him" win the Holy Bull and if any of the horses at 50-to-1 or better run well behind them then still try to lock in those inflated prices.

The risk is that if any of the $100+ horses wins (or runs a flashy race behind the champion) then that price will be gone as well, but that's a chance I'm willing to take since I think Shanghai Bobby is the most likely winner of this race but not of the Kentucky Derby.

If you like Sr. Quisqueyano or Clearly Now those prices might seem enticing now, but they're certain to be among the longshots in the Holy Bull. Let's say they're 20-to-1 and a win would reduce either's price for the Kentucky Derby to 50-to-1. A $2 wager on them to win the Derby now would return $452 on Sr. Quisqueyano and $502 on Clearly Now. A $2 wager on them to win the Holy Bull would return $42. Parlaying that on them to win the Derby gets you to $2,000+. Even if they dropped to 20-to-1 after a Holy Bull win you'd be better of parlaying.

Thus, there really isn't that much risk to giving up the big price if you really like them to win. Granted, you're still going to lose some odds if they run well, but it still makes sense to wait.

For those looking for some pari-mutuel future wager action, Churchill Downs' first pool will be February 8-10, which is an empty week as far as points races going but follows a busy February opening of the Sam F. Davis, Robert B. Lewis, and the Withers.

As a final aside, here is the previous ten champion two-year-old males and race and odds in their three-year-old debut. I think it's interesting that both Uncle Mo and War Pass bowed in meaningless races at 1-to-20 and then lost their next start before missing the Derby. That Shanghai Bobby shows up in the Holy Bull is a testament A) to the effectiveness of the new Derby points system, B) trainer Todd Pletcher's confidence in the champion, or both.

Hansen, Holy Bull, 9-to-10
Uncle Mo, Timely Writer, 1-to-20
Lookin At Lucky, Rebel, 11-to-10
Midshipman, off trail
War Pass, allowance, 1-to-20
Street Sense, Tampa Bay Derby, 6-to-5
Stevie Wonderboy, San Rafael, 3-to-5
Declan's Moon, Bob Lewis (nee Santa Catalina), 4-to-5
Action This Day, Sham, 19-to-10
Vindication, retired