The 21st century horseplayer trying to handicap the Kentucky Derby is equipped with tools that were almost unimaginable 25 years ago – unlimited replays of every prep race, lifetime past performances of every entrant with sophisticated speed figures, comprehensive coverage and videos of every entrant’s morning gallops and workouts, and detailed discussion and analysis of every conceivable angle and scenario surrounding the race. The explosive growth of technology and information makes the 1980s seems like the Dark Ages by comparison. Even professional racing journalists struggled to acquire the most basic information available today to any fan. The most prized invitation for a reporter during Derby Week was not to any of the galas and banquets but to an annual gathering of turf writers in a rented Holiday Inn room, where the author and handicapper Steve Davidowitz had laboriously assembled a videotape of all the 3-year-old stakes races. In those days before widespread simulcasting, much less replays on demand and racing networks and websites, this was the only way to get even one look at races you had not witnessed in person when they were run. So why, in the midst of this glorious new Information Age, is picking a Derby winner harder than ever? I think the answer is that the race itself, and the way that horses are prepared for it, has changed as radically as the tools available to horseplayers. Full fields of up to 20 horses in recent years has made a big difference. There is no longer such a thing as a Derby favorite who scares anyone off, and simply getting a horse to the Derby starting gate has become a badge of success for owners and trainers. Only nine lined up against Spectacular Bid in 1979 because few trainers wanted to run against a clearly superior horse. Today, Pegasus himself could be 1-10 and he would still have 19 opponents (and four on the also-eligible list). Larger fields mean more traffic, more chaos, and a larger pool of plausible contenders, especially for the minor awards that fill out trifectas and superfectas. Another reason is that Derby entrants today have made so many fewer starts than they used to by this point in their careers. Even without the in-depth coverage available today, we knew more about Derby horses’ capabilities because they had been tested more often, and had established a clearer pecking order among themselves through repeated meetings. There were fewer roads to the Derby, and fewer gaudy prep races that now make every winning owner think his horse belongs in the Kentucky Derby because he won a minor race with “Derby” in its name. There was a greater chance that horses had run close to their full capabilities by the time they got to the Derby just by making 10 or 12 starts. Now, we have to make a lot of guesses about horses who have run five or six times and are more eligible than their predecessors to make a sudden and sharp leap forward on Derby Day. This has become a staple of modern Derby handicapping, and it’s a highly speculative one: judging a horse’s chances less on what he has actually accomplished so far on the racetrack and more on whether he is poised to deliver a performance unlike any other he has turned in during his brief career. You can add the introduction of synthetic racing surfaces at a handful of tracks, and increased grass racing for young horses, to the changing landscape. A horse who had never won a race on the dirt would have been considered a no-hoper just a few years ago, but last year Animal Kingdom won the Derby in his first start on it and this year one of the favorites is Dullahan, a two-time Grade 1 winner on Keeneland’s Polytrack but 0 for 3 on the dirt. All these changes have combined to make it not only harder to select a Derby winner but also less rewarding to look to the past for guidance. Over the last decade we have seen one Derby “rule” after another broken by winners who did not seem to have the requisite foundation or recent experience. It seems silly to cling to old maxims in a rapidly-changing game. Tom Ainslie, the dean of American handicapping authors 50 years ago, advised players never to bet on a horse who had not run in the last 14 days. It was sound advice at the time, but today would disqualify the majority of horses on any given day of racing. The granddaddy of Derby rules will be put to the test on Saturday. No horse since Apollo in 1882 has won the Derby without racing as a 2-year-old, and that is precisely what Bodemeister will be trying to do, quite possibly as the favorite. There are good reasons to like him and to doubt him, but it’s risky to disqualify him on that basis alone, given that Derby history seems to be becoming ancient history with each passing year. • Each day during Derby Week, Steven Crist will answer a Kentucky Derby handicapping Question of the Day. Crist will select questions from Facebook, Twitter, his blog, or the comments on this article to tackle on DRF.com next Monday to Friday.