Flash back some 24 years and Shug McGaughey's long-term future on the first Saturday in May seemed like such a given.
Though his champion Easy Goer lost what was supposed to be his coronation, finishing second to eventual Horse of the Year Sunday Silence in the 1989 Kentucky Derby, all signs pointed to the would-be Hall of Fame trainer getting, at the very least, several more legitimate cracks at the American classic.
"Obviously there is a lot of water under the bridge from those days," McGaughey said this month. "I thought (a Kentucky Derby win) would happen a lot earlier so I wouldn't have to worry about it anymore."
Despite being backed by one of Thoroughbred racing's most esteemed operations in the Phipps family and conditioning numerous champions, McGaughey's Kentucky Derby presence has been shockingly scant. He has saddled just one Derby starter since 1989 in Saarland (2002) and only six Kentucky Derby starters total for his career.
Time and circumstance have dictated that a 3-year-old in McGaughey's barn needs to show him something beyond promising to even start the path to the Derby. Leading up to Saturday's Grade I Florida Derby at Gulfstream Park, McGaughey has become convinced graded-stakes winner Orb is worthy of that endorsement.
In a field slated to include reigning juvenile champion Shanghai Bobby and Holy Bull Stakes winner Itsmyluckyday, Phipps Stables and Stuart Janney's homebred colt Orb stamped himself as a potential favorite for Saturday's 11⁄8-mile test when he surged to a half-length victory over Grade I winner Violence in the Grade II Fountain of Youth Stakes at Gulfstream on Feb. 23.
Among the many people hit over the head by Orb's performance both that day and his allowance win going 11⁄8 miles at Gulfstream on Jan. 26 was McGaughey himself.
When he brought the son of Malibu Moon to Payson Park Training Center in Florida this winter, McGaughey admits he may have "underestimated" where Orb was in terms of development — and he wasn't optimistic Gulfstream's speed-favoring track would fit the bay colt's late-running style.
Instead of getting in a couple good allowance starts and heading to the Wood Memorial at Aqueduct in April as McGaughey thought might be the case, Orb has grown up seemingly by the day.
"He got sick right after he got down here so I kind of discounted him a little bit. But when I took him up to Payson everything just sort of changed for him," McGaughey said. "The first time I breezed him up there, I was pretty much ... I was pretty excited with what I saw.
"Then to come down (to Gulfstream) and with his style of running to be able to win two races the way he did over this track, is pretty remarkable to me. He's way ahead of where I thought he would be at this time."
McGaughey has handled his share of temperamental runners, and it appeared Orb would be another case study when he had gate issues in his first two losses at Saratoga and Belmont last season.
Since breaking his maiden at Aqueduct last November — defeating eventual Withers Stakes winner Revolutionary in the process — Orb's gate troubles have been behind him. McGaughey said Orb broke as well as he ever has in the Fountain of Youth and has become a professional around the barn.
"He's matured to the point where he is pretty much push button," McGaughey said during a teleconference Tuesday. "The horse who won the Fountain of Youth even is not the same horse I'm seeing today. I do think physically he's a lot further along now than he was then."
The 50 points Orb earned for his Fountain of Youth win as part of the new "Road to the Kentucky Derby" system that determines the field for May 4 all but guarantees he would be able to go forward to Louisville regardless of his finish Saturday.
In classic McGaughey style, he said that regardless of points, Orb still has to give him the final green light.
"A lot of guys it's their goal to get to the Derby and we don't really do it that way," he added. "I want to get there but I want the horse to take me. Hopefully, (Orb) will run well enough this weekend to take us there, but if he doesn't we're not running in it to be an also-ran."
What: Kentucky Derby prep race for 3-year-olds
Where: Gulfstream Park in Hallandale Beach, Fla.
Purse: $1 million (Grade I)
Distance: 11⁄8 miles
Derby points: 100 to winner, 40 for second, 20 for third, 10 for fourth.