LOUISVILLE, Ky. – Chad Brown will have to wait at least another year to win his first Kentucky Derby, but that won’t necessarily preclude him from enjoying Derby Day 149. Brown will send out his champion filly-mare sprinter Goodnight Olive as a heavy favorite in the Grade 1, $750,000 Derby City Distaff as the once-beaten mare looks to further extend her dominance of a division she topped last year. Goodnight Olive will have Irad Ortiz Jr. back aboard when she makes her second start of the year after she picked up right where she left off by capturing the Grade 1 Madison at Keeneland last month to extend her winning streak to seven. “She came out of the Madison in great shape,” Brown said of Goodnight Olive, a 5-year-old Ghostzapper mare owned by First Row Partners and Team Hanley. “She’s had two works since then, and both were outstanding. We’re excited about having her ready for this one.” Goodnight Olive has not been defeated in more than two years, a stop-and-start span that began after she lost her March 2021 debut at Gulfstream Park. Since then, she has scarcely been challenged, capping a perfect 2022 with open-lengths victories in the Grade 1 Ballerina and Grade 1 Breeders’ Cup Filly and Mare Sprint before returning with a Madison score that was easier than it might look on paper. Using a familiar stalk-and-pounce style, she drew clear in midstretch in that comeback race and held on to win by a length. Goodnight Olive will break from post 2 when she faces five others in the seven-furlong Derby City Distaff, the fourth of 14 Saturday races and the first of nine straight stakes on the card. Post time for the Derby City Distaff is 12:04 p.m. Eastern. :: KENTUCKY DERBY 2023: Derby Watch, point standings, prep schedule, news, and more Brown, for all his overwhelming success – he’s a four-time Eclipse Award-winning trainer (2016-19) – has yet to win the Derby in seven tries. He doesn’t have a starter this year after recently eliminating the Champagne Stakes winner Blazing Sevens from consideration following a third-place finish in the April 8 Blue Grass Stakes. Brown also has contenders in the Grade 2 Distaff Turf Mile and the Grade 2 American Turf on the Derby card. Wicked Halo and Matareya, 4-year-olds exiting their first start of the year, figure as the top threats to slow down the Goodnight Olive juggernaut. They were the respective one-two finishers in the March 31 Matron at Oaklawn Park after enjoying highly productive 3-year-old seasons of contrasting forms. Wicked Halo came on strong in the latter half of the year, winning four straight stakes before finishing third to Goodnight Olive in the Nov. 5 BC Filly and Mare Sprint at Keeneland. Matareya was sensational early in reeling off wins in the Beaumont, Eight Belles, and Acorn prior to ending her season in August with a third-place finish in the Test. Wicked Halo, a Winchell Thoroughbreds homebred, will be ridden from post 3 by Tyler Gaffalione. Matareya, a Godolphin homebred, will have Flavien Prat up from post 5. Their matchup in the six-furlong Matron at Oaklawn was a terrific launch point for both fillies, with Wicked Halo proving narrowly best after Matareya got first run turning for home. After the Matron, Wicked Halo’s trainer, Steve Asmussen, said: “This is a great starting point. We can dream big all year.” Even in defeat, Matareya sparked high hopes for what lies ahead, trainer Brad Cox said this week at his Barn 22 headquarters. “Flavien didn’t think she cared a whole lot for the track at Oaklawn,” said Cox. “I do think she got a good bit out of it; she’d been off a while. I thought she ran very well, and she’s trained very well here since then. She does like Churchill. I like the outside post. “She had a nice trip at Oaklawn from the inside post, but I’m thinking the extra distance and being outside the other fillies might help her along this time. I think she’ll improve off the one start and hopefully we can get the job done Saturday.” :: DRF Kentucky Derby Package: Save on PPs, Clocker Reports, Betting Strategies, and more. Rounding out the lineup are Hot and Sultry, Travel Column, and My Destiny. Of those, maybe Travel Column has the best chance to bump up the exotics payoffs after finishing fifth in an allowance race at Keeneland on April 14, her first start of the year. This is the 37th Derby City Distaff, which was renamed in 2020 after previously being known as the Brown & Williamson (1987-1994), then the Humana Distaff. It’s the opening leg in an all-stakes pick five wager (races 4-8). :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.