A year older and wider, Bold Act on Friday at Keeneland tries to win the Sycamore Stakes for the second year in a row. Bold Act broke from post 3 under Jamie Spencer before winding his way through traffic and capturing the 2023 Sycamore in his North American debut. Now 4, Bold Act has gone 3-0-0-2 in three North American stakes this year – losing twice as an odds-on favorite – and this time will break from post 11 under Luis Saez in the Grade 3, $300,000 Sycamore. That’s a difficult position in a 1 1/2-mile Keeneland grass race, which encompasses three turns and has a short run into the first of them. And Bold Act will need things to go his way if he’s going to perform at a higher level than in his last three starts. The Godolphin homebred trained by Charlie Appleby refused to settle in the Elkhorn this past April at Keeneland, finishing third, and behaved similarly when fourth on May 18 in the Louisville. Bold Act settled better in his most recent outing, the June 15 Chorleywood overnight at Churchill Downs, but his late run only netted third. Ten others are drawn inside Bold Act in a competitive renewal of the Sycamore. None starts for a hotter barn that Tawny Port, whose trainer, Christophe Clement, won three turf stakes in two days last weekend in New York. In fact, Clement has excelled in turf stakes throughout 2024, compiling a record of 25-15-18 from 92 runners, good for a 27 percent strike rate and a $2.24 return on investment. :: Play Keeneland with the most trusted information in horse racing! All Access Past Performances, Picks, Betting Strategies and more. Tawny Port absolutely fits the spot, and while he’s winless from six starts during 2024, Tawny Port finished second or third in five of them. Of some concern is his fifth-place finish in this race a year ago, Tawny Port’s only previous Keeneland grass race. Tawny Port exits a third in the Turf Cup at Kentucky Downs. The race’s second-place horse, Highway Robber, rates a strong Sycamore chance. Trainer Brian Lynch upon meeting his horse coming back to be unsaddled following the Turf Cup was overheard to say, quizzically, “Pretty far back, wasn’t he?” Indeed, Highway Robber, who brought a hint of positional pace to races between one mile and 1 1/8 miles, dropped back to last of nine in the early stages of the 1 1/2-mile Turf Cup. A field-best second half-mile in 46.71 seconds propelled Highway Robber into contention, and a field-best 25.08 final quarter-mile (an uphill finish accounts for the slow time), got him within a half-length of victorious Grand Sonata. Highway Robber has improved all year, hitting a peak two starts back going as far as 1 1/4 miles for the first time, and running even better last out in his 1 1/2-mile debut. Tyler Gaffalione rides for the first time. Sugoi won the Louisville in May, won his lone previous Keeneland grass start in a 1 1/8-mile allowance race four Octobers ago, and will try to race wire to wire under Florent Geroux. Trained by Mike Maker, a two-time Sycamore winner, Sugoi can win if left alone on a slow pace. Ohana Honor, who’s 7-2 on the morning line, and Utah Beach, listed at 15-1, each won 1 1/2-mile second-level turf allowance races here in the spring. While Ohana Honor jumped up to finish third in the Grade 1 Manhattan four months ago, Utah Beach should improve considerably making his second start following a four-month layoff. His comeback run over 1 1/16 miles last month in New York clearly was no more than a prep for this longer race. :: Bet the races with a $200 First Deposit Match + FREE All Access PPs! Join DRF Bets. Verstappen two springs ago at Keeneland won the Elkhorn, another 1 1/2-mile turf contest, but hasn’t seen racing action since March. Five-year-old Verstappen is exposed, but 4-year-old Dataman could hit his highest level in his first start over a distance this long. Dataman improved in two starts this spring and comes to the Sycamore after a pair of troubled trips. Dataman is drawn well in post 4, while the 3-1 morning-line favorite and defending Sycamore champ, Bold Act, either will drop to the rear of the field or find himself stuck wide. There’s little reason to bet on a repeat. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.