Friday May 29
Penn Mile Stakes (Grade 3) – Race 6 at Penn National – Post Time 7:51 PM Eastern
Top Win Contender(s): Immortalised, Alpyland
Exactas in second: Honey Dutch
Immortalised has won all three of his two-turn turf races, all in a row. The last race was the Cutler Bay Stakes. Immortalised is the only one of two horses among the field that won their last race. The other horse was Classic Nofty, who just won an allowance race. Immortalised will sit in third early, behind Bonsai Warrior, who stretches out off a sprint, and Honey Dutch, who has been first or second in each of his seven two-turn turf races. However, Runaway Again doesn’t kick well, finishing second or third in six races. Hall-of-Fame jockey John Velazquez was aboard on Immortalised last two races and rides again. Immortalised will therefore be in the perfect spot behind the two early horses and will be able to pass them both in the stretch for his fourth straight win.
The other horse I think has a chance to win, if all the other six run, is Alpyland, who finished fourth in the tougher Grade 1 American Turf Stakes. Prior to his last race, he won the Columbia Stakes, and he won two of three races before that, including the Dania Beach, where he beat Honey Dutch. Alpyland won three of five turf races and has a strong chance to rebound in this easier race. Jockey Javier Castellano was aboard in both the Columbia and the American Turf.
Handicapper Picks
Win bets: Immortalised, Alpyland at 2 to 1 or higher.
Exacta: Immortalised, Alpyland over Immortalised, Alpyland, and Honey Dutch.
Saturday May 30
Eclipse Stakes (Grade 2) – Race 7 at Woodbine – Post Time 4:20 PM Eastern
Top Win Contender(s): Maycocks Bay, Jokestar
Other contender: Runaway Again
Maycock’s Bay has the only “early” pace in the field, so he should be able to control from start to finish. He has started first or second in all but one of his last seven races. He was off an 11-month layoff when he finished second in February, where he led early, then battled through the last quarter to the finish, and was beaten by a nose. On April 16, Maycocks Bay led easily, but it was too fast a pace, and he finished third. Both of the recent races were on turf, and he ran on all-weather for the first time, but his pedigree is great for the surfaces. As I said, Maycock’s Bay is going to be in the front, and with a slower pace than in his last race, he should win this year’s Eclipse Stakes.
Jokestar has either won or finished second in four races since trainer Kevin Attard took over. Last November, Jokestar finished second in the Grade 3 Autumn Stakes, and in December, he finished second in the Valedictory Stakes, both on all-weather. He then won the Post Time Stakes on conventional dirt in February. He finished a half-length behind Parchment Party, who has four straight wins in the U.S. If Maycocks Bay can’t lead from the start, Jokestar should win it all.
Runaway Again has won three of five route races. He had been on a layoff for three months until February, when he ran a sprint, which he had never tried, where he rallied from seventh and finished third. It was just a prep for this race. He has won two of four all-weather routes, and he is a four-year-old, so Runaway Again has a shot to improve while the other two are five-year-olds. He is also a closer who can have a shot if Maycock’s Bay can’t lead from the beginning.
Handicapper Picks
Win bets: Maycocks Bay, Jokestar at 5 to 2 or higher.
Runaway Again at 7 to 2 or higher.
Exactas:
Box Maycocks Bay, Jokestar, Runaway Again
Box Maycocks Bay, Jokestar
Jacques Cartier Stakes (Grade 3) – Race 9 at Woodbine – Post Time 5:20 PM Eastern
Top Win Contender(s): Possiblemente, G T Five Hundred, Playmea Tune
Possiblemente, except for his first career race in 2022, he has raced all two-turn races (27 races) until his three recent races. Before then, he had a good record of 7-7-4 in 28 races. When the horse was changed to trainer Joe Sharp this year after he finished third at a one-mile all-weather race, Sharp saw something about Possiblemente, and he put him into a sprint on an all-weather surface. That effort was on February 18 when he earned his first win after 16 months, a career-best effort earning a 107 Equibase Speed Figure. That was no fluke, as he won his next race on March 12, another sprint on all-weather. Then Sharp put Possiblemente into a tough race, the Grade 2 Turf Sprint at Churchill Downs on May 2, where he rallied from 10th to fifth, just one length behind. He ships from Kentucky and back to all-weather, and if he repeats either of his races in February and March, he can win.
G T Five Hundred has also won four in his last five recent races, all of which were sprints on all-weather. He won the Forego Stakes in February with a career-best 114 figure, the same time as Possiblemente earned his 107 race figure. He earned a 108 figure in January and a 101 figure in December. After the Forego, he didn’t run as well as he did on March 7 in the Big Daddy Stakes, but he rebounded to win the Thorncliffe Stakes on May 3. That was his first race ever at Woodbine. He only earned a 90, not good enough to beat Possiblemente if that horse repeats any of his last races. However, G T Five Hundred can run faster as he did in his races in the winter, and can run as well as Possiblemente.
Playmea Tune has won five of 10 all-weather races and four of eight at Woodbine. The win not at Woodbine came in the 2025 Forego, the same as G T Five Hundred this year. Since then, Playmea Tune has won one race in eight starts, but four races were on conventional dirt, one on turf, and one was a two-turn race. His best effort since the 2025 Forego was in the 2026 Forego, where he was the second choice at 5 to 2. He was last early, then eighth on the turn, he was still seventh at the eighth pole, and still he had no path until the sixteenth pole when it was clear, and he flew, but he was too late and finished fourth, a nose behind the third horse. With a better trip today, Playmea Tune has a shot.
Handicapper Picks
Win bets: Possiblemente at 5 to 2 or higher.
G T Five Hundred and 3 to 1 or higher.
Playmea Tune at 7 to 2 or higher.
Exacta: Box Possiblemente, G T Five Hundred, Playmea Tune