Analysis: Sir Winston raises red flags in the Woodchopper Stakes

Six months after winning the Belmont Stakes, Sir Winston returns in Saturday's one-mile Woodchopper Stakes for 3-year-olds on the Fair Grounds turf. From a betting standpoint, there's more than one red flag to consider with the tepid 7-2 favorite.

For one, Sir Winston lacks a win on the lawn. In his lone turf try, he ran ninth, losing by 11 ¾ lengths in a Saratoga maiden race. Afterward, he was sent to Woodbine and improved on synthetic by breaking his maiden and winning the Display Stakes, before tackling the Derby trail on dirt.

Sir Winston failed to make the Kentucky Derby, but he finished a fast-closing second to Global Campaign in the Peter Pan Stakes (G3) and captured the Belmont.

In addition to being on the dirt, those races ran at longer distances than he'll go in Saturday's return. Sir Winston also lacks a win at a mile or less.

Notice he broke his maiden at one mile and 70 yards and won the Display at 1 1/16 miles before moving forward with faster figures at longer distances.

His career-best 119 TimeformUS Speed Figure came in the 1 ½-mile Belmont Stakes, while he also earned a 116 in the Peter Pan.

In terms of pedigree, his dam, La Gran Bailadora owns zero turf wins, too. All her wins came on either dirt or synthetic, although she has turf blood.

It's clear Sir Winston's connections wouldn't mind losing this race. Trainer Mark Casse likely has bigger plans, as this is just a starting point for the classic winner.

Sir Winston is not an A or B type of horse for me. He is a toss.

The rail entry Flying Scotsman, meanwhile, is interesting at 12-1.

Cross out Flying Scotsman's recent attempts in the American Derby (G3) at Arlington Park and the Saratoga Derby Invitational. This ridgling is loaded with sprint influences on his dam side as the half-brother to Leigh Court, Star Hill and Bon Raison, making those two longer routes out of his range.

But as seen in his races last year, Flying Scotsman is proven at one mile. He beat a current star in Omaha Beach in a one-mile maiden at Santa Anita. Afterward, he won the Cecil B. DeMille (G3) at Del Mar by 4 ¼ lengths.

Flying Scotsman cuts back to one mile again and gets to save ground on the rail. Given his two off-the-board finishes this year, he will offer value.

Another good option is Tracksmith, who also will enjoy the cutback.

In the Commonwealth Stakes (G3) at Churchill Downs, Tracksmith took dead aim on Mr Dumas in the stretch after saving ground on the turn and hung late. He still kept second, but he had no excuse not to mow him down.

Two races ago, Tracksmith also hung for second in the nine-furlong Jefferson Cup on the same course, and three races ago he hung for fourth in the Virginia Derby (G3). Note the side comments state he ran “one-paced.”

Tracksmith's last win came four starts ago in the one-mile Frisk Me Now Stakes at Monmouth Park. He mowed down an uncontested leader in War Treaty.

Notice how he only needed a hand ride in the stretch run. 

Tracksmith is also the great grandson of Xtra Heat, an ultra-talented filly sprinter who finished second in the 2001 Breeders' Cup Sprint. His short-winded pedigree underneath may explain why he hangs in the stretch.

While Tracksmith is 6-1 and probable to go lower, he is usable. 

A third solid option in this overflow field is Louder Than Bombs. Two races ago, he also competed in the Commonwealth Turf as well, but received an aggressive ride that did not work out. With Spectacular Gem setting a fast pace, Louder Than Bombs moved alongside him on the far side and put his head in front.

According to TimeformUS, the 48.61 and 1:13.13 fractions were fast enough to be marked in red, and those numbers understandably affected Louder Than Bombs in the stretch as he faded to seventh. He only lost by 3 ¾ lengths.

Louder Than Bombs is capable of a more conservative strategy, as his earlier races show, as well as his recent closing second in a Turfway Park optional claimer. He also experienced notable trouble in that Turfway race.

At double-digit odds, Louder Than Bombs is a worthy inclusion on tickets.

No matter which horses readers side with, though, almost any pick is better than taking Sir Winston off a layoff in a race too short for him over a surface where he hasn't won. With such a large field to choose from, look beyond the morning line favorite.