Jamie Begg admits to “messing around on the rail” at various times this spring at Belmont Park touting the potential of a rather plain chestnut colt whose main accomplishments to that point didn’t exactly scream classics contender.

The colt owned two wins – a dead-heat maiden race and the $100,000 Display Stakes over Woodbine’s synthetic track in the waning days of Toronto’s racing schedule for 2018 – but not much else. He finished off the board in his first four starts on dirt, yet Begg knew something was there. And the assistant to trainer Mark Casse didn’t come down from his beliefs to friends, colleagues and anyone that might listen.

“I kept telling people we were going to win the Belmont with this horse,” Begg said Saturday in the fading daylight at Belmont Park.

Begg stated the opinion to Belmont-based trainer Tom Morley, a good friend of another Casse assistant David Carroll (who had Casse’s Preakness winner War Of Will in the barn) and got a quick retort. 

“Mate, you have a Belmont winner but he’s not chestnut,” said Morley, “and David Carroll has him in Kentucky.”

In front of 56,217 fans who turned out on a perfect Long Island afternoon for the 151st Belmont Stakes and a deep undercard, Sir Winston proved Morley wrong and Begg right, upsetting War Of Will and eight other 3-year-olds to close the 2019 Triple Crown. Under Joel Rosario, the 10-1 fifth choice won by a length over favored Tacitus with Joevia third as War Of Will faded to ninth as the winner covered 1 1/2 miles in 2:28.30.

Begg can take credit for being right about Sir Winston – and Rosario. The third-generation horseman mentioned the colt to the jockey’s agent Ron Anderson before the Grade 3 Peter Pan Stakes at Belmont May 11.

“Look,” Begg told Anderson. “I’ve got a horse here that I think is a Belmont-type horse. You need to ride him.”

Anderson gave Begg the call, Rosario got aboard for the key Belmont prep and the son of Awesome Again finished second (beaten 1 1/4 lengths by Global Campaign) after a hard-charging final quarter in the 1 1/8-mile stakes. Rosario got to know the horse a bit more in two breezes before the Belmont, and told Anderson Sir Winston belonged.

“This horse likes this track and he has a chance,” said the jockey, who won the 2014 Belmont with Tonalist.

Anderson credit Begg with knowing what he had.

“Jamie, this kid’s a wizard,” the agent said. “He’s a really smart kid. He’s brilliant, trust me.”

SirWinstonBelmontFinishBegg didn’t pump his chest a bit after the Belmont’s 12 furlongs were finished, even after Casse and the rest of the winning connections invited him up to the podium for the extended made-for-TV trophy presentations.

Casse also wanted his 32-year-old New York-based assistant to earn his due and attend the post-race press conference in the Belmont basement. Walking up the horse path in the tunnel, before a member of the gate crew joked, “So you’re a rock star now?” Begg was asked if he knew where to go and if he’d attend the presser.

“Wait, can you say no to it?” he fired back before making the short walk and taking his place next to Casse in the interview room.

More than once Casse said Begg did a “tremendous job” with Sir Winston first during the winter in Ocala and later this spring at Belmont. Casse also praised the colt, a second-generation homebred for Tracy Farmer out of the Grade 3-winning Afleet Alex mare La Gran Bailadora.

“He’s an amazing little horse,” Casse said. “If at this time last year, if you had asked me to rate our top 20 2-year-olds, he would have been about 16th or 17th. But I’m very proud of him because he’s kind of what our operation represents, and that is I feel like we develop horses. We run horses. The first two times he ran, he got beat 10 or 20 lengths.”

Sprinting on the dirt at Churchill Downs in June, it was 13 3/4. Going long on the turf at Saratoga in July, it was 11 3/4. After the latter, Casse had a conversation with Farmer about patience.

“Don’t give up on him,” the trainer told the owner. “It’s crazy, but I see something. Let’s just give him some time to develop.”

The trainer was encouraged because, even though the horse would lose he would finish. He’d try, he’d make up ground, he’d hint at a quality around the corner.

Well-traveled winner
The sixth Belmont Stakes winner to use the Peter Pan as a prep since Coastal in 1979, Sir Winston went to Casse’s string at Woodbine and graduated the maiden ranks by finishing in a dead heat with Inclusive going 1 mile and 70 yards on the synthetic track in September. Sir Winston followed with a third in the Grade 3 Grey Stakes in late October and a win – by a length over Inclusive – in the Display in early December.

Casse closed his northern barns for the winter and Begg traveled to Ocala, Fla., to help work with the large group at Casse Training Center. The Grade 3 Withers back in New York at Aqueduct Feb. 2 was picked for Sir Winston’s 2019 debut, after a conversation between Casse and Farmer.

“Look, he doesn’t really train like a good horse, but I think we have to give him a shot,” Casse told his owner. “We may get beat 30 lengths. I really can’t tell you, but if you're OK with that, let’s do it."

Farmer didn't hesitate, “Yeah, let’s give it a try.”

Sir Winston finished fourth at 33-1, the longest odds of the seven in the field, and 5 lengths behind winner Tax.

“He ran well at the Withers,” Casse said. “There wasn’t a lot of speed. He really came running. (Then we) took him home to Ocala.”

Close enough in the Withers to entice Casse that he might have another serious classics contender to go with the leader of the operation, War Of Will, Sir Winston was aimed for other Kentucky Derby points races.

He followed the Withers with a fifth in the Grade 2 Tampa Bay Derby. He runner failed to earn any points, but impressed Casse while finishing  4 lengths behind winner Tacitus.

“If we could get him to the Kentucky Derby,” Casse said before the Tampa race, “I’m not promising you that he’ll win, but he’ll run really well.”

Afterward, it was much of the same, only with confirmation from his jockey.

“Julien Leparoux has ridden for me for years and he doesn’t get excited,” Casse said. “He rode this horse in the Tampa Bay Derby and about the sixteenth pole this horse kicked in really hard and he was running over the top of horses.” 

Leparoux offered a simple, “This is a really good horse.”

After Tampa, Sir Winston finished a well-beaten seventh in the Grade 2 Toyotal Blue Grass at Keeneland, never making up any ground after a bump at the start and finishing 19 1/4 lengths behind winner Vekoma. The Kentucky Derby was out, and the Preakness didn’t really make sense. Never one to give up and knowing Farmer loves a plan, Casse changed direction.

“What about the Peter Pan? He’ll love Belmont,” the trainer told the owner. “He’ll love the big turn, a mile-and-an-eighth, and if he comes running, we’ll run him in the Belmont.”

Sir Winston breezed twice at Belmont before the Peter Pan – a half in :50.54 April 24 and 5 furlongs in 1:01.48 May 3.

Begg noticed some differences in the colt when he shipped into Team Casse’s barn near the Morning Line kitchen in the Belmont stable area, where the late Hall of Famer Allen Jerkens trained for years.

“He’s definitely matured and filled out,” Begg said. “When you see him with some of those horses in the Belmont he’s not one of those bigger, strapping colts. He’s kind of plain chestnut. For him he’s filled out more, he looks more mature and I’m sure he probably has more to do. He still kind of looks a little immature.”

Sir Winston earned his way into the Belmont with a strong second in the Peter Pan. Fifth and 11 lengths back after the opening half, he closed with a rush while wide into the lane but couldn’t catch the winner. Casse estimated he ran the Peter Pan’s final quarter-mile in just over 23 seconds.

“If there’s a horse that will go a mile-and-a-half, it’s Sir Winston,” Casse said told anyone who would listen during Belmont Week. “This horse ran the last quarter-mile in 23 and 2, going a mile-and-an-eighth on dirt? That’s amazing.”

Big opportunity
The Belmont afforded Sir Winston the opportunity to make two consecutive starts at the same track since last fall at Woodbine. The $1.5 million classic also would be his toughest test, even though this year’s Belmont didn’t include disqualified Kentucky Derby winner Maximum Security, or adjudged Derby winner Country House.

A field of 10 lined up, led by Wood Memorial winner and elevated Derby third Tacitus and Preakness winner War Of Will. Intrepid Heart, third in the Peter Pan for two-time Belmont winner Todd Pletcher, Preakness eighth Bourbon War and Japan’s Master Fencer, who earned buzz for his solid run through the lane to finish 4 lengths behind Maximum Security in the Derby, were also in the field.

Joevia, sent off 21-1 off a win in Monmouth Park’s Long Branch the day after the Peter Pan, took the initiative from the inside post and led into the first turn just ahead of Tax with Spinoff, War Of Will and Tacitus wide into the opening bend.

Rosario quickly found a spot along the rail from post 7 and rode the inside path around the first turn and through the opening quarter in :23.92. The only rivals behind Sir Winston on the turn were Bourbon War and Master Fencer and they stayed that way through the half in :48.79.

Everfast, runner-up in the Preakness, made the first move under Luis Saez approaching 6 furlongs in 1:13.54, inching along the inside and behind Joevia and Tax with Spinoff and War Of Will still to the outside. Jose Ortiz, aboard Tacitus, found himself parked wide on the backstretch and outside Intrepid Heart with a half-mile to run and past 1 mile in 1:38.27. Rosario liked his spot following Saez, and they were less than 4 lengths back while running seventh past the half-mile pole.

“He broke real good. I got into the spot where I wanted to be,” Rosario said. “I was able to save ground the whole time. I was in a good spot. After that, it was all him. I knew he was going to win the race, the way he was moving.”

Rosario got to know Sir Winston a bit in the time between Begg’s cajoling with Anderson and the Belmont. The veteran rode him in the Peter Pan and in the colt’s two serious workouts before the Belmont.

The first came the Saturday of Memorial Day Weekend, two weeks removed from the Peter Pan and two weeks before the Belmont. Casse wasn’t on hand, but told Begg how it should all work. Not wanting to leave anything to chance, Begg treated Rosario like any breeze rider – outfitting the winner of 2,700 races with a radio. 

“I’ve never been so nervous,” Begg told Casse beforehand. After the work, 5 furlongs in 1:01.48 with Farmer’s 3-year-old stakes-palced filly Catch A Thrill, Begg sent his boss a video.

“Did you put a radio on Joel?” Casse asked.

“Yep,” Begg replied. “I didn’t want him to screw it up.”

Casse laughed, and called it “A-plus work” for a horse that’s “never been much of a workhorse.”

Sir Winston and Rosario followed that move with a solo half in :50.16 May 31, eight days before the Belmont.

TacitusBelmontJoevia and Tax continued to battle for the lead around the far turn with Spinoff three paths out, War Of Will four paths out and Tacitus six paths out and shuffled toward the back of the field as the sun-splashed crowd prepared to meet the field with a deep roar.

Rosario came off the rail leaving the quarter pole, getting the jump on the back-pedaling War Of Will. Tacitus (at right with Jose Ortiz) reconnected with the field toward the end of the bend and continued to advance while Rosario angled Sir Winston to the outside of Tax. Sir Winston accelerated in the clear, passed Tax and finally Joevia to take the lead at the eighth pole. The winner edged clear in deep stretch while Tacitus got up for the second spot over the fading Joevia and Tax with Master Fencer making another late run to nab fifth.

Casse, who watched the race from the owners’ box area with his wife Tina and youngest son Colby, found himself in the awkward position of watching one of his horses charge to the win while the other backed up through the field. War Of Will wound up ninth, beaten 7 1/4 lengths in the longest classic decided by a dozen lengths front to back.

“It was emotional,” Casse said. “Because War Of Will, he got his Preakness win, and it’s like your son, you don't want to see him (lose). It’s hard. It's like having two kids and rooting.

“I would think that if anybody knows me, they probably could see that emotion in me. As excited as I am, and believe me, the Belmont is big to me. It’s huge to win, but it still hurt that War Of Will didn’t run better. So, yeah, I’m still a little emotional about that.”

Begg felt the emotion, too, having worked with both colts at various points of their careers.

War Of Will started at Belmont last spring, an unraced 2-year-old bought by Casse’s brother Justin Casse out of a French breeze-up sale for Gary Barber. The Preakness winner didn’t stay on Long Island long before shipping with most of the stable’s top runners and prospects to Saratoga for the summer, but long enough to make an impression.

Sir Winston left more of a mark on Begg, who grew up in Canada at his family’s Windways Farm, breeder of 1996 Queen’s Plate winner Victor Cooley and Grade 1 winner El Brujo and co-owner of 2015 Canadian Horse of the Year and Breeders’ Cup Juvenile Fillies Turf winner Catch A Glimpse. Begg watched Sir Winston develop this spring, from a colt he touted to a colt who backed it up.

Begg thought back to those light-hearted conversations with his peers while walking back to the barn area with Colby Casse, first through the paddock, past the racing office and finally through the tunnel that comes out by the test barn. Morley had already shouted a, “You called it, you called it,” of congratulations, but Begg could still hardly believe it.

Last summer, when War Of Will breezed a sharp three-eighths as an unraced 2-year-old, Justin Casse texted Begg something about the colt being a half to a Grade 1 winner and Begg responded, “The Grade 1 winner might end up being a half to him.” In racing, nobody truly believes those things even if they say them, even if they are confident. The list of variables is too long. 

“Really it was one of those things where you’re being half-facetious,” Begg said. “I hoped it, but when you say things like that you’re never actually as confident as you let people think you are. I guess I’m getting lucky with that stuff . . . You bury all the things you say all that time that aren’t true. You forget those ever happened and just remember the things that came true.”

Saturday at Belmont those beliefs became facts thanks to a plain chestnut colt that did something extraordinary on one of the world’s biggest stages.