Saffie Joseph Jr. has come far in a relatively short time since leaving his native Barbados and arriving in South Florida with two horses in 2011.

Now, he is bidding for a threepeat as leading trainer at Gulfstream Park’s Championship Meet. He has turned back Todd Pletcher each of the last two years after Pletcher had rattled off a remarkable 18 consecutive titles.

In another testament to the strength of Joseph’s barn, he will be well represented on Pegasus World Cup Invitational Stakes Presented by Baccarat day. He will saddle Big Ass Fans Breeders’ Cup Dirt Mile third-place finisher Skippylongstocking and O’Connor in the $3 million Pegasus World Cup at Gulfstream. O’Connor, a 7-year-old son of Boboman, comes off consecutive victories in the Oct. 28 Hagyard Fayette Stakes at Keeneland and the Dec. 30 Harlan’s Holiday Stakes.

He sends out Accomplished Girl and Sister Lou Ann in the $500,000 Thoroughbred Aftercare Alliance Pegasus World Cup Filly & Mare Turf Invitational Stakes.

Joseph discussed his rise to prominence and his Pegasus prospects during a question-and-answer session conducted on behalf of America’s Best Racing.

PEDULLA: How is Skippylongstocking faring coming into the Pegasus?

JOSEPH: We gave him a little break after the Breeders’ Cup Dirt Mile and he’s doing well. Obviously, he’s drawn post 12. That is disadvantageous but it is what it is. You can’t worry about that. Hopefully, we will work out a trip.

PEDULLA: How did you evaluate his third-place finish in the Dirt Mile?

Multiple graded stakes winner Skippylongstocking (Coady Photography)

JOSEPH: I thought he ran well. Cody’s Wish was the best horse on the day. A mile is a little on the short side for him. This race, a mile and an eighth, is probably his preferred distance. We feel like we have a chance if he’s able to overcome the draw. Hopefully, we work out a trip [with jockey Tyler Gaffalione].

PEDULLA: It looks as though O’Connor has been a project since he came under your care two years ago. Have you finally figured him out?

JOSEPH: We thought a lot of him early on. He won his [North American] debut and was kind of inconsistent after that. The last two races he’s been the horse we think he is. He’s going to need to improve again, but he’s entitled to do that.

PEDULLA: Can Accomplished Girl move forward after her second-place finish to Full Count Felicia in the Dec. 30 Suwannee River Stakes?

JOSEPH: She’s going to need to. She ran credible last time, just got beat. I thought if she was able to stay inside she could have reversed the results. But she had to go outside and go around everybody. This is a sixteenth longer. I think it’s within her reach. Whether she’s good enough, we’ll find out.

PEDULLA: Sister Lou Ann ran third in the Suwannee River. She has wins on turf, dirt, and synthetic. Does she have a shot?

JOSEPH: Everything went her way [in her last start], easy fractions, but they ran by her still. She ran her race, but she just wasn’t good enough. She’s going to need to improve quite a bit to beat these horses.

PEDULLA: What would it mean to you to win the $3 million Pegasus World Cup?

JOSEPH: It’s a race we want to win. It’s at the top of the list. It’s home. It’s a Grade 1, huge purse. Just the atmosphere of the Pegasus, the vibe it creates with the concert afterward, it gets a different crowd to racing, which is what racing needs. I think it’s one of the coolest vibes, if not the coolest, of any race day. I enjoy it.

PEDULLA: Do you believe in home-course advantage?

JOSEPH: Yeah, I do. Any time a horse doesn’t have to ship, it’s an advantage for the horse. Most definitely. Most ships to Florida are 20 hours. Any time you don’t have to do that, it’s definitely an advantage for any horse. You run right out of your stall.

PEDULLA: What does it mean to you that you have been the leading trainer at Gulfstream Park’s Championship Meet for consecutive seasons?

JOSEPH: I’m just thankful for the opportunities. I am thankful for all of the opportunities that owners give us. It’s quite simple. Owners make trainers. If you look at top trainers, they have good owners.

PEDULLA: What divisions will you have this year?

JOSEPH: We’ll keep some in Kentucky, some in New York, here, and Monmouth [Park] also.

PEDULLA: Monmouth is an addition?

JOSEPH: Yes. We were there once. I think we’re going to go back this year. It makes sense because of where it’s located.

PEDULLA: What are your ambitions?

JOSEPH: My ambition is to get better every day and make the whole team better.

PEDULLA: Do you feel there is a Derby out there for you?

JOSEPH: Most definitely. I feel we’re going to win the Derby one year. Fingers crossed. We need to get the horses. Once you get the horses, everything takes care of itself. We know when we get a good horse that we can take care of it.