He thought he was going to San Diego with a handful of teammates to run some routes, work out and build some camaraderie. Any old hotel would have done, but the Grand Del Mar was on another level. It hosted LeBron James' wedding.
"I mean it was nice," Jackson said.
If Dak Prescott was going to ask teammates to travel to Del Mar, he was going to do it right. The Cowboys were less than two weeks away from traveling to Oxnard, California, for the start of training camp on July 27, but the quarterback wanted to get in a little bit of work with some teammates before the 2019 season began. The reason for the trip was equal parts football and chemistry, and it showed how Prescott continues to evolve into the leader Dallas knew it was getting when it drafted him in 2016.
Prescott took care of more than just the hotel. He took care of the players' transportation and all of their meals in San Diego. He secured Cathedral Catholic High School for workouts. He had people on hand to help stretch his teammates. He had people in place to help with their lifting and running, too.
They each received a pair of Apple AirPods and an Apple Watch, courtesy of the quarterback.
"That's what leaders do, right?" Prescott said.
Even when guys tried to pay for something, Prescott said no.
"We tried to chip in where we can, just so you don't feel like a guy just chintzing off somebody else," tight end Blake Jarwin said.
Jason Witten, Amari Cooper, Randall Cobb, Allen Hurns, Dalton Schultz, Jarwin and Jackson joined Prescott for three days. Other players were invited but could not make it for a variety of reasons, such as Michael Gallup attending the wedding of teammate Leighton Vander Esch.
Workout sessions commence
In the morning, some time around 8:30, they met in the hotel lobby and made the 10-minute drive to Cathedral Catholic. Players were surprised by the impressive facilities on the high school campus.
One day, they worked with Les Spellman of Spellman Performance. Spellman's group broke down each player's running style in terms of ground time, air time and stride length.
"He loved the detail," Spellman said of Prescott. "He wants to know why. He wants to understand. He told us he wants to rush for more yardage and he really wants to get faster so he was incredibly interested in why we do what we were doing. We weren't just teaching, 'OK, just run.' It was teaching progression from the ground up and it takes a lot of reps. Even when the other guys were running, he was watching their reps and how that applied to him."
What struck Spellman was how Prescott interacted with everybody. Spellman has worked with 3DQB, the quarterback gurus Prescott has been with the past two years, and has been around professional athletes in other sports.
"Just his actions, like being the first guy in the huddle, breaking the guys down, watching them, coaching the other guys, getting them lined up -- he was incredible," Spellman said. "I had never met Dak, so I didn't know what to expect. I've been around a lot of other guys, other quarterbacks, and it's hard being the quarterback because you always have to be leading. But Dak was the first in line to do every drill."
Beyond training, the rest of the trip was about football. The group worked with Prescott's coach from 3DQB, John Beck, who spent five years in the NFL and has been part of the renowned program run by former Major League pitcher Tom House that includes quarterbacks such as Tom Brady, Drew Brees and Matt Ryan.
For a few hours, the Cowboys players ran different routes, took a break and then ran some more. For Prescott, the details involved his footwork and building his throwing motion from the ground up to improve his accuracy.
"Me and him connected on every single ball except one," Cooper said. "Over the course of those two days, it was over a hundred balls. So I'd say that's pretty consistent."
The sessions weren't scripted but Prescott knew what he wanted to work on with each receiver. Prescott practiced more downfield throws with Witten, something they did not do much of together in 2016 and 2017.
"It wasn't necessarily strenuous, back-to-back routes, just going and going, but it was talking through routes: 'All right, well, you run this route, let's see how you want to work out. This is how I want to throw it,'" Prescott said. "When you're there with that many guys, you can go a couple of hours long and that's how it was. It was great. It was definitely beneficial."
Witten's year away with ESPN's Monday Night Football gave him a different perspective on Prescott.
"A lot of quarterbacks [hold workouts], but I think he's just so purposeful. It's, 'We're going to get better,'" Witten said. "It wasn't just we're running routes, but we're working through our 'fastball,' terms, we're doing hurry-up, on-the-ball and we're going down the field. He's always had the intangibles of leadership, just constantly trying to become better, you know? He pushes that envelope of what that looks like. Every great player I've been around, they seem like their expectations are so much higher than what anybody else can put on them. He fits in that mold."
Camaraderie off the field
When the players went back to the hotel, they drank, sat around the pool and ate dinner. They played Tom Fazio's Grand Golf Club course, often so late into the night that the sprinklers came on.
Prescott shared a cart with Witten.
"A lot of different conversations," Witten said. "It was relaxed. Beautiful weather. Great setting. It was football talk, but a lot of other things. Talked about life. That's where the real relationships come alive."
Said Prescott: "The training is one thing. You know you're going out there, spending a few hours training, hammering it, talking about how I want you here on this route or what I'm thinking on this route and vice versa. But when you leave there, play a couple rounds of golf, you have dinner, those type of things, those conversations. The tight ends getting to know the receivers better. Me getting to know them better. All that pays off in the end when it comes to crunch time in a game. You can look at a guy and you know you put in time, that camaraderie and you create a relationship that it's easy at that point."
Building relationships is where Prescott thrives. He studied educational psychology at Mississippi State and worked on his master's degree in workforce leadership.
"What makes people tick, how to get people going, how to find their purpose," Prescott said. "Just my interest in how the human mind works, and everybody's is different."
Prescott turned 26 on July 29, the first day of full-padded practices, but he has seemed much older from the time he took over for an injured Tony Romo in 2016.
Prescott has made an effort to relate to everyone: from teammates to the athletic training staff to interns in the equipment room. When he visited the Cowboys before the 2016 NFL draft, owner and general manager Jerry Jones said the coaches told him Prescott was like the "Pied Piper," with how people followed him around.
"His ability to connect with people is unique. The best leaders I've been around in all walks of life have that," coach Jason Garrett said. "Anybody you bring out to the practice fields afterward: 'Dak, can you say hi to my family? This is my cousin.' He just comes right over. He just has this great way about him, and he was raised really well. He's a really good person, and I think that comes out. It comes out in his leadership and how he connects with our football team."
It is more than just getting it -- whatever it might be.
"It's the way he works in general," Jarwin said. "If you watch him in the weight room or watch him in the film room and especially during practice, he's always working to get better. That's something we can all look to and learn from."