In the hours after Ray Serrano and Louisville City FC had defeated Greenville Triumph SC in the Third Round of the Lamar Hunt U.S. Open Cup, the Moses Lake, Wash. native was talking with his brother about what could come next.

“He was like, ‘what if you guys drew against Seattle? You know, that'd be crazy, right?’” Serrano told USLChampionship.com recently. “The following day was the drawing. I called my brother as soon as that happened. I was like, ‘wow, this is exactly how you planned it out.’

“It's pretty cool.”

This week, Serrano and Memphis 901 FC’s Nighte Pickering will see the U.S. Open Cup take them back to the places where their respective journeys have brought them.

The familiar faces of friends and family members will be in the stands to offer support as both players look to prove something in addition to helping their teams eliminate top-flight opponents in the historic tournament.

For both players, the opportunity couldn’t have arrived at a more opportune moment.

Now 21 years old, Serrano turned pro with the Tacoma Defiance when they were still known as Seattle Sounders 2 and made his debut in the 2018 USL Championship season. Currently in his third season at LouCity, he’s off to the best start to a campaign in his career with three goals and three assists in seven league appearances as the Championship club heads to face the four-time Open Cup title winner Seattle Sounders at Starfire Stadium on Wednesday night.

“This game means everything to me, to be honest,” said Serrano. “I’m going to be playing in front of coaches that I used to train in front of back when I was in Seattle, and most importantly in front of my family.”

For Pickering, Tuesday night will see a return to the venue from which the 19-year-old decided to depart two years ago. Electing to turn pro with 901 FC in 2022 after coming through the FC Dallas Academy, the United States youth national team striker will have a chance to add to his Open Cup resume after scoring the winner in Memphis’ victory against Atlanta United FC a season ago.

“I was excited to go back home to Dallas, be at Toyota Stadium, and obviously for our team to play against an MLS opponent,” said Pickering. “It’s really good for us, and really good for our club. … We played Atlanta last year in the Open Cup and that was one of our one of our best games of the season. So, it’s exciting to draw another MLS team away, going to their stadium, and we’re hoping to get a result on the road.”

SIMILAR JOURNEYS, DIFFERENT EXITS

For both Serrano and Pickering, the moment they became part of the Sounders and FC Dallas Academy programs was a transformational moment.

As young teenagers, the focus and level of professionalism that surrounded them had a major influence on the players they have become. In Pickering’s case, current FCD assistant coach Peter Luccin’s experience at big European clubs such as Paris Saint-Germain and Atlético Madrid as a player provided insights the young Texan was eager to take on board.

“They treat you like a pro at such a young age,” said Pickering. “I moved over to Dallas when I was 12 years old, starting with the U-13 Academy, and as soon as you start even at U-13, they treat you like a pro. It’s a pro environment. You’re training at the same facility as [the First Team]. So, I think it was a great experience for me to be over there, just because you’re getting this amazing treatment and these amazing facilities. It’s giving you all the tools to be as good as you can be.”

For Serrano, there were the likes of former Sounders Director of Player Development Marc Nicholls – now the Technical Director of the Columbus Crew – and the age-group coaches who helped pave his pathway in the system.

“My very first coach, U-14, U-15, was Sean Henderson, and then my U-16, U-17 coach was Chris Little,” said Serrano. “I’d say without them, I wouldn’t be in the place that I am today because of how much they helped me out in the Academy and pushed me every day at training.”

The similarities continued throughout their pathways.

As both players became among the best in their age groups at their respective clubs, overseas trips saw both achieve success on the field. Serrano recalls being part of a Sounders Academy squad that went to England for the 2017 Youdan Trophy that defeated Everton in the Final, while one of Pickering’s memorable experiences was being part of the FC Dallas U-15s who won the 2019 Bayern Campus Cup in Germany, defeating the hosts in the final.

But then there was a dividing point.

For Pickering, as much as he was achieving in Dallas’ Academy – including call-ups to the U.S. youth national team program – he felt his progress was beginning to stall. While there was a clear path forward within the club to move into reserve team North Texas SC and continue on a path to the First Team, the departures to success in the USL Championship of former FCD Academy products Jonathan Gomez to Louisville City FC and Matthew Corcoran to Birmingham Legion FC got Pickering’s attention.

“I was 17 years old,” he said. “I’ve been in the in the academy for five years at that time. I’d had some First Team training, I had been training with North Texas, but just at that time in my path it didn't look like at that moment I was going to be going into the First Team or getting a contract anytime soon.

“So, I just talked to my agent and decided to go to use the USL path, because many players before me had done that too. He informed me that it’ll be a good a good opportunity to go USL and get some pro experience young and build yourself so that you can go get transferred somewhere else one day. … So, I just pulled the trigger on that decision.”

At the end of the 2021 season, however, while Serrano was still under contract with the Defiance the pathway to the Sounders’ First Team remained closed. For both parties, it felt like time to move on and for Serrano to find a new route to his professional aspirations.

Enter USL Championship powerhouse Louisville City FC.

“Louisville came with some interest, and I think it was just the next step for me,” said Serrano. “I think it helped me, just to have another perspective on in my football career, because I came here and I see players putting food on the table for their families and playing with more experienced players in the league in the USL Championship. I think it was the right fit for me.”

MAKING THE LEAP

Serrano’s departure from the Pacific Northwest for the first time in his life brought its challenges, most notably a season ago. After logging three goals and three assists in his first season for LouCity in 2022, his 2023 campaign was partially derailed by an injury in preseason which hindered him from finding a rhythm when he returned to training.

That led to a conversation with LouCity Head Coach Danny Cruz at the start of last offseason that Serrano credits for the path he’s on now.

“[Cruz] asked me one question that really stood out,” said Serrano. “He said, ‘Are you making my decision easy to play you? Are you making my decision easy to roster you?’

“That’s something that really stuck with me during the whole offseason, and during the whole offseason I really focused on myself. I was with my family. But outside of seeing my family, I really was just focused on myself to the point where I wouldn’t even really see my friends, to be honest. I really wanted to come back this year and prove a point.”

With his play and commitment on both sides of the ball, Serrano has made Cruz’s decisions easy so far this campaign. He’s started all seven of LouCity’s league contests and is well on course for a career year, one that could propel him to a bigger stage in the years to come.

Pickering, for his part, remains certain his decision to join Memphis was the right one for his aspirations. Including scoring on his debut for 901 FC, he’s recorded seven goals and four assists in 46 appearances, logging 1,698 minutes for the club in the Championship’s regular season and playoffs. 

Last year he also provided the extra time game-winner for Memphis in its upset of Atlanta and has been part of this year’s United States U-19s squad that is building toward the Concacaf Men’s U-20 Championship in August. As part of the Championship’s next wave of teenage talent, the experience he’s gained with 901 FC has proven invaluable.

“The most important thing I’ve gained is just the professional experience, because I think the USL is a really underrated league,” said Pickering. “You’re grinding with these older guys, and you learn a lot from them because they have so many years in the game. They’ll tell you little tricks and little tips and stuff that you didn’t already know playing in the academy that you learn after you play in the pro game.”

EYES ON THE PRIZE

While the future looks bright for both Serrano and Pickering at this point, the opportunity this week brings against the clubs their journey began at is one for each to relish.

After last year’s upset of Atlanta – accomplished in extra time, but in impressive fashion as Memphis outshot its hosts 30-10 and recorded 10 shots on target overall – Pickering and 901 FC are looking for another chance to claim the “Cupset” spotlight.

“It would mean a lot, because the Open Cup is such a prestigious competition,” said Pickering. “When you’re going into it, and we’re playing an MLS team, obviously all you want to do is upset them and go out there and show like we can we play against you guys too. … It would mean a lot for our club. I know the fans would really enjoy it. And all the guys are going to be really, really wild for that game.

“Who knows what happens, but we have that confidence in ourselves that that we can go out there and play any team.”