Old Heads and Young Ones: Oakland’s Roots Go Deep in the Open Cup

One photo said it all.

Wide young eyes locked on a grown-up in the foreground. Eager teens, some looking younger than that – and most getting their first taste of the pro game that night, listened intently. It’s not a classroom (exactly) nor is Neveal Hackshaw a teacher (precisely). He’s the Oakland Roots captain who, at 28, is worlds wiser – and he outlined the way forward on a hard night in the East Bay. 

“For some it was their first time playing in the Open Cup and in the first team too, so it’s tough,” said Hackshaw, born in the heart of the Caribbean in the southern corner of Arima on the island of Trinidad, out amid the doubles stands near the Piarco Airport. “I had to keep them calm and motivated. To let them know they belong here and don’t sweat it if you make a mistake.

“We’re all in this together,” he added. 

This, right here, is the essence of Oakland Roots, the second-division USL Championship side founded in 2018 who, simply, ooze cool. Steeped in the radical love of the area, with brotherhood at its core, each one teach one is the unspoken bond around Pioneer Stadium. 

Hackshaw is a sturdy defender, 30 times capped for his national team. He’s kicked around a bit in the USA’s lower leagues, through Charleston and Indianapolis after an apprenticeship as a youngster in the fires of the T&T Premier League in Port of Spain. You learn quick on the streets around the neighborhood of La Horquetta where he grew up, and in Trinidad’s Hasely Crawford Stadium, where he played for North East Stars. So being down early in an Open Cup Third Rounder, trailing the talented amateurs of El Farolito, wouldn’t rattle him. He’s been in and out of enough close calls to know circumstances are made to be changed by those with the guts to change them.

Young & Old

But the young ones – thrilled by the call-up and full of energy – are a different story. Their slates are clean. A hiccup can grow, nerves can take over, and, before you know it, your Cup run can be done on the wrong side of an upset. There were five of those kids, prospects from the club’s academy and talent lab known as Project 510, on the bench that night. 

Edwin Rodriguez (17) and Tomas Caminos (18) stayed there, but Eli Wachs, Kieran Bracken Serra (both 18) and – most notably – Ali Elmasnaouy (19) all entered the field and made their presence felt.

“I was just warming up the whole time. I felt like, ‘man, if I go in I feel like I can really do something’,” said Elmasnaouy, who came on in the 85th minute with the game tied and extra-time looming. “When the coach called my name, that’s when the nerves really hit me. My heart started beating fast.”

Elmasnaouy, who graduated high school last year, took his deep breaths. He went through his routines and got out there to do what he knows how to do. “Once you’re in there and you get your first few passes done, then you’re kind of in the game and on the task and doing your thing.”

Out there on the field from the start was Hackshaw, his afro-crown glorious. Shirt stuck to him on the muggy night. He was battling in the trenches against a familiar opponent, known to all in Bay Area soccer circles as amateur in name only. El Farolito have some outstanding players, like Dembor Benson, and they know every trick in the book.

“They were growing in hope, you can just feel it out there,” said Hackshaw about El Farolito, who took the lead in the 12th minute through that same Benson and held it through to the stroke of halftime. “These games are tough; it was really hard. I’ll not lie.”

Grind Required

Guillermo Fernando Diaz leveled the score for the Roots just before the halftime whistle went, calming the fans who Hackshaw calls the “12th man out there for real.” Then, when El Farolito’s Edgard Kreye was sent off early in the second half, the game really became a grind. Coach Noah Delgado, with options thin and an opponent trying to waste time and muck it to a shootout, turned to his babies on the bench.

The extra 30 minutes of OT was a pure slog. The fans – a huge part of the puzzle at Oakland Roots – were doing their all to help lift the boys to victory. “The fans are different over here,” said Hackshaw, reminded of the supporters from back home in Trinidad. “They always have our backs no matter what.”

Elmasnaouy, embraced by the crowd from his first seconds on the pitch, agreed: “They’re extra, just an added element,” he said of them. “I just love it. All the hype. It makes it all so much more.”

It’s the Cup, so someone needed to be the hero. Elmasnaouy, with a wide smile when he thinks back to the game, his pro debut, was going to be that man. It was fitting for the teenager who grew up a few minutes from the Roots’ homebase in the East Bay. He had family there on the night too – including his dad, who he calls a “soccer maniac” and who hails from Morocco and introduced his son to the game.

“I just remember scoring and running toward the stands and there they were – my whole family,” said Elmasnaouy, who remembers falling to his knees when the call came confirming his first pro contract. “It was such a special moment in a lot of ways. We needed that win to move on. And so many guys contributed to it.”

Hackshaw contributed. No doubt. He smiled, tired and happy, at the final whistle. Thrilled to be moving on, eager to get some ice on the bruises he’d earned. He looked on as the boys had their moment.

Building Brotherhood

“They practice with us all the time, you get to know them – we have a relationship. They know me and I know them,” said Hackshaw. “It’s always great to see young guys come in and make a difference.”

For Elmasnaouy and the other young ones it was a singular moment to be savored. “We all celebrated together, which was super special,” said Elmasnaouy, who felt the sting of losing with project 510 in last year’s Open Cup. “We’d all been battling together for years, and then we were called up and we helped get this win – it’s hard to put into words.”    

Moments come and moments go. This one is something to build on for the youngsters who helped grind and survive El Farolito. The fruit of their efforts is a date with the local side from Major League Soccer – where the Roots will go from being favorites-under-threat to underdogs-with-nothing-to-lose.

“It’s a chance to fight and show who we are,” said Hackshaw, a little smile on his face, knowing Roots fans snapped up all the away tickets in minutes for the May 7th game at the Earthquakes’ homebase in San Jose. It’s just a quick 25 miles or so for the Oakland fans, who smell a Cupset on the Bay breezes. “These Cup games, they’re all like finals so if you show up willing to work and win, then you got a shot.”

While Hackshaw, the veteran, readies for another fight, the kids, with a taste for the possibilities, buzz with anticipation. They want more. “We all grew up going to Quakes games,” Elmasnaouy said, his eyes glowing. “It's a great challenge for us but we’ll have confidence we can beat them and keep on going.”

Fontela is editor-in-chief of usopencup.com. Follow him at @jonahfontela on X/Twitter.