Ben Olsen knows the Open Cup.
The ups and downs. The chaos. And, of course, the glory.
“You just have to keep on keepin’ on in this thing,” said the 47-year-old Dynamo boss, who won an Open Cup in 2023 with the Houston-based MLS side and ten years before that as coach of D.C. United. “The Open Cup is always a wild ride and no matter what, if you want to win, you have to hang in there.
“It’s always interesting,” Olsen added with a sigh.
Interesting. It’s a word he uses a lot. And it seems to contain an infinity of meanings. Especially when talk turns to how his D.C. United side of 2013 won the Open Cup, when they were mired in last place in MLS, to salvage what would have been an irredeemable season of misery.
“Winning it [the Cup] in 2013 saved my job, and that’s no exaggeration,” said the current Dynamo boss, who also won the Open Cup with D.C. United as a player in 2008. “It was a horrible season. Everything spiraled away from us. But the Open Cup kept us together as a group and gave us a north star during really, really tough times.
“It adds up when you have so many losses in a row,” Olsen said about a 2013 season he calls “fascinating” and his “most valuable” as a leader. “The Cup kept us from imploding.”
Olsen started resting players in league games that year so they’d be fit and ready for midweek Cup action – where hope still sprang forth. And the opportunity to win a trophy in a year defined by hardship (three wins, 24 losses and no chance at the playoffs) was all-important for the former USMNT midfielder.
“He [Olsen] is the master at motivating players,” remembered Bill Hamid, the current Miami FC (USL Championship) goalkeeper, who was named Man of the Match in that 2013 Open Cup Final, played away at Real Salt Lake and won 1-0 by the underdog visitors from D.C.. “He’s got that heart of a lion.”
Hamid calls that Open Cup Final win “one of the biggest moments” of his career and he puts most of the credit for it at the feet of Olsen.
The coach brought his master-class motivational abilities to the fore again a decade after that 2013 victory. But in 2023 he had a decade of coaching experience built up and “a lot of leaders” in his Houston Dynamo side. Among them were Mexico legend Hector Herrera and Panama star ‘Coco’ Carrasquilla.
“He’s a strong communicator – and he has a lot of respect for his players,” was the assessment of Herrera, who captained the side to a win in the 2023 Open Cup Final away at an Inter Miami side missing their injured superstar Lionel Messi. “He always wants what’s best for the team.”
The Open Cup’s ability – unique in American sports – to be a launching pad for outsiders and Cinderellas is important to Olsen. He valued the tournament as a player, as part of the all-conquering D.C. United sides of the late 90s and early 2000s, and he still does so to this day.
“Trophies talk,” said Olsen, in charge of a Dynamo team that ran the gamut of Open Cup challenges en route to victory in 2023: A win away at lower-league opposition (Tampa Bay Rowdies) and two more at home in games influenced by red cards (1-0 down a man over Sporting Kansas City and 4-0 up a man over Minnesota United). “When the fans see you holding a trophy, it’s special.
“And that doesn’t go away,” added Olsen, who, this year, has guided his Dynamo team to a 4-1 OT Round of 32 win over a talented Phoenix Rising side (Division II, USL Championship) on the road in Arizona.
“I’m romantic about the Open Cup,” insists Olsen, whose 2025 Dynamo – without the services of Carrasquilla and Herrera but still boasting 2023 stars like Griffin Dorsey, Amine Bassi, Artur and Erik Sviatchennko – are down near the bottom of the MLS Western Conference standings in the early stages of league play. “It could be improved, of course, but I’d hate to see it go away.”
Fans of the Dynamo, like Olsen himself, also know the distinct charms of our Open Cup. Five years before their 2023 triumph on the road in South Florida, they watched their 2018 veteran captain DaMarcus Beasley lift the trophy into the hot air around the downtown Shell Energy Stadium with a rookie-year gleam in his eye – a final moment of celebration to cap a storied career.
The result saved then-coach Wilmer Cabrera’s job in a season in which the Dynamo missed the playoffs. It also gave the club’s fans a taste of winning something for the first time since 2006 and 2007 when they claimed back-to-back MLS titles.
It’s no surprise then that Olsen – a man who uses the word glory considerably more than some of his other favorites – always sees opportunity in the Cup. “They’ve experienced it here [the fans, winning the Open Cup] and so it resonates for them. They know what it’s all about and what it means.”
There’s a certain amount of hang-on-for-dear-life energy in the Open Cup. Ask Olsen about it and he’ll shrug and half-laugh. “You survive long enough and you start to smell an opportunity to put up a Cup and that’s a rare thing you don’t want to miss out on,” added the coach, who, you get the sense, might be a bigger fan than he lets on of the roller-coaster rides the Open Cup provides.”
“We want to continue a culture of winning here,” he said, ahead of a 2025 Open Cup Round of 16 date on the road against fellow MLS Texans Austin FC (LIVE on Paramount+). “Winning helps. Each win matters – so does getting into the Last Eight or the Last Four and competing for Cups. Every game is a chance to push this club forward.
“You only get so many chances to raise a trophy in a career, if you’re lucky,” added Olsen, giving a low-gear glimpse of that motivating thunder he’s known for. “A lot of players go their whole career and never get the chance for that one night of glory.
“It’s rare,” he concluded, a knowing echo in his voice as he sits on the precipice of another opportunity in this country’s most historic competition. “I’ve been lucky enough to have a few of those nights, and you don’t want to let them slip away.”
Fontela is editor-in-chief of ussoccer.com/us-open-cup. Follow him at @jonahfontela on X/Twitter.