Some players are difference-makers. They change games, no matter who they play for, helping turn slim losses to draws and disappointing draws to wins.
Juan Carlos Obregon Jr., captain of USL League One side Westchester SC, is one of these players.
“The mindset is different,” he said of playing in the Open Cup, a single-elimination tournament where a winner is required every time out. “It’s always win or go home. Winner takes it all, so you end up in situations where anything can happen and you have to put in your best performance at all times.”
Open Cup games require a healthy dose of winning attitude. Belief. Whether you’re playing against a team from a division below you, above you – or from the same level. And Obregon has been making all the difference for his first-year Div. III pro side in the first two Rounds of this year’s Open Cup.
He scored the only goal in Westchester’s First Round game, out on the road against historic amateur spoilers FC Motown in New Jersey on March 18. It was the first game in the history of the club, part-owned by USMNT star and 2017 Open Cup Runner-up Tyler Adams, and Obregon’s cool spot-kick ten minutes from time kept it from turning into a debut to forget.
In the Second Round, he wasted no time making his mark early – scoring the opening goal in a 3-2 win over another complicated amateur outfit in three-time Open Cup-Champion NY Pancyprian Freedoms.
The versatile forward, who’s happy to drop into the creative hole between midfield and frontline, has his fingerprints all over the team’s passage to the Third Round of the 2025 U.S. Open Cup. The New Yorkers now face a road trip to USL Championship (Div. II) side Detroit City FC and one of the toughest road tests in American soccer at the cauldron of Keyworth Stadium in Hamtramck.
It won’t be lost on the veteran Obregon, playing in his second year in this country’s professional Division III, that he’s going up against a club from the USL Championship (the sanctioned Division II) and a side, on paper at least, from a world above. He played three seasons in that USL Championship (closer to his stated dream of the big time of MLS) with Hartford Athletic and the Pittsburgh Riverhounds.
“I feel like most of the teams in League One can compete with teams in the USL Championship if I’m being honest,” said Obregon, who helped another League One side, Charlotte Independence, to the Round of 32 of last year’s Open Cup – a run that included a Cupset of USL Championship side Rhode Island FC in which he scored twice. “You see that proven out in the Open Cup every year, with teams from lower divisions beating those from above.”
Far from bitter about landing in USL League One, the 27-year-old brings a desire to improve every day to his work. He exudes an admirable commitment to the required grind.
“You just have to keep grinding every day, go at it hard every single day,” said Obregon, a leader in the new Westchester SC side along with former NY Red Bulls midfielder and Jamaica international Kemar Lawrence. “It’s not always easy, results go against you, and maybe you’re not getting exactly where you want to be, but it’s a process. Not every setback is a failure. Just keep going and going.”
Born and raised in Brooklyn, Obregon came up in the game in the concrete jungle of New York City. “I remember early on, you know, playing in the parks around the city in this great, diverse soccer environment.”
Obregon showed a rare talent early on. An ability to influence an outcome in a variety of ways. Carving open a defense with a clever pass. Scoring the crucial goal. Hustling in the middle of the park, winning individual battles, to help imperceptibly turn the tide of a game. His list of attributes was lengthy as a youngster – and it remains so today.
After a pair of seasons at Sienna College, he signed with Mexican side Necaxa, where he got a taste of the pro game with the club’s youth side and scored six goals in 24 appearances. It wasn’t the only time he’d have successes on foreign fields. He also spent a season with Motagua in Honduras, his parents' birth country.
There, amid what he calls “the huge passion” for the game in Central America, he found a level of celebrity he’d not seen in his previous stints in Connecticut or the Rio Grande Valley of Texas.
“I got to play in the Concacaf Champions Cup against Mexico’s Pachuca, who we beat,” he said of the 2023 season he spent with Motagua, scoring once in seven starts. “The fans in Tegucigalpa were very passionate. You're like, kind of like a celebrity down there when you play, which isn’t like here in the USL Championship and USL League One. You walk out on the streets and people will recognize you.”
Obregon holds being called into the Honduras Under-23 National Team that took part in the Tokyo Olympic Games of 2020 as one of the highlights of his career – even though Covid-19 forced events to be contested behind closed doors. “We won a game against New Zealand at the Olympics so that was like a dream come true,” he said of the tournament, where – despite beating the Kiwis – Honduras finished bottom of their group.
Obregon never gave up on being called into the Honduran senior national team, who he says were “always keeping an eye” on him and his progress. And the nod finally came last year, when he helped Charlotte Independence to the USL League One playoff quarterfinals, a deep run in the Open Cup and scored a personal-best 20 goals across all competitions.
Now the focus is on taking Westchester SC, in sixth place in the league (with games in hand) and thriving in the Open Cup, as far as possible in the club’s first year of life.
“You know, players kind of tend to come to me and ask for advice. And if I see if a player is struggling in some aspect, I put my arm around them and offer some wisdom,” he said of the role of captain at a new club. “I look to be a leader on the team with my experience.”
A win in this Third Round in Detroit would set up a date with a Major League Soccer team in the Round of 32 (the stage when all 16 competing MLS teams join the party). For Obregon, who reached that stage last year with Charlotte, and ended up on the losing end of a 3-0 result to 2019 Open Cup Champs Atlanta United, it’s an opportunity he relishes.
“Representing your league and your club is the highest responsibility,” he said. “It's always exciting to play against players at the level where you want to be.”
Fontela is editor-in-chief of ussoccer.com/us-open-cup. Follow him at @jonahfontela on X/Twitter.