Khaled El-Ahmad is still scarred from what happened at Wembley Stadium in May 2023.

Minnesota United’s Chief Soccer Officer was in a similar leadership role at Barnsley in England when his team played in the League One Final against Sheffield Wednesday in front of 72,492 fans at London’s iconic venue.

The match was a heartbreaker for El-Ahmad. Barnsley was playing for promotion into the Championship — the second tier of English football — when it lost 1-0 on a header in the 120th minute. The deciding goal came in the last action of the match.

Eighteen months later, El-Ahmad felt elements of post-traumatic stress from that match when watching the Loons advance past Real Salt Lake in the MLS Cup Playoffs in early November. (Both matches going to penalty kicks didn’t ease his heart rate nor desire to avert his eyes at the biggest moments in the shootout.) He will likely feel pangs of it again when MNUFC plays Los Angeles Galaxy in a Western Conference semifinal game Sunday evening in Carson, Calif.

That League One Final is so engrained in El-Ahmad that he brought it up during introductory meetings with Loons staff when he first joined the club in January. It’s a prime example of what percolates his competitive juices, and how it can simmer in preseason or postseason.

At the time of Barnsley’s defeat, El-Ahmad was angry and criticized what he felt should have been a penalty for Barnsley early in the second half. It didn’t materialize despite a VAR check, but minutes later a Barnsley player was sent off for a red card, forcing it to play one man down for the final 70 minutes.

El-Ahmad told ITV post-match: ‘(It’s) a tough loss. Absolutely robbed by the referee.”

Barnsley failed to earn promotion out of League One the following season in 2023-24 and are vying for it again this season, but with El-Ahmad in a new job, he knows how fleeting these moments can be.

“Playoffs for me is just so many emotions,” El-Ahmad told the Pioneer Press in an interview earlier this month. “Mostly ending with a heartbreak.”

El-Ahmad took over Barnsley in 2021. The team was in the Championship division, but was relegated in 2022. He said a lot of work was necessary behind the scenes to put the squad in a position to fight for promotion. With that promotion on the line at Wembley, his college friends from their time together at Wisconsin-Milwaukee had flown to London for the game. Match day also happened to be one of his two daughters’ birthdays.

El-Ahmad has had to endure other bitter playoff defeats, including New York City’s 7-0 pounding by Toronto across two legs of the MLS Cup Playoffs in 2016, as well as defeats in penalties in the Swedish Cup final and in the NCAA tournament during his playing days.

This history has El-Ahmad — who was included in NYCFC’s MLS Cup win in 2021 — cherishing the ability to make a run in these MLS Cup Playoffs during his first year with MNUFC.

“I’m trying to also enjoy and be proud of what we have achieved by being where we are,” El-Ahmad said of United. “And going towards Galaxy with kind of little bit of an enjoyment, because ultimately everyone’s going to be disappointed, except one team. And the closer you get to the final, the more disappointed you are gonna be.”

El-Ahmad has worked to bring collaborative processes to MNUFC, but that’s not how he prefers things on game day. “Probably would want to watch it alone, but that space is rarely provided (at Allianz Field),” he said.

So, El-Ahmad has been watching the playoffs with colleagues as well as family, including one of his daughters falling asleep on his shoulder during a match. “That was a completely different dynamic,” El-Ahmad said with a smile.

During matches, El-Ahmad tries to pluck out trends, intricacies and nuances. He will watch the coaches’ and players’ behavior and body language, and examine how tactics are executed.

“There are aspects where emotions just take control, sure, when you win or when you lose, but I try to be analytical,” he said.

El-Ahmad will then rewatch the game on video and consult the club’s data reports on that specific match and over a string of matches. He will let it settle for at least a day, if not longer, before communicating with head coach Eric Ramsay.

El-Ahmad breaks up MNUFC’s year into at least six phases, starting when he arrived in preseason, the season’s start with interim head coach Cameron Knowles to when Ramsay joined in March, the long summer winless drought with injuries/absences, the fall surge up the West standings and now the playoff run.

Given the rollercoaster, “I’m excited to be where we are,” El-Ahmad said. He credited Ramsay’s ability to get players such as Carlos Harvey to switch from his regular midfield spot to center back defender as an example of the team’s progress.

“I would say the biggest credit to the coaching staff is kind of that togetherness and belief and getting everyone to buy into what we want to do,” El Ahmad said. “The tactical adjustments by being compact, smart, gives us a strong foundation to, over time, also build and improve our game. … But I said this year is going to be somewhat of a hybrid — in various ways we play or adaptability or tactically, and that’s exactly what we show. And I also think that’s been our strength.”