Former Union coach Jim Curtin left lasting moments from his time in Philly. Here’s 10.

For 11 seasons, Jim Curtin guided the Union to a level of success achieved just once in the first five years of the club’s existence prior to the Oreland native’s takeover. Perhaps that’s why the news of his firing by the Union on Thursday sent shock waves through the American soccer sphere, especially considering the club just agreed to be on the hook to pay him for two more seasons — to now coach elsewhere.

It was 10 years of highs and lows — and some scratching and clawing — to kick-start a reign of success with the club, interspersed with a few interesting moments sprinkled in.

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Here are the top moments from Curtin’s run on the Chester waterfront.

Before Curtin established himself as a top American coach on the professional level, he helped mold the early beginnings of the Union’s youth academy, lauded as one of the best in the country. It has brokered multiple players to overseas clubs, and arguably the biggest American prospect hopeful in recent memory in Cavan Sullivan. It was Curtin who served as an architect of what that system would now become.

Just two years into his run as manager, the Union qualified for the 2016 MLS playoffs despite falling in the first round to Toronto FC. That trip under Curtin would be the first time the club qualified for the playoffs since the 2011 season.

After sporting director Ernst Tanner gave Curtin a one-year extension ahead of the 2019 season, he followed it up with one of the finest seasons to date in the club’s history, with the Union sitting in first place in the East for a good chunk of the season and qualifying yet again for the MLS Playoffs. At the end of that season, Tanner gave Curtin a two-year extension.

It was a pandemic year but it was one of the finest for the Union under Curtin. The end of it saw Curtin and the club earn a trip to the CONCACAF Champions League. In the team’s debut in the Champions League, the Union defeat Costa Rica’s Deportivo Saprissa, giving Curtin his 100th win as coach.

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That same year, Curtin would go on to be named the MLS Coach of the Year for the first time. He’d earn the same honor during the 2022 season after leading the club to its first-ever MLS Cup. More on that later …

By 2020, the club was in desperate need of a trophy. It teased both itself and its fans into believing that the Lamar Hunt U.S. Open Cup trophy would be it after qualifying for the final on three separate occasions. However, behind an MLS-best 14-4-5 (47 points) record, the Union would capture MLS’ Supporters Shield, given to the club that finished with the League’s best regular season record. Technically, they’d capture a replica of it before the actual one arrived as a makeshift Captain America shield was what Curtin and the Union used to celebrate the title, with the actual never making it to Subaru Park.

» READ MORE: Jim Curtin wasn’t surprised by Gregg Berhalter’s firing, and still wants to help the USMNT some day

It’s well documented the vitriol diehard Union fans have for the New York Red Bulls but for about three straight seasons from 2020-22, the rivalry definitely became heated between MLS’ other franchise representing the Big Apple in NYCFC. In 2021, it was NYCFC that defeated the Union en route to an MLS championship, but Curtin orchestrated a team that ran it back in 2022 to defeat NYCFC at home in the Eastern Conference final and book its first trip to the MLS Cup.

The numbers don’t lie. Year over year, the Union’s salary cap is one of the lowest in MLS, ranking at the bottom of the table among the League’s 30 teams. However, Curtin and his staff were able to acquire and coach up players that gave the Union perennial playoff appearances for seven consecutive seasons.

» READ MORE: How Jim Curtin developed a culture of success and style for the Union

Starting out in 2014, Curtin had to toe the company line. That meant well-pressed suits on the sideline and having to weave in archaic ideas from senior management and ownership. But under a new sporting director in Tanner who better served as that buffer between the team and the front office, Curtin developed a culture both on the field and off that fueled a great deal of the club’s success.

After an unforgettable run to the MLS Cup final, the Union played one of the most memorable games against Los Angeles Football Club. Curtin ran out a lineup that went back and forth, with the club nearly winning it in regulation until a stoppage-time header from LAFC’s top player Gareth Bale pushed the game into overtime and a shootout round. In the shootout, it was Philly vs. Philly as Union penalty kick takers when up against former Union goalkeeper and Cinnaminson, N.J. native John McCarthy. McCarthy, who Curtin brought into the club in 2015, stymied three PKs en route to becoming the first goalkeeper to enter as a substitution and win MLS Cup MVP.