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Former San Jose Earthquakes and KC Wizards defender Jimmy Conrad, (12), plays for the USMNT and fights off Panama's Jorge Luis Dely Valdes for the ball during the first half of the Gold Cup final at Giants Stadium Sunday, July 24, 2005, in East Rutherford, N.J. (AP Photo/Gregory Bull)
Former San Jose Earthquakes and KC Wizards defender Jimmy Conrad, (12), plays for the USMNT and fights off Panama’s Jorge Luis Dely Valdes for the ball during the first half of the Gold Cup final at Giants Stadium Sunday, July 24, 2005, in East Rutherford, N.J. (AP Photo/Gregory Bull)
Jason Mastrodonato is a sports reporter for the Bay Area News Group.
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As the San Jose Earthquakes take the field in Kansas City for a 6:30 p.m. PT kickoff on Wednesday night and begin their quest to win an MLS playoff game for the first time since 2012, one former Earthquakes star will be watching the game with internal conflict.

Call it the Jimmy Conrad Derby.

The former United States Men’s National Team captain began his MLS career in San Jose and won an MLS Cup with the Earthquakes in 2001 before he was traded to KC. He said he’ll be watching Wednesday’s game like a “mom who just wants both teams to have fun.”

The Earthquakes infamously dealt Conrad to Kansas City for a second-round draft pick after the 2002 season. It was in KC that Conrad became an MLS legend, being named to the All-Star team six times, earning four MLS Best XI selections and being named the 2005 MLS Defender of the Year.

Today, Conrad calls the Bay Area home. He’s the technical director and an assistant coach for the San Francisco Glens, a minor league soccer team, and he’s a friend of Earthquakes head coach Luchi Gonzalez. The two played together briefly in San Jose more than 20 years ago.

But when it comes to which side Conrad favors, he’s a bit nervous to say that Kansas City has his heart.

“My time in San Jose was awesome,” he said by phone this week. “Then I got traded away. I never saw it coming. I don’t hold it against them. But when I went to KC I blossomed. I accomplished so much when I was there. I’m in their Hall of Fame. If you go to their stadium, my name is up there. As much as I love what San Jose has done for me as a player and my continued relationship now, I still have a lot of tethered to my time in KC. I have to say KC is my club.”

Still, Conrad said he’s been impressed with how quickly the Quakes bounced back from being the worst team in the Western Conference last year to making a playoff appearance this season, Gonzalez’s first as the head coach.

“Having been on the Quakes when Luchi got drafted to us, there was something about him,” Conrad said. “He was a student of the game. The details mattered to him. I really appreciate that about him then and I probably appreciate it even more now that he’s the coach. You can see his personality on the team. There’s a sense of care and a warmth to him. Luchi is a special human being.”

The Quakes will have their hands full going up against KC on Wednesday night. San Jose won an early-season matchup, 3-0, back in April, then KC got revenge with a 3-0 win at home in August.

KC is entering Wednesday’s game as one of the hottest teams in MLS, having won six of its last nine contests.

“Kansas City has done really well, and we recognize that,” Gonzalez said Tuesday. “Probably the perception and the expectation out there is that because we’re not home and they are, and with their form and their talent, that we aren’t supposed to get through. We’ll embrace that. It’ll drive our motivation and mentality.”

Gonzalez’s club hasn’t won a game since Sept. 16, having tied in four consecutive matchups to squeeze into the playoffs as the No. 9 and final seed.

“With four consecutive ties it proves that they have some resilience to them, they know how to stay in games,” Conrad said. “If they’re not playing well they can still grind out results. But can they take their chances when they come? There’s something to be said that they haven’t been beaten in a little while. You need that. You need to be tough.”

In their most recent appearance in the MLS Playoffs in 2020, the Quakes also played against KC and lost in penalty kicks, 3-0.

Wednesday night, there will be no extra time. If the game is tied after 90 minutes, it goes straight to PKs.

“That first goal is so important,” said Conrad. “If they can go get that first goal that really changes KC’s approach and I wonder what that looks like. You have to punch them first.”

The winning team will move on to play against the top-seeded St. Louis City FC in a best-of-three series that begins on Sunday in St. Louis. Either San Jose or Kansas City will host the second game of the series. The Quakes haven’t hosted a playoff game since 2012 and have never hosted a playoff game at PayPal Park.

They finished their regular season 10-14-10. Argentinian winger Cristian Espinoza led the squad with 13 goals and 13 assists, participating in 67% of the team’s goals, tied for highest in MLS this season and the highest percentage in club history.

Sporting KC, which began the year without a win in its first 10 matches, finished the season 12-8-14. They’re led by Mexican forward Alan Pulido, who has a career-high 14 goals in 28 games.

The game can be streamed globally on MLS Season Pass via Apple TV or be heard on local radio via 810 AM (English) and 1370 KZSF (Spanish).

The Quakes will also be hosting a watch party at Old Wagon Saloon in San Pedro Square.