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The punch, air kiss and a walk-off walk: Reranking the greatest moments in City Series history after Christopher Morel’s walk-off home run

Christopher Morel’s walk-off, three-run home run off Gregory Santos on Wednesday at Wrigley Field will go down as one of the greatest — or worst — moments in the 26-year history of the City Series, depending on your rooting interest.

For Cubs fans it was an epic moment in a pennant race made even more joyous by Morel’s jersey-off display as he rounded third base. For Sox fans it was another reminder of how badly this train wreck of a season has gone.

Either way, it will be talked about whenever the crosstown rivalry is renewed, just like all the other memorable moments.

Here’s our updated countdown of the top 10 City Series moments.

10. Caruso’s rain-delay home run, 1999

Perhaps more surprising than even Nick Madrigal’s basket-hugging solo home run Wednesday was the two-run shot by slap-hitting Sox shortstop Mike Caruso off Cubs closer Rick Aguilera at Wrigley Field.

The game-winning home run followed a 3 1/2-hour rain delay that sent most Cubs fans to the local bars. Police were called when hundreds tried to get back in after play resumed. A few thousand wet and well-oiled Sox fans who stuck around took over the ballpark.

The Sox sweep started the Cubs on a disastrous stretch that ultimately cost manager Jim Riggleman his job.

9. The Pick, 2000

During the Sox’s turnaround year in a rebuild, reliever Sean Lowe picked Mark Grace off first base to end the eighth inning with the tying run on third and Cubs slugger Sammy Sosa batting. Grace argued it was a balk, but the Sox got a hometown call.

“Now it’s like that?” Lowe said. “When have we ever had (umps) come out and (say), ‘Oh, we’re in Comiskey, we’re going to make a call’?”

8. Big Z vs. D-Lee, 2010

Cubs starter Carlos Zambrano and first baseman Derrek Lee engaged in a first-inning shouting match in the dugout that was caught on camera. Big Z was upset with the Cubs’ fielding during a four-run inning.

“If you’re not going to play for me, then I’m not going to play for you,” Zambrano yelled.

Lee, the team’s most respected player, told Zambrano to pipe down.

“He was upset some of our players didn’t dive for those balls,” manager Lou Piniella said. “A few of those balls were hit really hard, and one was in the seats with two strikes. Regardless, he was ranting and raving and out of control.”

7. Section 508 brawl, 2007

Fights between Cubs and Sox fans have been a longstanding tradition over the years, particularly at Sox Park.

Even Sox manager Pedro Grifiol admitted Tuesday to sneaking a peek at a fight in center field during the first round of the City Series last month on the South Side.

The mother of all Cubs-Sox fan fights took place in Section 508 in the upper deck at U.S. Cellular Field during a game in 2007. Cubs reliever Bob Howry said it was full of “haymakers” from both sides.

“A guy grabbed a girl by the hair and threw her down three rows,” he said. “I was like, ‘Wow.’” Howry said he disapproved of the fight but couldn’t turn away.

6. Walker’s walk-off walk, 2004

On a wild Fourth of July at Wrigley, Sox slugger Carlos Lee homered off LaTroy Hawkins to tie the game in the ninth before Cubs second baseman Todd Walker coaxed a bases-loaded walk from Damaso Marte in the bottom of the inning to give the Cubs a 2-1 win and a series sweep. Walker was down 0-2 in the count before drawing the walk-off walk.

“It’s like being thrown into the lion’s den with no way out,” he said. “It’s not the way you draw it up. Those are the types of at-bats that give people heart attacks.”

5. The Air Kiss, 2001

Sox infielder Jose Valentin homered off Cubs reliever Will Ohman in the seventh and turned to the TV camera in the dugout to imitate Sosa imitation by tapping his heart and blowing an air kiss to Cubs fans.

“Let (Valentin) do whatever he feels like doing,” Cubs manager Don Baylor said. “Guys want to do that, let ‘em showboat. If they get drilled eventually, that’s part of (the game).”

Valentin refused to apologize for stealing Sosa’s trademark home run reaction. Sosa said he approved of the imitation.

4. Kerry Wood’s farewell, 2012

Word spread before the game that Wood had decided to retire in his 14th season. He struck out Dayan Viciedo with his final pitch at Wrigley Field and walked off to a standing ovation from both Cubs and Sox fans.

Wood’s young son, Justin, ran out of the dugout and embraced his dad, who carried him off the field in perhaps the most heartwarming moment in City Series history.

“We don’t all get to choose when; we don’t all get to have a say in it,” Wood said afterward. “But I was fortunate enough to play this game a long time and play in a wonderful city in front of the best fans in baseball. It was just time.”

3. A.J.’s revenge, 2006

In Round 2 of the City Series at Wrigley, with two outs in the ninth and Cubs fans on their feet, Sox catcher A.J. Pierzynski launched a three-run home run off closer Ryan Dempster to shock the ballpark and propel his team to an 8-6 win.

Pierzynski had become Public Enemy No. 1 at Wrigley after the fight with Michael Barrett in May and was booed loudly every time he came to the plate.

2. Morel’s shirtless walk-off, 2023

“It’s my time,” Morel said after shaking Wrigley’s foundation with a walk-off homer off Santos and doing a Magic Mike impersonation on the basepaths in Wednesday’s 4-3 Cubs win.

The Cubs offense had been lifeless for two days against Sox pitching until the ninth-inning rally, ignited by a Cody Bellinger double. The timing of the shot heard ‘round Wrigleyville, during a pennant race on a warm, mid-August night, made Morel’s home run that much sweeter for Cubs fans.

1. The Punch, 2006

Stop us if you’ve heard this one before.

Pierzynski gets punched in the head by Barrett at the Cell, igniting a crosstown brawl that rivals any in baseball history. You can’t mention the City Series without talking about A.J., whether you loved or hated him. In a mostly forgotten side story, Sox manager Ozzie Guillen later claimed that Dempster said Sox coach Joey Cora bit Jacque Jones on the foot during the brawl.

“Wow, when you’re in the ballgame, you have shoes on,” Guillen said. “If Joey Cora is going to bite somebody, I hope he’s not dumb enough to try and get his feet.”

The only way to top this crazy day would likely occur in a Cubs-Sox World Series. Reliable sources indicate that’s not imminent.