That's a lot of angst for those who have long followed the local teams but have never lost their incredible enthusiasm. Yet as far as Cubs fans on the North Side and White Sox fans on the South Side are concerned, never the twain shall meet.
"There's a huge difference in the fan bases," said Ron Kittle, a former White Sox outfielder and designated hitter who was on a Saturday morning panel with another pair of fellow former White Sox, Carlos May and Mike Huff. "Cubs fans have iPhones and send text messages during the games. White Sox fans watch the games.
"I'm a longtime season-ticket holder at Wrigley Field, so I should know. When I go to Wrigley, I go there to watch the game. Nobody around me is paying attention. I don't want to get hit in the noggin [by a ball] because of somebody who can't catch."
On Sept. 23, 1908, Fred Merkle, who had been on first base, failed to touch second base on what should have been a walk-off single for the New York Giants at the Polo Grounds as fans flooded the field to celebrate. Cubs second baseman Johnny Evers called for the ball and stepped on the base for the force. Umpire Hank O'Day saw the play from home plate and called Merkle out. The game ended in a tie due to the commotion and darkness, and the mistake by Merkle loomed large at the end of the season, as the Cubs and Giants finished tied on the final day. The Cubs won the makeup game to claim the National League pennant.
That may seem like ancient history, but it's still a big part of Chicago's loveable baseball lore. The Cubs have lost in the World Series seven times since then, but haven't been back since losing to the Tigers in 1945.
Then there's the matter of the 1919 Black Sox scandal when the White Sox were charged with throwing that World Series to the Reds and eight of those players, including Shoeless Joe Jackson, were banned forever from the game. The White Sox have been back to the World Series only twice since then, losing in 1959 and winning in 2005.
The 10-year anniversary celebration of their sweep of the Astros is coming up later this summer. But the fact is, after 1917, they never won again in Comiskey Park, their iconic ballpark that was closed in 1990 and subsequently torn down. Wrigley Field was opened in 1916, and the Cubs have never won a World Series there, either.
Both teams retooled during the offseason and hope sprung eternal. The White Sox, though, are slogging through a 32-41 season, currently in last place, 12 games behind the Royals in the American League Central. The Cubs and Wrigley have been refurbished. Despite a 39-34 record, they are in third place, 10 1/2 games behind the Cardinals in the NL Central, but still in position to grab a Wild Card spot.
Left-hander Steve Trout is one of 177 players -- 88 pitchers -- to have played for both franchises. Three of them are on the current rosters: Edwin Jackson now on the Cubs; and Jeff Samardzija and Geovany Soto for the White Sox.
Trout was the eighth pick overall by the White Sox in the 1976 Draft, but he had his best year playing for the ill-fated 1984 Cubs, finishing 13-7 with a 3.41 ERA.
Put on the spot and asked whether he preferred pitching for the White Sox or the Cubs, Trout responded: "Day-time baseball was the best part of it for me. The White Sox had better fights in the stands, but the Cubs had prettier women in the bleachers. You had to love day-time baseball."
Wrigley wasn't equipped with lights until Aug. 8, 1988. It cost the Cubs home-field advantage against the Padres in 1984, the last of the best-of-five League Championship Series. The Cubs had the better regular-season record, but because the networks wanted a night game on Saturday, only the first two games were played earlier in the week at Wrigley.
The Cubs outscored the Padres 17-3 to win those games. Awaiting in the World Series was the Tigers, the same team the Cubs beat in 1908 and lost to in 1945, the last time they had made it to the postseason. It wasn't to be. The Padres swept the three San Diego games.
"My dad [Dizzy Trout] pitched against the Cubs in the 1945 World Series," Trout recalled. "And we had won the first two games of the playoffs, as you know. It was going to be his son going back against the Tigers all those years later. But crazy things happened in San Diego. That was the biggest letdown I've ever had and most of the '84 guys ever had. It just didn't work out."
The White Sox hadn't made the postseason after losing the 1959 World Series to the Dodgers until Tony La Russa led them into the ALCS in 1983. Kittle had 35 homers and 100 RBIs for that team, which lost to the Orioles. A decade later, Huff was a member of the 1993 team that lost in the ALCS to the Blue Jays, the deepest the White Sox would advance in the postseason until 2005.
For Huff, who grew up in the Chicago area and went to Northwestern University, his trade from the Indians to the White Sox was a dream come true.
"Being traded, I went from this incredible low to this high, coming back to my hometown," said Huff, a former outfielder who played only three seasons for the White Sox. "I grew up on the North Side rather than the South Side, but to be back in Chicago was just incredible."