Cubs legends on what a World Series title would mean to them and the city of Chicago

As the 2016 Cubs aim to end 108 years of futility, they're being watched and cheered on by some of Chicago's all-time greats—all of whom were unable to break the team's World Series drought.
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Billy Williams was one of four future Hall of Famers who formed the core of the Chicago Cubs' roster in the late 1960s and ealry 1970s, but despite all that talent the team never did reach the playoffs, much less the World Series, in that time. After retiring in 1976, Williams remained a Cubs fan and he endured the hardship of watching the team fall short in eight different postseasons. So when Chicago closed out a 5-0 victory last Saturday night to secure the franchise's first National League pennant since 1945, Williams was ecstatic beyond words.

“After that double play, I jumped up and shouted, 'Oh Lordy, we made it,'" Williams said as he got ready to leave his Cleveland hotel room for World Series Game 1 at Progressive Field on Tuesday night. “I’m happy for the Cubs fans who have suffered for so long. I can’t believe it. It hasn’t sunk in yet, but I’m watching TV and it says the Cubs are in the World Series.

"'The Cubs in the World Series,' has a nice ring to it," he added. "They deserve to go, but it is still hard to believe."

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Maybe believing will be easier when the Indians and Cubs play this weekend in 102-year-old Wrigley Field, starting with Game 3 on Friday. It will be the first World Series game at the Friendly Confines since 1945, two years before Jackie Robinson integrated baseball. (Cleveland has been to the World Series five times since 1945 and last won it in '48.)

Except for the early days of the Fall Classic, Chicago's history is littered with losing and playoff heartache. The first World Series was in 1903, and the Cubs played in four of the first seven, winning titles in '07 and '08 and losing in '10. Since 1910, they have been to the World Series in '18, '29, '32, '35, '38 and '45. That’s when the futility began.

Of the 16 teams that were in baseball in 1945, each has been to the World Series multiple times since then. Consider that the Yankees have won 26 pennants in that time; the Cardinals have won 11. Washington, a city that hasn’t hosted a World Series since 1933 or had a World Series winner since 1924, would have to go without a championship appearance until 2040 to match the Cubs’ drought.

Former Chicago players hope that the Cubs going to the World Series can forever change the narrative of the team as "Loveable Losers.". Hall of Fame pitcher Ferguson Jenkins, the NL Cy Young winner in 1971 with 24 wins and a 2.77 ERA in 325 innings, says there is no curse except for the fans always reliving the history.

“Winning the World Series would be a relief for Cubs fans," he says. "It would get rid of all kinds of mystique about not being able to win, always hearing about 1908. The Cubs had great teams in the playoffs but didn’t win. When that happens you sometimes get a label that you can’t win. All that will go by the wayside now."


Jenkins, who joined Williams and the late Ernie Banks and Ron Santo as Cooperstown-bound members of that '69 team, knows first-hand about great Cubs teams that fell short. In 1969, Chicago carried a nine-game lead into mid-August but collapsed down the stretch and finished in second place, eight games behind the Mets. But that '69 team isn't the only one to leave Cubs fans' heartbroken. Even some of the Chicago team's that made the playoffs suffered painful endings. Consider:

• In 1984, the Cubs won the first two games of the best-of-five NLCS against the San Diego Padres, but lost the next three games, including a walk-off loss in Game 4 and a defeat in Game 5 aided in part by a groundball through the legs of first baseman Leon Durham.

• In 2003, the Cubs led the Florida Marlins, three games to two, in a best-of-seven NLCS going back to Wrigley Field with Kerry Wood and Mark Prior—their two best pitchers—in line to start. They wound up watching the World Series on TV after blowing leads in Games 6 and 7.

• In 2007 and '08, the Cubs were swept in the Division Series, first by the Diamondbacks and then by the Dodgers despite leading the NL with 97 wins in the former season.

Mark DeRosa played on both of those latter two teams, and even lived in Wrigleyville, the neighborhood near the ballpark, so he was immersed in the undying passion Cubs' fans have for their team. "It reminds me of the Cape Cod League or American Legion when the whole town came out to support the team,’’ DeRosa says. “If the Cubs win the World Series, it will be the greatest sports moment ever."

As the 1984 season began, the Cubs still hadn't been to the postseason since winning their last pennant since '45. When Rick Sutcliffe was traded from Cleveland to Chicago on June 13, 1984, he didn’t know much about the Cubs’ history. But he soon learned. Sutcliffe was on the mound for Chicago's division-clinching 4–1 win in Pittsburgh on Sept. 24. As he headed to the bullpen before the game to warm up, he noticed two Cubs fans—a father and son—holding a sign that read, “39 years of suffering is enough."

“I give you my word, I’m going to make it all worthwhile," Sutcliffe told the man and his son.

Sutcliffe gave the kid his warm-up ball, then delivered on his promise with a two-hit complete game win against the Pirates, striking out nine without a walk as the Cubs wrapped up the NL East. After the traditional champagne-soaked clubhouse party, Chicago's players went back on to the Three Rivers Stadium turf and watched a live video of Cubs fans celebrating at Wrigley.

“Wrigley Field was surrounded with fans," Sutcliffe said. “Imagine the worst traffic jam you’ve ever seen. They were screaming. It was sheer joy. And that was just from winning the division. It was bigger than we realized."

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Sutcliffe’s favorite story is from when the Cubs returned to Wrigley Field. A group of players from 1969, including Jenkins, Santo and Banks—the other three Hall of Famers on that team—were in the clubhouse waiting for players to arrive before a game.

“Ron Santo grabbed me by the shirt collar—he was a strong man—and told me, ‘I can never repay you for helping these fans forget what happened in 1969,'" Sutcliffe says. "That’s probably what I would say today to (team president) Theo Epstein. I don’t know if any of us know what it would be like if the Cubs won the World Series."

But Cubs players know how baseball defines the community around Wrigley Field, and even though they didn’t get a chance to win a World Series, the players are big-time fans.

Hall of Fame outfielder Andre Dawson, now a front-office executive with the Marlins, played six of his 21 big-league seasons with Chicago after signing with the team as a free agent before the 1987 season.

“Cubs fans are so deserving of a championship, and if they win, the jubilation would be epic because there are people that have been waiting a lifetime for the Cubs to win a championship," says Dawson, who was named the 1987 National League MVP after leading the league with 49 home runs and 137 RBIs. “I started in Montreal, but the Cubs supported me, made me feel like family. They helped get me on my feet. It was wonderful to be embraced the way I was embraced."

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Another Cubs Hall of Famer, second baseman Ryne Sandberg, can relate. The 1984 NL MVP loves to point out that of his 9,282 career plate appearances, only six weren't in the Cubs’ blue-and-white pinstripes (those came as a member of the Phillies, who drafted him in '78 and traded him to Chicago in '82). Sandberg played on the Cubs teams that lost in the playoffs in 1984 and '89, but being with the Cubs' community is what it is all about these days.

“You never forget the feeling of not getting to the World Series," Sandberg says. “Yes, it sticks with you. Time and time again, I see former teammates and we talk about it. It feels like we are all on the same page: We enjoyed the regular season, but we were disappointed in not making the World Series.

“I’ve spent 34 years associated with the Cubs, and part of the reason I’ve stayed in baseball is because I want to be part of a World Series winner," he adds. "This year, the Cubs have all the pieces to do that."

DeRosa said that while former players are pulling for the Cubs to win and will be happy if they do, there’s another emotion attached to what is happening. "There’s one percent of me that is jealous of the players" who get a chance to win the World Series for the Cubs, he said.

Williams played his 16th and final season for Chicago in 1974 and eventually became the team's batting coach. Always, though, he was a Cubs fan. As Chicago beat the Giants and the Dodgers in the first two rounds of the postseason, he thought back to 1969 and how Santo and Banks would enjoy this weekend. But his emotion turned quickly to giddiness.

“It’s exciting," Williams says. “This team has pitching, defense, speed, bats. And they’re young, so they’re going to be around awhile."

Mel Antonen, a former USA TODAY baseball writer, is a reporter and analyst for MASN-TV, the network of the Washington Nationals and Baltimore Orioles, and for MLB Network Radio on Sirius-XM.