I asked Paul Sullivan if he knew anything about I.E. Sanborn.

“No, never heard of him,” Sullivan said.

Well, Sanborn has the distinction of being the last sportswriter in the Chicago Tribune to write the story of the Cubs winning the World Series. On Oct. 15, 1908, Sanborn’s story detailed how the then powerful North Siders claimed their second straight title.
“Wow, I didn’t know that,” Sullivan said.

Now in 2016, Sullivan, the long-time Tribune baseball writer, or someone else at the paper, could be in line to follow up Sanborn a mere 108 years later with a front-page byline about the Cubs finally winning that long-awaited World Series. The Cubs are the favorites going into post-season play, and my hometown is ready to explode if they can pull it off — or implode if there is another epic heartbreak. Indeed, anxiety is so high, they should pass out Xanax to fans entering Wrigley Field for Game 1 on Friday night.

Sullivan, my old Tribune teammate, pointed out he actually has somewhat been down this road before. With the Cubs ahead late in Game 6 of the 2003 National League Championship Series against Florida, he had a lead written about them finally reaching the World Series for the first time since 1945.

“We were all on deadline, and we’re all doing our stories about them going to the Series,” Sullivan said. “I remember thinking how weird it was to be the person in the Tribune writing about the Cubs going to the World Series.”

Of course, that lead never went beyond Sullivan’s computer. Not after the whole incredible and unthinkable Steve Bartman thing happened, creating the all-time story of Cubs despair.

Sullivan, though, wasn’t surprised. A lifetime of following (he watched games with legendary owner Bill Veeck in the Wrigley bleachers) and then covering the Cubs has conditioned him to expect the worst. Case in point: When he took over the Cubs beat for the Tribune in 1997, he witnessed them go 0-14 to start the season.

“Yeah, that was an interesting way to start a new beat,” Sullivan said. “They were out of it two weeks into the season. You’re thinking, ‘OK, what am I going to write now?’”

Sullivan was forced to figure it out several times while covering Cubs on a full-time basis through 2013. Now he continues to be around them for most of their games as the Tribune’s baseball columnist. He is the author of “The Weight” for the Tribune, a series of long-form stories detailing various passages throughout the season.

“It’s got to be the most unique beat in sports because of the whole drought thing,” Sullivan said. “Everyone says, ‘You’ve got the greatest job in the world. You get to watch the Cubs every day.’ You can’t really argue with them, even though it’s still a job.”

From a beat reporter standpoint, Sullivan prefers the team to either be really good or really bad. He said the job is tougher when they are in between.

“I would much rather cover a really bad team than a team that’s .500,” Sullivan said. “You can rip them more when they are terrible. The fans know they’re bad, and they want you to say they’re bad. People in Chicago won’t tolerate it if you sugarcoat a bad team.”

Ultimately, Sullivan says he wants interesting people to cover. He recalled the late 90s hoopla that surrounded Sammy Sosa “was like a beat unto itself.” He enjoyed being around former manager Dusty Baker because he “was so quotable.”

Sullivan also has high praise for current Cubs manager Joe Maddon.

“He’s the best manager we’ve ever had as far as access,” Sullivan said. “He’s like (Chicago icon Mike Ditka) as far as charisma. I’ve never seen him upset with the media, and he gets asked a lot of stupid questions. I think he understands our jobs.”

Maddon and his players will begin the quest to finally end the century-plus frustration in Wrigley. Sullivan has his own favorite statistic that shows the Cubs futility through the years.

“There’s only been four beat reporters for the Tribune to cover the Cubs in the postseason in more than 70 years (since their last World Series appearance in 1945),” Sullivan said.

Current Tribune Cubs beat reporter Mark Gonzales already has experience in writing about a World Series winner in Chicago. He covered the White Sox’s run in 2005.

That was my ultimate moment as a lifelong White Sox fan. Yet even I have to admit the Cubs winning the big one after all these years would be a bigger story.

However, when I asked Sullivan if he could imagine writing a story about a Cubs World Series winner, perhaps in an attempt to temper expectations, he said, “I’m not even going to go there.”

Indeed, Sullivan, like everyone else in Chicago, is all too familiar with how these stories end for the Cubs.