Pitcher Jon Lester spent nine seasons with the Boston Red Sox, watching as a city and a region burdened by decades of dispiriting postseason losses had its championship renaissance. In his second season as a Cub, Lester cannot help seeing the similarities between Chicago and Boston.  “In Boston, no matter how good the Patriots, Celtics or Bruins are, it’s sort of a Red Sox town,” he said. “I feel the same thing is true in Chicago. No matter how good any other team is, it always comes back to the Cubs.”  Lester has also assessed the two fan bases and sees considerable differences.  “East Coast versus the Midwest,” he said. “It’s not the full, up-in-your-face, fast-paced type of city and fan as you get in Boston. Here, everybody is a little slower, a little more laid-back. But the passion is still there. Both ballparks are packed every night, and everybody is yelling.”  While much of the Cubs’ roster was built with shrewd acquisitions of young talent, Lester was perhaps the final pivotal piece added when he spurned multiple other suitors, most notably the Red Sox, to sign a free-agent contract before the 2015 season worth $155 million. He was rejoining the architects of Boston’s multiple championships: the Cubs’ president for baseball operations, Theo Epstein, and General Manager Jed Hoyer. Lester brought with him the gravitas of a 3-0 World Series pitching record and a 0.43 earned run average in those games.  There were other bonds to his Boston days.  Lester is one of two cancer survivors in the Cubs’ clubhouse. In 2006, he was told he had a form of non-Hodgkin’s lymphoma, but returned to win the game that clinched the World Series for the Red Sox in 2007.  Cubs first baseman Anthony Rizzo was told he had Hodgkin’s lymphoma in 2008, when he was an 18-year-old Red Sox minor leaguer.  Lester and Rizzo first met in the Boston clubhouse shortly after Rizzo received the diagnosis, with Lester offering his counsel on how to approach the chemotherapy and the mental challenges of confronting the disease.  Eight years later, they have been reunited as Cubs and have developed a big-brother-little-brother bond. Lester had a 19-5 record this season, the best winning percentage for a National League pitcher. Rizzo is a leading candidate for the league’s Most Valuable Player Award after slugging 31 home runs and driving in 101 runs.  All around the Cubs’ clubhouse, Lester has become a seasoned, valued voice, perhaps because of his Boston experiences or maybe because Lester had to overcome so much more off the field. But he is not reluctant to discuss the subject that never goes away in Chicago: the Cubs’ curse.  “I’ve told the guys we have to talk about it, because you can’t stick it in the back corner of a dark room and never acknowledge it,” Lester said, standing at his locker. “That’s how bad things creep in. This city has waited a long, long time. For whatever reason — a goat or a black cat — things haven’t worked out.  “But we’ve talked about wanting to be the team that wins the World Series — a Cubs World Series.”  Lester looked across the team’s clubhouse, toward the long, serpentine footpath that leads to the home dugout and the cozy grounds of Wrigley Field, built six years after the Cubs’ last World Series victory.  “There is a reality that we are facing,” Lester said. “It is the team’s history. But history gets updated all the time.”  A mime once came to lead the Cubs’ pregame stretching drills. A player rode his bike from his home to the ballpark like a Little Leaguer, in complete uniform. Another day, the team stepped onto the field to find live bear cubs frolicking in the grass.  All the shenanigans came from the fertile, experimental mind of Cubs Manager Joe Maddon, a grizzled and usually half-shaven former scout, minor league hitting coach and manager and first-base coach who waited 31 years to be put at the helm of a big-league club.  Before the 2015 season, when he was 60 years old, Maddon agreed to become the Cubs’ manager and shoulder the weight of history that came with the job. The new sheriff in town gave his team a set of nonmarching orders. As he described them last week:  “I don’t have any rules or regulations other than I want you to run hard to first base and I want the pitchers to work on their defense. There are no dress codes; I think they’re nonsensical. The concept of being late is overblown. You can’t really be late for anything.”  In less than two years, Maddon’s freethinking philosophy has elevated him to cult-figure status in Chicago, where his Zen-like preachings are emblazoned on T-shirts sold all over the city.  John Baranowski, a 45-year-old longtime Cubs fan, was wearing one of Maddon’s signature T-shirts that read “Do Simple Better” as he prepared to enter Wrigley Field last week. Baranowski likened Maddon to a baseball swami delivered to Wrigley by divine intervention to reverse the Cubs’ curse.  “Is there anyone better to fix an insanely pressure-filled, against-the-odds situation than a guy who lives to defy what people say is supposed to happen?” Baranowski said. “This is the perfect guy. He doesn’t care about the stupid curse.”  Maddon, whose regular-season record with the Cubs is 200-123, may have saved his most important, if atypical, managerial ploy when it comes to the famed curse. He refuses to shy from it.  At Wrigley Field, he had a wall leading from the team’s clubhouse to the dugout inscribed with this Maddon maxim: “Don’t let the pressure exceed the pleasure.”  Maddon is not going to allow more than a century of postseason despair to ruin his good time.  “For me, the word ‘pressure’ should be an absolute positive and not a negative, because if people are throwing that pressure out at you, that means there’s really something good attached to whatever you’re trying to accomplish,” he said. “Pressure lives in the future, not the present tense. If you can live in the moment, then you can enjoy the pleasure of it.”  Sitting at his office desk beneath the Wrigley Field grandstand, Maddon shook his head.  “Listen, I’ve wanted to do this since I was 6 years old, and now I’m going to get here and be miserable?” he said. “No, man, I don’t get that way of thinking at all.”
Anxiety and excitement are in the air in Chicago with the Cubs still seeking their first World Series title since 1908.