CHICAGO — Joe Maddon pops out of the trendy downtown hotel where he's spending the season in a bi-level top-floor suite, and he hops into his pickup the valet has waiting for the 20-minute drive to work at his new gig that he says couldn't be going better.He looks much the same as he did during his nine years in Tampa Bay — well, except for the scraggly attempt at a beard he'll explain later. He says many of the same things, about the mind being stretched, not letting the pressure exceed the pleasure and every night not being an oil painting, all while still dropping in the occasional non-sequiturs "Woof!" and "Poom!" for emphasis.And he tells you, several times, that once he learned his way around the city, adjusted to the frequent day games and accepted the unpredictability of the weather, the job managing the Cubs isn't all that different from managing the Rays."Once you get the hang of how all this works, it's no biggie," he said. "It's baseball, man. It's baseball."But then, with the famed stadium now in view, he tells you how different it really is.From the dedication of a thus-far friendly fan base that creates a citywide vibe he puts on par with European soccer allegiance, to the large crowds that provide a "playoff feel every night," to Wrigley Field itself, which he says — forget Fenway — is the majors' best ballpark."Reporting to work every day, here, is unique," Maddon said. "I hope I never get used to this."It has been nearly 10 months since Maddon made the shocking decision to opt out of the final year of his contract with the Rays. And it's just more than four months into the first season of the five-year, $25 million deal he signed with the Cubs, and he has the young and inexperienced team 62-48 and positioned — maybe a year earlier than expected — to make the playoffs, the requisite step to winning that elusive first World Series championship since 1908.It would seem like the move has gone about as well as it could have."I think it has," Maddon said.Not that he'd necessarily admit so anyway, but Maddon, sitting now in his cramped office with photos of Bruce Springsteen and Jackie Robinson and a Wes Lang print on the walls, insists there are no regrets.At least not on his part, a subtle acknowledgement to the Rays' reaction to his departure and the tampering accusations they asked MLB to investigate, with nothing found."Oh no, just that some people may have gotten upset, that's it," he said. "I never intended to hurt anybody's feelings or just hurt anybody. That was not the intent, obviously, at all. That's not who I am."I just hope that moving forward, everybody understands it was in the best interests of everybody. The Rays have been able to get a lot of good new young faces involved there, also, which is probably going to be better for them, too."I think it's one of those win-win situations. I think everybody benefitted from the move."He still keeps tabs on the Rays games and in touch with some personnel, though he said he wasn't aware that he'd been basically scrubbed from the Trop — photos, elevator wrap and most references to him removed despite the team's first and only four playoff appearances."That's too bad," he said, adding that "I'll always be a member of the Rays in my heart, absolutely. Just like with the Angels. It's no different. I was fortunate to start with the Angels, then go to the Rays, and now I'm here. Every place has been a great stop."Maddon, 61, has brought along most of what worked with the Rays, such as the relaxed and casual atmosphere, themed road trips (Blackhawks jerseys, shorts and sport coats to Miami, pajamas and onesies for an upcoming redeye flight) and clubhouse entertainment (bringing in a magician, though so far no live animals).Strategically, too, as he uses the same matchup-based philosophies with his lineup and bullpen and plots defensive shifts similarly. Also, he has former Rays bench coach Dave Martinez and Rays '08er Eric Hinske on his staff.Maddon didn't want everything to sound exactly the same, though, so he has been using a different catch phrase, "Respect 90," in general reference to running hard to first base, and sporting a T-shirt that reads, "Do Simple Better."In addition to the fortune and fame (including T-shirts in his likeness and a TV commercial for Binny's liquor store chain), the setup Maddon has here is pretty good. He gets to ride his bike along the lake and has top restaurants and bars, world-class shopping and scenery and, yes, his requisite Starbucks, all within walking distance of the boutique hotel that is so him.But there are things he misses about the Rays and Tampa Bay, where he still has his offseason home and his soon-to-be 1-year-old restaurant, Ava."I really enjoy living there," he said. "I miss the people that we worked with a lot. … You don't miss the Trop. To be very honest, I don't miss the Trop at all. I just hope they get a new ballpark. But you miss everything else about it, the wonderful people, the organization."Maddon has seen, and heard, enough to have a sense what it would be like if he were the manager who ended the Cubs' 100-year-plus World Series drought. "Crazy is not a strong enough word," he said. "It'll be that 100 times over."Just being in the race has shown him that, based on the reaction he gets from Cubs fans whenever he heads out on the town."They're very nice, really respectful. And they really love their Cubs," he said. "They always start out with, 'No pressure but … ' and I always love that. None taken. And they always want to talk about how their dad or their grandpop or grandmom never saw a championship. I'm always respectful of that and tell them we plan to change that."Which brings us back to the semblance of a beard.Shortly into the season, Maddon said someone told him that all coaches and managers who won championships in Chicago, at least somewhat recently, had mustaches — Mike Ditka with the Bears, Phil Jackson with the Bulls, Ozzie Guillen with the White Sox and Joel Quenneville with the Blackhawks (over the Lightning)."So since facial hair is the key, I thought I would take it the next level," Maddon said. "I'm trying. I've always been challenged. But I'm not giving up on it." Contact Marc Topkin at firstname.lastname@example.org. Follow @TBTimes_Rays.