The very best Joe Maddon moments of the 2016 season

Throughout Joe Maddon's managerial career, his mostly consistent success has been accompanied by inconsistent and often nontraditional methods. To get his teams to bond, for example, Maddon advocates dressing up for themed road trips rather than spending more time in the batting cage.

It's a philosophy that boils down to a simple mantra: finding comfort in the uncomfortable. And it's this paradox that reflects his regimented, carefree personality.

Here's a look at the Cubs' chase for a historic season from behind Maddon's signature wayfarers:

Who wears short shorts? The Cubs wear short shorts!(June 22)

While the theme for the Cubs' 11-game stretch away from home is self-explanatory, there's an important caveat that can't be missed: If a player or coach wears sandals, painted toenails are a must.

"[First-base coach Brandon] Hyde's daughter was excited," Maddon said. "She was very excited about painting Daddy's toenails last night."

Maddon hangs out with Bill Murray (June 13)

Born in the Chicago suburbs, comedian Bill Murray has been a lifelong Cubs fan. During a recent Cubs series in Atlanta, Murray and his brothers hung out with Maddon.

"He's naturally a very funny guy, but then he has a serious side," Maddon said. "He wanted to know a little bit about Hazleton [Pennsylvania] last night, so I gave him the whole rundown. ... Just a nice, interesting, easy conversation, and whenever the opportunity popped up for him to say something clever, he did. He didn't miss a beat with that. Really a nice man, really easy to be with."

Maddon on the freedom he gives his players (June 13)

A players' manager can be seen as a visionary or a pushover. Maddon's reputation is shaping up to be the former.

"The freedom component really works in our favor," Maddon said. "I don't have any rules. But there's no reason to have any. The boys take care of business on a daily basis. And if anything is going awry, somebody out there will address it."

Comfort is key when it comes to themed road trips (June 4)

Themed road trips have become a staple of Maddon's teams. In honor of the NBA Finals, Cubs starter Jon Lester and strength coach Tim Buss got the team personalized track suits for its early-June trip to Philadelphia. For the manager, the trip was, fittingly, all about comfort.

"I intend on wearing it as often as the weather will permit. I intend to pack very lightly on this trip and bring T-shirts and sneakers and toothpaste."

Cubs welcome mariachi band for Cinco de Mayo(May 5)

Before the start of a four-game series against the NL East-leading Washington Nationals, Maddon used traditional Mexican music to serenade his players before the game.

Maddon reveals his most-desired dinner guests(May 4)

In a wide-ranging Q&A with ESPN Chicago beat writer Jesse Rogers, Maddon said he wants to eat with authors Pat Conroy and Mark Twain, as well as Bruce Springsteen because you "have to have some rock 'n' roll in there." He also discusses his views on baseball's unwritten rules and how the Cubs have avoided losing streaks in 2016.

The importance of "venting"(May 3)

While he prides himself on his relaxed demeanor, Maddon advocates for venting as an important stress-reliever.

"It's always fun to vent, isn't it? We've all been there. You have to vent on occasion. It's the worst thing you could possibly do for your health, long term, is to hold that stuff in. So I wanted to get it out."

The "minimalist zany suit" road trip (May 2)

The Cubs' first themed trip of the season was a classic. With the team and coaching staff decked out in colorful and eccentric formal wear, one moment stood out to the Chicago skipper.

"It's typified by [bullpen coach] Lester Strode sitting in front of me in the airplane -- sans alcohol, none -- singing his butt off because he thought he looked so hot," Maddon said. "Hat on backwards, great-looking suit, tie tied perfectly, singing out loud on the airplane. That, to me, said it all."

"Try not to suck" shirts cause controversy in St. Louis(April 20)

Late last season, Maddon informed then-rookie Javier Baez to "try not to suck" when advising him on how to best stay in the Majors. The slogan quickly became a team favorite, and Maddon printed it on shirts to benefit his Respect 90 charity, which supports sports for kids in inner-city Chicago.

But when the Cubs visited St. Louis, the shirts were initially banned from Busch Stadium for the first game of the series.

"I'd love to know why they're offensive in any way, shape or form," Maddon said of his shirt. "Anyone that thinks it's offensive has a dirty mind."

Cubs open new clubhouse facilities(April 13)

Maddon welcomed almost all of the updates to the club's facilities at Wrigley Field. But he couldn't hold back from jabbing star first baseman Anthony Rizzo and his use of a new cryogenic chamber.

"I've heard about this little egg that simulates the mother's womb back there, so apparently Rizzo is the first guy to jump back into the womb."

Maddon on dealing with the pressure of delivering a World Series to Cubs fans(April 3)

The Cubs entered the season as favorites to take their first World Series crown in over a century. And while some may shy away from that pressure, Maddon wouldn't have it any other way.

"It makes the day even more fun," Maddon said. "Why would you want to go with 10,000 in the ballpark and predicted to finish last? Why would you ever want to be there? I've been there. It's no fun. I'd much rather [have] a raucous ballpark with a great fan base with great expectations. And trying to live up to those, not because you're trying to satisfy anyone's urges but because you're a major league baseball player, you're a professional and your goal is to win and that's what you want to do. If your motivation comes from the outside in, it's not going to work."

Bear cubs visit Chicago Cubs(March 25)

To break up the monotony of spring training, Maddon will often bring in some special guests to visit the team. It's safe to say none were cuter than two bear cubs that came to the team's facility in Mesa, Arizona.

Maddon's preseason antics(March 23)

Mimes, dress-up days, jokes, hippies, a karate expert breaking a block of cement on Maddon's chest with a sledgehammer: It all happened during spring training this year for the Cubs.

"That's just the way we start the day," Maddon said.

Maddon dishes on his clothing philosophy(March 21)

What does Maddon want his players to wear on the road? It's very simple.

"If you think you look hot, you wear it," Maddon said, smiling. "I've always rallied against the fact that [the] previous generation really frowns upon non-collared shirts, which I've never understood. They've always been in favor of the collared shirt and that being more acceptable than the non-collared shirt. I've never understood that logic when it comes down to dress. The $5,000 suit on the airplane ride makes no sense to me."

Chicago bans smokeless tobacco (March 16)

While Maddon stopped chewing tobacco over a decade ago and does not advocate its use, Chicago's move to ban the substance rubbed the manager the wrong way.

"I'm into personal freedoms," Maddon said. "I don't understand the point with all that. Just eradicate tobacco period if you're going to go that route. I'm not into over-legislating the human race, so for me I'll just have to listen and learn."

Maddon values rest, despite youthful stars(February 29)

With a bevy of young stars, Maddon could be tempted to play them all every day, giving even more rest to the roster's aging veterans. But for young players especially, Maddon believes rest has more value as a mental break than a physical one.

"I don't care what birth certificates say," Maddon said. "I'm living it [the grind] myself. I believe in keeping the mind sharp. If the mind is sharp, the body will follow."

Chicago brings back Dexter Fowler in secret (February 25)

For most of the offseason, it was widely believed that Cubs center fielder Dexter Fowler would join another club. Then, as spring training was getting underway, Maddon brought in one of his special guest speakers. Fowler showed up after resigning with the club, surprising his teammates.

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