A. Messerschmidt/Getty Images
But while it is hard to imagine the Cubs without Maddon now, it might have never have happened if the Tampa Bay Rays didn't concede to a "ballsy" demand by Maddon when he interviewed for their managerial vacancy in 2005.
In November, 2005, the then-Devil Rays had just finished their eighth straight season of at least 90 losses, had parted ways with manager Lou Piniella, and Stuart Sternberg had just taken over as the principal owner. One of the finalists for the vacany managerial position was Los Angeles Angels bench coach Joe Maddon.
Maddon had lost out on the Boston Red Sox managerial opening after the 2002 season, a job that was coincidentally given to now-Cleveland Indians manager Terry Francona. So you'd forgive Maddon if he would be hesitant to make any bold demands of the Devil Rays.
But that is not Maddon's style.
You see, Maddon already had an important appointment during the 2006 season - his girlfriend's law school graduation - and Maddon was not going to miss it.
Here is how Maddon described the demand a few years later for "ESPN the Magazine":
"One of my favorite Rays memories is my first one. When Matt Silverman and Andrew Friedman interviewed me in 2005, I made a special request. 'If I get the job, can I have two days off next May to attend my girlfriend's law school graduation?' Jaye and I weren't married yet.
I know, it was pretty ballsy of me. But they smiled and assured me it would not be a problem. So when I did get the job, I knew I was going to the right place."
Curiously, the Devil Rays won both of those games as bench coach Bill Evers filled in against the then-Florida Marlins.
But it is amazing how history can turn on simple things. Many teams would not have agreed to the demand. If Maddon had not been hired by the Devil Rays, maybe he gets another job elsewhere, or maybe not. But more importantly, even if he were managing another team, maybe he would not have had a weird opt-out in his contract that let him leave the Rays for the Cubs in November, 2015.
And if that doesn't happen, maybe the Cubs aren't in the 2016 World Series.