Maddon didn't know at the time that those good things would become a personal complication, but they have.
Maddon's talented, wide-eyed Cubs have flashed the promise of a dynasty in the making, which showed last weekend when they took two out of three from the Cardinals in a pulsating series at Wrigley Field. But now, here come McCutchen and the Pirates this weekend, and the Cubs have to state their case all over again.
In baseball, like in life, it's often tougher to break through than to get to the point where a breakthrough is possible, and that's the challenge presenting these Cubs at the crossroads.
As great of a season as they've had, they're the third-place team in the NL Central (with the third-best record in the Major Leagues). They're headed into the playoffs as a Wild Card team -- and nobody is going to want to play them with their loaded lineup and the Jake Arrieta/Jon Lester combination at the front of the rotation -- but they'll be unfulfilled a year from now if they can't push their way past the Cardinals or the Pirates.
Not that they'll have to wait a year.
MLB's postseason format has the Cubs lined up to face the Pirates in the Wild Card Game presented by Budweiser, with the winner then getting a crack at the Cardinals in the best-of-five NLDS. The storyline for this weekend's series will be whether the Cubs can wrest home field advantage away from the Pirates for the one-game showdown, although by sweeping a four-game series in Colorado and winning their last six, the Bucs have left the Cubs in one of those dreaded must-sweep situations.
Wherever the Wild Card Game is played, nothing would be sweeter for Cubs fans than to run a gauntlet through the Pirates and the Cardinals. But anybody who thinks that's going to be easy hasn't been paying attention. At least not for long.
Sure, the Cubs lead the Pirates in the season series, 10-6 -- if they can make up the 3 1/2 games they trail in the standings, they'd host the Wild Card game because of the tiebreaker edge -- and have gone 6-3 against both the Pirates and the Cardinals since the All-Star break. But that's an awfully small sample size.
How about this one? Over the last three seasons, the Cardinals have 283 regular-season wins, while the Pirates have 274. That ranks 1-2 in the Major Leagues.
You can see why they aren't going to politely step aside and hand the keys over to Anthony Rizzo and Kris Bryant.
While the Pirates have had the Cubs in their peripheral vision all season, it's the Cardinals they've been focused on. After going 1-1 in the win-or-go-home Wild Card games the last two seasons, they really, really want to avoid it altogether this year.
They had climbed within 2 1/2 games of the Cardinals before the Cubs arrived in Pittsburgh on Sept. 14, but now are 3 1/2 back, in part because the Cubs won the last three games in that four-game series. Chris Coghlan also took out Pirates shortstop Jung Ho Kang with a hard slide breaking up a double play, and while it was considered a clean play, you know that it hasn't been forgotten in the Pittsburgh clubhouse.
The Pirates head home to face St. Louis after the weekend series at Wrigley Field, but they aren't likely to get caught looking ahead. The Cubs, who have gone 31-14 since moving Addison Russell to shortstop, are guaranteed to have the full attention of everyone they play.
Along with the Mets, the Cubs and Pirates have had the most productive lineups in the NL since the All-Star break. Like the Cardinals, the Pirates have a significant bullpen advantage over the Cubs, who allowed Arrieta to throw 123 pitches to finish off his three-hitter on Tuesday rather than bringing in Hector Rondon or Pedro Strop. You have to think that Hurdle would have called on Mark Melancon, who locked down his 50th save on Thursday in Colorado.
Starling Marte has had a tough season, but returns to Wrigley Field hot after a 13-hit series, which tied Pie Traynor for the most by a Pirate. He and McCutchen, along with Neil Walker, Pedro Alvarez, Gregory Polanco and former Cub Aramis Ramirez, will be a stern test for the Cubs' pitchers, including Arrieta and Lester
Luckily for fans, if not hitters, all the big guns are lined up to pitch in the series.
Gerrit Cole, the Pirates' likely Wild Card starter, faces Lester on Friday, with Arrieta -- the best pitcher in the Majors since the All-Star break (10-1, 0.86 ERA in 13 starts) -- getting A.J. Burnett in the Sunday night finale. That game will present high drama if the Cubs win the first two.
Everything that happens will be a prelude to the one truly defining contest, the one on Oct. 7. It will hang over Wrigley Field like fog off Lake Michigan.