The club lost eight of nine games. Kenney and Hendry, in their adjacent offices at Wrigley Field, began questioning.
"Should we have done something different?" Kenney said. "What about this? What about that? Should we have done something at the [Trade Deadline]? Ultimately, we've just got to turn it over to manager Lou [Piniella]. He either gets us there, or he doesn't."
Piniella and the players allayed their fears by locking up the National League Central on Saturday. A management team led by Kenney and Hendry in ties and Piniella in uniform was as big of a reason for back-to-back division titles as the 25-man roster they put together.
"It's Jim, it's me, but really it's everybody," Kenney said. "This is my sixth year, this is the best organization, from Lou to the coaching staff, from [vice president of player personnel] Oneri [Fleita] to the development league, Jimmy bringing [assistant general manager] Randy [Bush] in. It's allowed Jim not to take every road trip with the team and stay back and work on things like getting Jimmy Edmonds. It really is a collective effort."
It starts at the top with Kenney, who continues to juggle day-to-day duties with the weight of selling one of baseball's most storied franchises. To his credit, he's kept the two separate and not let the uncertain future of ownership affect the current club.
He's got another duty now, locking up Hendry, who's signed through this year, and Piniella, who's under contract through next season.
"I'm going to keep teeing up good decisions for the organization long-term," Kenney said. "Really, Lou and Jim are no different than the players. They're talent for the organization. We should do smart, long-term arrangements for them. Ultimately, it'll be me teeing it up, and a new owner possibly saying yes or no. But Jimmy deserves an extension, and so does Lou, in my opinion."
Hendry has made magical moves. Center field could have been a black hole with the early struggles of Felix Pie. Hendry found diamonds in the rough in Edmonds and Reed Johnson, whom their previous teams gave up on.
"People thought it was a gamble," Kenney said of the Edmonds signing. "But when you know the player, it's not a gamble with Edmonds."
While Milwaukee buzzed over a deal for CC Sabathia, Hendry countered by acquiring Rich Harden from Oakland without dealing a top-line prospect. He likes the group he put together, and not only because of the on-field performances.
"I just felt good about them as a group all year -- I never heard any selfishness, Cy Youngs, All-Star Games, batting titles, nothing," Hendry said.
Fleita worked wonders in the Minor Leagues. Dominating setup man Carlos Marmol was once a catcher. All-Star catcher Geovany Soto was once a third baseman. Fleita urged both position switches.
Then there's Piniella, who, at 65, hasn't lost his winning attitude. He made it work with Ryan Dempster and Kerry Wood switching places. He's moved Mark DeRosa around the field and the batting order with success everywhere. When high-priced right fielder Kosuke Fukudome struggled, he wasn't afraid to bench him.
"The credit for these guys this year is that, from the beginning, people picked us," Kenney said. "We basically went wire to wire. I think that's harder than coming in under the radar."
The next step for the front office is to make these celebrations routine. With this group, that's not too much to ask.
"I've told Jim Hendry this, I've told Crane Kenney this, this team here should dominate the National League Central the way the Yankees and the Red Sox have dominated the American League," Piniella said. "That's not to take anything away from the teams in our division, because they're all good, competitive teams, and they've got good ownership, and they're well managed. But we're a big city. There's no reason why our team here can't be in this position for a long time to come."
Nick Zaccardi is an associate reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.