Or was the best team architect the man who dramatically overhauled his roster and oversaw an amazing worst-to-first transformation? In that case, your pick would be World Series-winning Red Sox GM Ben Cherington, who last week was named the Sporting News' Executive of the Year.
"Obviously, you think a lot about winning. You think a lot about getting into the postseason and doing well in the postseason," Cherington said at the annual General Managers Meetings in Orlando, Fla. "That's something we talk about all the time, and think about all the time, and work toward all the time. Thankfully, we were able to do that this year. And when things like that happen, other things come along with it."
Cherington might be the frontrunner for the Executive of the Year GIBBY Award. But there are plenty of other worthy options to choose from, and fans can vote to help influence the outcome.
This year's postseason clubs are well-represented on the list of finalists. Detroit's Dave Dombrowski, Cleveland's Chris Antonetti, Atlanta's Frank Wren, Cincinnati's Walt Jocketty, Pittsburgh's Neal Huntington and the Los Angeles Dodgers' Ned Colletti round out the list.
Major League Baseball's A-listers will take home 2013 GIBBY Awards -- the ultimate honors of the industry's awards season -- based on votes by media, front-office personnel, MLB alumni, fans and the Society for American Baseball Research.
This year's GIBBY Awards feature nominees in 22 categories. Individual honors will go to the MLB MVP, in addition to the year's best starting pitcher, hitter, closer, setup man, rookie, breakout hitter, breakout pitcher, comeback player, defensive player, manager, executive and postseason performer.
GIBBYs also will be awarded for the year's top play, storyline, hitting performance, pitching performance, oddity, Cut4 topic, regular-season moment and postseason moment, from MLB.com's Must C highlight reels.
In the past five years, fans have cast more than 50 million votes across the various GIBBY categories, none of which was restricted to individual league affiliation. Fan voting runs through Dec. 1.
Winners will be presented their GIBBYs at the MLB.com Greatness in Baseball Yearly Awards extravaganza during the Winter Meetings next month in Orlando, Fla.
As Cherington recently pointed out, there's more behind being Executive of the Year than simply making the right moves in the offseason or pulling off smart Trade Deadline deals.
"I consider this to be an award for the organization, not for me," Cherington said of the TSN honor. "I also sort of see it as usually an organization that does work over a period of time, not necessarily one year."
Cherington fits the bill, having shed $264.7 million in salary in one massive trade, made in 2012 with an eye on '13. He filled out his roster with shrewd offseason pickups like Mike Napoli, Shane Victorino, Stephen Drew and Koji Uehara. Boston won 97 games, finished first in the American League East and rolled on to a World Series championship.
The GM on the other side of that huge trade last year was Colletti, who turned the Dodgers into the National League West champs. Los Angeles acquired Adrian Gonzalez, Carl Crawford and Hanley Ramirez in mega-deals last year before signing Zack Greinke and Hyun-Jin Ryu in the offseason and adding starter Ricky Nolasco before the July 31 non-waiver Trade Deadline.
But the NL's best team belonged to Mozeliak, whose Cardinals won 97 games and finished atop the highly competitive NL Central en route to the pennant. What's more, St. Louis has won primarily with a roster of homegrown talent, particularly its lights-out pitching staff.
Huntington's Pirates weren't far behind the Cardinals in the division, and the way Pittsburgh snapped its 20-season playoff drought may have been the story of the season. Huntington put together an impressive homegrown core, but he bolstered that with veteran players like Francisco Liriano, A.J. Burnett, Justin Morneau and Marlon Byrd.
Let's not forget the Reds, who secured 90 victories and made the postseason for the third time in four years. For that, and for picking up leadoff man Shin-Soo Choo and his incredible on-base ability, Jocketty deserves consideration.
Rounding out the NL contenders, there's Wren and the Braves. Wren was tasked with replacing Chipper Jones over the offseason, and his big trade for Justin Upton and batting title runner-up Chris Johnson went a long way toward doing that. Atlanta finished with 96 wins and ran away with the NL East crown.
When it comes to roster turnover, Friedman may be the best in the business. The Rays won 92 games -- as always, on a small budget -- and made the playoffs for the fourth time since 2008. They relied on homegrown young players, low-cost signings like James Loney, quiet trades like the one that brought in Yunel Escobar, and major trades for prospects like AL Rookie of the Year Wil Myers.
Beane and the A's might still be the industry standard for small-market success. Oakland and its "Moneyball" architect won 96 games and took home a second straight AL West title despite having one of the game's lowest payrolls.
Another one of baseball's most respected executives is Dombrowski, whose Tigers franchise has reached the postseason in three straight years for the first time since 1907-09. With a tough lineup from top to bottom and an untouchable starting rotation, Detroit won 93 games and finished atop the AL Central.
Antonetti's Indians weren't far behind the Tigers, however, winning 92 games and securing an AL Wild Card berth. Cleveland reached the postseason for the first time in six years thanks to a crew assembled through big offseason signings like Nick Swisher and Michael Bourn, and under-the-radar additions like Scott Kazmir and Ryan Raburn.