That's A Damn Good Question

Which 16-year dynasty reigns supreme: Patriots or Yankees?

The New England Patriots have defied nearly everything about the NFL, especially its insistence that championship-level teams get dragged back to the pack sooner rather than later. For 16 years they have outperformed and outsmarted a system built around parity and equal opportunity, inspiring fans to search for a modern equivalent in a different sport.

When it comes to all things New England, New York is the first and last place to look for a rival. And in this case, the 1996-2011 New York Yankees belong in the conversation with the 2001-2016 Patriots.

Scott Pioli/Nick Caserio vs. Brian Cashman

This is a tough one to call, given Belichick's final say in personnel. Both sides have had their hits and misses, though high-schoolers' eligibility makes pre-draft evaluations in baseball tougher. Pioli didn't succeed while running his own program in Kansas City but has bounced back to help another former Patriots staffer, Thomas Dimitroff, put the Falcons in the Super Bowl. (Caserio has yet to go out on his own.) Cashman gets credit for four of the Yanks' five titles (he was Bob Watson's assistant for this first one), for weathering Boss Steinbrenner's storms, for flying solo in New York for such a long time and for transitioning to a promising Yankees youth movement without suffering a losing season along the way. He has had significant financial advantages over his football counterparts and, for the most part, he has taken advantage of them. Edge: Yankees

Kraft vs. George/Hal

Kraft made it to seven of his eight Super Bowls in the designated 16-year period, and the Steinbrenners made it to seven of their 11 World Series in theirs. George Steinbrenner is best-known as a founding father of free agency, even as an impetuous owner who twice got himself banned from baseball, once for life (though he was later reinstated). Whereas Torre had to manage Steinbrenner's personality in the post-suspension phase of George's reign, Kraft has been the one to soften Belichick's rough edges, accept his quirks and give him the requisite space to lead as he sees fit. Kraft saved the Patriots from moving to St. Louis in the 1990s and then found his sweet spot as an owner after feuding unnecessarily with former coach Bill Parcells. Steinbrenner could be an obstacle between the Yanks and winning. But for the Patriots, two years ago, when Kraft marched into New England's first Super Bowl news conference and set a defiant and helpful Deflategate tone for the week, Kraft removed an obstacle between the Patriots and ring No. 4. Edge: Patriots
 
(ESPN.com)