There's no guarantee that either of these guys wins a single ring -- this could be a 1 to 0 edge when all is said and done. Not a slight to either talented youngster -- that's just the truth. Forced to choose one, though, I will go with Derek Carr. I considered three factors in my decision-making process:

**1)** Who is the best QB? [Derek Carr](/player/derekcarr/2543499/profile) wins that at this point.

**2)** Who has the best head coach and staff? I will call that even.

**3)** Which organization has done the best job obtaining players? Clearly, both teams have done well here, but I will give the [Raiders](/teams/oaklandraiders/profile?team=OAK) the edge.

Carr and the Raiders win two of my three categories, so the Oakland QB gets my vote. But everyone in the entire league will have to wait for Bill Belichick and Tom Brady to hang it up! The Cowboys are better constructed to have a long, sustained run of success. They have a spectacular second-year running back in Ezekiel Elliott and a young offensive line that's the best in the business. They are still adding pieces to the defense, but I'd like to think that, as this team continues to build around Dak Prescott, Dallas will have a 5-to-7-year run.

When I look at Oakland, most of the major players are already in their prime and I don't know how much longer that can go. With the exception of Amari Cooper, everyone on offense is older. I just think Dallas is better prepared to have a long run, so I'm going with Prescott. I really like both of these players, but I have to side with family. I do hope it's close, though. Something like: Derek 8, Dak 7.

In all seriousness, Derek and the Raiders have the edge right now because they have game changers on both sides of the ball -- with a number on offense and Khalil Mack on defense. With Dallas, I don't see a defensive player right now who can change the outcome of a game. Until the Cowboys get someone who can, I'm giving the one-ring edge to Derek. To appropriately answer this question, one needs to look at the surrounding team and situation, not just the quarterbacks. While the Raiders look like the more likely contender for 2017, with blue-chip players on both sides of the ball, those players ( Derek Carr, Amari Cooper and Khalil Mack) will all need massive new contracts in the near future. Those paydays could hamper the front office's ability to help the team get over the hump. Meanwhile, Prescott is costing the Cowboys pennies, allowing them to make a run at top free agents in the coming years.

So while I expect both to make it to the big game, Prescott might have the better shot at multiple rings. The fact Dak and Derek are so talented and so young is kind of a scary prospect. Not for opposing NFL franchises, but for us mere mortals who no doubt will have to deal with Raiders and Cowboys fans for the next decade. Not only are there tons of them (especially here in Southern California), but they often aren't shy about letting you know that their team is doing well. (Especially when you consider fans of both franchises are likely Warriors fans, too. Raiders supporters, obviously, for geographical reasons. Cowboys backers, for front-running reasons.)

So, yeah. I was stalling. Because it's really tough to figure out an answer to this question. I mean, it's so hard to win a Super Bowl. And, at times, somewhat random. I mean, jeez, Brad Johnson and Trent Dilfer are Super Bowl quarterbacks. Dan Marino is not. Peyton Manning was carried to a Super Bowl 50 victory by a great defense. So it's not always on the quarterback. And yes, I'm stalling right now because I'm really having a tough time trying to reach a decision here. I like both quarterbacks. I feel like Derek will have many battles with Marcus Mariota to represent the AFC in future Super Bowls. Dak will be going up against Jameis Winston.

Give me Derek. Mostly because I don't want Cowboys fans to be happy. Am I incredibly biased? Yes. But at least I'm up front about it. Who'll end up with MORE rings? Sorry to be a curmudgeon, buzzkill or otherwise, but at this point, either guy oughta be thrilled at the prospect of winning even ONE ring. You see, while it's quite easy for talent evaluators to declare on draft day a QB will win "multiple titles," the inconvenient reality remains this: There's only ONE Super Bowl-winning quarterback each calendar year. (That means at least 31 other QBs finish the season disappointed.) Assuming a high-end NFL QB plays a decade-and-a-half, that ring math says his chances of winning it all figures to be ... problematic.

None of the above is intended to diminish Carr, Dak or any of the other ring-less QBs. It's just that winning a Lombardi is hard, Trent Dilfer notwithstanding. After the Patriots' reign of terror over the NFL's 31 teams comes to an end, it will be the Raiders' turn to torture the league. Derek Carr showed the football cognoscenti he can play like an MVP candidate with a receiving duo that includes 23-year-old Amari Cooper.