For the purpose of keeping this grounded in some sense of reality, this won't be a list of simply the best head coaches. That list would be ludicrous. This will just be those head coaching candidates that are free agents or will likely be very soon. We will start from the most dreamy and work our way down from there.
Ah, yes, the Oakland Golden Boy. The beloved "one that got away". The man who every Raider fan sees in their dreams on Christmas Eve night in place of sugar plums. Good ole "Chucky" is the last great Raider coach. He wasn't the last to take them to the Super Bowl but when the Raiders got there, he was waiting on the opposite sideline to teach them it was not a good idea to photocopy the same playbook he used while he was there. He was the Phoenix that rose the Raiders from the ashes in the late 90's and back to glory. His juggernaut team came within a Tony Siragusa belly flop one year and a tuck rule snow job the next of reaching the Super Bowl. Then his and Al Davis' egos clashed and he was traded to the Buccaneers for a first round pick. Now bygones are bygones and the door appears to be cracked for his return to where it all began.
"The Chin" has been that guy who most teams would drop their current head coach in a hot second if he were to put his name back in the ring. He left on top and he is still relatively young (55). He would command instant respect from his team as well as any prospective coordinators. He spent 15 years as the head coach in Pittsburgh and has an outstanding career record of 149-90-1 over that time. He has one Super Bowl, 2 conference championships, and 9 division championships in that time.
Reid's time in Philadelphia is really more of a case of needing a change in scenery than anything. He has been the Eagles' head coach for 14 seasons. In that time, he has put together a 130-91 record with 7 division championships, and one trip to the Super Bowl. His Eagles team made the playoffs nine times under him, reaching the NFC title game five times. Reggie McKenzie knows him because Reid was an assistant coach in Green Bay during McKenzie's first few seasons in the Packers' front office. Reid, much like Cowher, would command a great deal of respect from his many years as a successful head coach. And with Ron Rivera likely out in Carolina, Reid could very well ask for him to join him as Raiders defensive coordinator. Rivera was Reid's linebackers coach for five seasons from 99-03.
Whisenhunt has had a raw deal of late in Arizona. He began his coaching career there in Kurt Warner's third season with the team. Whisenhunt's arrival turned that franchise around. After ten straight losing seasons, they were 8-8 in his first season. They were a playoff team in his second and third season with the team. It was their first playoff appearance in over ten years and it was the team's first back to back winning seasons since 1984. But Warner retired three seasons ago and since then, the quarterback situation has been a mess. First it was Derek Anderson, then a combination of Kevin Kolb, John Skelton, and other less qualified fill-ins. He actually rode that combination to an 8-8 record last season. But this season the team is back to being a losing team and Whisenhunt's time in Arizona could be up. He might just make some lucky franchise very happy.
He was a hot name on the coaching market last offseason and ultimately turned down the chance to leave Oregon for the pros. He will be courted aggressively again this offseason with many teams hoping to capture the kind of speed and domination that he has engendered with his Oregon Ducks. Some believe he will opt to stay at Oregon for now because he is still holding out for that elusive National Championship. He lost to Cam Newton and Auburn in the National Championship two seasons ago and a late loss to Stanford this season kept the Ducks out of the Championship game this year. He knows with Marcus Mariota at quarterback, the sky's the limit for the Ducks and he may opt to stay to lift that crystal football before he heads to the big stage of the NFL. Then again, he could strike while the iron is hot and make the switch following the Ducks trip to the Fiesta Bowl.
Dennis Allen must be on this list. He is still the head coach and signs point to him remaining the head coach next season. He was a hot commodity last offseason when the Raiders hired him. He wasn't some obscure signing no one else wanted. He was the choice of Reggie McKenzie and a budding young coach in the eyes of the NFL world. Having him return would give the Raiders some continuity. Many people are angry with the "regression" of the team and have asked for his untimely release. That is the way of Al Davis. He wanted progress and instant results. Going from 8-8 to what could be 4-12 would have been unacceptable to him and it would mean starting over again with another new head coach. McKenzie appears willing to let his new head coach have some leeway to build the team and struggle during the rebuild. That measured approach could pay off. No way to know without letting it play out. As hard as that might be for Raiders fans who are used to "Off with his head!" philosophy each year.