OK, well Bill Callahan went to the same superbowl with the team that Jon Gruden built (And Jon Gruden totally outcoached him in the game of 'borrowed teams'). And by the way, that Raider team he built was one of the 2 or 3 elite teams in the AFC for several years. (And if not for the infuriatingly dumb 'tuck rule', he may have gotten to a superbowl with them, himself)
There might be a 1st time, but it won't be Gruden. 1, His players don't like him. Tuna and Bellicheater break their players balls, but their players would lay down in traffic for them 2, He won with Dungy's team and has not won a playoff game since 3, He's failed to develop a qb 4, His last 5 drafts have been downright disappointing 5, His offenses have been in the lower half of the league for 6 straight years So I do think it can happen, but it's a lot more likely to happen for Cowher, Homgren, or Shanny
1) A) This is very speculative in nature. B) Stuff like this always comes out when things are going bad. Bellicheat and Parcells both have had plenty of players who didn't like them. It didn't mean those same players didn't bust their asses for them. 2) True, but he also built a superbowl calibur team in Oakland (one of the elite teams in the AFC for several years) and he EASILY could have gotten to several superbowls with them, himself, if it weren't for A) the moronic tuck rule and B) The Ravens 2000 defense (Remember his Raiders hosted that vaunted defense in the 00-01 AFC Championship game and lost 16-3 after Tony Saragusa knocked Rich Gannon out of the game in the 2nd quarter) And, by the way, his 'borrowed team' kicked Bill Callahan's 'borrowed team' all over the field in that Superbowl. He earned that SB ring fair and square. 3) Bruce Allen was the General Manager and deserves AT LEAST half of the blame for not drafting a young QB besides Chris Simms. (Who looked like he might be pretty good until he injured his neck) 4) See # 3. 5) He has consistendtly had one of the least talented offenses in the NFL. Again, the General Manager's name is Bruce Allen, NOT Jon Gruden. As for coaches not being able to win a second championship with a second team . . . It would have happened with Holmgren already but the refs totally screwed him with awful call after awful call going against his Seattle team against the Steelers in the Superbowl. (If that game is officiated correctly, the Seahawks beat the Steelers that day and Holmgren has a second superbowl championship with a second team, while big ben and Cohwer have nothing)
Would I rather have a 45 year old coach who has won a Super Bowl or another coordinator with no head coaching experience at any level above Aussie semi-pro? Hmm, let me think about that for a minute.
I would love to see John Gruden come to NY and whip our boys into shape both mentally and physically. Unfortunately we have ZERO interest in him for some unknown reason.