Found November 20, 2012 on Awful Announcing:
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Like clockwork, the yearly rumors of Jon Gruden's departure from the ESPN booth to coaching are starting up in full force once again.  In 2012, the sheer number of reports and rumors circling around Gruden have been more voluminous than ever before.  (Putting to doubt the "exclusivity" of that exclusive five year contract Gruden signed with ESPN, naturally.)  Everyone with a league source from the NFL to Pop Warner has Gruden returning to coaching next year. It's becoming more and more clear that Gruden will leave the ESPN booth sooner rather than later.  If this is indeed the last days of Gruden's ESPN tenure in the Monday Night booth, ESPN is already planning a successor.  From Richard Deitsch at Sports Illustrated, the leading candidate appears to be Trent Dilfer... "So what happens if Gruden bolts at the end of the season? SI.com contacted a half-dozen ESPN staffers on Sunday and Trent Dilfer appears to be the leading in-house candidate to replace Gruden. Steve Young would also get consideration.  "I'd actually be surprised to hear that Steve would want the job," said an ESPN staffer who has worked with both Dilfer and Young. "I'm pretty sure Trent wants it." [...] Dilfer served (perhaps endured is the better word) as the analyst alongside Chris Berman for the Chargers-Raiders season opener, and he also worked the Monday Night Football season-opening doubleheader in 2011. He's considered a rising star by ESPN's NFL production executives. Both Dilfer and Young are cerebral broadcasters, but Dilfer is thought to be the better fit in the booth as a game analyst. If Gruden goes, Dilfer would be a smart fit. He has a bigger long-term upside than Gruden because he's already willing to be critical of coaches and players when the situation calls for such transparency." Trent Dilfer would be a better fit than his MNF postgame counterpart Steve Young in the broadcast booth, but Dilfer didn't particularly impress me in his one appearance earlier this season.  Granted, Dilfer was working with Chris Berman, but he used a few bizarre analogies and generally got caught up in Berman's antics. Dilfer's smart, you can tell he knows what he's talking about, but the way he comes across on screen has never resonated with me.  Maybe it's a personal preference more than anything and he'd blossom working next to a pro like Mike Tirico.  At least with Dilfer, you'd be getting an analyst that would tell it like it is without showering unconditional love on everyone who moves to protect his possible return to the league that has been the hallmark of Jon Gruden's career. It's unfortunate that "this guy" and Gruden's effusive praise will be what he's most remembered for as an analyst.  His work at the QB camps and NFL Drafts were really good, but he couldn't quite make that next critical leap as a game analyst.  Instead of really developing into an elite analyst, Gruden has always protected his return to coaching. Honestly though, the best option for ESPN moving forward in a hypothetical post-Gruden world is Gruden's former analyst partner for multiple years - Ron Jaworski.  Jaws has the experience, the pedigree, and the talent.  He was moved to the studio to make room for Gruden this season, but it's clear ESPN and Monday Night Football would be better off with Jaworski in the long haul.  Nobody can break down X's and O's better for television viewers than Jaws. If Gruden does leave his media career behind, it's Ron Jaworski that should get the call to fly solo in the Monday Night Football booth.  Maybe that's the decision that should have been made all along. [Sports Illustrated]
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