As you know, it’s been a pretty interesting week for the Dawg Pound. Cleveland set sail on several of its top evaluators while bringing in a new GM, Andrew Berry, who, though highly regarded, was also part of a previous unsuccessful Browns regime.

Berry, 32, gets the unenviable task of turning around a team that has missed the playoffs 17 straight seasons and has had only two winning seasons since it was reconstituted in 1999. The problems are various and substantial. However, I see three as most pressing.

  • One of the head coaches on the sidelines Sunday, San Francisco’s Kyle Shanahan, was Cleveland’s offensive coordinator five seasons ago. Until Dec. 31, the Browns’ GM, John Dorsey, was the man who built the other team, the Chiefs. Meanwhile, Green Bay went to the NFC Championship game with a defensive coordinator, Mike Pettine, who was Cleveland’s head coach as recently as 2015. None of them got more than two years in Cleveland. Why in the world would a talented coach or executive come to Cleveland?
  • The GM prior to Dorsey, Sashi Brown, was tasked with making analytics front and center in Cleveland. He tried without success, and his reward was getting unceremoniously dumped after just two years. Meanwhile, the presumed architect of all things analytical, Chief Strategy Officer Paul Depodesta, remains. Is Berry going to have the flexibility to experiment until he finds the right mix? Will DePodesta allow that?
  • I get it that, more and more, you better have instant results to last more than a year in the NFL. Still, during the ownership of Jimmy Haslam, five head coaches have had at least one full season. Just oneHue Jackson — got more than two years. Meanwhile, Berry is the fifth GM Haslam has hired. Not one of them so far — not Michael Lombardi, Ray Farmer, Brown or Dorsey — has gotten more than two seasons. That’s high-octane dysfunction.

At the end of the day, I think Berry’s biggest obstacle will be trying to satisfy an owner that doesn’t know what he wants. Berry has a five-year deal, but most certainly won’t live to see the end of it unless he either (a) has immediate success or (b) is able to convince Haslam that it’s a big job turning around an NFL team, and it doesn’t happen overnight.

Today, for our Friday Wrap, we asked dozens of NFL scouts what they think Berry’s toughest job will be. We got several meaty responses, and we’ll present them today at 6:30 p.m. CT when the Wrap goes out to thousands of people across the industry (and you, if you register here).

Meanwhile, you can let it be known your feelings on which of the three issues is the biggest in our Twitter poll, which you can access here. We’ll continue accepting responses until late this afternoon. Please vote!