21. Duke Tobin/Mike Brown, Bengals
After nearly hacking the system with safe drafts and limited free agency adventurism, the Bengals have tumbled back to the bottom of the pile. The past four seasons have produced zero playoff appearances and a .328 winning percentage. With owner/GM Mike Brown not about to fire himself, the team’s options boiled down to “luck” or a change in philosophy. They got both this offseason. Brown finally opened the purse strings on the open market before accepting his gift of Joe Burrow at No. 1 overall. Brown even refused to trade A.J. Green, opting to set Burrow up for rookie success instead of bagging an extra pick or two. In theory, that was not a smart long-term move, but it could still pay dividends. A frightening number of otherwise talented quarterbacks fail to overcome early-career chaos. Burrow will have the supporting cast to build confidence right away. Going on 85, perhaps Brown is finally ready to stop holding himself back and embrace full-bodied roster building that relies not just on acing the draft, but actually spending a dollar or two.
22. Mike Mayock/Jon Gruden, Raiders
Jon Gruden is the man behind the curtain, but Mike Mayock’s first two drafts have been all over the map. Whereas No. 4 overall pick Clelin Ferrell was one of 2019’s least-impactful first-rounders, Josh Jacobs was one of the most. This spring, Henry Ruggs ably filled a need at No. 12, but like Ferrell before him, Damon Arnette was a jaw-dropping reach at No. 19. Elderly for a rookie (24), Arnette moves glacially slow for a corner, checking in with 4.56 wheels. Despite his advanced age, he “didn’t show up for some post-season meetings” at Ohio State. Mayock and Gruden sent similarly mixed messages in free agency, where they made Marcus Mariota one of the highest-paid backups at any position. Derek Carr needed to be challenged, but not by the worse version of Derek Carr. At the mercy of his hundredmillionaire boss, it is going to be difficult for Mayock to break through the noise in Vegas.
23. Steve Keim, Cardinals
The easy part — taking Kyler Murray — is over for Steve Keim. What comes next? As it turns out, it was drafting yet another defensive tweener in the first round. There is no reason Isaiah Simmons can’t be a star. The same was also true of previous Keim selections Haason Reddick and Deone Bucannon. That is to say nothing of the players who actually had positions, like Josh Rosen, Robert Nkemdiche and Jonathan Cooper. Shaky drafter or not, Keim still managed to win his second consecutive offseason, acquiring DeAndre Hopkins for the price of David Johnson and a second-round pick. He also snagged Kenyan Drake for a bag of footballs last October. Keim was just fine when he had an engaged Bruce Arians to drag him along. The core of Kliff Kingsbury, Chandler Jones, Murray and Hopkins may be ready to do the same thing.
24. Bill O’Brien, Texans
Bill O’Brien doesn’t lose confidence in his shot. Like J.R. Smith, he will never stop letting it fly. Also like Smith, he will need someone else to get him a ring. Whereas O’Brien is stodgy on the sideline, he is hyperactive in the front office. The man simply cannot stop making trades, treating draft picks like a credit card with no limit. So far, it hasn’t come back to bite him. With BOB in the ascendancy in personnel matters, the Texans have piled up 21 victories over the past two years. They have done so while shedding blue-chip talent, most egregiously a cost-controlled DeAndre Hopkins for David Johnson. BOB has managed to assemble a decent post-Nuk receiver corps, though it required surrendering a second-round pick for Brandin Cooks and paying 30-year-old Randall Cobb $27 million. BOB is clearly playing for the now, even though any well-thought-out “win now” plan would not involve trading DeAndre Hopkins. The Saints have found success living in the moment. With O’Brien, it feels like an 0-of-11 from behind the arc waiting to happen.
25. Jason Licht, Bucs
Jason Licht has three coaches and zero playoff wins to show for six years on the job. That he has yet to be pink slipped with that résumé is a remarkable act of front office survival. After attempting to build around 2015 No. 1 overall pick Jameis Winston, Licht has now resorted to the get rich quick scheme of 43-year-old Tom Brady. Licht needs Brady to accomplish things that have literally never been done before for the move to pay off. To Licht’s credit, he has put the weapons in place for Brady to do so. He also leveraged Brady’s arrival into a zero-downside acquisition of Rob Gronkowski. 2019 Licht stroke of genius Shaq Barrett is back via the franchise tag. The Bucs are not lacking for high-end talent. Licht desperately needs Brady to be the missing piece. If he’s not, someone else will be assembling the Bucs’ puzzle in 2021.
26. Dave Gettleman, Giants
Dave Gettleman finally ran out of big bets to make this offseason, instead settling into filling out a roster that is now quintessentially Gettleman. The first-round running back and high-risk quarterback prospect have been joined by a meat and potatoes left tackle, Andrew Thomas. Although he once again refused to trade down, Gettleman came out of the first two days of the draft with strong value. “Strong value” isn’t how anyone would describe questionable 2019 trade acquisition Leonard Williams on the franchise tag, but that is the kind of hog mollie luxury Gettleman can afford with Daniel Jones on his rookie contract. The same is true of CB James Bradberry, whom Gettleman drafted in Carolina and showered $43.5 million on in free agency. Despite Gettleman’s old school approach, his fortunes are decidedly modern. They live and die with Jones, who was plagued by turnovers as a rookie but supported by big plays. Season two will signal Jones’ future while sealing Gettleman’s.
27. Joe Douglas, Jets
Joe Douglas arrived in New York with a great reputation. He immediately set about letting Adam Gase tarnish it. Nothing has been more damaging than the Jamal Adams affair. The young defensive cornerstone took great offense to his placement on the trade block last October. Douglas insisted he was never made available, but something got lost in the Gase translation. That is Douglas’ biggest problem. Gase feuds with far too many of his players, creating tricky front office situations and locker room landmines. Minus Gase’s numerous imbroglios, Douglas had a decent first offseason. No. 11 pick Mekhi Becton arrives with monstrous upside as the Jets’ left tackle of the future. The same is true of raw-but-explosive No. 59 overall pick Denzel Mims. Douglas committed to upgrading Sam Darnold’s atrocious offensive line, but the third-year pro still has far too few weapons. Darnold’s shaky setup and Gase’s never-ending intrigue are dangerous trap doors for Douglas. If he can make it out of 2020 alive, he will be on to something in the league’s toughest market.
28. Ryan Pace, Bears
When you are a general manager, you pass on great players. That is part of the deal. You would still rather be known for the picks you made than the ones you didn’t. So is life for Ryan Pace after he traded up for Mitchell Trubisky. As Patrick Mahomes and Deshaun Watson have ascended to the top of the NFL, Pace has tread water in the middle. His one year in the fast lane, 2018’s 12-4 campaign, brought Khalil Mack but mortgaged future assets. The Bears have been limited to just 12 total draft picks over the past two years, zero of which came in the top 40. That is no way to build a roster without a franchise quarterback. Things have scarcely been better in free agency, where Pace backed up the Brinks truck for 30-something veterans Robert Quinn and Jimmy Graham. A pass rusher coming off an 11.5-sack effort is one thing. But a tight end who looked dead legged for a division rival last season? Mystifying. Meanwhile, Pace neither spent nor drafted to address his troublesome offensive line. Even for the best GMs, building a roster is more art than science. Through six years, Pace has yet to paint a pretty picture.
29. Dave Caldwell, Jaguars
Dave Caldwell has been a part of seven rosters in Jacksonville. They have won more than six games once. In a league where good men get sent packing after one bad year, Caldwell has somehow survived six of them. There are alibis, of course. A stone-aged Tom Coughlin spent the past three seasons poisoning the well, focusing on things like how an injured Leonard Fournette stood on the sideline. How bad was Coughlin? By the time he was fired in December, over 25 percent of grievances filed by the NFLPA were against the Jaguars. “You as players may want to consider this when you have a chance to select your next club,” the union warned in a memo. Caldwell wasn’t going to be able to overcome that. It’s just unclear why the Jags didn’t make a clean break, sending Caldwell and coach Doug Marrone packing along with Coughlin. Most of Caldwell’s biggest calls — Luke Joeckel, Blake Bortles, Dante Fowler — were duds. The Jags’ Coughlin-influenced drafts of 2017-19 were bad. One of Caldwell’s best decisions, selecting Jalen Ramsey, went down in Coughlin flames. Basically, if Caldwell was so good, why did the Jags big foot him with Coughlin? A team that was crying out for a fresh start will instead try to back the Jeep out of the mud one final time.
30. Bob Quinn, Lions
Do you have strong feelings about Bob Quinn? Does anybody? Where are the impact players? Where is the plan other than cycling through people Bill Belichick allowed to walk in free agency? Why was Jim Caldwell fired after back-to-back 9-7 seasons only to be replaced by Belichick’s least impressive mini-me, Matt Patricia? Nothing has gone right for Caldwell since his Patricia galaxy brain, with Patricia proving more adept at chasing off talent (Darius Slay, Quandre Diggs) than cultivating it. Not that Quinn has been killing it. His 2017 first-round pick, Jarrad Davis, just had his fifth-year team option declined. Quinn continues to overinvest in the running game. To a comical degree — Trey Flowers, Duron Harmon, Justin Coleman, Danny Shelton, Danny Amendola and literally eight others — Quinn only seems interested in ex-Patriots on the trade and free agent markets. How about instead of co-opting someone else’s identity, you create your own? This is the Detroit Lions. It’s going to take a big thinker to turn things around. Quinn only seems capable of copying someone else’s thoughts.
New Hires (Alphabetical Order)
Andrew Berry, Browns
The Browns’ latest savior briefly got away. Andrew Berry traded up from Browns vice president of player personnel to Eagles vice president of football operations in 2019. The 33-year-old has been lured back as the league’s youngest general manager. Each of Berry, chief strategy officer Paul DePodesta and coach Kevin Stefanski will report separately to owner Jimmy Haslam, which doesn’t seem like the best way to set Berry up for success, but this is the Browns after all. A Harvard alum with a bachelor's in economics and master's in computer science, Berry arrives lab-created for a modern GM. It won’t be the first time in Cleveland. The trick is achieving some sort of harmony with the rash and imperious Haslam. Berry had a strong first offseason, addressing last year’s season-ruining offensive line by signing Jack Conklin and stealing Jedrick Wills at No. 10 overall. He found draft value all down the board. Berry needs time. He would be the first to get it under Haslam.
Ron Rivera, Washington
Underappreciated for much of his nine-year tenure in Carolina, Ron Rivera has been rewarded with the league’s most thankless job. It would be one thing if Rivera merely had to man the sideline for a franchise that has won one playoff game in the 21st century. He also has to fill the power vacuum in the front office and clean up owner Daniel Snyder’s myriad off-the-field messes. How exactly is this man supposed to focus on football? More importantly, why does Washington want his focus elsewhere? Personnel was never Rivera’s forte in Carolina. As they have learned the hard way in Washington, a toxic culture will ruin everything. Rivera is the man for that job. Actually assembling the football team that has to go out there and play games? Your guess is as good as Washington’s.