6 NFL Coaches Who Tried Playing General Manager and Destroyed The Roster

by Jeremy Block - 7/31/2026

NFL coaches who tried playing GM and destroyed the roster Chip Kelly

Usually, most NFL teams run smoother when the head coach actually focuses on coaching and leaves roster management to someone else. The second an owner hands a head coach the keys to the personnel department, franchises can set their watch for disaster. First-round picks vanish into thin air, All-Pros get dealt for pennies on the dollar, and washed-up veterans get handed bags of cash because they played well for the coach six years prior.

By the time ownership realizes their head coach has no idea how to evaluate talent or manage a salary cap, the franchise is already set back half a decade. Here are six NFL coaches who tricked their owners into giving them full GM authority and immediately torched the team.

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Mike Ditka, New Orleans Saints (1999)

In 1999, Mike Ditka decided he wanted Texas running back Ricky Williams so badly that he treated the Saints’ draft capital like a stack of casino chips. Ditka somehow convinced Saints ownership to trade away their entire 1999 draft class, plus their first and third-round picks in 2000—just to move up to the fifth spot and grab Williams. Eight draft picks for one player—and he wasn’t even a quarterback. Think about that for a second.

Then came the iconic magazine cover of Ditka and Williams posing as a bride and groom, which proved to be the peak of the entire experiment. Williams ran for 884 yards as a rookie while the depthless Saints finished just 3-13 on the season. Ditka got fired right after the season, leaving New Orleans trapped under a mountain of draft debt while Washington rode those picks all the way to the bank. Williams eventually became a star, but mostly in Miami—making Ditka’s one-man draft night stunt one of the most hilariously reckless executive moves in NFL history.

Bill O'Brien, Houston Texans (2019-2020)

When Houston gave GM Brian Gaine the boot in the summer of 2019, they handed Bill O'Brien full administrative control, forgetting that roster construction requires actual strategic planning. O'Brien immediately went on a roster-wrecking tear that felt like season mode in Madden.

He kicked things off by shipping pass-rusher Jadeveon Clowney to Seattle for a third-round pick and two backups—Jacob Martin and Barkevious Mingo. Yeah, that actually happened. Keep in mind, Clowney was coming off a 38-tackle, third-consecutive Pro Bowl selection season. Next, O’Brien decided to dump two first-rounders and a second-rounder to Miami for tackle Laremy Tunsil.

The crazy thing is, it didn't stop there. He out-did himself in March 2020, when he traded DeAndre Hopkins, arguably the best wideout on Earth at the time, to Arizona for a broken-down David Johnson and a second-round pick.

While Hopkins led the NFL in catches during his first year in Arizona, Johnson recorded just 4.7 yards per carry in Houston. O'Brien was fired just four games into the 2020 season after an 0-4 start, leaving behind a gutted Texans team trapped under zero cap space and no draft picks.

Chip Kelly, Philadelphia Eagles (2015)

Who can forget Chip Kelly’s infamous run in Philadelphia? Kelly spent his first two years putting up back-to-back 10-6 records, and owner Jeffrey Lurie was so impressed that he stripped GM Howie Roseman of his authority prior to the 2015 season and handed Kelly the keys to the kingdom. Big mistake.

Having already cut Pro Bowl receiver DeSean Jackson the previous spring, Kelly used his new GM power to dismantle what was left of an already playoff-caliber roster. In a single off-season, he traded All-Pro running back LeSean McCoy for an injury-prone linebacker Kiko Alonso, flipped Nick Foles for Sam Bradford, and dumped Pro Bowl guard Evan Mathis. To replace his stars, he handed big-money contracts to DeMarco Murray and cornerback Byron Maxwell (who couldn't even cover a blanket).

Kelly thought he had all the answers, but he was completely out of his wheelhouse. The Eagles collapsed to 6-9 before Kelly was booted out the door before Week 17. Roseman was immediately pulled back into the GM chair, scrubbed the roster clean of Kelly’s mistakes, and built a Super Bowl champion just two years later.

Jon Gruden, Oakland Raiders (2018)

When Mark Davis handed Jon Gruden a 10-year, $100 million deal to come out of the Monday Night Football booth in 2018, Gruden made it clear he was running the whole show. He quickly pushed out GM Reggie McKenzie, traded away McKenzie's best draft picks, and eventually replaced him with TV draft analyst Mike Mayock.

Gruden’s first order of business? Trading away Khalil Mack, a former Defensive Player of the Year and the beating heart of the franchise, right before Week 1 of his first season. A few weeks later, he sent wideout Amari Cooper to Dallas for a first-rounder without even telling his players—leaving many of them to find out by checking Twitter after practice.

Gruden then used his free agency budget to load up on washed-up veterans who were stars during his first coaching stint in the late '90s. By the time Gruden resigned four years into his decade-long deal, he left behind a 22-32 record and a roster that had to be completely blown up all over again.

Mike Shanahan, Washington Redskins (2010-2013)

Dan Snyder handed Mike Shanahan total control of Washington's football operations in 2010, hoping a two-time Super Bowl winner would fix decades of losing. Instead, Shanahan orchestrated one of the most toxic eras in franchise history.

The main disaster came in the 2012 draft trade for Robert Griffin III, where Shanahan coughed up three first-round picks and a second-rounder to St. Louis just to climb up to the No. 2 spot. Griffin took the league by storm as a rookie, sure, throwing for 3,200 yards his rookie season, but the relationship between Shanahan and his superstar quarterback took an immediate nosedive.

Shanahan then left Griffin injured on the field during a 2012 playoff game until his knee completely buckled, sparking an ugly, public feud that tore the entire organization apart. Shanahan spent his final months leaking stories to the press and battling with his locker room before getting fired with an ugly 24-40 record—leaving Washington with no draft picks and a broken franchise quarterback.

Hue Jackson, Cleveland Browns (2016-2018)

Hue Jackson somehow talked Cleveland ownership into giving him the reins over roster decisions during a full franchise rebuild, and the result was by far the most miserable two-year stretch any Browns fan has ever been forced to watch. Jackson went 1-31 over his first two seasons, including an 0-16 season in 2017.

Jackson’s roster input forced Cleveland into a hilariously bad game of quarterback musical chairs, cycling through Robert Griffin III, Cody Kessler, Kevin Hogan, and DeShone Kizer. The dysfunction didn’t stop there; at the 2017 trade deadline, Jackson tried to trade a 2nd and 3rd round pick for Bengals backup AJ McCarron, only for Cleveland's front office to “accidentally” fail to file the paperwork in time to stop him.

When he wasn't throwing his quarterbacks under the bus during postgame press conferences, he was waging a passive-aggressive war against GM Sashi Brown. After Brown got the ax, new GM John Dorsey drafted Baker Mayfield No. 1 overall in 2018, but Jackson spent eight games ripping into his rookie QB before finally getting fired.

Jackson immediately joined the Bengals coaching staff, and spent his post-firing media tour claiming ownership incentivized him to lose—which is a bold call for a coach who went 3-36-1 and blamed everyone else for his dumb decisions.

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Start:	July 31, 2026 @ 10:10 PM
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6 NFL Coaches Who Tried Playing General Manager and Destroyed The Roster

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