CHICAGO – JANUARY 21: Virginia McCaskey, team owner of the Chicago Bears and her son Michael McCaskey receive the George S. Halas trophy from Hall of Fame running back Tony Dorsett and Terry Bradshaw following the Bears 39-14 against the New Orleans Saints during the NFC Championship Game January 21, 2007 at Soldier Field in Chicago, Illinois. The Bears won 39-14. (Photo by Jonathan Daniel/Getty Images)Ever since her father’s passing in 1983, the only daughter of legendary Pro Football Hall of Famer George Halas, Virginia Halas McCaskey has served as the Bears’ principal owner—at least in name.There are a lot of different McCaskey in the kitchen that is the Bears’ front office, but the chairman, George H. McCaskey, is the one ultimately calling most of the shots…
And… let’s just say that it doesn’t typically go well for him or the rest of the McCaskey clan.
The Bears—despite inhabiting one of the largest metropolitan areas and serving one of the largest markets in the game, with a diehard fanbase to boot—are regularly run like a mom-and-pop shop!
The McCaskey’s entire family fortune is tied up in the team, so they don’t have the financial flexibility that some of the other owners around the NFL—many of which are backed by massive groups with significant resources—do.
And the folks in charge in Chicago continue to make the same boneheaded mistakes year in and year out.
It does look like they are starting to turn the page ever so slightly with the latest regime that they put in charge of football ops… but… I don’t know. The Bears definitely have some of that Cowboys – what can go wrong, will go wrong – to them, and it feels like we are just waiting for the shoe to drop on this latest iteration of the team.
And all of that dysfunction and the subsequent shortcomings tie back to the failings of the ownership group!
Best – Art Rooney II, Pittsburgh Steelers
MIAMI GARDENS, FLORIDA – OCTOBER 23: Owner Art Rooney II of the Pittsburgh Steelers walks on to the field prior to the game against the Miami Dolphins at Hard Rock Stadium on October 23, 2022 in Miami Gardens, Florida. (Photo by Eric Espada/Getty Images)
The Rooney Family is synonymous with the Pittsburgh Steelers organization—and really the wider NFL brand as well. Art Rooney Sr. founded the Pittsburgh Steelers in 1933. Initially named the Pittsburgh Pirates, the team was, as we know, later renamed the Steelers to reflect—you guessed it—the city’s deep ties to the steel industry.
The team struggled in its early years, but once Rooney Sr. Hired Chuck Noll to lead the team on the sidelines, everything changed. They won four Super Bowls in six years and became the model of consistency—something that has lived on as the team has been handed down… First, it was to Dan Rooney, and now, it is Art Rooney II.
The Steelers have remained one of the most stable franchises in the NFL, known for their consistent performance and long-term coaching tenures—and they have done more than their fair share of winning.
You can tell when you hear Steelers players, present and former, talk about Art in the media, how impactful his presence on the team is.
Worst – Jimmy Haslam, Cleveland Browns
HOUSTON, TEXAS – JANUARY 13: Cleveland Browns co-owner Jimmy Haslam looks on prior to the AFC Wild Card Playoffs between the Cleveland Browns and the Houston Texans at NRG Stadium on January 13, 2024 in Houston, Texas. (Photo by Carmen Mandato/Getty Images)
The Cleveland Browns aren’t exactly the pinnacle of success in the NFL, but it is hard to argue that their fortunes haven’t somehow gotten worse since Jimmy Haslam purchased the team in 2012.
He is the prototypical “impulsive” rich-guy owner and his rash decision making has continued to cause issues for the team.
He fired Tom Heckert as General Manager and Pat Shurmur as head coach after taking over the team—instead hiring Michael Lombardi and Rod Chudzinski to assume those roles.
They make it all of one year.
The next duo, Ray Farmer and Mike Pettine? They make it two years.
This is just one example of a long line of terrible decisions made by Haslam. After all, we are talking about the guy that both drafted Johnny Manziel in the first round, reportedly overruling the player personnel execs in the front office AND put Deshaun Watson on that ridiculous 200-plus million fully guaranteed contract, the first of its kind after his fallout with the Houston Texans.
Simply put, this guy is just about as bad as it gets – and any success that the Browns manage to muster up in the coming years is in spite of Haslam!
Best – Jeffrey Lurie, Philadelphia Eagles
TAMPA, FLORIDA – SEPTEMBER 25: Philadelphia Eagles owner Jeffrey Lurie is seen on the field prior to a game against the Tampa Bay Buccaneers at Raymond James Stadium on September 25, 2023 in Tampa, Florida. (Photo by Mike Carlson/Getty Images)
After finally getting over the hump and capturing a long-awaited Super Bowl for the City of Brotherly Love, it became official… Jeffrey Lurie established himself as one of the best owners in the NFL.
Ever since his tenure began in the mid-90s, the Eagles have largely fostered a culture of success and stability within the Philadelphia Eagles organization.
Lurie’s success stems from his strategic approach to leadership and management. He has a keen eye for hiring the right personnel at the right time. Think about his decision to bring in head coach Doug Pederson and general manager Howie Roseman.
Both played pivotal roles in the team’s Super Bowl run.
Lurie has also managed to flexible and seems to know when to change course rather than go down with a bad idea for pride’s sake.
Eagles fans are tough to please… and I’m sure Lurie still has some haters out there… after all, Philly fans will hate on just about anything.
But between his experience, demeanor, and understanding of the game—he is easily one of the top five owners in the league, no questions asked.
Also Read: NFL Owner Calls Out His Entire Coaching Staff, Puts Them On The Hot Seat Entering The 2024 Season
Worst – David Tepper, Carolina Panthers
CHARLOTTE, NORTH CAROLINA – FEBRUARY 01: Carolina Panthers Owner David Tepper speaks with the media as the Carolina Panthers introduce Canales as their new Head Coach at Bank of America Stadium on February 01, 2024 in Charlotte, North Carolina. (Photo by David Jensen/Getty Images)
Since acquiring the team in 2018, Tepper’s leadership has been characterized by a lack of continuity and poor decision-making.
We aren’t just talking about the crazy decision to move up and sacrifice a boatload of valuable draft capital to take Bryce Young number one overall over C.J. Stroud, but, frankly—really basic stuff… like his inability to get along with other execs or his coaches.
Or his unwillingness not to pour drinks on his own fan’s head!
You are the owner of an NFL franchise, my man! Get it together!
Not to mention that this is a guy who is supposed to be some epic-deal-making financier, yet his failed practice facility project in Rock Hill, South Carolina, resulted in a massive loss for the organization and no practice site for the team!
Court documents say Tepper’s company — GT Real Estate Holdings — spent $282 million on the now-defunct facility and claimed it would take another $500 million to finish the project.
Tough.
All things considered, David Tepper might be one of the worst owners in the NFL today! His team has been terrible, and he has turned himself into a laughingstock!
Best – Steve Bisciotti, Baltimore Ravens
BALTIMORE, MARYLAND – NOVEMBER 16: Baltimore Ravens owner Steve Bisciotti looks before the start of the Ravens and Cincinnati Bengals game at M&T Bank Stadium on November 16, 2023 in Baltimore, Maryland. (Photo by Rob Carr/Getty Images)
Steve Bisciotti is easily among the top in the league when it comes to running a professional organization.
Off the field, Bisciotti is highly respected for his player-centric philosophy.
Year in and year out, he continues to invest in top-notch facilities and support systems for his most valuable asset, so much so that the franchise is regularly recognized across the league.
His commitment to creating a positive work environment has been instrumental in attracting and retaining top talent. It may sound like an HR software commercial, but it is the truth about the Baltimore Ravens organization.
Biscotti has created such a strong infrastructure and culture that players want to go there—and, more importantly—they want to stay there.
He has also proven to possess a great eye for management talent, namely head coach John Harbaugh and GM Ozzie Newsome, both of whom are tops in the league at their respective positions.
It is hard to do a much better job than Steve Biscotti… Once this team gets back over the hump and he lifts his second Lombardi Trophy—people will really start to put some respect on his name around the league!
Worst – Woody Johnson, New York Jets
DENVER, COLORADO – OCTOBER 08: New York Jets owner Woody Johnson looks on before the game against the Denver Broncos at Empower Field At Mile High on October 08, 2023 in Denver, Colorado. (Photo by Justin Edmonds/Getty Images)
Woody Johnson’s tenure as the owner of the New York Jets has been fraught with instability, poor decision-making, and cough cough. Tim Tebow!
Placing Johnson among the worst owners in the NFL is a no-brainer… Ever since he acquired the team in 2000, Johnson’s leadership… if you dare to call it that… has been abysmal.
This has resonated throughout the organization in numerous ways, including a lack of continuity, questionable management choices, and outright poor performance.
It has to be painful as a Jets fan to watch his erratic decision-making play out… Whether it was bringing in a bozo like Adam Gase to coach the team—and for some reason keeping him over everyone else when things went south… Or… Or failed “big-named” acquisitions like the Brett Favre deal or up until this point—the Aaron Rodgers trade.
Everything that Johnson touches seems to turn to trash.
And the Jets fans, passionate as they are—are one of the best groups out there at letting the world know exactly how they feel about their favorite team’s terrible owner.
Best – Robert Kraft, New England Patriots
LAS VEGAS, NEVADA – FEBRUARY 11: Owner Robert Kraft of the New England Patriots reacts before Super Bowl LVIII between the San Francisco 49ers and Kansas City Chiefsat Allegiant Stadium on February 11, 2024 in Las Vegas, Nevada. (Photo by Steph Chambers/Getty Images)
Robert Kraft is widely regarded as one of the best owners in the NFL, thanks to his transformative impact on the New England Patriots since purchasing the team in 1994.
Save the last few seasons post Tom Brady… his ownership turned the Patriots from a laughingstock to the model of sustained success and excellence in the league.
Kraft’s decision to hire head coach Bill Belichick away from the rival New York Jets in 2000 was a masterstroke, leading to an unprecedented era of dominance.
Together, Kraft and Belichick—and soon Brady—would build a dynasty spanning two decades, during which they won six Super Bowl titles and consistently competed at the highest level.
Kraft’s commitment to creating a winning culture extends beyond just the front office.
Over the years, he has invested heavily in state-of-the-art facilities and support systems, ensuring that players and staff have the resources they need to succeed.
Obviously, things aren’t quite what they used to be in Foxborough, but the fact that Kraft was able to have sustained success at the level he did for as long as he did is a marvel in and of itself!
It wouldn’t be right to publish a list of the top five owners in the NFL and leave him off… Not yet, at least! We’ll give him a few more years of grace while he tries to right the ship in New England!
Worst – Jody Allen, Seattle Seahawks
PORTLAND, OREGON – JANUARY 31: Jody Allen, chair of the Portland Trail Blazers, looks on during the game against the Milwaukee Bucks at Moda Center on January 31, 2024 in Portland, Oregon. (Photo by Steph Chambers/Getty Images)
Since assuming control of the Seattle Seahawks following her brother, Paul Allen’s, death in 2018, Jody Allen’s leadership has raised concerns about the franchise’s direction and future.
Despite once being regarded as one of the top organizations in the league operationally—the Seahawks have begun to lag behind other franchises in terms of player support systems and amenities, contributing to a less-than-optimal environment for players and staff.
Jody—or whoever she appointed to handle key personnel decisions—has also really struggled.
Say, for example, the abrupt firing of longtime head coach Pete Carroll and general manager John Schneider, who were instrumental in the team’s Super Bowl victory and responsible for a decade-plus long span of the best football that the organization had ever seen.
Obviously, the play on the field had started to decline in recent years, but that was largely due to the organization dysfunction and their inability to execute in the front office more so than Carroll’s ability to run the show on the field.
It is a tough state of affairs in the Pacific Northwest… Even the 12th Man, the moniker for the Seahawks’ generally extraordinarily passionate fanbase, has grown increasingly disillusioned with the team’s direction and the ownership’s inability to provide a clear path forward.
And unfortunately… there is no end in sight for the mess up there.