
His methods regarding the NFL salary cap are being monitored
The word “loophole” is derived from thin slits that were built throughout the stone walls of castles. The openings provided enough space for an archer to shoot arrows out of without being hit by the castle’s attackers. The top of the opening was a long narrow slit for vision while the bottom had a round hole for the arrows, called a loop which means “to encircle.”
The context of the word today means “to take advantage of something already there.”
One famous loophole that was implemented was the way to circumvent “Raine’s Law” during the 1920s. The New York law stated that on Sundays, restaurants and saloons could not sell alcohol unless food was purchased at the same time. To exploit this, the establishment sold the customer a sandwich to go along with his beverage of choice, then took it away after one bite, and then sold the same sandwich to the next customer. Using this system, a few sandwiches would often last an entire day, without any rules or laws being broken.
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Cleveland Browns GM Andrew Berry has shown he is a master of manipulating the NFL’s salary cap. Often, he will place future contract money and convert it into a signing bonus, to which the player receives his funds anyway, and it does not affect the salary cap as much and his use of void years has been used as an example around the NFL.
Having Jimmy Haslam’s money to throw around is very helpful in this process.
Take Myles Garrett’s new contract extension. It includes reasonable salaries for 2025 and 2026, then pays the star defensive end a $29.2 million option bonus that kicks in 2026 and over $39 million in 2027.
Breakdown of DE Myles Garrett’s contract extension with the Browns https://t.co/fqnX0Wsl7r
— Dawgs By Nature (@DawgsByNature) March 20, 2025
The league is intrigued by Berry’s math and may be interested in doing something about it.
During the owner’s meetings held recently in Minneapolis, NFL commissioner Roger Goodell spoke about the league’s future and mentioned possible reforms to the financialization of the salary cap. The NFL’s current Collective Bargaining Agreement (CBA) was ratified in 2020 and expires after the 2030 season.
Goodell stated:
“The two areas that we spent time on were really the cap system itself, the integrity of that system, how it’s working, and where do we need to address that in the context of collective bargaining, when that does happen. That was a very lengthy discussion.”
A lot has changed since the 2020 season. For one, the schedule has added a 17th game, and the league is moving towards adding an 18th contest. This year, there will be 16 international regular-season games as the current CBA only allows for 10 per year. Costs keep rising, including team operations. New stadiums and new practice facilities are being discussed.
Teams are worth billions.
If you think about what Goodell has hinted at, the owners appear to be unhappy with the current split of revenue between players and ownership. With the salary cap now at $279.2 million per club, there are some ownership groups that believe they are spending too much on player salaries.

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Right now, there is peace between owners and players. But, if nothing else, the league seems to have placed the NFLPA on notice that changes are on the horizon, and the method used for the salary cap will change.
Goodell explained:
“There are no formal plans on any discussions. We obviously continue to be in close communication with the union on a variety of matters, but no start of negotiations have been set or are under consideration really at this point. We did spend time today talking, at length, about areas of our Collective Bargaining Agreement that we want to focus on.”
Goodell has identified several clubs that the league has stated their front offices skirt around the current salary cap, which gives them an advantage. Are there loopholes? Or should this be construed as creative mathematics instead?
The Browns are certainly in Goodell’s sights.
Berry uses several inventive methods that aren’t exactly textbook in regards to the cap. As previously described, signing bonuses as well as the conversion of contract funds into signing bonuses are Berry’s favorite ploy. He will also dabble in voidable years, which will maximize its year-to-year financial outlook.
But none of these tactics are against league financial rules. Yet.
Today, NFL clubs make a ton of money. A huge chunk comes via TV contracts, which have expanded to streaming services. The league looks at revenue sources from every angle.
When the new CBA comes up for negotiations, it will most likely be messy. A team like Cleveland will be affected the most because it has exposed loopholes that nobody else considered or pursued. If the league changes its financial rules, the Browns and Berry will have to adjust.
Now, if the franchise could only figure out how to be that successful on the field.