Contrary to Popular Opinion: Five NFL Transactions That Won't Work Out

Illustration by Thomas Dyson

There are trades, and then there are TRADES. There are free agent signings, and there are FREE AGENT SIGNINGS.

Sometimes a team needs to fill a couple of spots of need. Sometimes a team needs depth at a position. These moves are necessary, even if they are not existential.

Sometimes moves are quantum leaps, like trading for Matthew Stafford or Micah Parsons, or signing Sam Darnold or Saquon Barkley.

We have seen some transactions this offseason that are going to really change some franchises and make them more competitive. Note the Chiefs signing Kenneth Walker (what was Seattle thinking?) or the Rams signing Trent McDuffie (or maybe the Rams signing the other Chiefs cornerback, Jaylen Watson, was even more genius).

The rich got richer. And Jaylen Waddle to the Broncos? That could be the most impactful move of the offseason and could change everything in the AFC.

But some trades and signings are not going to work out, no matter how much press or excitement there may have been surrounding those transactions.

Here are the top five flops, in no particular order.

Baltimore Ravens Sign Trey Hendrickson

Yes, I agree that this may have made more sense than going through with the Crosby trade. Hendrickson is slightly less expensive and did not cost the Ravens any draft picks, especially two first-round picks.

Hendrickson, at 31, has recorded 14 or more sacks in three of the five years he played for Cincinnati. In the other two years, he did not reach double-digit sacks.

Here is what is going to happen. Hendrickson is going to get hurt fairly early in the season. You can feel it coming for Baltimore. I would guess he will be injured within the first eight games. He will not have double-digit sacks, he won’t be around for the playoffs, he won’t stop the run, and he won’t be worth $30 million a year.

It isn’t that he has had a terrible injury history—it is just that he is going to start having one, and he is going to do it on Baltimore’s dime.

Miami Dolphins Sign Malik Willis

As a Bears fan, I can tell you that Malik Willis is dangerous. Subbing for Jordan Love several times in 2025, Willis can really move with his legs, and his accuracy can be absolutely soul-crushing at times, even if his overall stats don’t fully reflect that.

I definitely believe that Willis deserved a starting role, but it is a gamble given that he has thrown just 155 passes in four years. If you surround Willis with playmakers, you have the recipe for a very good offense that could contend for a playoff spot in a very difficult AFC East division. At $22 million a year, Willis is a steal if it works out.

However, the Dolphins went the opposite direction. They released Tyreek Hill, and they traded Jaylen Waddle. Now this feels like a stopgap solution while they rebuild the entire franchise, including the defense. It feels like Willis is there to keep the team serviceable until they find their playmakers and their next franchise quarterback. Willis is the fall guy.

Tua might not have been the answer for the Dolphins, but if you are going to tank the next several seasons, do you do it with $99 million in dead money from releasing Tua (plus more from Waddle)?

We’ll see how it works out, but from a fan perspective, this doesn’t put the Dolphins or Willis on the road to success. Putting an unproven quarterback in charge of a rebuild is a disaster scenario. Willis could have done wonders in Atlanta or Pittsburgh.

New England Patriots Sign Romeo Doubs

New England made it to the Super Bowl last year, and maybe that moment was just a little too big for Drake Maye. However, he is a real franchise quarterback who nearly won MVP last year.

He probably should take fewer sacks.

But that is not the point. In almost Chiefs/Bills/Mahomes/Josh Allen fashion, he willed his team to the championship game without a rock-star supporting cast. Let’s face it—Eddie Van Halen needed David Lee Roth, and Keith Richards needed Mick Jagger.

And Drake Maye needed Romeo Doubs? That just doesn’t sound like the same league. If New England had grabbed A.J. Brown, Michael Pittman Jr., or even Mike Evans, that could have created real fireworks. The Bills grabbed DJ Moore—that was a big move. Stefon Diggs was starting to look like his old self (85 receptions, over 1,000 yards), and off-field issues aside, he could have been even more productive this year.

As Eddie Murphy would say, the Patriots needed a Ritz, and they got the same old crackers. They needed Randy Moss, and they got Doubs.

Doubs is solid, averaging around 700 yards and maybe 55 catches per year. Those are not WR1 numbers. But that is not what the Patriots needed. If they don’t make other moves this offseason, this starts to sound like the Bills’ offseason story over the last few years.

Houston Texans Sign David Montgomery

The Texans have been on the verge of joining the top echelon of the NFL for a couple of years now. The defense is absolutely loaded and looks formidable against any offense. The receivers are a handful (when healthy), especially with Nico Collins, Tank Dell, and now Christian Kirk.

C.J. Stroud is a good quarterback. Some consistency would be nice, and a return to rookie form would be great. But the talent and experience are there.

Running back was a key issue last season and a missing piece to make the Texans a complete team. Joe Mixon was a great fit, but he was out all last year, and apparently the Texans have lost confidence in him. Is David Montgomery the answer?

I don’t think so. Montgomery can still break tackles, catch passes, and is excellent at the goal line. But is he going to grind out 100 yards every game?

No.

In fact, he probably hasn’t been that guy for a year or two. I always believe a player’s former team knows things we don’t (see Dalvin Cook or Kirk Cousins). They let Montgomery go because he wasn’t going to perform the way they needed. Even if he and Jahmyr Gibbs made great music together at one time, it looks like that band is breaking up. Gibbs is going solo.

Montgomery is destined to be the player who has a few great games each year but mostly averages just over three yards per carry.

What’s worse is the cost to the Texans—a lineman and two draft picks. That’s a hefty price that likely won’t pay dividends.

Kenneth Walker or Travis Etienne was probably the better call.

Las Vegas Raiders Sign Tyler Linderbaum

If the rich got richer, the poor continue to stay poor. I could have nominated every move the Jets made this offseason (see Geno Smith). I could have also called out the Chiefs signing Justin Fields. If Mahomes misses time, should the Chiefs just forfeit?

But instead, I’ll pick on the Raiders.

The Raiders needed a lot this offseason, including an offensive line, wide receiver help, and defensive upgrades.

Yes, center is an important position, and there was a run on centers this offseason. Getting the best one was always going to be competitive and expensive. But did you have to pay 50% over market value? It didn’t seem necessary.

Instead, the Raiders spent most of their cap space on defense. Not a terrible strategy—but they needed to upgrade the offense as well.

If the plan is a multi-year rebuild, I get it. But not saving money for a quality receiver or additional offensive line help feels like negligence.

The Raiders will likely draft a quarterback in round one and fill other holes, but those are always risks.

They may have a great center, but the cost—$27 million per year—could create major cap issues when they need to invest in a WR1 or left tackle.