The NFL's five toughest contract extension talks of the summer

It took a while for Jordan Love. No, we’re not talking about the three seasons from 2020-22, when he mostly sat on the bench behind Aaron Rodgers, stewing in a special brand of frustration that is now apparently reserved for all Packers star-quarterbacks-in-waiting.

We’re talking from Week 11 last season (Nov. 19) to the evening the Packers were eliminated from the playoffs on Jan. 20 when Love was – get ready to gasp – the NFL’s best quarterback.

What else to call the guy who apparently “got it” after all those years on the bench and delivered 23 touchdowns and three interceptions in leading the Packers to the postseason, and a playoff win before being eliminated in the divisional round?

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That notable stretch did it for the Packers. It convinced them they have a budding franchise quarterback on their hands.

And now they have to pay Love like it because he’s in the final year of his contract and wanting an extension.

Negotiations between the sides are expected to reach a conclusion before the start of the regular season and probably even before that. The sides aren’t really leaking information on the topic, which suggests all is on course.

(Trade secret: Leaks typically come when one party or the other is dissatisfied).

But being on course and being easy are two different matters. This Love contract negotiation isn’t easy because while Love was, as you just read, arguably the best quarterback in the NFL late last season, it is a very small sample size.

So the sides have to come to agreement on potential more than past performance.

That’s what makes some of the big contract extensions currently being negotiated so tough at times. They typically involve outstanding players with outstanding agents negotiating with very good teams.

So it’s not just about whether a guy is good anymore. We know they’re good. But are they going to be great?

And it’s not just about being great. Because they also must be great in big games.

Oh, and, it’s also not all about being great in big games, but the contract numbers typically being discussed here have to deliver championships.

So some of these negotiations with big-name players who are undoubtedly very good get undoubtedly very prickly. Love’s looming deal is like that. And here are more:

QB Dak Prescott: Both sides are saying all the right things. Prescott went so far recently as to state, “I don’t play for money,” and that he’s never cared for it. This while his representatives are trying to make him the NFL’s highest-paid quarterback.

The Cowboys, meanwhile, are saying they have no expectation of losing Prescott, which they must know is indeed possible via free agency next year if he doesn’t sign an extension. So it seems this should be easy and get done. 

But it isn’t done. And cannot be easy because the Cowboys have this lingering question about what Dak Prescott they’re getting? Are they getting the guy who led the NFL with 36 TD passes last year? Or the guy who has struggled in the playoffs, including in a loss to Green Bay in the wild card round last season? 

What should happen: It would be a huge surprise if the sides simply agree to let it all play out and do a deal when Prescott either balls out or bombs next postseason. But there is so much danger involved in that course – such as Dallas losing its QB or Prescott getting hurt and going to free agency injured – that cooler heads will prevail, and an extension should be done by the first week of September. 

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WR CeeDee Lamb: The Cowboys would have been wise to get this done already because the longer they wait, the higher the price has gone and it may go higher. If they had signed Lamb to an extension that averages, say, $30 million per season to make him the highest paid wide receiver along with Tyreek Hill back in March, the Cowboys would have actually saved money. 

They could have avoided the $17.9 million cap charge currently on their books for 2024, and they could have avoided the price hike for a top receiver that A.J. Brown has brought with his extension, which averages $32 million per year.

What should happen: Dallas should pay. The draft is over and they don’t have a better receiver on the roster. A trade would not likely give them a better player at the position, unless they’re trading for Jefferson. And, by the way, if a Jefferson deal gets done before Lamb, that will also drive up the price for Lamb. So the Cowboys should do a deal. 

QB Tua Tagovailoa: I was the first to report the Dolphins and their quarterback were working on an extension that would “easily” surpass $50 million per season on an annual average – and some Dolphins fans just about lost their minds.

Except that’s exactly what is still going to happen barring a total collapse in negotiations, in which case Tagovailoa will play on his fifth-year option. But an extension will definitely be over the $50M annual average threshold. 

That is dangerous because Tagovailoa is good. But he hasn’t been great in that he’s 4-8 against playoff teams the past two seasons and, generally, he’s part of the problem in those losses. 

What should happen: The Dolphins have to pay. They’ve committed to him publicly and to ownership. There is no available backtrack by management that says we changed our minds. And the going rate for QBs who deliver 28-30 TDs in a season and are among the completion percentage and ratings leaders is, well, somewhere on the $50 million plateau. 

It could work or backfire. But that’s the spot the Dolphins have put themselves in.

WR Brandon Aiyuk: He’s had two outstanding seasons back-to-back and that means he should probably be among the top 10 highest paid receivers because those years came with new QB Brock Purdy in the lineup and the future is bright.

But …

The 49ers have a ton of highly paid players already, including fellow receiver Deebo Samuel. The Niners have to find a way to thread the needle on a fair reward for Aiyuk and not have Samuel get upset and demand a raise if he has a better year in 2024.

(Yes, this happens in the NFL).

The other thing is, even with Aiyuk, the Niners have fallen short of winning it all. And they just drafted a potential replacement in Ricky Pearsall. Aiyuk, meanwhile, has no compunction about going elsewhere if he doesn’t get what he believes is the right deal.

So lots of leverage on all sides.

What should happen: Look, sometimes players have to move on. Aiyuk can be dynamic, but he’s not Tyreek Hill or Justin Jefferson or perhaps even Lamb. So maybe he has to hit the market to see that he would slot in behind those guys while the 49ers get another draft to replace him.

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