Pretty sure they only own him like 11.5M.
The rest of his cap hit has come from all the previous years of reworking his contract.
If they tagged him, I don't think it would be quite $20M. Pretty sure the tag numbers are based off the top 5 base salaries and there's only 1 QB who has a base salary of $20M. Looks like it would be closer to 14M.
http://www.spotrac.com/top-salaries/nfl/quarterback/
So he's really only looking at having $25M in play for this season and next season.
If I had to guess what the hold up would be, it would be the structure of the contract and not the dollar amount.
I'm just guessing but I think Dallas is probably looking at more backloading than Tony or his agent would be comfortable with at his age. He really only has maybe 2-3 years before we have to wonder when he might slow down a little and that might be a little optimistic.
If his base salaries for the next 2 years are pretty low and his base salaries in the final 2 years are really high to where Dallas gets significant cap relief by cutting him, I think he'd be selling himself short by agreeing to it.
Lets take 5 years, $80M as a hypothetical example. SB of $4M per year leaves $60M in base salaries (not gonna work with roster bonuses or anything like that) that needs to be accounted for.
Code:
Base Salaries By Year (Cap Hit) [Dead Money]:
2013: $3M ($7M)
2014: $6M ($10M)
2015: $13M ($17M) [$12M]
2016: $18M ($22M) [$8M]
2017: $20M ($24M) [$4M]
On a deal like this he would make $23M in year 1 when including his SB and he'd make another $19M over the next two seasons if he stayed with the team. With $4M per year in dead money for each year that he doesn't play, you can pretty much be assured that he's going to make it through 2015. The team would only see about $5M in cap "savings" by cutting him before 2015 and you probably won't be able to win a bidding war for another QB in free agency while having his cap number be just $5M.
In total, he'd make about $42M in the first three years of the contract but that's about all he could reasonably be sure that he'd see. I doubt he's going to decline in 2013 to a point where cutting him is an option and even a bad year in 2014 would be written off as a down year. Combined with minimal cap relief, he'll be on board for 2015.
In 2016 however, the team would get about $14M in relief by releasing him and he wouldn't see that $18M in base salary and at 36 years old and sitting in the position of being cut it's unlikely he could get a contract that would be anything close to paying that much.
This would be my guess of the sticking point. How the numbers are structured. He'd be a fool to settle for a contract that is really "cap friendly" up front because it means that it is "cap unfriendly" on the back end which ultimately puts him in the position of needing to get the team deep into the playoffs or into a Superbowl or he's going to be cut.
I've said it before that players who shoot for the moon on contracts are idiots. Nate Clements, DeAngelo Hall, and I'd even say Flacco. Just idiots. I don't think there's any chance in hell that Flacco sees year 5 of that contract unless the total cap space available goes way up. Outside of a 4 game stretch, that guy hasn't been anything close to a $20M cap hit QB and in year 5 he's gonna count for $31M of cap space? IMO, he'd have to play as well as he did during the playoff run for like 3 seasons in order to warrant that kind of cap hit. I think that's impossible so I don't see him getting beyond year 4, if he makes it there. Cutting him would provide cap relief after year 3, albeit a small $3M but getting $3M in space is a lot better than paying $28M for a player who isn't worth it.
With that said, I don't think he sees 1/3rd of that money. I'm skeptical he makes it to year 4 which means he'd get about half overall. Players that accept these contracts put the burden on themselves to be great. For year four and at a cap hit of $28M, Flacco better be the best damn QB in the NFL or as Ric Flair would put it, he better be "The Man".
People say Tom Brady took some sort of discount and I don't necessarily agree. I think he actually did the smartest possible thing he could do and that is pretty much guarantee that he sees the end of his contract, provided he stays healthy and wants to play. His cap hit this year of $13.8M is 1.2M less than his highest cap hit over the span of $15M in 2017. At $15M, Brady doesn't even have to be the best QB in the league to be worth the cap space. It's likely he doesn't even have to be Top 5 at his position to be worth the cap space. Even if he was 75% of what he currently is, he's still better than more than half the league. If healthy and he wants to play he'll see the end of it because he hasn't backed himself into a corner where he better be Godly in order to justify his cap hit. His cap hit is pretty much constant from here on out. The team won't have to factor in some giant increase and his cap hit is very reasonable.
I suppose if you take a stab at what his total amount could have been he might be giving a discount. He probably could have gotten $100M but playing out the remainder of your career and making $70M is a hell of a lot better than playing 3 years and only coming out with $50M, sitting on the market as a 40 year old player.
For this very reason I think Romo would be wise to take a lesser overall deal that has a little more in guaranteed money. It makes his cap number far more reasonable, makes his dead money less likely to provide cap relief if he were cut which means the team is less likely to cut him and it gives him an opportunity to reach the end of the deal and realize the total amount of the contract.
If you look at the 5 year, $80M with $20 in SB and assume he was cut after year 3 he would ultimately end up with just over half of that contract. In total $42M.
Lets look at taking less total and a little more in guarantees. I'm just gonna say 5 years, $65M with $25M in SB that looks like this.
Code:
Base Salaries By Year (Cap Hit) [Dead Money]:
2013: $5M ($10M)
2014: $7M ($12M)
2015: $9M ($14M) [$15M]
2016: $9M ($14M) [$10M]
2017: $10M ($15M) [$5M]
In this case, he'd make $30M this year and $16M over the next 2 seasons. That's $4M more than he would make on the 5 year, $80M contract but it comes with the benefit of not putting himself in a position where his play absolutely has to justify his 4th year cap hit. It also puts him in a position where the team gets very little cap relief by cutting him before the 4th season. On the more total money contract, the team sees relief of $14M on top of a cap hit of $22M. On the lesser overall contract the team only gets $4M in relief and is only faced with a $14M cap hit.
Even if he played out the 4th year, I think he'd be hard pressed to keep up production to warrant his cap hit on a backloaded contract and ultimately would be cut at the age of 37. There'd he be, free agent at 37 years old and having only earned $60M of his total $80M contract. This opposed to playing out the 5th year and earning the total $65M that he signed for. All the while the team can plan for his cap hit to remain relatively steady and won't be forced to deal with a huge spike 2-3 years down the road.
I've said it for a while, I think players who go for every last dollar they can get are absolutely stupid. Think of all the giant contracts that have been signed by Haynesworth, Clements, DeAngelo Hall (Oakland) and some others and think of how many actually played those things out. DeAngelo Hall is a prime example. He signed for so much in Oakland and like an idiot had so little money guaranteed that when they cut him like a couple of months into the contract he basically shorted himself tens of millions of dollars. Nate Clements signed for $80M but from the looks of things he only came away with a little over $30M after only playing 4 years. Compare that to Hall who signed with the Commanders after 2008 and while having signed for $25M less he walked away with $6M more at the conclusion of his 4 year stint with the Skins.
The trade off for all those eye-popping numbers is a lack security. When you shoot for the moon, you better be able to justify the big fat cap numbers that come a couple years down the road or else you're out the door because your small guaranteed amount couldn't save you. When you start thinking in a realistic fashion and take significantly less overall money with a greater amount guaranteed, then you've increased your chances of hitting those last couple years where your base salary is likely at it's highest but is also at a reasonable amount that gives the team a cap hit that is both justifiable and manageable.
When you're cut after a few seasons because your cap number is too high, you aren't getting another crack at a big contract. You're taking way less and ultimately you lose out.
IMO, Romo and Dallas would be best served to sign a reasonable contract with a good amount guaranteed, allocate the cap space as evenly as possible and enjoy the next 5 years.