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The Succession Plan of the Dallas Cowboys
Looking down the road and wondering if there is light at the end of the tunnel.
BOB STURM
JAN 31, 2024
There will come a day when the Dallas Cowboys are no longer overseen by Jerry Jones. Discussing someone running out of time on this planet is never a pleasant topic, but the reality, even for billionaires, is that there will be an end at some point.
When individuals depart from this world, the Earth continues its rotation on its axis, and life persists for everyone else. A succession plan is in place where these influential individuals pass on the leadership to the next in line. Often, as is the case with the Dallas Cowboys, this responsibility is handed down to the firstborn son.
Stephen Jones is on the verge of turning 60 and has been part of the organization since his father assumed control of the team in 1989. Every step he has taken thus far has been in preparation to assume control of the entire operation when the time arrives.
So, I am frequently asked a variation of the same question when discussing the Cowboys:
“Do you think things will be any different when Stephen is running this thing?”
And almost every time I reflect on it, my thoughts turn to the Chicago Blackhawks.
Bill "Dollar Bill" Wirtz served as the owner of the Chicago NHL franchise for over 40 years, and his tenure was far from successful. He embodied the classic old-school owner, notorious for driving away his best players over time due to relentless disputes over every last dollar. Whether it was Bobby Hull, Denis Savard, Chris Chelios, or Jeremy Roenick, the outcome was invariably the same – these players ended up in different uniforms.
He transformed a great hockey city into a much less desirable one. Infamously, Wirtz prohibited home games from being broadcast on Chicago television, effectively suffocating the fanbase. In the modern era, fans were compelled to resort to radio broadcasts, applying outdated methods from 1955 to the year 1995. It was sheer madness. For about 40 years, the city wondered if they would ever witness another Stanley Cup victory (a scenario that may sound familiar).
In 2007, Wirtz succumbed to a brief battle with cancer, and the franchise transitioned to his sons, particularly his son Rocky. Within less than a month of his father's passing, Rocky took immediate action by broadcasting all home games on television and actively working to regain the city's hockey interest. While the emergence of young talents like Jonathan Toews and Patrick Kane undoubtedly fueled the subsequent golden age of Blackhawks hockey, marked by Stanley Cup victories in 2010, 2013, and 2015, it was the son's endeavor to signal that the doors were now open.
Did the passing of the father trigger a renaissance? It is a somber and uncomfortable thought, but the timing appears too coincidental to dismiss any potential connection.
Now, let me clarify. That anecdote doesn't perfectly align here. The Cowboys are not lacking in fans and operate their business at an All-NFL level, effectively attracting customers to spend both money and time with them. The Cowboys and the Wirtz Blackhawks share little in common, aside from enduring long championship droughts and implementing a father-son succession plan.
However, considering the stark differences in how Bill Wirtz and his son viewed the world and how Rocky Wirtz demonstrated a clear vision for doing things differently, is it fair to ponder what changes Stephen might bring? I mean, didn't Stephen prevent his dad from drafting Johnny Manziel? Doesn't that suggest he's more adept at this?
While I'm unsure about Rocky Wirtz's visibility within the organization before his father's passing, we have distinct indicators of how Jerry and Stephen compare. Over the past decade, Stephen has taken on a more prominent role in various situations, and based on the evidence, I'd venture to guess that he'll be the sole candidate to succeed his father as the team's GM. I suspect he considers himself a "qualified football man" due to his lifelong involvement in the sport, akin to his father's background.
In my opinion, the most significant indicator of whether Stephen sees things differently than his father might be best assessed through the lens of Dak Prescott's contract. While I could use several other contracts to tell this story, the gravity of "spring 2024" and the alignment of various factors with that specific transaction prompt me to focus solely on it, despite Stephen's prominent involvement in other deals:
At the same time, we must be careful about making sure we don’t assign all of the blame for bad moves to Jerry and Stephen, while giving all the credit for good moves to guys like Will McClay who the public adores. I realize that is the game these organizations play so that nobody truly knows who wanted which move and should shoulder the blame, but it is tough to pin things down. Again, let’s just view this through the lens of Dak’s current situation.
HOW THE COWBOYS BOTCHED THE PRESCOTT CONTRACT
The Cowboys thrust Prescott into the role of opening day starter for his rookie season in 2016 out of sheer necessity. The team faced the loss of not one, but two different quarterbacks in the preseason, and neither replacement was anywhere near ready. Kellen Moore was sidelined for the entire year, and Tony Romo appeared to be out for at least two months. Faced with limited options and buoyed by Prescott's strong performance in the initial preseason, the Cowboys opted to take a chance.
Prescott delivered three consecutive strong seasons, establishing himself as a cornerstone player for Dallas by the end of 2018. This marked the first opportunity to secure a contract extension (in February 2019), and with a proactive and intelligent approach, the negotiation could have proceeded smoothly. However, no contract negotiations since Stephen assumed a more prominent role seem to have been straightforward, from my observation. I have three quick thoughts on this:
In December of 2018, I thought $20 million a year might cut it. It might have been laughed out of the room, but I thought the fully-guaranteed part might get their attention. At that point, it had never been done.
Instead, Dallas allowed him to play his 2019 with no extension and a contract that paid him $2.1m in 2019. In June of 2019, Philadelphia worked out an extension with Carson Wentz and in September of 2019, the Rams did the same with Jared Goff. They had a 5th year option for the 2020 season because they were 1st rounders and then built 4-year extensions for 2021-2024 with that flexibility and forward thinking. They even had a chance to use 2019 to spread the money out. In other words, they thought this through and made a smart decision – even if both QBs would be moved within 24 months.
In 2019, Dallas did absolutely nothing with Prescott and his future.
In 2020, they slapped him with a tag of $31.4 million and did absolutely nothing beyond that.
In 2021, they used the tag again which is a simple 120% of the first tag. That means it was 37.7m for that year. From there, they built a 4-year contract that was accepted and averaged $40 million per season.
By doing nothing for 24 months, they allowed the QB marketplace to explode from $25m per season to $40 million. Since 2021, it has gone from $40 to $55 million with Joe Burrow’s latest. Procrastination comes at quite a price.
Stephen was asked by my friend Pat Doney of NBC5 about his biggest mistake:
“Probably would have signed Dak the first time around…and it would have been better for everybody.”
No kidding.
(I added the following video after I published it the first time - This emerged last week from “About Them Cowboys” podcast from the Athletic) It is the story of Stephen on the phones during the draft and his lack of basic knowledge of the players in the league. I have checked on the story and believe it to be true. Again, I wish it wasn’t.)
(Now, back to our story as it was originally published:)
But, they got it done. Four years for $160m on March 8, 2021 it was agreed and signed.
I think most of us with math classes in our past can quickly see that this suggest he is to be paid $40 million a year for the next four years with more than three seasons guaranteed. I use AAV to demonstrate he now makes $40 million as nine newer contracts have raced past him and two more are his equal. We can say he is amongst the 12 highest paid QBs and belongs with those around him.
Which again, is the truth. Dak agreed to those numbers. Once he signs the deal and they pay him on time, how they account for that money against the league’s salary cap is completely up to Stephen Jones and his office.
This goes back to my analogy of paying rent on an apartment. If you work out a deal with your landlord on $1,000 a month, you can pay him $12,000 in January and nothing the rest of the year.
If he's amenable, you might consider paying him $12,000 in December and nothing else throughout the year. In theory, any agreement can be reached as long as he receives his $12,000 within that specific year. That's how the salary cap operates – you have the flexibility to smooth it to the average or simply pay it outright. Additionally, you can make payments without accounting for them, a strategy employed by Dallas with Romo and now with Prescott. This approach has, however, complicated their future decisions significantly.
As of now, Prescott has fulfilled 75% of his contract, yet Dallas has only accounted for 40-45% of his earnings against the salary cap. Despite having just one season remaining on his deal, which they have been contemplating since 2018, the cap accounting for 2024 is set to be nearly $60 million, with an additional $40 million in 2025. It's worth noting that this is a cap situation, not an issue of funds owed to Prescott (he already has the money).
So, when you hear that he has them painted into a corner, it is only partially true.
They cannot trade him (like Wentz or Goff) and they cannot tag him in 2025. I have no idea what they were thinking on those two provisions, but again, this contract has been bungled at every turn.
But, the other part? They held the paint brush the entire time! They did this out of their own thinking. That is how they did it with Romo – learned nothing – and are doing it again with Prescott. They have shoved so much money into ‘24 and ‘25 that they have closed off most escape routes in the event that they don’t think he is their QB to get them a Super Bowl.
Yes, they can help 2024’s cap without an extension. They can take a chunk (around $18 million) and push it into 2025, but the reality is that if 2024 is his last season here, they will face about $50 million in dead cap in 2025. Of course, if they extend him, they still have to account for the $40 million in 2025 ON TOP of a new deal that starts around $50m a year.
Does your head hurt more than your chest does right now?
The question we began exploring approximately 2,300 words ago centered on whether Stephen would fare better in this role than his father. This question often occupies my thoughts, reminiscent of the 2019 training camp where I heard Stephen discuss various matters, from Ezekiel Elliott's location in Cabo to Jaylon Smith's deal, Amari Cooper's situation, and the impending contract negotiations with Dak Prescott. Throughout these conversations, he frequently emphasized how "players need to accept their piece of the pie," seemingly convinced that there exists a universe in which players should willingly accept less for the greater good. This stance, however, contrasts sharply with the reality that Stephen himself has never compromised on any front and exhibits no intentions of doing so.
In attempting to negotiate with Elliott, Lawrence, Cooper, and Prescott, it appeared that Stephen's bluff was unsuccessful in each instance. Reports abound about not even engaging with these agents before crucial deadlines, highlighting a pattern that raises concerns about whether lessons have been learned and mistakes avoided.
While the resolution for Prescott remains uncertain, it is clear that they had the option to finalize the original deal sooner. Even if they didn't, they had the alternative of making timely payments, allowing them the flexibility to walk away with minimal dead money. Instead, they are left with a substantial $100 million to account for, severely limiting their strategic options.
Not only did they botch his first deal, but they did it in such a way that they might find the easiest solution is to do another one to fix it.
I used to describe the Jerry Jones Cowboys this way:
“Nothing ever changes because nothing ever changes.”
Now, I am actually wondering if the biggest change possible around here would even bring real change.
I wish I had better news, but when it comes to the biggest deals around here, they don’t seem to ever learn from their biggest mistakes.
Looking down the road and wondering if there is light at the end of the tunnel.
BOB STURM
JAN 31, 2024
There will come a day when the Dallas Cowboys are no longer overseen by Jerry Jones. Discussing someone running out of time on this planet is never a pleasant topic, but the reality, even for billionaires, is that there will be an end at some point.
When individuals depart from this world, the Earth continues its rotation on its axis, and life persists for everyone else. A succession plan is in place where these influential individuals pass on the leadership to the next in line. Often, as is the case with the Dallas Cowboys, this responsibility is handed down to the firstborn son.
Stephen Jones is on the verge of turning 60 and has been part of the organization since his father assumed control of the team in 1989. Every step he has taken thus far has been in preparation to assume control of the entire operation when the time arrives.
So, I am frequently asked a variation of the same question when discussing the Cowboys:
“Do you think things will be any different when Stephen is running this thing?”
And almost every time I reflect on it, my thoughts turn to the Chicago Blackhawks.
Bill "Dollar Bill" Wirtz served as the owner of the Chicago NHL franchise for over 40 years, and his tenure was far from successful. He embodied the classic old-school owner, notorious for driving away his best players over time due to relentless disputes over every last dollar. Whether it was Bobby Hull, Denis Savard, Chris Chelios, or Jeremy Roenick, the outcome was invariably the same – these players ended up in different uniforms.
He transformed a great hockey city into a much less desirable one. Infamously, Wirtz prohibited home games from being broadcast on Chicago television, effectively suffocating the fanbase. In the modern era, fans were compelled to resort to radio broadcasts, applying outdated methods from 1955 to the year 1995. It was sheer madness. For about 40 years, the city wondered if they would ever witness another Stanley Cup victory (a scenario that may sound familiar).
In 2007, Wirtz succumbed to a brief battle with cancer, and the franchise transitioned to his sons, particularly his son Rocky. Within less than a month of his father's passing, Rocky took immediate action by broadcasting all home games on television and actively working to regain the city's hockey interest. While the emergence of young talents like Jonathan Toews and Patrick Kane undoubtedly fueled the subsequent golden age of Blackhawks hockey, marked by Stanley Cup victories in 2010, 2013, and 2015, it was the son's endeavor to signal that the doors were now open.
Did the passing of the father trigger a renaissance? It is a somber and uncomfortable thought, but the timing appears too coincidental to dismiss any potential connection.
Now, let me clarify. That anecdote doesn't perfectly align here. The Cowboys are not lacking in fans and operate their business at an All-NFL level, effectively attracting customers to spend both money and time with them. The Cowboys and the Wirtz Blackhawks share little in common, aside from enduring long championship droughts and implementing a father-son succession plan.
However, considering the stark differences in how Bill Wirtz and his son viewed the world and how Rocky Wirtz demonstrated a clear vision for doing things differently, is it fair to ponder what changes Stephen might bring? I mean, didn't Stephen prevent his dad from drafting Johnny Manziel? Doesn't that suggest he's more adept at this?
While I'm unsure about Rocky Wirtz's visibility within the organization before his father's passing, we have distinct indicators of how Jerry and Stephen compare. Over the past decade, Stephen has taken on a more prominent role in various situations, and based on the evidence, I'd venture to guess that he'll be the sole candidate to succeed his father as the team's GM. I suspect he considers himself a "qualified football man" due to his lifelong involvement in the sport, akin to his father's background.
In my opinion, the most significant indicator of whether Stephen sees things differently than his father might be best assessed through the lens of Dak Prescott's contract. While I could use several other contracts to tell this story, the gravity of "spring 2024" and the alignment of various factors with that specific transaction prompt me to focus solely on it, despite Stephen's prominent involvement in other deals:
- The Dez Bryant extension fiasco of 2015
- The entire Greg Hardy journey
- The selecting of Ezekiel Elliott and Jaylon Smith in 2016
- Keeping Jason Garrett as head coach at least five seasons too long
- Drafting Taco Charlton over TJ Watt for ridiculous reasoning
- The top-of-market extensions of Ezekiel Elliot and Jaylon Smith in 2019
- Trading Amari Cooper for nearly nothing during the WR boom
- Misplaying the DeMarcus Lawrence contract disagreement badly
At the same time, we must be careful about making sure we don’t assign all of the blame for bad moves to Jerry and Stephen, while giving all the credit for good moves to guys like Will McClay who the public adores. I realize that is the game these organizations play so that nobody truly knows who wanted which move and should shoulder the blame, but it is tough to pin things down. Again, let’s just view this through the lens of Dak’s current situation.
HOW THE COWBOYS BOTCHED THE PRESCOTT CONTRACT
The Cowboys thrust Prescott into the role of opening day starter for his rookie season in 2016 out of sheer necessity. The team faced the loss of not one, but two different quarterbacks in the preseason, and neither replacement was anywhere near ready. Kellen Moore was sidelined for the entire year, and Tony Romo appeared to be out for at least two months. Faced with limited options and buoyed by Prescott's strong performance in the initial preseason, the Cowboys opted to take a chance.
Prescott delivered three consecutive strong seasons, establishing himself as a cornerstone player for Dallas by the end of 2018. This marked the first opportunity to secure a contract extension (in February 2019), and with a proactive and intelligent approach, the negotiation could have proceeded smoothly. However, no contract negotiations since Stephen assumed a more prominent role seem to have been straightforward, from my observation. I have three quick thoughts on this:
- The 49ers will be having this exact conversation in 52 weeks with Brock Purdy at the end of his 3rd season they can enjoy the talks about $50 million a season moving forward.
- The Cowboys never actually enjoyed any years of Dak Prescott’s cheap seasons because they were paying off Tony Romo’s dead money off in 2017-2018 and it was quite significant. Basically, he cost $40 million from ‘16-18 without ever starting a meaningful game for them. His body had broken down – Which probably should have told them the continuous acts of “pushing money forward” game can backfire badly. It did and they learned absolutely nothing.
- I actually laid out a contract on December 7th of 2018 under the following terms:
In December of 2018, I thought $20 million a year might cut it. It might have been laughed out of the room, but I thought the fully-guaranteed part might get their attention. At that point, it had never been done.
Instead, Dallas allowed him to play his 2019 with no extension and a contract that paid him $2.1m in 2019. In June of 2019, Philadelphia worked out an extension with Carson Wentz and in September of 2019, the Rams did the same with Jared Goff. They had a 5th year option for the 2020 season because they were 1st rounders and then built 4-year extensions for 2021-2024 with that flexibility and forward thinking. They even had a chance to use 2019 to spread the money out. In other words, they thought this through and made a smart decision – even if both QBs would be moved within 24 months.
In 2019, Dallas did absolutely nothing with Prescott and his future.
In 2020, they slapped him with a tag of $31.4 million and did absolutely nothing beyond that.
In 2021, they used the tag again which is a simple 120% of the first tag. That means it was 37.7m for that year. From there, they built a 4-year contract that was accepted and averaged $40 million per season.
By doing nothing for 24 months, they allowed the QB marketplace to explode from $25m per season to $40 million. Since 2021, it has gone from $40 to $55 million with Joe Burrow’s latest. Procrastination comes at quite a price.
Stephen was asked by my friend Pat Doney of NBC5 about his biggest mistake:
“Probably would have signed Dak the first time around…and it would have been better for everybody.”
No kidding.
(I added the following video after I published it the first time - This emerged last week from “About Them Cowboys” podcast from the Athletic) It is the story of Stephen on the phones during the draft and his lack of basic knowledge of the players in the league. I have checked on the story and believe it to be true. Again, I wish it wasn’t.)
(Now, back to our story as it was originally published:)
But, they got it done. Four years for $160m on March 8, 2021 it was agreed and signed.
I think most of us with math classes in our past can quickly see that this suggest he is to be paid $40 million a year for the next four years with more than three seasons guaranteed. I use AAV to demonstrate he now makes $40 million as nine newer contracts have raced past him and two more are his equal. We can say he is amongst the 12 highest paid QBs and belongs with those around him.
Which again, is the truth. Dak agreed to those numbers. Once he signs the deal and they pay him on time, how they account for that money against the league’s salary cap is completely up to Stephen Jones and his office.
This goes back to my analogy of paying rent on an apartment. If you work out a deal with your landlord on $1,000 a month, you can pay him $12,000 in January and nothing the rest of the year.
If he's amenable, you might consider paying him $12,000 in December and nothing else throughout the year. In theory, any agreement can be reached as long as he receives his $12,000 within that specific year. That's how the salary cap operates – you have the flexibility to smooth it to the average or simply pay it outright. Additionally, you can make payments without accounting for them, a strategy employed by Dallas with Romo and now with Prescott. This approach has, however, complicated their future decisions significantly.
As of now, Prescott has fulfilled 75% of his contract, yet Dallas has only accounted for 40-45% of his earnings against the salary cap. Despite having just one season remaining on his deal, which they have been contemplating since 2018, the cap accounting for 2024 is set to be nearly $60 million, with an additional $40 million in 2025. It's worth noting that this is a cap situation, not an issue of funds owed to Prescott (he already has the money).
So, when you hear that he has them painted into a corner, it is only partially true.
They cannot trade him (like Wentz or Goff) and they cannot tag him in 2025. I have no idea what they were thinking on those two provisions, but again, this contract has been bungled at every turn.
But, the other part? They held the paint brush the entire time! They did this out of their own thinking. That is how they did it with Romo – learned nothing – and are doing it again with Prescott. They have shoved so much money into ‘24 and ‘25 that they have closed off most escape routes in the event that they don’t think he is their QB to get them a Super Bowl.
Yes, they can help 2024’s cap without an extension. They can take a chunk (around $18 million) and push it into 2025, but the reality is that if 2024 is his last season here, they will face about $50 million in dead cap in 2025. Of course, if they extend him, they still have to account for the $40 million in 2025 ON TOP of a new deal that starts around $50m a year.
Does your head hurt more than your chest does right now?
The question we began exploring approximately 2,300 words ago centered on whether Stephen would fare better in this role than his father. This question often occupies my thoughts, reminiscent of the 2019 training camp where I heard Stephen discuss various matters, from Ezekiel Elliott's location in Cabo to Jaylon Smith's deal, Amari Cooper's situation, and the impending contract negotiations with Dak Prescott. Throughout these conversations, he frequently emphasized how "players need to accept their piece of the pie," seemingly convinced that there exists a universe in which players should willingly accept less for the greater good. This stance, however, contrasts sharply with the reality that Stephen himself has never compromised on any front and exhibits no intentions of doing so.
In attempting to negotiate with Elliott, Lawrence, Cooper, and Prescott, it appeared that Stephen's bluff was unsuccessful in each instance. Reports abound about not even engaging with these agents before crucial deadlines, highlighting a pattern that raises concerns about whether lessons have been learned and mistakes avoided.
While the resolution for Prescott remains uncertain, it is clear that they had the option to finalize the original deal sooner. Even if they didn't, they had the alternative of making timely payments, allowing them the flexibility to walk away with minimal dead money. Instead, they are left with a substantial $100 million to account for, severely limiting their strategic options.
Not only did they botch his first deal, but they did it in such a way that they might find the easiest solution is to do another one to fix it.
I used to describe the Jerry Jones Cowboys this way:
“Nothing ever changes because nothing ever changes.”
Now, I am actually wondering if the biggest change possible around here would even bring real change.
I wish I had better news, but when it comes to the biggest deals around here, they don’t seem to ever learn from their biggest mistakes.
