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Answering biggest questions about Khalil Mack trade to Bears

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Riddick: Mack trade is 'huge win' for Bears (1:37)

Louis Riddick reacts to the Raiders trading Khalil Mack and says Oakland can't rely on draft picks to replace him. (1:37)

It happened. It actually happened. The bizarre silence about Khalil Mack's contract ended and the rumors suggesting the Oakland Raiders would deal away their star pass-rusher shockingly came true Saturday, as Oakland traded him to the Chicago Bears for a package built around two first-round picks. Mack, now the NFL's highest-paid defensive player after agreeing to six-year extension worth $141 million, including $90 million guaranteed, goes to the Bears along with a 2020 second-round pick and a conditional 2020 fifth-round pick. The Raiders get a 2019 first-round pick, 2019 sixth-round pick, 2020 first-round pick and 2020 third-round pick.

It's an absolutely stunning trade. Even in a league in which trades are becoming more common and stars like Marcus Peters are being dealt in the middle of their rookie contracts, Mack is the most accomplished player in the prime of his career to be traded since the Broncos acquired Champ Bailey in 2004.

This is an enormous bet from both sides. The Bears are assuredly about to hand Mack a blank check, while the trade suggests that the Raiders' checkbook might be under lock and key. So many questions came to mind as I tried to figure out this swap. Let's go through them and see what we can figure out about the biggest trade in recent league history.


Is this a logical trade for the Bears?

It depends. The 2017 Bears weren't crying out with a desperate need for a pass-rusher. Chicago quietly finished 14th in defensive DVOA, which was buoyed by the league's sixth-highest sack rate. You might chalk that up to blitzing given the lack of a big-name pass-rusher like Mack on the roster, but Akiem Hicks & Co. were fourth in the league in sack rate when they didn't blitz. Hicks's 8.5 sacks made him the only player on the team to top 4.5 sacks, but the Bears were effective in getting after the quarterback as a whole.

There are reasons to think the Bears might have declined in this category in 2018, though, without adding a player. In addition to moving on from expensive reserves like Pernell McPhee and Lamarr Houston this offseason, Vic Fangio's defense was unusually effective at turning pressure into sacks. While the Bears were sixth in sack rate, they were 19th in the league in pressure rate. When the defense got pressure on opposing quarterbacks a year ago, Chicago sacked those passers 25.6 percent of the time, above the league average of 21.9 percent.

Teams with a gap between their sack rate and pressure rate tend to decline the following year. ESPN only has pressure data going back through 2009, but from 2009 to 2016, 45 teams placed 10 or more spots higher in the sack rankings than their position in the pressure rankings. (The Bears, of course, were 13 spots higher.) Those teams saw their sack ranking decline the following year by an average of just under seven spots, suggesting the Bears would have found it difficult to keep their sack rate as high in 2018.

By adding Mack, then, the Bears get one of the highest floors for any pass-rusher in the league. He has topped 10 sacks and 20 knockdowns in each of the last three seasons, which amount to three-quarters of his professional career. There's nothing in his track record saying that production is fluky or likely to decline beyond the typical attrition rate of pass-rushers. He's still only 27 and hasn't missed a game. The last time Fangio had a pass-rushing combination this good was in San Francisco with Justin Smith and Aldon Smith, the latter of whom racked up 33.5 sacks from 2011 to 2012.

The on-field fit is just peachy. Mack was beloved in the Oakland locker room; certainly, Bruce Irvin doesn't appear to be very happy about the move. You get the feeling that the Raiders might be throwing a Sterling Shepard-esque party for Mack getting a massive new contract, even if Mack won't be there to join in the festivities.

Mack is going to get a massive extension as part of this deal. If anything, his representatives can ask for more than they were asking from the Raiders as part of a deal because the Bears have less leverage to work with. Can you imagine the Bears trading two first-round picks for Mack, only to let him leave in free agency for the maximum return of a third-round compensatory pick? Of course not. You have to imagine the Bears were in contact with Mack's representation during these trade negotiations, but during those initial discussions and in the ones that have followed, the Bears are basically going to pay whatever Mack wants. There are no issues there, either; he deserves to be among the three or four highest-paid defensive players in all of football.

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Raiders to trade Mack to Bears

Adam Schefter reports on the Raiders trading DE Khalil Mack to the Chicago Bears.

Is there a 'but' coming?

Yes. The issue is that the combination of the contract and the trade adds up to a ridiculous price tag. The goal of any NFL contract from management's perspective is to pay a player less than his production is worth to the team. We acknowledge this in talking about quarterbacks on rookie contracts, which has been the most important asset in the game going back to the beginnings of the new CBA in 2011 and its draft rules.

Teams rarely trade two net first-round picks in moving up for rookie quarterbacks, who offer the most surplus value of any player in the league. The moves up for Patrick Mahomes and Deshaun Watson, for example, included two first-round picks in a swap to move up for one first-round pick. The last trade a team made in which it lost a net of two first-round picks (without considering the non-first-rounders) was the Robert Griffin trade in 2012.

When you draft a quarterback in the first round and land on a star, you create surplus value. The Eagles got MVP-caliber play from Carson Wentz in 2017 before the former second overall pick tore his ACL. Top-tier quarterbacks were getting paid $25 million or so per year last season, but Wentz was at their level while only costing the Eagles about $6 million on the cap. That extra $19 million can go elsewhere on the roster, and even after trading a bunch of draft capital to move up to grab Wentz, the Eagles were able to parlay that savings into deals for guys like Alshon Jeffery and Tim Jernigan. Even after Wentz went down, the roster general manager Howie Roseman built was strong enough to win the Super Bowl with Nick Foles.

The Bears are hoping to do this same thing with Mitchell Trubisky, of course, and Trubisky's four-year, $29-million deal is letting them spend money at other positions. They would probably have second thoughts about this Mack deal if they were still paying Mike Glennon $16 million per season to be their starter or went in a different direction with their quarterback position last offseason.

The difference between those rookie quarterback deals and this swap is that the Bears aren't acquiring Mack on a rookie contract. They're going to be paying him essentially what the market would give him on a veteran deal. Unless he's the Defensive Player of the Year four seasons in a row, the Bears aren't going to get much at all in the way of surplus value on this contract. At best, given the way the top of the defensive market will grow, they're probably looking at $10 million to $15 million over the next four to five years if everything breaks right, and even that's assuming Mack continues to play at an extremely high level and doesn't get injured.

Paying two first-round picks for the right to possibly gain $15 million in excess value just doesn't make economic sense. Teams don't value their draft capital that way. The upside in trading for a quarterback like Wentz, as an example, is a totally different economic proposition. The Eagles sent less capital to Cleveland than the Bears sent for Mack and came away with a quarterback whose upside was somewhere in the range of $100 million in excess value over five years.

The downside, of course, was also much smaller; if Wentz failed, the Eagles would have been out no more than $26.7 million. If Mack gets hurt or struggles in Chicago, the Bears could be paying tens of millions of dollars per year for a player who actually costs them money. Wentz is the best-case scenario for this example, but the same logic applies to Mahomes, Trubisky and Watson, all of whom cost much less to acquire in draft capital than Mack and offer the same mix of a higher ceiling and a far less dangerous floor.

To be worth two average first-round picks on top of his market-value contract, Mack would have to be worth, as an educated guess, something in the range of $15 million more than his actual deal with the Bears over each of the next five seasons. If he gets Aaron Donald-level money and hits $23 million per year, Mack probably has to play like a $38 million-per-year player to make the economics work in this swap. That's just not humanly possible.

To think about it in terms of opportunity cost, the Bears are foregoing a chance to grab two players in the first round at market-friendly prices in their own right over the next few years. Chicago is hoping that rookie inside linebacker Roquan Smith turns into a superstar. Smith is signed to a four-year, $18.5 million deal after the Bears took him with the eighth overall pick. When Eric Kendricks and Benardrick McKinney signed extensions this offseason, the first four years of their respective deals came in with an average of just over $40 million in new money. The Bears are giving up the opportunity to get bargain deals with those two first-round picks and will have to otherwise find players to fill the positions those first-rounders would have filled.

The Bears are paying an enormous premium, then, to sign a player they wouldn't otherwise have access to. General manager Ryan Pace's drafts have produced some useful players, but his first-round picks have included Kevin White, Leonard Floyd and Trubisky before adding Smith this offseason. It's still too small of a sample size, but White has been a nonfactor due to injuries, and Floyd hasn't yet lived up to expectations due to injuries. Pace landed a hit with Hicks, but his free-agent additions have mostly been misses, including a dreadfully bad class last offseason.

The Bears are paying two first-round picks and forfeiting a ton of surplus value because Mack is too good to get wrong. Is it an efficient use of assets? Absolutely not. They're valuing Mack as being worth more than Aaron Rodgers over the next five years, and that just isn't the case. Is it the best these Bears could have done with $23 million or so per year in cash and two first-round picks? Quite possibly.

Do teams that trade two first-round picks for veteran players look back fondly on their decision?

Ask a Bears fan. The last time a team sent two first-round picks away in a swap for a veteran was in 2009, when Chicago sent two first-round picks, a third-rounder and Kyle Orton to the Broncos for Jay Cutler and a fifth-round pick. Cutler was coming off a Pro Bowl season with the Broncos and was three weeks away from turning 26; it was a rare opportunity to acquire a Pro Bowler in the prime of his career at a position of great need and importance.

Cutler threw 26 interceptions the next season and never made the Pro Bowl again. The oft-frustrating Cutler certainly had his moments and often took more flak than he deserved, but it's fair to say that Cutler never lived up to the player the Bears thought they were acquiring. The Broncos were able to parlay the picks into a bevy of selections, two of which turned into future starting wide receivers Eric Decker and Demaryius Thomas.

The same is true for many of the veterans with this lofty price tag. ESPN Stats & Information found nine other instances of a player changing hands for two first-round picks since 1986, a list that doesn't include restricted free agents like Sean Gilbert and Wilber Marshall, who cost their new teams two first-round picks as compensation. I've gone through those trades and found how long each star lasted in their new city as well as the eventual return for those players. In many cases, the teams ended up drafting a more effective player than the guy they dealt:

I would argue that after Walker, Mack would be alongside Dickerson as the most accomplished players in this group at the time they were traded. It's also worth noting that none of these trades netted the acquiring team a superstar for years to come; the closest example is Dickerson, who had a great first season-and-a-half with the Colts before declining and eventually forcing his way out of Indianapolis. The two young quarterbacks, Cutler and Jim Everett, were the only ones to last more than five years with their new team.

This should be enough to inspire some skepticism that the Bears' move is a stroke of genius, but it's important to note that many of these trades came in an era in which the league, frankly, was a lot dumber about the value of draft picks. (This applies to all American sports.) When you look at the more recent trades, Mack is clearly a better player than Joey Galloway, Keyshawn Johnson and Ricky Williams were at the time of their trades. He's better than Cutler, although Cutler plays at a more valuable position.

Do teams really trade young superstars like this very often? Does it work out?

No, this doesn't happen very often. Over his first four seasons, Mack made three Pro Bowls and was a first-team All-Pro twice. Awards aren't perfect measures of player quality, but there aren't any bad players who have pulled off that feat. Since the AFL-NFL merger of 1970, 53 players have made it to at least three Pro Bowls and been a first-team All-Pro twice during the first four years of their career. Thirty-eight of them are eligible for the Hall of Fame, and 25 are actually enshrined in Canton.

Teams don't let go of those players often. Many of them spent either their entire career or the vast majority of their career with one team. A few others, including recent examples like Darrelle Revis and Richard Seymour, were dealt midway through their second contract with their original franchises. Those don't really compare to the Raiders dealing Mack before the end of his rookie contract.

I can find just four examples of players with a similar pedigree to Mack who were dealt this early in their careers. One is Dickerson, who was traded away during the middle of his fifth season, during a contract dispute. Two of the others were Chargers wideout John Jefferson and Eagles tight end Keith Jackson. Jefferson made one further Pro Bowl and was out of football by 30. Jackson made two Pro Bowls and retired after his age-31 season.

The third was Jerome Bettis, who was traded to Pittsburgh after just three seasons with the Rams, was a first-team All-Pro in his first season with the Steelers, and went on to play for a decade with Pittsburgh. Mack fits more in the first group than he does with Bettis, but you get the idea here: This is something close to a once-in-a-decade move, and no team has traded away a player like this so early in his career in more than 20 years.

So why are the Raiders trading a franchise pass-rusher?

This is a difficult question to answer, and it's easier to disqualify bad arguments than it is to find the right one. To start, the idea that the Raiders didn't have the cash on hand to sign Mack seems absolutely bizarre. The Raiders have known for three years now that a Mack deal was coming due this summer, and they spent hundreds of millions of dollars along the way, including $55 million on contracts this offseason alone. It would have taken approximately 10 minutes to raise the cash flow to sign Mack if owner Mark Davis failed to balance his checkbook. This should be a non-starter.

It also seems unlikely that this is Reggie McKenzie's doing. The Oakland general manager liked Mack enough to draft him with the fifth overall pick in 2015 and was excited about locking him up to an extension as recently as last November. McKenzie was telling fans not to panic about the holdout on Aug. 1.

We've heard plenty of reports that coach Jon Gruden is the one making personnel decisions in Oakland, which is reinforced by the choices the Raiders have made this offseason in adding veteran after veteran in free agency. (McKenzie did this early in his tenure with Oakland, but that was out of the sheer reality that players in their prime didn't want to play for the Raiders at the beginning of their rebuild.) Multiple reports suggested that McKenzie didn't want to trade Mack and that Gruden is in charge of the organization. Given that Gruden has a 10-year, $100 million contract and McKenzie is halfway through a four-year extension for far less than that, we shouldn't be surprised.

When I wrote about Gruden's track record in January, I found that there was a big gap between Gruden the coach and Gruden the personnel evaluator. The former ESPN commentator took over de facto control of personnel in Tampa Bay after the 2003 season and was a relatively poor drafter. It would be difficult to argue that the roster he left after the 2008 season was better than the one he inherited, either as a coach in 2002 or as personnel chief in 2004.

If we focus specifically on the defensive line, Gruden really didn't put much of an emphasis on investing up front during his time shopping for the groceries. Cap constraints led Gruden to release Warren Sapp after the 2003 season, and while edge rusher Simeon Rice stuck around, the Bucs cut him to save $7.3 million after he suffered a shoulder injury during the 2006 season. Rice would later refer to Gruden as a "scumbag" for lying to him about his future with the team.

The Bucs got by with players like Greg Spires, Dewayne White and 34-year-old free-agent Kevin Carter at defensive end. Gruden signed Chris Hovan to a one-year deal and then re-signed him to a five-year, $17.5 million contact after he impressed on the interior, but he also traded away former first-round pick Booger McFarland halfway through his contract extension. Gruden's most notable investment along the defensive line was Gaines Adams, who the Bucs took with the fourth overall pick in the 2007 draft. Adams was traded after Gruden left town and played one season with the Bears before dying of a heart condition.

Reports have suggested that Gruden thinks he can make better use of the $20 million-plus the Raiders might have spent on Mack by splitting it across multiple players, and his track record with the Buccaneers suggests that the Raiders might approach things in a similar fashion. Andrew Hawkins also tweeted out an interesting quote from former Gruden quarterback Jeff Garcia about his old boss:

Gruden's argument might very well be that the Raiders weren't very good on defense with Mack in the lineup. Oakland's defense ranked 26th in DVOA during Mack's rookie season and improved to 15th during his breakout 2015 campaign, but over the last two seasons, the Raiders fell to 22nd and then 29th. McKenzie's draft picks on defense simply haven't worked out: Oakland hasn't gotten yet much out of first-rounders Gareon Conley (who was injured for most of his rookie season) and Karl Joseph. Second-rounder Mario Edwards hasn't developed after missing most of his 2016 season with injuries, and subsequent second-rounders Jihad Ward and Obi Melifonwu have been even less impressive. Ward was dealt to the Cowboys this past offseason, while Melifonwu was cut and cleared waivers before returning to the Raiders.

At the same time, though, recognizing that the defense is bad and trading Mack is like having a bunch of holes in the roof of your house and reacting by tearing up the foundation. The Oakland defense isn't going to get better by trading Mack, and while they like rookie third-rounder Arden Key, there's no obvious replacement for Mack on the roster. If the Raiders play their cards right, they might be able to turn the two first-rounders and $22 million they save on Mack into four viable NFL starters. Of course, given their recent past on defense and Gruden's run as personnel chief in Tampa, they don't appear to be great card-players.

What does this tell us about the Bears and Raiders (and the rest of the league)?

From the Bears' perspective, they are basically all-in with this core of players for the foreseeable future. Chicago was set to have $45 million in cap room next offseason, but a huge chunk of that will likely go toward the Mack extension. The Bears will also be down their next two first-round picks, so they'll be missing key assets which might have helped them shape their roster around that core.

Most specifically, as Brian Burke noted on Twitter, the Bears don't have a first-round pick to use to either draft a quarterback or trade for one if Trubisky fails to develop. It's obviously way too early to judge Trubisky, given that he only started 12 games in a very limited scheme last season, but it's also not as if he played as well as Dak Prescott did during his rookie campaign. We still have no idea whether Trubisky is going to be a successful NFL quarterback. Pace's long-term job security was already probably all-in on Trubisky turning into a useful passer. Now, there's no question.

The Bears were already one of the most likely teams in the league to improve this season. Trading for Mack obviously doesn't hurt those odds. After the news came out Saturday morning, Chicago went from 100-1 to win the Super Bowl to 40-1, while their over-under for the season jumped from 6.5 wins to 7.5 wins.

As for Oakland, trading Mack seems to be a suggestion that Gruden thinks his roster isn't good enough to win in a wide-open AFC West this season, which should help the Broncos, Chiefs and Chargers. You could make an argument that it might be prudent for a guy with a 10-year contract to think about the long term, but it's not as if Mack was a 34-year-old on his last legs. There was every reason to think that Mack would have been a star for the Raiders for years to come, stretching well past their scheduled move to Vegas in 2020.

There's also going to be a chilling effect in play here. Fans and media members often overrate how important it is to re-sign players on bad teams -- remember that McKenzie was widely criticized after letting Houston and Jared Veldheer leave in the spring of 2014 and didn't come to regret either move -- but Mack is not the typical player. Are the Raiders going to pay Amari Cooper as he approaches the end of his rookie deal? If you're a free agent looking to sign with the Raiders in a couple of years and you see players like Conley and Key breaking out, will you have faith that Gruden is going to pay those guys market value to stick around? Would you be willing to take the plunge and find out? Even if the Raiders end up being right to make this trade, they're taking a ton of heat for making it in the first place.

As quarterback salaries continue to rise at a faster rate than the salary cap, we're going to see more situations like the one the Raiders were facing with Mack and Derek Carr under contract. It would have cost somewhere around $48 million per year to keep those two guys in town, or nearly 27 percent of the salary cap. I won't fault you for saying the Raiders should have bit the bullet and made cutbacks elsewhere, but it's clear Gruden wasn't comfortable doing so.

Many of the league's best-compensated pass-rushers are on teams that either have a quarterback on a rookie contract or an otherwise-undervalued deal. Aaron Donald is with Jared Goff. Chandler Jones is with Josh Rosen, although Sam Bradford is on a big short-term deal. DeMarcus Lawrence is with Prescott. Fletcher Cox has Wentz. Von Miller, Calais Campbell and Geno Atkins are working with three of the lower-paid veteran quarterbacks in Case Keenum, Blake Bortles and Andy Dalton, respectively.

The Vikings are an obvious exception with Everson Griffen and Kirk Cousins, and the Saints have Cameron Jordan making close to top-tier money with Drew Brees. The Vikings are also arguably the best draft-and-develop team in the league over the last five seasons, and the Saints had huge holes on their defense before nailing the 2017 draft. Teams can have a star quarterback and a star edge rusher making huge sums of money and do well, but it's not enough to win.

Finally, this deal continues to illuminate the value of rookie quarterbacks. The Bears aren't even sure (or shouldn't be sure) if they have a good one in Trubisky, and they could have chosen to roll their cap space over into the future, but the actual cash they're saving at the position and the mere possibility of being set at quarterback allowed them to take a huge swing at a known franchise player in the prime of his career. Even if you think they paid an enormous premium to acquire Mack, the Bears traded for a 27-year-old player at a critical position who appears to be on a Hall of Fame career path today. If you're ever going to overpay, that's the sort of player you max out your bank account to acquire.

For the Raiders, meanwhile, they're left with a huge hole in their heart and a whole lot of uncertainty. Oakland shouldn't have based its decision to trade Mack on what happened at quarterback, but Carr unsurprisingly took a step backward last season and suddenly looks like he might be a liability at $25 million per season.

The margin for error is a lot more comfortable when the starting quarterback is making $1.3 million per season, as Carr was before his extension. Will teams get more aggressive about opting out of deals for midtier quarterbacks and use their cap space elsewhere while using their draft picks to trade for cheap passers in the draft, as the Rams and Eagles did two years ago? Would that have kept Mack in Oakland at the expense of his former quarterback? We'll never know, but with Carr owed no guaranteed money after the season and Gruden clearly rebuilding the roster in his own image, it's unclear whether the Raiders' core that won the AFC West in 2016 might be scattered around the league this time next year.