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Could there be a method to Raiders madness in waiting until last minute to sign Khalil Mack to extension? As the season creeps ever closer Derek Carr Jersey , and Khalil Mack is still not in house, the questions get more and more frequent as to how this situation will resolve itself. If at all.The big question tends to be ‘Will Khalil Mack’s holdout go into the season?’ Most seem to think it will not. But no one really knows for sure. Mack’s leverage lies in the threat that it could.Even if he does report before the season begins, there is the question of whether that would be because he got the extension he wanted or despite not getting it. And if he reports without a new deal, will we then be looking at another holdout next offseason with an increasingly disgruntled player?And as much as the rest of the league is getting worked into a lather about the possibility they could land the best defensive player in the league on a trade, that scenario just seems too far-fetched to actually happen. The reports are that teams have offered as much as a first round pick and a high pick and Reggie McKenzie has turned them down.Ideally, of course, Mack would get his deal before the season, return to the team and remain with the Raiders for what would figure to be the rest of his career.Knowing that is what the Raiders want, it leads to the question of why have they not had negotiations since February and are now seemingly playing chicken with their best player?In the interest of giving the Raiders the benefit of the doubt here, I have a potential scenario.It’s very likely Khalil Mack’s people gave the Raiders their target number back in February. At that time, the Raiders either said they can’t do that, or alternately said they wanted to hold off and play things by ear. Knowing that missing time in the offseason for Mack is not a big deal, they were in no real rush.A few weeks later, Jon Gruden began furiously adding free agents. By the time he was done, there were some 25 new free agent signings. Most of them weren’t making a lot of money Reggie Nelson Jersey , but it all adds up.I have said all offseason that extensions, even big ones, such as Khalil Mack is seeking, don’t necessarily raise the cap number in the season upcoming. That’s because the extension hasn’t kicked in yet, so the team can decide what kind of money they want to count against the cap until then.Look at Aaron Rodgers’ 2018 cap number after having just signed a 4-year extension that averaged $34.5 million per season.The caveat here is we know Reggie McKenzie likes to front load his contracts as much as he can so as to limit kicking the can down the road and/or risking being saddled with dead money should he wish to release a player after a couple seasons. That won’t be so easy with Mack seeking a lot of guaranteed money but I see no reason why he would care about that. Does anyone really doubt that Mack with earn every penny he receives?Even though the Raiders may not have to raise Khalil’s cap number this season, they may want to because it will allow them to lower his cap hits in future seasons. Just as he did with Derek Carr, who will make $25 million this season and then have his salary go down each season after. They were able to do that by adding to his cap number on the final year of his rookie contract, before his extension kicked in.Let’s say the Raiders are looking to bring Mack’s cap number up from its current $13.8 million to right about what he is looking for on his yearly average. Let’s say $22 million. That’s what he was said to be asking this offseason and that’s about what Aaron Donald just received from the Rams.With some of the cuts the Raiders have made recently, they are sitting at $7.1 million in cap space according to Over the cap. The expected trade or release of Mario Edwards Jr would add another $1.3 million to that to put them at about $8.4 million. Add that to the $13.8 million Mack is making now and you have鈥?$22.2 million.There are a lot more cuts coming too, some of which currently count in the top 51, which means even more money available under the cap.Also consider that Khalil Mack doesn’t count against the roster until he reports. Not reporting until, say, two days after the cut down day (Monday) would allow the Raiders to keep a player for one more day after the initial frenzy of players get claimed off waivers, which might make it easier to stash them on the practice squad. In theory, of course. And Mack would be back just in time to start preparing for the season opener.Also Kolton Miller Jersey , don’t discount the simple concept that deadlines spur actions. Both Mack and Aaron Donald were holding out seeking new deals. Donald got his record deal today on a 6-year, $135 million deal with some $87 million guaranteed.I don’t think they were both staring down each other waiting for the other to make a move first, but you have to figure with Donald’s deal done, it sets the market which could be the trigger that sets Mack’s deal into motion. I don’t think either Mack or Donald were worrying about who signed last and thus leapfrogging the other to be the highest paid defender in the NFL. That’s the kind of stuff agents care about so they can attract new clients. And both agents will be able to make that claim, even if the title only lasts a few days. These players aren’t sitting around obsessing over being the richest in their sport. They’re football players, not the Wolf of Wall Street (I mean, Mychal Kendricks aside). They just want to get market value for their services as two of the top pass rushers in the league. That means surpassing previous highest paid defender, Von Miller. Donald blew Miller’s $19.5 million per season out of the water. Mack’s deal should do similar.This whole scenario has a lot of people sweating near the end, but that doesn’t necessarily mean things won’t come together at the 11th hour. It could. I am not predicting it will. Though my gut tells me one way or another, Khalil Mack will take the field for the season opener. For whatever that’s worth.Follow @LeviDamien Sometimes timing is just too good to be a coincidence. Thursday Charles Woodson announced to the world that he was leaving ESPN where he had been a desk anchor for three years. And there is no logical reason why ESPN would have made that decision as CWood is well liked, has a great on-camera presence, and is headed to the Hall of Fame in a couple years. ESPN loves it when their current employees are inducted into the Hall of Fame.No, CWood it seems unlikely would leave unless he had something else lined up. He ended his farewell message to ESPN with “I’ll see you next season somewhere. Stay tuned.”My first thought was another TV gig. He was always destined for TV, which is why ESPN snatched him up with a quickness immediately following his retirement in 2015. But maybe Woodson has other plans. Maybe he wants to take a shot at coaching?It wasn’t so long ago we saw Jon Gruden as someone who wouldn’t leave the booth. Likewise it was hard to envision Mike Mayock stepping away from being the most respected draft analyst in the world. But both ended up joining the Raiders.When Gruden first started entertaining the idea of returning to the sideline, he said the only team he would coach for was the Raiders. He felt like he had unfinished business in Oakland after the unceremonious ending that saw him traded to Tampa for two first round picks.Woodson was among those in attendance for Gruden’s introductory press conference in Alameda as Gruden was the head coach in Oakland when Woodson was drafted and was the starting cornerback for all four years Gruden was Raiders head coach. And they shared a network for two years. Woodson was the first player Gruden mentioned among the many greatson hand that day.Back in 2013 P.J. Hall Jersey , Charles Woodson was 36 years old and had just been released by the Packers. He wasn’t ready to end his career, so he took a few visits. When he got to Oakland, he had a mob of excited fans ready to keep him from leaving. And he signed on, playing three more seasons, not missing a start.For Woodson, it was also a return to the place he spent the first 8 years of his career, playing for fans who adored him, and just up the road from his winery in Napa. The Ohio native had become a California guy.Three days ago, when the news was flying around about whether the Raiders would play in Oakland or Santa Clara next season, Woodson chimed in with his support for the team to stay in Oakland for its final season before leaving for Las Vegas in 2020. “LET’S DO IT” he said in all caps.“LET’S”Even with his ardent support for Jon Gruden, the Raiders and the City of Oakland, the Raiders already had a Defensive Backs coach. Derrick Ansley, who was hired away from Alabama to join Gruden’s staff was in place. Yeah, about that...Friday multiple reports had Ansley taking the Co-Defensive Coordinator job at the University of Tennessee. Could it be? ... Is it possible? ... These two job changes are related? Could Charles Woodson be joining the Raiders coaching staff? Is he even ready to handle that job? We may soon find out.Follow @LeviDamien