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Oakland has long been a place in the NFL that winning forgot.

Other NFL outposts are filled with the sorrow, and worse, indifference that comes with losing. But for various reasons they don’t feel quite the same as Oakland’s prolonged stretch of stink. The Raiders have gone 11 years without qualifying for the playoffs. That’s tied with the Browns and behind only the Bills, a 90s juggernaut that did everything short of actually winning a Super Bowl, and now Buffalo has gone 14 years without a playoff berth.

But the NFL is a place where the future must always be the focus. I suppose that’s a generic statement about all sports, but the feeling is emphasized with 16-game seasons that fly by at warp speed. When we look at that future, there’s at least sprinklings of hope in Cleveland and Buffalo. Though they just lost Jairus Byrd and questions still surround E.J. Manuel, the Bills have youth and promise throughout their offense and an overbearing pass rush. Meanwhile, the Browns just signed Karlos Dansby and Donte Whitner, Josh Gordon is the most explosive young receiver in the game, and in May they have 10 draft picks to plug various other holes including the fourth overall pick and five selections in the first three rounds.

The Raiders? They started free agency with over $60 million in cap space, and then watched as their best players departed.

General manager Reggie McKenzie quickly found himself in an odd position with little solution when this offseason started. To be exact, he had $64.3 million in money to spend when free agency began earlier this week, cash granted to him when a significant chunk of his 2013 roster was destined to leave.

In total Oakland had 14 impending free agents, which is where our story of confusion begins.

Franchise tag? Nahhhhh

Chief among those free agents were Jared Veldheer, LaMarr Houston, and Rashad Jennings. They can also be referred to as the Raiders’ top three players at any position, and even better, all three are currently under the age of 28. Fans can reasonably accept the reality of a rebuild if youth is present on the roster. Youth leads to hope even during dire times, and hope leads to interest, and interest fights indifference. That’s a crucial math equation for a team which has won only eight games over the past two years, and just 49 over the last decade. Really.

That consistent failure has led to a predicable though hurtful existence for McKenzie: the amount of money you have is irrelevant when top free agents don’t want to take it. Football players enjoy money, but they also think winning is great fun too. Preferably they’d like to go to a place where they can have both, and with their stench that’s hovered for over a decade Oakland isn’t that place.

But there’s a solution the NFL has built in for this exact scenario: the franchise tag. Applying it costs a premium by design, but its purpose is to secure a core player and prevent him from hitting the open market. Then afterwards a long-term deal can be negotiated that lowers a cap hit.

McKenzie had more than enough funds available to pay for a tag attached to either Houston at $12.6 million, or Veldheer at $11.2 million. Despite his mound of cap space he chose to do nothing, presumably because those prices were too high. At some point the risk associated with overpaying for one core player is drastically reduced, and the Raiders passed that at about, oh I dunno, the $40 million cap space mark.

If he was staunchly against the franchise tag due to an extreme overpayment, McKenzie was validated when Veldheer and Houston signed with Arizona and Chicago respectively, and they did it for identical five-year contracts that will pay $35 million. That’s a combined 2014 cap hit of $14 million, and McKenzie could have resigned himself to overpaying out of necessity by handing them a combined, say, $18 million, and he still would have walked away with over $48 million in cap space remaining.

A limping backfield

Then there’s Rashad Jennings, a running back who is the same age as fellow 2014 free agent Maurice Jones-Drew, but he’s not the same football age due to his lack of abuse.

While filling in for the oft-injured Darren McFadden, Jennings finished 2013 with 1,025 total yards on just 199 touches (and only 163 carries). That’s an average of 5.2 yards per touch, and it includes a four-game stretch between weeks 9 and 13 with 553 yards. Yet still Jennings — the Raiders’ best offensive player — wasn’t deemed worthy of a payment, even when his asking price and the contract he eventually agreed to with the Giants was worth only $14 million over four years, a cap hit of $3.5 million.

That’s a few pennies for McKenzie, yet CSN Bay Area reported that he let Jennings leave town without much of a fight. What exactly is worth fighting for to this man? Ohhh yeah…

Chasing the old and injured

Instead of ponying up whatever extra cash was required to secure the far fresher Jennings, McKenzie thought it was wise to cheap out and spend only $1.75 million on Darren McFadden. That’s the same Darren McFadden who has never played a full season, and he’s missed 19 games over just the past three years. Even when he was healthy this past season McFadden averaged only 3.3 yards per carry, and he’s light years removed from this…

“He’s the closest thing I’ve seen to Eric Dickerson” is a thing that was actually said once about McFadden.

With young talent like Houston and Veldheer unwilling to rot away at market price in Oakland during their prime years, McKenzie has been left chasing the NFL’s equivalent of the golden girls. He just spent $11 million for two years of Justin Tuck, who’s fading and is about to turn 31 at the end of this month. For just over $3 million more he could have snatched Michael Johnson, and instead he gets a veteran who pushed during a contract year in 2013 to record 9.5 sacks during the final six games. That’s a mirage and not the real Tuck, as over the previous 37 games he had all of 10.5 sacks.

McKenzie signed LaMarr Woodley, the now former Steeler who’s still effective off the edge when healthy, but that health part has been a problem. Woodley’s last double-digit sack season was in 2010, and he’s missed 14 games over the past three years. Woodley and Tuck are band-aid, short-term solutions, which isn’t how you rebuild.

McKenzie also pursued 32-year-old Jason Hatcher, and soon-to-be 31-year-old Donald Penn is reportedly in for a visit today while the search for a left tackle continues. Penn is a fine run blocker, but Tampa’s decision to cut him was made easier when he gave up 11 sacks this past season according to Pro Football Focus, the second most among left tackles.

Just like a year ago when Jason Hunter was signed fresh off a torn triceps along with a very vintage Charles Woodson at 36 years old, settling for aging veteran reclamation projects is the most Raiders thing.

The new Davis is the same as the old Davis

Al Davis has a storied NFL legacy, but a younger generation only remembers his later years. Mostly they remember the meddling and his overbearing nature. Mostly, they remember this…

His son Mark was supposed to be different, and until earlier this week he was. McKenzie dramatically overpaid for Rodger Saffold, but he was still a critical left tackle signing. Then ownership trumped the GM and overturned the contract, citing a bogus shoulder problem.

In the first hours of free agency the Raiders signed Saffold to a five-year contract worth $42.5 million, $19.5 million of which was guaranteed. Though Saffold is a fine left tackle and a solid replacement for the departed Veldheer, it was a steep sum of cash. But whatever, because again, mildly to not-so mild overspending isn’t a concern for the Raiders.

Then something completely inexplicable happened: the deal was overturned because Saffold failed his physical due to a shoulder problem. The same shoulder problem that didn’t keep him out of a single game during the 2013 season (he did miss three games, but because of a knee issue). The injury originated in the preseason when Saffold dislocated the shoulder during Week 2 of August football. He missed one exhibition game and then was on the field the next week.

Between then and the conclusion of the Rams’ season Saffold had two physical examinations, one at the end of training camp, and one during the standard exit physicals players go through before they depart for the offseason. Neither exam by Rams doctors and trainers revealed a lingering shoulder problem, and certainly not one serious enough to nix a trade.

As Saffold’s agents told the St. Louis Post-Dispatch, that wasn’t good enough for Mark Davis, even after Rams executive vice president Kevin Demoff had a specialist double-check Saffold’s MRI. Nope.

Saffold has since re-signed with the Rams, and now the tackle market is bare.

***

How will this end?

Woodley and Tuck are the sort of players the Raiders have to settle for right now. They’re veterans who may have upside left if they can either stay healthy (this especially applies to Woodley), or if they can slow the descent of their career. They’re the kind of players good teams add as final pieces, like DeMarcus Ware in Denver, and not the core.

Drafting has to improve, and now. That’s how successful franchise are built, yet over the past five drafts (only one of which was under McKenzie) the Raiders didn’t even have their first-round picks in 2011 and 2012 due to trades acquiring Carson Palmer and Richard Seymour. The recent history of Raiders draft failures has been well-documented, between McFadden, JaMarcus Russell, Darrius Heyward-Bey, and Michael Huff. All bitter, fiery flameouts.

But for the even more recent history and failure to retain the assets they’ve developed, we can look specifically at the 2010 draft. The first three rounds went as follows: Rolando McClain, LaMarr Houston, Jared Veldheer. One is another first-round bust, but the other two are ascending young talents who will now keep doing that elsewhere.