Mark Davis beamed in delight not knowing what the future held.
The Raiders owner finally got his man after years of chasing then-Monday Night Football color analyst and former Super Bowl-winning head coach Jon Gruden to take over the franchise he once led when Al Davis still cast a voluminous shadow over the entire organization.
"Once a Raider, always a Raider—never been more appropriate than today," Mark Davis said in an opening statement on that fateful day during Gruden's introductory press conference. "This is a big f'n deal."
At the time, the hiring dominated headlines. Gruden received a contract somewhere in the vicinity of 10 years and $100 million, according to CBS Sports' Jason La Canfora. Gruden denied that his contract was worth $100 million, but he certainly didn't come cheap.
Three years later, Davis' investment in the man he admittedly called an infatuation looks like one of the worst in professional sports, because Gruden hasn't done anything to make the Raiders a viable contender.
"Over these six years, everyone knows that I've been infatuated with him, or whatever, to get him here, but they really didn't know how deep our conversations were going," Davis said. "Somebody asked me what was harder: to get the 31 votes to move to Las Vegas, or to get Jon Gruden? And by far to get Jon Gruden was the toughest."
Initial euphoria has devolved into severe disappointment with an 18-29 record since the start of the 2018 campaign.
A first-year rebuilding period is acceptable. Turnover always occurs as a new regime implements its vision. However, the idea of a coach stepping out of the booth after being out of the day-to-day grind for nine years and then coming back with expectations of having the same success was flawed from the start.
The game evolves. Yes, Gruden spent his time poring over tape, keeping similar routines and calling games as a broadcaster, but it's not the same as leading on a daily basis, making in-game adjustments and knowing what it takes to win in today's NFL.
Things started to go wrong when Gruden and Co. agreed to trade Khalil Mack and a second-round pick in the '19 class to the Chicago Bears for a pair of first-round draft picks and an added third and sixth before the season even began. A few months later, the Raiders won the "Best Transaction" award at the '19 Sloan Sports Analytics Conference at MIT for the move.
Here's the thing about a trade of this type and magnitude: Execution ultimately defines who the winner is. Essentially, the Raiders gave up one of the game's best defenders for what turned out to be running back Josh Jacobs, cornerback Damon Arnette and wide receiver Bryan Edwards.
Mack has been named to the Pro Bowl every year he's worn a Bears jersey. While Jacobs is an exciting young runner and plenty of potential can be found in the Raiders' other picks, Las Vegas isn't better without the 2016 Defensive Player of the Year. Even worse, the team invested a top-four draft pick in another edge-rusher, Clelin Ferrell, and still can't get to opposing quarterbacks on a consistent basis.
In fact, the Raiders defense has ranked bottom 10 in sacks each of the last three seasons.
Seven weeks later, the organization flipped two-time Pro Bowl wide receiver Amari Cooper to the Dallas Cowboys for a '19 first-round draft pick. Cooper has gone back to the Pro Bowl twice since donning a star-emblazoned helmet.
Ultimately, previous general manager Reggie McKenzie was forced out before the end of the 2018 campaign—which created yet another conundrum.
Gruden handpicked Mike Mayock as McKenzie's successor. Technically, Davis had to sign off on the move. But it was clear from the start that Gruden wanted to be involved in the process as the face and most powerful person within the organization. According to NBC Sports Bay Area, the Raiders' hire, who turned out to be Mayock, answered to Gruden.
Thus, all personnel decisions couldn't be pawned off on anyone else.
Ferrell has improved this season, but the duo's first draft pick has managed 6.5 sacks through 26 games. For comparison, fellow defensive ends Nick Bosa and Chase Young each heard their names called among the top four picks in the last two classes. Bosa posted nine sacks as a rookie, while Young already has 6.5 in his first campaign.
Sure, the Raiders can point to Jacobs as one of the league's best ball-carriers, though one can argue the value of a first-round running back in a pass-first league. The team had a third first-round pick in Gruden and Mayock's first class. Safety Johnathan Abram missed all but one game as a rookie with a torn rotator cuff. The physical downhill defensive back has been a subpar performer in his second season, particularly in coverage.
To be fair, some of the franchise's later picks—cornerback Trayvon Mullen, defensive end Maxx Crosby, tight end Foster Moreau and wide receiver Hunter Renfrow—are solid contributors. Still, the Raiders needed more after trading Mack and Cooper.
Gruden and Mayock made the same mistake twice by reinvesting in the position with premium assets after trading away top performers in their primes. These types of moves signify poor roster management. But they weren't even the worst part of the brain trust's decision-making process.
After Cooper's departure, the Raiders made a massive blunder the following offseason by trading third- and fifth-round draft picks to the Pittsburgh Steelers for Antonio Brown.
As a Raider, Brown barely practiced after suffering frostbitten feet due to a cryotherapy mishap. The receiver then got into a spat with the league over wearing his outdated helmet. Mayock fined the veteran for not practicing despite being cleared to do so. The two got into a verbal altercation. Brown apologized and said he was ready to be part of the team only to demand his release the very next day. The Raiders cut the receiver before the '19 campaign began.
The '20 draft didn't redeem Gruden or Mayock, either. This year's 12th overall pick, wide receiver Henry Ruggs III, ranks fifth on the squad with 23 receptions. Arnette, who was generally viewed as a reach with the 19th overall pick, has been wildly inconsistent. The Raiders traded their third selection, Lynn Bowden Jr., to the Miami Dolphins before he ever played a down in silver and black.
Las Vegas can't continue missing on high-profile selections. The organization has made eight first- or second-round draft picks since Gruden took over, with only two—Jacobs and left tackle Kolton Miller—being solid additions so far.
And the coach hasn't redeemed himself with a quality on-field product.
It's not just the overall record that's a problem.
Over the last two seasons, the Raiders started 6-4 and 6-3, respectively. They had wins over quality opponents, thus placing them in the early playoff hunt, only to see everything fall apart both times. Last year, Gruden's squad lost five of its last six games. The Raiders are enduring an identical skid right now with one game left to play.
To take these issues a step further, how the Raiders lost is even worse because they're not playing to win. Las Vegas' last two losses serve as a microcosm of what's gone wrong with Chucky at the helm.
Last weekend, the Raiders lost 30-27 in overtime to the Los Angeles Chargers despite having the ball at the 5-yard line during the extra frame. Instead of going for the touchdown and an outright victory on fourth down, Gruden chose to kick a field goal. The Chargers scored the game-winning touchdown on the very next drive. Going for it would have won the game at that very moment or pinned the opponent against your own end zone. The Raiders didn't achieve either by taking the field-goal attempt.
Saturday, the Raiders trailed by a point to the Dolphins late in the fourth quarter but had the ball near Miami's goal line. Again, Gruden played for the field goal. In certain situations, an argument can be made in favor of a team kneeling before scoring a touchdown, as Jacobs did, to run out the clock. In this particular situation, two factors didn't work in Las Vegas' favor. First, the Raiders had to score to win. They weren't guaranteed to convert the field goal and should have taken the touchdown to ensure a lead. Just because Daniel Carlson converted doesn't mean it was the right decision. Second, the Raiders couldn't run out the entire clock.
As such, a strange confluence of factors including a busted coverage and ill-timed facemask penalty worked in the Dolphins' favor when they got the ball back. Miami completed the improbable comeback with a game-winning 44-yard Jason Sanders field goal with one second remaining.
Adding insult to everything else, the NFL fined the Raiders $500,000 and Gruden $150,000 and stripped the team of a sixth-round draft pick last month because the team and coach didn't adhere to NFL COVID-19 guidelines, per Yahoo Sports' Charles Robinson.
The Raiders have reached the point where the coach needs to honor his word from two years ago.
"If I can't get it done, I'm not going to take their money," Gruden told USA Today's Jarrett Bell.
Well, the coach hasn't gotten it done, and Davis should reconsider his options despite his earlier elation.
Brent Sobleski covers the NFL for Bleacher Report. Follow him on Twitter, @brentsobleski.