When Jon Gruden and the Raiders traded star defensive end Khalil Mack to the Chicago Bears in 2018, it left the Raider Nation stunned. Mack, who was able to stuff the run at DE and rush the passer to devastating effect at DE and outside linebacker, had quickly become one of the most highly decorated defenders in Raiders history — including once earning first-team All-Pro honors at both DE and OLB in the same year.

But questions about his upcoming contract expiration led to an offseason holdout and the new/old coach’s decision to deal him before he ever played a down for Gruden 2.0.

Gruden, of course, was no stranger to a big trade — he, after all, was part of the biggest deal in franchise history.

(In the details that follow, bold indicates players drafted by the Raiders.)

(Photo of Khalil Mack with the Raiders in 2018.)

The Khalil Mack trade, Sept. 1, 2018

The Mack trade, made by Oakland’s then-General Manager Reggie McKenzie, broke down this way:

To Chicago:

• Khalil Mack, DE/OLB;
• Round 2 pick, 2020;
• Conditional Round 5 pick, 2020 (conditions met).

To Oakland:

• Round 1 pick, 2019 (No. 24 overall);
• Round 6 pick, 2019 (No. 196 overall);
• Round 1 pick, 2020;
• Round 3 pick, 2020.

How has the trade worked out for the two teams?

Khalil Mack: In Chicago, Mack has played in 30 games over the 2018 and 2019 seasons (starting 29) and registered a combined 94 tackles and 21 sacks, earning two more Pro Bowl selections and leading the Bears to a 2018 playoff berth. The Bears also got him signed long-term, which the Raiders either couldn’t or wouldn’t do, and they seem to be more than getting their money’s worth — no surprise, given Mack’s superlative play on the field and immaculate reputation off it during his time in Oakland.

Round 2 and conditional Round 5 picks, 2020: The Bears have yet to use either of the picks they received as part of the trade, with the second-round pick currently slated for No. 43 overall in the upcoming 2020 NFL Draft and the fifth-rounder’s overall slot yet to be determined due to compensatory picks and other factors.

Round 1 pick, 2019: The Raiders received the No. 24 overall and No. 196 overall picks from Chicago in 2019.

With the 24^th overall pick, the team selected running back Josh Jacobs from Alabama, the first RB chosen in the 2019 NFL Draft and the consensus top RB available.

Jacobs didn’t disappoint in his first year in Silver & Black, rushing for a team rookie record 1,150 yards, with seven touchdowns in 13 starts, while catching 20 balls and earning (at the time of this writing) at least one Offensive Rookie of the Year honor. All this despite playing through a shoulder injury for much of the season.

Round 6 pick, 2019: New GM Mike Mayock stayed busy on Draft Day 2019, moving up and down the various rounds repeatedly, while moving players in and out of Oakland.

As a result, the Raiders traded the 196^th pick, along with former starting guard Kelechi Osemele, to the New York Jets for the No. 140 overall pick in the fifth round. (Osemele was eventually released after a controversy over an injury.) The Jets took cornerback Blessuan Austin of Rutgers — who broke Raiders receiver Hunter Renfrow’s ribs with a tackle in Week 12 of the season — with that 196^th pick.

The Raiders then traded the 140^th pick to the Jacksonville Jaguars as part of a deal that enabled Jacksonville to move up in the second round. The Raiders traded second-, fifth- and seventh-round picks, Nos. 35, 140 and 235 overall, to the Jaguars for second- and fourth-round picks, Nos. 38 and 109 overall. The Jaguars took offensive tackle Jawaan Taylor of Florida at No. 35, RB Ryquell Armstead of Temple at No. 140 and defensive tackle Dontavius Russell of Auburn at No. 235.

Further complicating the return for Mack, the Raiders traded both picks they got from Jacksonville. They first traded No. 38 overall to the Buffalo Bills so Buffalo could move up in the second round, sending the No. 40 overall pick along with the No. 158 overall pick in the fifth round. Buffalo took G Cody Ford of Oklahoma. The Raiders, finally picking in the second round, took CB Trayvon Mullen of Clemson with the 40^th pick.

However, they traded the 158^th pick to Dallas, along with their own No. 218 overall pick in the seventh round, to move up to No. 149 overall in the fifth round. That’s where the Raiders landed Hunter Renfrow, the WR from Clemson. Dallas took CB Michael Jackson of Miami at No. 158 and RB Mike Weber of Ohio State at No. 218.

The Raiders also traded Jacksonville’s No. 109 pick, moving down in the fourth round through a deal with the Indianapolis Colts. The Colts sent the Raiders picks No. 129 and 135 (compensatory) in the round for that 109^th pick, then chose strong safety Khari Willis of Michigan State. With pick No. 129, the Raiders chose CB Isaiah Johnson of Houston.

And, of course, they traded pick No. 135. That pick went to the Atlanta Falcons in exchange for pick No. 137 in the round and pick No. 230 in the seventh round. Atlanta took DE John Cominsky of Charleston (W.Va.) at No. 135. With pick No. 137, the Raiders chose tight end Foster Moreau of LSU, and with pick No. 230, they took DE Quinton Bell of Prairie View A&M — the only draft pick who failed to make the 2019 squad.

Round 1 and Round 3 picks, 2020: For the Raiders in 2020, the first-rounder from Chicago is No. 19 overall, while the third-round slot has yet to be determined, but should fall in (approximately) the mid- to late 80s overall.

The Jon Gruden trade, Feb. 18, 2002

The amazing thing is that the Mack trade is not the most famous (or complicated) trade in Raiders history. It isn’t even close. And, while the most famous — or, infamous — trade in Raiders history also involved Gruden, it wasn’t the coach making the trade, it was the coach being traded.

As every Raiders fan knows, Gruden, in his first go-round with the team, led it to the playoffs in 2000 and 2001. But, by the offseason between 2001 and 2002, Al Davis had apparently tired of sharing the spotlight with the fiery young coach, and decided to allow the Tampa Bay Buccaneers to hire him away.

Davis, however, exacted a high price for Gruden:

• Round 1 pick, 2002 (No. 21 overall);
• Round 2 pick, 2002 (No. 53 overall);
• Round 1 pick, 2003 (No. 32 overall);
• Round 2 pick, 2004 (No. 45 overall);
• Cash, reportedly $8 million.

Of course, Gruden led the Bucs to Super Bowl XXXVIII that very season, 2002-03, where he defeated the Raiders and his right-hand man-turned-replacement, Bill Callahan.

But the trade had on-field repercussions for the Raiders for years to come.

Through subsequent trades, the Raiders were still reaping the benefits of the Gruden trade in some way, shape or form for more than a decade.

Here’s how:

Round 1 and Round 2 picks, 2002: The first picks the Raiders received in the trade wound up being No. 21 and No. 53 overall in the 2002 NFL Draft, before Gruden had even coached a game in Tampa Bay.

Oakland moved up in the first round on Draft Day, however, trading the 21^st pick, along with the No. 89 overall pick in the third round to the Washington Redskins for the 18^th overall pick. With the No. 18 pick, the Raiders chose CB/kick returner Phillip Buchanon of Miami. The 21^st pick wound up with the New England Patriots, who chose TE Daniel Graham of Colorado, while the 89^th pick wound up with Jacksonville, which took LB Akin Ayodele of Purdue.

With the No. 53 pick, the Raiders took OT Langston Walker of California.

What became of them?

Buchanon played three seasons for the Raiders, primarily as a starting CB and punt returner, known for both making and giving up big plays. Over his 36 games with the team, he produced 11 interceptions and returned four for TDs, while returning 72 punts for an 11-yard average and three more TDs. Nevertheless, the Raiders eventually tired of his mercurial play — Hall of Fame teammate Tim Brown once infamously said, “Phillip giveth and Phillip taketh away” — and traded him to the Houston Texans for second- and third-round picks in 2005, Nos. 47 and 78 overall. (See below for more.)

Walker played five years for the Raiders, starting 33 of 66 games, including all 16 in 2006, before signing a big-bucks free agent contract with Buffalo before the 2007 season. After two years in Buffalo, he was cut and returned to Oakland, playing 22 games with 17 starts, including all 15 games he played in 2010, his last year in the NFL. Although he spent all or parts of four season as a starter in Oakland, the 6-foot-8 Walker may be primarily remembered for his kick-blocking prowess.

Round 1 pick, 2003: As painful as losing the Super Bowl to Tampa in January 2003 was, the further salt in the wound was that the Raiders’ picks in the first round of the 2003 NFL Draft became their own No. 31 pick, next-to-last in the round as the league runner-up … and the No. 32 overall pick, last in the round because it came from the Super Bowl champion.

With that 32^nd overall pick, the Raiders chose DE Tyler Brayton of Colorado.

Brayton lasted five years in Oakland, but, after starting all 16 games as a rookie during the dreadful 2013 season, saw his chances of success derailed when the Raiders fired Callahan as head coach and new defensive coordinator Rob Ryan shifted the team from a 4-3 defense to a 3-4 and attempted to move the 280-pound Brayton to outside linebacker. Brayton started all 15 games he played in 2014, but struggled to keep up in pass coverage (as might be expected) and was benched in 2015, starting only three games. He moved back to DE in 2016 and started 13 games, but spent 2017 back on the bench and signed as a free agent with the Carolina Panthers after the season.

Round 2 pick, 2004: The Raiders’ final “original” pick from the Gruden deal wound up the No. 45 overall pick in 2004, as the Buccaneers had slumped to 7-9 and then 5-11 in the years after their Super Bowl win. With that pick, the Raiders took C Jake Grove of Virginia Tech. Grove was essentially the starting center for the team over five injury-prone seasons, but only played (and started) 16 games once in that stretch, in 2006. He signed a free-agent contract with the Miami Dolphins after the 2008 season, essentially switching places with Dolphins C Samson Satele, who Miami traded to the Raiders for draft picks.

The fallout in 2005: Having traded Buchanon in the days leading up to the 2005 NFL Draft, the Raiders continued to wheel and deal with the picks involved — not just on Draft Day, but for years to come.

At the 2005 draft, the Raiders packaged the 47^th pick, one of the two acquired for the CB, with another young veteran, TE Doug Jolley, and two more picks, Nos. 182 and 185 in the sixth round (both previously acquired in trades). That package was sent to the Jets for pick No. 26 overall in the first round and pick No. 230 in the seventh round. The Jets took kicker Mike Nugent of Ohio State with the 47^th pick and RB Cedric Houston of Tennessee with the 182^nd pick. The 185^th pick wound up with Jacksonville, which took KR Chad Owens of Hawaii.

The Raiders then traded up in the first round, sending the 26^th pick along with pick No. 105 overall in the fourth round to the Seattle Seahawks for pick No. 23 overall. Seattle took center Chris Spencer of Mississippi at No. 26 and OT Ray Willis of Florida State at No. 105. The Raiders, meanwhile, chose CB Fabian Washington of Nebraska at No. 23 (in another infamous note, local Cal QB Aaron Rodgers was still on the board, with the Green Bay Packers taking him at No. 24).

The Raiders did keep the 78^th overall pick from the Buchanon deal, selecting LB Kirk Morrison of San Diego State.

The Raiders also traded the other pick they received from the Jets, sending the 230^th pick to the New England Patriots along with a fifth-round pick in the 2006 NFL Draft, for the No. 175 pick overall, the first pick in the sixth round. With that pick, the Raiders took DT Anttaj Hawthorne of Wisconsin, who had seen his draft stock plummet after a failed drug test. With the 230^th pick, the Patriots took quarterback Matt Cassel of USC. Hawthorne lasted two seasons in Oakland, spending much of his rookie year on the practice squad and then the offseason in NFL Europe, before playing 16 games as a sophomore reserve. He was cut in camp in 2007.

The fallout in 2006: The Raiders’ fifth-round pick, sent to New England as part of the Hawthorne deal, wound up No. 136 overall. The Patriots chose OT Ryan O’Callaghan of Cal with the pick.

The fallout in 2008: Washington played three years in Oakland, starting the first two, before being benched and subsequently traded to the Baltimore Ravens for the No. 125 overall pick in the fourth round of the 2008 NFL Draft. With that pick, the Raiders chose WR Arman Shields of Richmond. Shields, who had been hurt as a senior in college, missed his rookie year due to injury despite a strong pre-draft Scouting Combine, and failed his physical prior to his second season, never playing a game for the Raiders.

The fallout in 2010: Morrison, meanwhile, became a five-year starter in Oakland, primarily at middle linebacker. He played in all 80 games from 2005 to 2009, starting all but one, and breaking the 115-tackle mark each season. He was traded to Jacksonville during the 2010 NFL Draft, along with the No. 153 overall pick in the fifth round, for the No. 108 pick in the fourth round. Jacksonville took DE Austen Lane of Murray State at No. 153. The Raiders took WR/KR Jacoby Ford of Clemson at No. 108.

The speedy Ford played for the Raiders from 2010 through 2013 (injury-prone, he played only eight games in 2011 and missed the entire 2012 season), but never broke into the starting lineup on a regular basis, starting only 13 of 38 career games. He caught 57 passes, including three TDs, primarily as a deep threat, while rushing 19 times and scoring twice on end-arounds. He got his most work as a return man, bringing back four kickoffs for touchdowns, including three in 2010 (both team records), and averaging 25 yards a return over 75 career kick returns, while also returning nine punts.

When Ford left the Raiders as a free agent after the 2013 season, he was the last remaining tie to the original Gruden deal, a dozen years before.

Gruden, meanwhile, was long gone from Tampa Bay, having been fired after the 2008 season. He won 60 total games in Florida, 57 in the regular season and three during the Super Bowl championship season. He posted four winning seasons out of seven overall, and lost both playoff games his teams qualified for after that magical 2002.

In 2018, after nearly a decade in broadcasting, Gruden returned to the Raiders’ sideline … and started his second stint with a bang, trading Mack and bringing this Project full circle.

(Editor’s Note: As we work to reboot and redesign the Raiders Research Project for 2020, early-year content may not reflect the final plans for the site in terms of both functionality and content. Please bear with us. ~ Ace)

Sources: Raiders publications; Ourlads Scouting Services publications; Raiders.com, ChicagoBears.com, NFL.com, The Athletic, Pro-Football-Reference.com and Wikipedia.com.

All photos (except as noted) by Bob Carr Photography; used with permission.