Oakland Raiders: 15 best free agent acquisitions of all-time

With free agency just around corner, let's take a look at the 15 best free agent acquisitions in Oakland Raiders history.

Lazy loading placeholder

Rich Gannon, Oakland Raiders. (Photo By Eliot J. Schechter/Getty Images)

Arguably the most important offseason in Oakland Raiders history is less than a month away and fans everywhere are waiting in anticipation. Obviously, fans are keen on looking for the next star in this year's crop of free agents. But why not take a look at some of the best pieces of business in franchise history?

Like any other NFL franchise, the Raiders have had some big time free agent acquisitions, but they have also had their fair share of misses. Remember DeAngelo Hall? Yeah, me, too. Nonetheless, let's keep it positive and look at which players the Raiders struck gold on.

Obviously, this ranking will be based on how well the player performed as a member of the Raiders. Statistics mixed with evaluations of team success during their stint will be considered heavily in ranking these players.

Let's start with some honorable mentions. Guys like Jeff Hostetler, Pat Swilling and Lee Smith were all great free agent pickups, but they barely miss the cut here. The first name on the list is one of my favorite players to ever sport the Silver and Black, and a huge reason for the Raiders turning the corner in 2016.

Lazy loading placeholder

Justin Tuck, Oakland Raiders. (Photo by Brian Bahr/Getty Images)

15

Justin Tuck

DE | (2014-15)
Justin Tuck Logo

First and foremost, Justin Tuck may not be the most talented player on this list, but his impact on the Raiders was tremendous. After spending the first nine years of his career with the New York Giants, Tuck joined the Raiders in 2014 after signing a two-year, $11 million contract. The hope was that the veteran defensive end would bolster the defensive line and give the Raiders a consistent presence off the edge.

So it turned out, the Raiders ended up selecting Khalil Mack with their fifth overall pick in the 2014 NFL Draft, a month after they signed Tuck. Oakland also drafted Justin Ellis and had young linebackers in Sio Moore and Ray-Ray Armstrong.

All four of the those players benefited heavily from having Tuck on the team. He was able to teach them the little things, like how to stay focused and how to deal with the daily toll the NFL has on its players.

Clearly, this two-year deal came at the tail end of Tuck's career, but Tuck still had a decent run with Oakland. In 2014, he tallied five sacks and two forced fumbles with 43 tackles to boot.

Unfortunately, he missed 11 games in 2015 due to injury and only recorded one sack. Tuck retired shortly after the 2015 season.

The best way to sum up how Tuck helped the Raiders was in a Thursday night game against the Kansas City Chiefs. After what was essentially a game-winning sack by Sio Moore, Moore and Mack were celebrating in the backfield while the Chiefs were about to hike the ball, resulting in an offside penalty.

Tuck was there to call timeout and save the Raiders from collapsing, resulting in the first win in Derek Carr's career. He may not have had incredible sack totals, but Tuck was a huge reason behind the culture shift in Oakland from 2014 to 2015.

3 of 16
Lazy loading placeholder

Donald Penn, Oakland Raiders. (Photo by Joseph Garnett Jr. /Getty Images)

14

Donald Penn

OT | (2014-Present)
Donald Penn Logo

Donald Penn is the first of several offensive linemen to make this list. Apparently, the Raiders have a knack for signing offensive linemen in free agency.

After making his name with the Tampa Bay Buccaneers, Penn decided to remain a pirate, signing with the Raiders in 2014. His original deal was for two years and $9.6 million, yet the tackle remains on the roster in 2019. Obviously, the deal worked out for both sides.

From day one with Oakland, Penn was the starting left tackle. For the first three seasons as a Raider, Penn didn't miss a single game, starting in all of them.

Unfortunately, Penn missed the Raiders' lone playoff game during that stretch after the 12-4 regular season in 2016. At the time, Penn was one of the longest tenured NFL players to have not played in a playoff game.

After 2016, Penn signed a contract extension for two more seasons and $14 million, that would later be upped to $21 million after a brief holdout after the 2017 season.

After Kolton Miller's selection in the 2018 NFL Draft, Penn lost his spot starting at left tackle. Showing his versatility, Penn moved to the right side, but due to injury, he only played in four games in 2018, opening the door for Brandon Parker to fill his place.

Whether or not Penn returns to the starting lineup in 2019, his time in Silver and Black was great. He earned Pro Bowl honors twice during his stay in 2016 and 2017. Penn was a huge part of an offensive line that was deemed top-three in the NFL during that period.

4 of 16
Lazy loading placeholder

Zack Crockett, Oakland Raiders. (Photo by Robert B. Stanton/NFLPhotoLibrary)

13

Zack Crockett

FB | (1999-06)
Zack Crockett Logo

Running back? Fullback? Linebacker? Whatever he was, Zack Crockett was a great free agent acquisition for the Raiders in the early 2000s. At 6-foot-2 and 240 pounds, Crockett was a beast of a runner and proved to be an incredible goal line threat for the Raiders from 1999 to 2006.

Drafted by the Indianapolis Colts, Crockett spent three and a half seasons with them before signing with the Jacksonville Jaguars for the remainder of the 1998 season. That offseason, Crockett signed with the Raiders, beginning what would become a great eight-season run with the Silver and Black.

Although he was listed as both a running back and fullback, Crockett did most of his work as a fullback for Oakland. His powerful running style made him borderline unstoppable in goal-to-go situations. This fact is very clearly is proven by Crockett's statistics during his 13-year career. Specifically during his stint in Oakland, Crockett compiled 1,232 yards and 35 touchdowns.

Crockett was a pivotal piece in the playoff teams of the early 2000s, leading the Raiders in rushing touchdowns twice during his stay.

In seven playoff appearances with the Raiders, Crockett finished with 31 yards and three touchdowns, further proving how the tough-nosed fullback was used under Jon Gruden. Still a member of the Raiders organization as a scout, Crockett is easily one of the best signings in franchise history.

5 of 16
Lazy loading placeholder

Jared Cook, Oakland Raiders. (Photo by Thearon W. Henderson/Getty Images)

12

Jared Cook

TE | (2017-Present)
Jared Cook Logo

When it comes to tight ends, the Raiders have had some pretty great ones, two of which coming in as free agent signings. The first of two on this ranking is Jared Cook.

He joined the Raiders prior to the 2017 season after spending time with three teams in his eight previous seasons. One thing is for certain, the Tennessee Titans, the then-St. Louis Rams and the Green Bay Packers all were unable to truly unlock Cook like the Raiders did.

Whether that was due to necessity or usage or any number of variables, it is a fact. In only two seasons as a Raider, Cook emerged as one of the best pass-catching tight ends in the NFL. That is pretty odd for a player who had already spent eight years in the league. One would think his skill set would have been utilized at some point during that time.

Nonetheless, in 2017 Cook signed a two-year, $10.6 million contract with $5 million guaranteed. Cook easily earned that contract and made a strong case to be re-signed by the team. How that turns out remains to be seen in this upcoming offseason.

In the 2017 season, Cook posted 688 yards and two touchdowns, a solid total for a tight end. In 2018 however, he really came into his own, leading the Raiders in receiving yards with 896, tacking on six touchdowns for good measure.

A shrewd piece of business and a roll of the dice turned into a huge success. That is why Cook finds himself in the top-15 free agent signings in Raiders history.

6 of 16
Lazy loading placeholder

Tyrone Wheatley, Oakland Raiders. (Photo by Jonathan Ferrey/Getty Images)

11

Tyrone Wheatley

RB | (1999-04)
Tyrone Wheatley Logo

Another member of the early 2000s success, Tyrone Wheatley is one of the many great running backs to have donned the prestigious Silver and Black. A first-round pick of the New York Giants, Wheatley spent the first four seasons of his career in the Big Apple.

Luckily for the Raiders, Wheatley was cut by the Miami Dolphins following training camp. Due to an injury to Zack Crockett, the Raiders needed another powerful rusher to pair with Napoleon Kaufman.

Wheatley was a perfect fit in Oakland and very quickly became a fan favorite. He developed a good relationship with Jon Gruden as well, improving his position within the team. Over the next six seasons, the veteran running back would enjoy a lot of success.

Adept at both rushing and catching the ball out of the backfield, Wheatley opened up a lot of possibilities for the Raider offense. During his stay in Oakland, the Raiders made the playoffs three consecutive seasons, including a trip to the Super Bowl which resulted in a loss to the Tampa Bay Buccaneers, led by former Raiders coach Gruden.

Over six seasons, Wheatley rushed for 3,682 yards and 32 touchdowns, good enough for eighth all-time in Raiders history.

Undeniably, Wheatley is one of the best free agent signings the Raiders have ever made. He helped carry them to their most recent playoff success and Super Bowl appearance after largely striking out in New York. Wheatley is now the head coach of Morgan State, further proving how great of a football mind he is.

7 of 16
Lazy loading placeholder

Michael Crabtree, Oakland Raiders. (Photo by Lachlan Cunningham/Getty Images)

10

Michael Crabtree

WR | (2015-17)
Michael Crabtree Logo

Coming out of Texas Tech, Michael Crabtree was one of the most sought after wide receivers in his draft class. So much so that the San Francisco 49ers selected him with the 10th overall pick in the 2009 NFL Draft. Crabtree enjoyed a successful six seasons in San Francisco, helping them to a Super Bowl along the way, before joining the Raiders in 2015.

The Raiders needed to give their new franchise quarterback Derek Carr some more weapons on offense. In the 2015 offseason, they added Crabtree and fourth overall pick Amari Cooper to the fold, transforming the Oakland offense. The new pairing proved to be very successful, as both were able to thrive in a high-flying offense.

In Crabtree's three seasons as a Raider, he proved that he belongs in the record books of the Silver and Black. Not only did he bring a sure set of hands and jump-ball ability, he brought a swagger to Oakland that had been missing for many years. Yes, that may have cost him a bit, as it led to his release in 2017, but it was instrumental in his success with the Raiders.

Three seasons, 2,543 yards and 25 touchdowns later, Crabtree proved to be one of the most successful free agent acquisitions in Oakland history. He helped turn what was a very important corner for the franchise, helping them bridge the gap from 7-9 in 2015 to 12-4 in 2016. Without Crabtree, it is hard to imagine that Raiders team making the playoffs in 2016.

8 of 16
Lazy loading placeholder

Rod Woodson, Oakland Raiders. (Photo by Joe Robbins/Getty Images)

9

Rod Woodson

FS | (2002-03)
Rod Woodson Logo

Obviously, this ranking is based upon his time as a player, not a coach, as Rod Woodson has fallen out of favor with Raiders fans in recent times.

Due to some comments after being released from his duties as defensive backs coach and the infamous coin flip with the San Francisco 49ers, Woodson's name may not be the most popular among the Raider faithful. That aside, Woodson was one of the best defensive backs in Raiders history.

Woodson will be remembered mostly for the incredible 10 years he spent with the Pittsburgh Steelers, his time in Oakland was impressive considering the context. In 2002, the Raiders were loading up for a Super Bowl push, and Woodson happened to be available.

In that offseason, Oakland signed Woodson to a six-year contract. Unfortunately, Woodson only fulfilled two years of that commitment due to injuries.

Regardless of how it ended, Woodson was pivotal in the Raiders' Super Bowl appearance in 2002. At 37 years old, Woodson earned All-Pro and Pro Bowl honors during that season, as he led the league in interceptions with eight. Playing in the NFL at 37 is impressive enough, let alone starting at free safety and leading the league in interceptions.

The contract is the only bad aspect to this deal. It only looks that way because Woodson injured his knee and was unable to fully recover and failed a physical. Who knows, without the injury, maybe Woodson would go on to play into his 40s?

9 of 16
Lazy loading placeholder

Todd Christensen, Los Angeles Raiders. (Photo by George Rose/Getty Images)

8

Todd Christensen

TE | (1979-88)
Todd Christensen Logo

Earlier I mentioned the Raiders have had some pretty stellar tight ends in their time, but few were better than Todd Christensen. On second thought, no other tight end in Raiders history eclipsed what Christensen was able to do. Dave Casper is a close second, but he doesn't quite match Christensen.

Signed in 1979, Christensen was primarily used as a special teamer early in his stay with the Raiders. Eventually, he moved to tight end and well, the rest is in the history books.

His following nine seasons would be spent with the Raiders, both in Oakland and Los Angeles. In 1983, Christensen led the league in receptions with 92 and tallied 1,247 yards. That same season the Raiders won the Super Bowl, due in a large part to how well Christensen played that year.

Over the years he spent with the Silver and Black, Christensen totaled 5,872 yards, enough for fourth all-time in the Raiders' record books. He also hauled in 41 touchdowns as a Raider. nNot too bad huh for a fullback, turned tight end.

A two-time Super Bowl champion and a four-time All-Pro, Christensen is without a doubt one of the best signings in Raiders history. His transition to tight end was flawless and he helped lead the Raiders to a lot of success in the 1980s. One team's roster cut turned into legend for another. That's what they call good business.

10 of 16
Lazy loading placeholder

Kelechi Osemele, Oakland Raiders. (Photo by Brian Bahr/Getty Images)

7

Kelechi Osemele

G | (2016-Present)
Kelechi Osemele Logo

Yet another offensive linemen appears on this ranking, but don't worry, Kelechi Osemele isn't the last one. The former second-round pick of the Baltimore Ravens was one of the biggest free agent acquisitions in recent history for the Raiders. As it has played out, it has been one of the best signings ever for Oakland.

The Iowa State product has been nothing short of spectacular during his time with the Silver and Black. In 2016, Osemele signed a five-year, $60 million contract that would carry him through the 2020 season. Once a tackle, Osemele switched to guard and has held down the left guard position for the Raiders since his arrival.

A two-time Pro Bowler, one-time All-Pro and a Super Bowl champion, Osemele is one of the best offensive linemen in the business. Despite battling some injuries while with the Raiders, Osemele was a huge part of the Raiders' success in 2016. He and fellow guard Gabe Jackson were two of only four NFL guards in 2016 to not allow a sack. That is dominance.

Many teams pursued Osemele in free agency, but only the Raiders were lucky enough to land his services. Only 29 years old, Osemele has some more great football ahead of him. Already one of the best signings in Oakland history, the talented guard may have some more time to solidify that fact.

11 of 16
Lazy loading placeholder

Charlie Garner, Oakland Raiders. (Photo by Jed Jacobsohn/Getty Images)

6

Charlie Garner

RB | (2001-03)
Charlie Garner Logo

The final running back on this ranking, Charlie Garner comes in just outside the top-5, but only slightly. As is normally the case with running backs, Garner bounced around the NFL.

In the seven seasons prior to joining the Raiders, Garner spent time with the Philadelphia Eagles and across the bay with the San Francisco 49ers. Following his three-year spell with Oakland, Garner finished his career with the Tampa Bay Buccaneers.

When Garner joined the Raiders in 2001, it was hoped that he would be the final piece of the puzzle and would help push the Raiders to the Super Bowl. Pairing with Tyrone Wheatley, Garner did just that.

In three seasons, Garner put up some incredible numbers. He rushed for 2,354 yards on 513 attempts, enough for a ridiculous 4.6 yards per carry. But Garner provided value in the passing game as well, tallying 211 receptions for 1,905 yards. An absurd 4,259 all-purpose yards in three seasons, Garner was simply incredible for the Silver and Black.

After losing in the Super Bowl, the Raiders regressed heavily. Garner left after that season, but he was already over the dreaded age of 30.

His time in Oakland may have been somewhat short-lived in comparison to some others on this list, but he did more than enough to be named one of the Raiders' best free acquisitions of all-time.

12 of 16
Lazy loading placeholder

Charles Woodson, Oakland Raiders. (Photo by Jamie Squire/Getty Images)

5

Charles Woodson

DB | (1998-05, 2013-15)
Charles Woodson Logo

When it comes to being a Raider through and through, few come to mind more than the great Charles Woodson. I know what you may be thinking, the Raiders drafted him out of Michigan in 1998.

True, but the Raiders also re-signed him as a free agent prior to the 2013 season. For the purposes of this article, only his statistics and impact after being re-signed will be considered, but it is more than enough.

At 37 years old, Woodson left the Green Bay Packers, but wanted one last rodeo. What better place to retire than the team that gave him his start in the league?

Oakland welcomed him back with open arms, literally. After the signing, there was a group of loyal Raiders fans waiting to greet him at the facility. That should tell you all that you need to know about Woodson.

Moving from corner to safety, Woodson started in every game for the Raiders in his second stint. Tallying 10 interceptions, seven fumble recoveries and three sacks, Woodson played very well considering he was 37, 38 and 39 years old during his final three seasons.

More important than the stats, Woodson helped usher in a new era in Raider football. He brought heart and leadership to a young group in need of a vocal leader and taught a lot of the core how to carry themselves in the NFL. Woodson's impact on the Raiders overall was tremendous and he is easily a legend of the franchise.

13 of 16
Lazy loading placeholder

Jim Plunkett, Los Angeles Raiders. (Photo by George Rose/Getty Images)

4

Jim Plunkett

QB | (1978-86)
Jim Plunkett Logo

Of all the players the Raiders have signed during their franchise history, Jim Plunkett has to be among the most interesting of the lot. His story is incredible and his success is largely unparalleled. Yet it was hard to predict, as Plunkett was originally signed to be a backup quarterback. But let's back up a bit to get the full story.

Coming out of Stanford, Plunkett was selected first overall in 1971. After spending time with the New England Patriots and San Francisco 49ers, Plunkett was signed in 1978 to serve as a backup.

Actually, the only reason he ever got a chance to play was because starter Dan Pastorini broke his leg and young gun Marc Wilson wasn't ready for the big stage.

Plunkett led the team to two Super Bowl victories, both seasons in which he started as the second or third option. Actually in the 1980 season, Plunkett led the Raiders to four consecutive playoff victories, making history as the first Wild Card team to win the Super Bowl.

Perhaps unsurprisingly, Plunkett was named Super Bowl MVP, becoming the first ever Latino to earn that honor.

Unfortunately and wrongly, Plunkett has yet to be named to the Pro Football Hall of Fame. Hopefully that error is corrected while he is still able to accept the award in person, not posthumously like former Raider great Ken Stabler. Two Super Bowl championships and one Super Bowl MVP award to his name, Plunkett is one of the best free agent signings in Raiders history.

14 of 16
Lazy loading placeholder

Rodney Hudson, Oakland Raiders. (Photo by Ezra Shaw/Getty Images)

3

Rodney Hudson

C | (2015-Present)
Rodney Hudson Logo

The final offensive lineman to be ranked, Rodney Hudson is the first player in the top-three on this list. The current center of the Raiders, Hudson came to the dark side after spending the first four seasons with the rival Kansas City Chiefs.

In 2015, Hudson was one of the biggest fish on the open market. Being able to steal him from a division rival made it even sweeter for the Raiders to land the consistent center.

Since joining Oakland, Hudson has only missed three games. Frankly, consistent may be an understatement, but is there another adjective out there to describe Hudson? Maybe dominant.

In four seasons in Oakland, Hudson has only allowed two sacks. Yes, you read that right. Shockingly, he was only named a Pro Bowler in two of those seasons.

There may not be a better center in the league at the moment. From preparation to putting it all together on the field, few do it as well as Hudson. He is the glue that holds the offensive line together and is vital to any success the Raiders have.

Hudson's deal was for five years in 2015, so coming up in 2020 he will be a free agent. If the Raiders are smart, they should do anything in their power to keep Hudson in the Silver and Black until he is ready to retire.

Yet to turn 30, Hudson still has some good football years ahead of him. A great, no incredible signing, the Raiders are lucky to have Hudson on their side.

15 of 16
Lazy loading placeholder

Jerry Rice, Oakland Raiders. (Photo by Jed Jacobsohn/Getty Images)

2

Jerry Rice

WR | (2001-04)
Jerry Rice Logo

Similar to how Charles Woodson didn't really need any introduction, the same should be true for the greatest wide receiver of all-time. Everyone knows that he spent an incredible 16 seasons with the San Francisco 49ers, where he tallied nearly 20,000 receiving yards. Yet at the ripe old age of 39, Jerry Rice moved across the bay to play for Jon Gruden and the Raiders.

Pairing Rice with Raiders legend Tim Brown was fruitful, as both had tremendous seasons in the early 2000s. Rice helped the Raiders to two consecutive playoff berths, including one Super Bowl appearance in the 2002 season. His three seasons with Oakland were incredible, especially considering he was 40 years old when the Raiders made the Super Bowl.

In 2001 when he joined the team, Rice posted 1,139 yards receiving and nine touchdowns. He followed that up with 1,211 yards and seven touchdowns. One more time to really hammer the point home...he was 40 years old. That defies all football logic.

Statistics, a solid locker room presence, and a personality that helped sell tickets. Rice really was the full package, on and off the field. All things considered, Rice would top this list in a lot of other scenarios. Unfortunately, the Raiders made one better signing along the way. It just so happened to be the quarterback throwing Rice the ball.

16 of 16
Lazy loading placeholder

Rich Gannon, Oakland Raiders. (Photo by Jonathan Daniel/Getty Images)

1

Rich Gannon

QB | (1999-04)
Rich Gannon Logo

A bit of a journeyman quarterback, Rich Gannon bounced around the NFL before finding a true home in Oakland with the Raiders.

Drafted by the Minnesota Vikings in 1987, Gannon made stops with the Washington Redskins and the Kansas City Chiefs as well before being signed by the Raiders in 1999.

Named the starter right away, Gannon embarked on an incredible six-year journey with the Silver and Black.

Prior to 1999, Gannon's career-high in yardage was 2,305 yards. In his first season as a Raider, he threw for 3,840 yards and never really looked back.

In each of his first four seasons, Gannon passed for over 3,000 yards and was named to the Pro Bowl every time. In two of those, he was also named First-Team All-Pro.

Without a doubt, 2002 was Gannon's best season in the NFL, as he led the league in completions and yardage with marks of 418 and 4,689. Gannon helped carry the Raiders to the Super Bowl and was named the MVP of the league for his efforts, and deservedly so.

Next: Oakland Raiders: 15 greatest pass rushers of all-time

Gannon resurrected his career with the Silver and Black and helped lead them to their most successful spell since the Super Bowl winning teams in the 1980s. His total of 17,585 yards is third most all-time in Raiders history, only surpassed by Ken Stabler and Derek Carr. Without a doubt, Gannon is the best free agent acquisition in the storied history of the franchise.