Money Down the Drain: The 15 Worst Investments in Raiders History
February 27, 2023
Hunter Macias
In this piece, we examine the top 15 most regrettable signings in the history of the Las Vegas Raiders, highlighting some of the team's most costly mistakes in the process.
Free Agency
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If you're a Las Vegas Raiders fan, you know that free agency has been a mixed bag for the team over the years. While some moves have paid off big time, others have been downright disastrous, leaving fans scratching their heads and wondering what went wrong. In this blog, we'll be counting down the 15 worst free agent signings the team has ever made, taking a trip down memory lane and reliving some of the team's most regrettable decisions.
No. 15: Nick Kwiatkoski, Linebacker (3yr-$21M)
Disappointment in Signing Nick Kwiatkoski: How the Raiders Got It Wrong
When the Las Vegas Raiders signed Nick Kwiatkoski to a three-year, $21 million contract in March 2020, fans were hopeful that the linebacker would be the answer to the team's defensive woes. After all, the Raiders had struggled on defense for years, and Kwiatkoski seemed like just the kind of player they needed to turn things around.
Unfortunately, things didn't go as planned. Kwiatkoski's tenure with the Raiders was marked by injuries and underperformance, and less than two years after signing him, the team made the difficult decision to release him.
In his 20 appearances with the Raiders, Kwiatkoski made just 12 starts, a disappointing return on the team's investment. While he did play well in 2020, racking up an impressive 81 tackles, it wasn't enough to justify the hefty contract he had been given.
No. 14: Curtis Lofton, Linebacker (3yr-$18M)
When the Raiders signed Curtis Lofton to a three-year, $18 million contract, they were hoping to add a reliable and productive player to their linebacker corps. Lofton had built a reputation as an Iron Man of the sport, having not missed a single game in the six seasons prior to joining the Raiders. This made his signing an exciting prospect for the team.
However, things didn't go according to plan. Despite his reputation for durability and productivity, Lofton struggled to make an impact in his lone season with the Raiders. He was released after failing a physical, which was surprising given his history of durability in the NFL.
During his six seasons leading up to his arrival in Oakland, Lofton had consistently recorded over 100 tackles per season and forced at least one fumble per year. In contrast, his lone season with the Raiders saw him record a career-low 64 tackles and fail to force any fumbles. He was mostly used as a rotational linebacker, and failed to live up to the expectations set by his reputation.
Overall, the signing of Curtis Lofton represents a misstep for the Raiders in free agency. Despite his impressive track record, Lofton was unable to make a meaningful impact during his time in Oakland, leaving the team with a costly contract and little to show for it.
No. 13: Randy Moss, Wide Receiver (2yr-$16M)
In 2005, the Raiders made one of the most high-profile free agent signings in NFL history by acquiring wide receiver Randy Moss from the Minnesota Vikings. At the time, Moss was one of the most dominant receivers in the league, with a reputation for being able to make big plays and stretch the field with his speed and athleticism. The Raiders, in desperate need of a playmaker on offense, thought they had found the missing piece to their puzzle.
However, Moss's tenure with the Raiders was a massive disappointment. Despite playing in all 16 games, he managed just 42 catches for 553 yards and three touchdowns, and the Raiders finished with a 4-12 record. His lack of production was partly due to a hamstring injury that limited his effectiveness on the field, but it was also due to the fact that he simply wasn't a good fit for the Raiders' offense.
Moss had a reputation for being a diva and a disruptive presence in the locker room, and he clashed with head coach Norv Turner and several of his teammates. His effort and work ethic were also called into question, with reports that he was not fully committed to the team or the game of football.
To make matters worse, the Raiders gave up a first-round draft pick to acquire Moss, which turned out to be the 7th overall pick in the 2005 NFL Draft. The pick was used by the Vikings to select wide receiver Troy Williamson, who had a disappointing career but still ended up having more production than Moss did during his time with the Raiders.
In the end, the Raiders were forced to trade Moss back to the Patriots after just one season, and he went on to have a resurgence in New England, where he broke several NFL records and helped the team to an undefeated regular season in 2007.
Overall, the signing of Randy Moss was a disaster for the Raiders. They gave up a valuable draft pick and a significant amount of money to acquire a player who was a poor fit for their team and who ended up causing more harm than good. It's a cautionary tale of the dangers of making high-profile free agent signings based on reputation and star power, rather than fit and team need.
No. 12: Trent Brown, Offensive Tackle (4yr-$66M)
The Las Vegas Raiders made a huge splash in free agency when they signed Trent Brown to a four-year, $66 million contract in 2019. At the time, Brown was considered one of the best offensive tackles in the league and was expected to be a cornerstone of the Raiders' offensive line for years to come. However, Brown's tenure with the team was a disaster, and he has to be considered one of the worst free agent signings in the franchise's history.
The problems started almost immediately. In his first season with the Raiders, Brown played in just 11 games due to injury. Despite his limited playing time, he still managed to earn a Pro Bowl nod, but it was clear that he was not living up to his massive contract. The real problems, however, started in 2020.
Brown played in just five games in 2020 due to a combination of COVID-19 and an injury sustained from an IV mishap. His lack of availability severely hampered the Raiders' offensive line, and it became clear that he was not worth the money he was being paid. In March of 2021, the Raiders traded Brown back to the New England Patriots, along with a seventh-round pick, for a fifth-round selection in the 2022 NFL Draft.
There were several reasons why Brown was a terrible free agent signing for the Raiders. For starters, he was simply not worth the money he was being paid. $66 million is a massive contract for any player, but it's especially egregious for an offensive lineman who had only played one full season in his career. Brown's injury history should have been a red flag for the Raiders, but they chose to ignore it.
Another problem with the signing was the lack of impact Brown had on the team. When he was on the field, he was good, but he wasn't the dominant force the Raiders were expecting. In fact, his presence on the field may have been overstated due to the poor play of his replacements. When Brown was injured, the Raiders struggled to find a competent replacement, which made his absence all the more noticeable.
Finally, the circumstances surrounding Brown's departure from the team were less than ideal. It's never a good sign when a team trades away a player they signed to a massive contract just two years earlier. The fact that the Raiders were willing to part with Brown for a fifth-round pick speaks volumes about how they felt about his time with the team.
In the end, it's clear that Trent Brown was a terrible free agent signing for the Las Vegas Raiders. He was overpaid, injury-prone, and failed to have the impact the team was expecting. While it's easy to say in hindsight that the Raiders should have avoided the signing, it's a lesson that all teams should take to heart: sometimes, the biggest names in free agency are not worth the money they're asking for.
No. 11: Tyrell Williams, Wide Receiver (4yr-$44M)
The Las Vegas Raiders have made their fair share of bad free-agent signings over the years, and one that stands out is the acquisition of wide receiver Tyrell Williams. Williams signed a four-year, $44 million contract with the Raiders in March 2019, with the expectation that he would become a reliable target for quarterback Derek Carr. However, things did not go according to plan, and Williams' tenure with the Raiders can only be described as a disappointment.
Firstly, Williams was plagued by injuries during his time with the Raiders. He played in just 14 games over two seasons, missing significant time in both years due to a variety of injuries, including plantar fasciitis, a torn labrum, and a foot injury that required surgery. As a result, he was unable to establish any sort of rhythm with Carr and was never able to live up to the expectations that came with his hefty contract.
In the limited time that he was on the field, Williams failed to make a significant impact. In his first season with the Raiders, he caught just 42 passes for 651 yards and six touchdowns, which were all lower than his previous season with the Chargers. In 2020, he played in just two games before being placed on injured reserve, finishing the season with no catches and no touchdowns. This lack of production was especially disappointing given the amount of money that the Raiders had invested in him.
Moreover, Williams' contract was one of the factors that contributed to the Raiders' salary cap issues in 2020. His cap hit in 2020 was $11.1 million, making him the third-highest paid player on the team. The Raiders were forced to restructure several contracts and release some players to get under the cap, which had a negative impact on the team's overall depth.
In conclusion, the signing of Tyrell Williams was a misstep for the Raiders. His injury history and lack of production, combined with his high salary, made him a liability rather than an asset for the team. While the Raiders have made some successful signings in recent years, this one was definitely not one of them.
No. 10: Sean Smith, Cornerback (4yr-$40M)
In 2016, the Las Vegas Raiders made a big splash in free agency by signing cornerback Sean Smith to a four-year, $40 million contract. At the time, Smith was coming off a solid season with the Kansas City Chiefs, where he had four interceptions and 12 passes defended. The Raiders were looking to upgrade their secondary and believed Smith would be a significant addition to their defense.
Unfortunately, Smith's tenure with the Raiders was an unmitigated disaster. He struggled mightily in coverage, allowing opposing quarterbacks to complete nearly 70% of their passes thrown in his direction. He also failed to record an interception in his two seasons with the team, despite being targeted frequently. Smith's poor play was a significant reason why the Raiders' defense struggled during the 2017 season, finishing 23rd in the NFL in passing yards allowed per game.
To make matters worse, Smith was arrested for assault in the summer of 2017, leading to a four-game suspension at the start of the 2017 season. The incident further tarnished his reputation and raised questions about the Raiders' decision to sign him in the first place.
The Raiders eventually released Smith in March 2018, just two years into his four-year deal. He had played in only 29 games for the team and had little impact on the field. The $40 million contract that the Raiders had given him turned out to be a complete waste of money.
In conclusion, the signing of Sean Smith was a terrible move by the Raiders. He was a liability in coverage, failed to make an impact on the field, and had legal issues off the field. The team spent a significant amount of money on a player who ultimately did not contribute to their success. The signing of Sean Smith will go down as one of the worst free-agent moves in Raiders history.
No. 9: Kwame Harris, Offensive Tackle (3yr-$16M)
In 2008, the Oakland Raiders signed offensive tackle Kwame Harris to a three-year, $16 million contract, hoping he would be the solution to their long-standing issue of protecting their quarterbacks. Unfortunately, Harris turned out to be one of the worst free agent signings in Raiders history.
Harris had shown promise earlier in his career, having been drafted in the first round by the San Francisco 49ers in 2003. However, he never fully lived up to his potential, and by the time the Raiders signed him, he was already on the decline. He had a history of inconsistent play and was known for being penalty-prone, which should have been red flags for the Raiders' front office.
Once Harris arrived in Oakland, he continued to struggle. He was slow to pick up the playbook and was often out of position during games. He also had a tendency to commit costly penalties, which hurt the team's chances of winning. To make matters worse, Harris suffered a season-ending injury in the first game of the 2008 season, further demonstrating his lack of durability.
Harris was eventually released by the Raiders after just one season, during which he appeared in only 11 games. The team had invested a significant amount of money in him, and they had nothing to show for it. It was a disastrous signing that set the team back and highlighted the importance of thoroughly evaluating players before signing them to long-term contracts.
In the end, Kwame Harris was a terrible free agent signing for the Raiders. He failed to live up to expectations, and his time with the team was marred by poor play, injuries, and costly mistakes. The Raiders paid a high price for his services and received very little in return, making his signing a cautionary tale for any team looking to make a big splash in free agency.
No. 8: Gibril Wilson, Safety (6yr-$39M)
In the 2008 offseason, the Raiders made a big splash in free agency by signing safety Gibril Wilson to a six-year, $39 million contract, with $16 million guaranteed. Wilson had just come off a Super Bowl-winning season with the New York Giants, and the Raiders were hoping he could provide leadership and playmaking ability to their defense.
However, Wilson's time with the Raiders was a disaster. He struggled in coverage and was a liability in run support, often missing tackles and taking poor angles to the ball carrier. He was a poor fit in the Raiders' defensive scheme, and his poor play only exacerbated the team's defensive struggles.
In his lone season with the Raiders, Wilson started all 16 games, but recorded just one interception and 74 tackles. He was often out of position, leading to big plays for opposing offenses. The Raiders finished the 2008 season with a 5-11 record and the 27th-ranked defense in the NFL.
The following offseason, the Raiders cut ties with Wilson, designating him as a post-June 1st cut and taking a significant cap hit in the process. Wilson's tenure with the Raiders was a costly mistake, as the team had invested heavily in him and received little return on their investment. It serves as a cautionary tale for teams looking to make big free agent splashes without considering fit and scheme fit.
No. 7: Lamarcus Joyner, Safety (4yr-$42M)
Lamarcus Joyner, a former safety for the Los Angeles Rams, was brought in by the Las Vegas Raiders in 2019 to help bolster the team's defense. Joyner was signed to a four-year, $42 million contract, making him one of the highest-paid safeties in the league. However, his tenure with the Raiders was a disappointment, and he ended up being one of the worst free agent signings in the team's history.
Joyner was expected to be a versatile piece in the Raiders' defense, playing both safety and nickel cornerback positions. However, his play was lackluster, and he failed to make a significant impact on the field. In his two seasons with the Raiders, Joyner recorded just 83 tackles, two sacks, and one interception, hardly numbers worthy of his expensive contract.
The Raiders' defense struggled mightily in Joyner's two seasons with the team, finishing in the bottom half of the league in points allowed both years. Joyner's lack of playmaking ability and inconsistent performance were major contributing factors to the team's defensive struggles.
Another factor that made Joyner's signing a disappointment was the fact that he was brought in to be a leader on the defense, given his experience and success with the Rams. However, Joyner failed to live up to these expectations, and he struggled to take charge and make a difference on the field.
Joyner's tenure with the Raiders ended in March 2021 when he was released to free up salary cap space. His release came as no surprise to Raiders fans who had grown frustrated with his lackluster play and inability to make a significant impact on the team.
In conclusion, Lamarcus Joyner's signing was one of the worst free agent moves in the Raiders' history. Despite his high price tag and reputation as a versatile and experienced defender, Joyner failed to live up to expectations, and his tenure with the team was a major disappointment.
No. 6: Lamarr Houston, Linebacker (5yr-$35M)
Lamarr Houston was signed as a free agent by the Raiders in 2014, with high hopes of bolstering their defensive line. He was coming off a solid season with the Chicago Bears, where he had recorded six sacks and 41 tackles. The Raiders signed him to a five-year, $35 million contract, with $15 million guaranteed. It was a significant investment in a player who was expected to become a cornerstone of their defense.
However, Houston's tenure with the Raiders did not go according to plan. He struggled to adapt to the Raiders' defensive scheme and was unable to replicate the success he had enjoyed in Chicago. In his first season with the Raiders, Houston recorded just two sacks and 16 tackles. His performance was below expectations, and the Raiders were left with a player who was not producing at the level they had hoped for.
Things went from bad to worse for Houston in 2015 when he suffered a season-ending knee injury in the second game of the season. This injury ended his season and effectively ended his time with the Raiders. He was released in March 2016, just two years into his five-year contract.
Houston's signing was a significant disappointment for the Raiders. He was expected to be a dominant force on their defensive line, but instead, he was a liability. His lack of production and inability to stay healthy made him one of the worst free agent signings in Raiders history. The Raiders wasted a significant amount of money and resources on a player who was unable to live up to expectations. The signing of Houston was a cautionary tale for teams looking to make big moves in free agency. It's a reminder that not every big signing pays off, and teams must be careful when investing in players with high expectations.
No. 5: Aaron Brooks, Quarterback (2yr-$8M)
When the Oakland Raiders signed Aaron Brooks to a two-year, $8 million contract in 2006, they were hoping to find a replacement for veteran quarterback Kerry Collins. However, the signing of Brooks turned out to be a disastrous move for the franchise and one of the worst free agent signings in Raiders history.
Brooks had a reputation as a solid quarterback during his time with the New Orleans Saints, but his play quickly deteriorated after joining the Raiders. He struggled to pick up the offensive scheme and showed a lack of chemistry with his receivers, leading to poor performances on the field. In his first and only season with the Raiders, Brooks threw for just 1,200 yards, six touchdowns, and eight interceptions in eight starts.
Brooks' lackluster performance on the field was not the only issue the Raiders had to contend with. The quarterback also had a history of clashing with coaches and teammates, leading to a negative impact on the team's morale. Additionally, Brooks was known for his tendency to hold on to the ball for too long, resulting in sacks and turnovers.
After the disastrous season, the Raiders quickly released Brooks, leaving the team without a clear starter at the quarterback position. The signing of Brooks set the franchise back and contributed to the team's struggles over the following years.
In conclusion, the signing of Aaron Brooks was a poor decision by the Raiders' front office. The quarterback's poor performance on the field and negative impact on team morale make him one of the worst free agent signings in franchise history.
No. 4: DeAngelo Hall, Cornerback (7yr-$70M)
In the 2008 offseason, the Oakland Raiders made one of the worst trades in team history, by adding DeAngelo Hall to their roster after trading for him from the Atlanta Falcons. At the time, Hall was one of the most sought-after cornerbacks and was expected to bolster the Raiders' defense significantly. However, things did not go as planned, and the move quickly turned into a disaster.
The Raiders signed Hall to a seven-year, $70 million contract, with $24.5 million guaranteed. Unfortunately, Hall's performance on the field did not justify his massive contract. He played in only eight games for the Raiders, registering just one interception and eight passes defended, with no tackles for loss. Additionally, Hall struggled with penalties and poor coverage, allowing opposing quarterbacks to complete 81% of their passes when targeting him.
Hall's attitude off the field was also a significant issue for the Raiders. He clashed with head coach Lane Kiffin and frequently undermined his authority in front of other players. Ultimately, Kiffin was fired after just four games into the 2008 season, in part due to his inability to manage Hall's disruptive behavior.
In November of 2008, after only eight games with the Raiders, Hall was released and signed with the Washington Redskins. The Raiders' decision to release him was costly, as they still owed him $8 million in guaranteed money, making him one of the highest-paid players in NFL history to be released after just eight games.
In conclusion, the DeAngelo Hall signing was a disastrous move for the Raiders. Not only did they pay him an exorbitant amount of money, but his on-field performance and disruptive behavior off the field made it clear that he was not a good fit for the team. The Raiders' failure with Hall was a costly mistake that set the team back in their rebuilding efforts and further cemented their reputation as a franchise with a history of questionable personnel decisions.
No. 3: Larry Brown, Cornerback (5yr-$12.5M)
Larry Brown was a cornerback who was signed as a free agent by the Raiders in 1996, after playing for the Dallas Cowboys for six seasons. Brown was coming off an impressive season where he recorded six interceptions and was named the Super Bowl MVP. However, his tenure with the Raiders was far from successful, and he is often considered one of the worst free agent signings in franchise history.
Brown's disappointing stint with the Raiders began with his contract. He was given a five-year deal worth $12.5 million, which was a lot of money at the time, especially for a player who was already 31 years old. Brown's play on the field did not justify his hefty contract, and he struggled to replicate the form he showed during his Super Bowl-winning season with the Cowboys.
Brown was often burned in coverage, and opposing quarterbacks frequently targeted him as a weak link in the Raiders' defense. He only managed one interception in his two seasons with the team, and his poor play contributed to the Raiders' defensive struggles during that time. In 1996, the Raiders finished with a record of 7-9, and the following year they went 4-12, which was the worst record in the NFL that season.
In addition to his lackluster play on the field, Brown also had a reputation for being difficult to work with off the field. He clashed with his coaches and teammates and was often seen as a divisive presence in the locker room. His attitude and behavior were a far cry from the leadership and professionalism that the Raiders were looking for in a veteran player.
After two disappointing seasons with the Raiders, Brown was released by the team in 1998. He would go on to play for the Kansas City Chiefs for one season before retiring from the NFL. In retrospect, it's clear that Brown was not worth the money or the trouble that came with signing him as a free agent. He is now remembered as one of the biggest busts in Raiders history, and his signing serves as a cautionary tale for teams looking to sign high-priced veterans in free agency.
No. 2: Javon Walker, Wide Receiver (6yr-$55M)
When the Raiders signed wide receiver Javon Walker to a six-year, $55 million contract in 2008, they had high hopes for him. Walker was coming off a season where he had 1,084 receiving yards and eight touchdowns for the Denver Broncos. Unfortunately, things did not work out as planned.
Walker's time with the Raiders was plagued with injuries and off-field issues. He missed nine games in his first season with the team and finished with just 15 catches for 196 yards and one touchdown. The following season, he played in just three games before being released due to his inability to stay healthy.
Walker's off-field issues were also a concern. He was arrested for assault and battery in June 2008, just months after signing his lucrative contract. In addition, he was involved in a nightclub incident in Las Vegas that same year that left him unconscious and in the hospital.
The Raiders took a big risk in signing Walker, and it did not pay off. He was one of the team's worst free agent signings ever, as he was unable to stay healthy and make an impact on the field. His off-field issues only added to the disappointment of his short tenure with the team.
In the end, Walker's time with the Raiders was a forgettable one. He played in just 18 games over two seasons, catching 26 passes for 287 yards and one touchdown. The team released him in March 2010, and he never played in the NFL again.
No. 1: JaMarcus Russell, Quarterback (6yr-$68M)
Although JaMarcus Russell wasn't technically a free agent signing, his selection as the first overall pick in the 2007 NFL Draft was one of the worst moves the Raiders ever made. Russell was a highly touted prospect coming out of Louisiana State University and had all the physical tools necessary to become a successful NFL quarterback. However, his lack of work ethic, poor decision-making, and inability to take the game seriously resulted in one of the biggest draft busts in NFL history.
From the beginning, there were signs that Russell might not be the best fit for the Raiders. He held out for most of his rookie training camp, missing valuable practice time and causing friction with the team's coaching staff. Once he finally signed his contract, he struggled to learn the playbook and to adjust to the speed of the NFL game. Russell's work ethic was also a concern, as he was often seen as lazy and unmotivated.
Despite these red flags, the Raiders gave Russell every opportunity to succeed. He started 25 games over three seasons, but he never lived up to his potential. He completed only 52.1% of his passes and threw for just 18 touchdowns and 23 interceptions during his time with the team. He was also prone to fumbling the ball and had a habit of making poor decisions on and off the field.
Russell's off-field issues were also a major problem. He was involved in several incidents that called into question his maturity and dedication to the game. In 2010, he was arrested for possession of codeine syrup, a controlled substance. This led to his release from the Raiders and effectively ended his NFL career.
The Raiders invested heavily in Russell, both financially and in terms of draft capital. They signed him to a six-year, $68 million contract with $32 million guaranteed, making him the highest-paid player in franchise history at the time. In addition to the money, the Raiders also used the first overall pick in the draft to select Russell, passing on other highly touted prospects such as Calvin Johnson and Adrian Peterson.
In the end, the Raiders' investment in JaMarcus Russell was a complete bust. He was a drain on the team's finances, a distraction in the locker room, and a major disappointment on the field. His lack of work ethic and inability to take the game seriously ultimately led to his downfall, and he is now remembered as one of the biggest draft busts in NFL history. Although he wasn't technically a free agent signing, his selection as the first overall pick in the draft was one of the worst moves the Raiders ever made.