Sometimes, players just don’t work out with certain teams. This is when a team will cut their losses and either release the person altogether or trade the player. Not every athlete is lucky enough to be traded away or released, and this often comes back to haunt teams. Yet some of the greatest trades led to titles. Most tend to happen in the offseason as well.
The greatest offseason trades in sports history are numerous, but not all lead to a title. Some come close, such as the case of Randy Moss being traded to the New England Patriots for practically nothing. Upon arrival, Moss set records for the Patriots and NFL alike. The team even went 18-0 and ended up in the Super Bowl….only to then lose when it mattered most.
While the Pats would go on to far more Super Bowls and get several titles since then, this just goes to show that trades do not always work out. To us, the greatest off-season trades are always ones that lead to a title.
Our criteria for this list is pretty simple.
While a title did not have to happen the following season, the person traded did need to be a key part in helping the team win a championship. This means if the person retires, is released, or traded away again…they do not count.
We also did not count players who refused to play for the team that drafted them, forcing a trade to occur, such as Eli Manning. However, we did count ALL types of trades, including those that did not exactly involve “players.”
Now that this is out of the way, sit back and relax. For you are about to learn of the most amazing and greatest offseason trades in sports history.
30. Corey Dillon Traded To The New England Patriots
While we brought up the Patriots above regarding a huge Randy Moss trade, their trade for the All-Pro running back known as Corey Dillon was much bigger. During this point, the Pats had Kevin Faulk but needed a far better, more traditional back to help them out. Corey would be just what the doctor ordered. Dillon was traded from the Cincinnati Bengals in the summer of 2004.
By February of 2005, he was playing in Super Bowl XXXIX with the Patriots. He put up over 100 total yards and had a Touchdown in the game. Without Corey, they would likely not have gotten to the big game either. He helped them on the ground later on in the season and especially in the playoffs, taking some pressure off of Tom Brady and the New England defense. Dillon earned legend status in New England as a result.
One of the most forgotten things in NFL history is that Favre was not a lifetime Packer who decided to play for a few teams at the end of his career. In fact, Favre was not even drafted by them. The Mississippi native was actually drafted by the Atlanta Falcons with the 33rd overall pick in 1991.
Favre would play for the Falcons for a bit but by the summer of 1992, the team wanted to get rid of him. This was when Green Bay agreed to a deal with the Falcons to acquire Favre. Brett would go on to help the Packers win at Super Bowl XXXI. Favre managed to get three touchdowns in the game, thus proving to be the main reason they won. This is now known as one of the best offseason trades in NFL history.
During the 1987 NBA Draft, a lot of great players were drafted. A number of them are even in the NBA Hall of Fame today, including a man by the name of Scottie Pippen. During this draft, Pippen was taken 5th overall by the Seattle Supersonics. The same day, he was traded to the Chicago Bulls for the 8th overall pick that year, Olden Polynice. This also included some future draft picks too.
As we know, Pippen’s arrival in Chicago helped Michael Jordan out massively and allowed the Bulls to win 6 NBA Championships. Pippen was considered one of the greatest defenders in the NBA during his time and landed on 8 All-Defensive First Teams and was a 7-time All-Star. He’s also been voted as one of the Top 50 NBA players all-time. For his credit, Polynice had a relatively short NBA career.
Likely one of the most stunning trades of the 1990s happened on February 18, 1999, during the MLB off-season. The Toronto Blue Jays decided to trade away then 5-time Cy Young Award winner Roger Clemens to the New York Yankees. They’d get back Homer Bush, Graeme Lloyd, and the impressive David Wells in the trade. It was so stunning because Clemens was still at the top of his game, yet he wanted out of Toronto and demanded a trade.
Clemens eventually backed off of the trade demand but Toronto would send him away regardless. During the 1998 season, he was the MLB wins leader, AL Strikeout leader, MLB ERA leader, and reigning Cy Young Award winner. The Yankees clearly won huge. Clemens went on to help the Yankees win two World Series Championships in 1999 and 2000 respectively. He’d also go on to win 2 more Cy Young Awards.
In one of the most shocking trades of its time, Oscar Robertson was traded from the Cincinnati Royals to the Milwaukee Bucks in 1970. Keep in mind that Robertson may have been a 10-year NBA veteran by this point, but the 1964 NBA MVP was still one of the top players of his time. He led the league in assists 6 times during the 1960s and was voted a 9-time All-Star at this point.
Robertson’s arrival in Milwaukee helped the team out immensely. While he’d only play about 4 more years in the NBA before his retirement, he was able to help the Bucks win their first and only NBA Championship in 1971. This was in his very first season as a Buck too. The Royals would not even remain a team in the NBA after 1972.
25. Frank Robinson Traded To The Baltimore Orioles
When this trade happened, it sent shockwaves through the sport of baseball. In December of 1965, the Cincinnati Reds decided to trade away the former National League MVP, Frank Robinson to the Baltimore Orioles. Frank was not old or even playing badly. He was still one of the best players in Major League Baseball at this point.
The Reds would get back Milt Pappas, Jack Baldschun, and Dick Simpson. For his credit, Robinson would GO OFF in Baltimore during the 1966 season. Frank became the 1966 American League MVP and a Triple Crown winner. He’d also help the Orioles win the 1966 World Series Championship, of which he was the MVP of after the team swept the Dodgers. Oh yeah, he’d help the Orioles win another World Series Championship in 1970, just for good measure.
Steve Young was playing for the completely horrible Tampa Bay Buccaneers in the 1985-1986 season. The Bucs actually felt Young was a bust, so they drafted Vinny Testaverde with the #1 overall pick in the 1987 NFL Draft. That led to a trade that would send Young to the San Fransico 49ers to work as Joe Montana’s back-up. The Bucs would receive the 49ers’ Second and Fourth-Round draft picks in exchange for Steve.
An injury to Montana led to an opportunity for Young to start in 1991. Young would become the 1992 NFL MVP, lead the league in passing touchdowns, completion percentage, and passer rating. Yet in 1993 Montana was capable of returning and was made the starter, sending a rift in the locker room. Montana would ask for a trade and was granted it. Young went on to help the 49ers win Super Bowl XXIX as the starter. He also led the league in completion percentage 5 times, passer rating 6 times, and passing touchdowns 4 times.
23. Wilt Chamberlain Traded To The Los Angeles Lakers
Wilt Chamberlain is one of the greatest players in NBA history. The man averaged over 50 points a game. With the 76ers, he was a 7-time NBA scoring champion and led the league in rebounds 6 times at that point. This is along with several NBA MVP awards. Chamberlain was the reigning NBA MVP in 1968 and even came off of winning an NBA Championship in 1967.
Yet on July 9, 1968, he was traded to the LA Lakers. The 76ers would get Darrell Imhoff, Jerry Chambers, and Archie Clark in the deal. Chamberlain would get a new contract from the Lakers’ owner Jack Kent Cooke, paying him a then-unprecedented $250,000. Wilt would remain dominant in the league and help the Lakers get to 5 NBA Finals and eventually help them win an NBA Championship in 1972. Chamberlain was also named the Finals MVP.
While it is quite uncommon normally, coaches have been traded in sports a number of times. One of the most prominent happens to be Jon Gruden, who served as the Oakland Raiders coach from 1998-2001. He’d compile a good 40-28 record at this point, yet Tampa needed a new coach and wanted Gruden. However, the Raiders did not want to release him from his deal. This led to an agreement between the two teams. The Tampa Bay Buccaneers would trade their 2002 & 2003 first round draft picks, their 2002 & 2004 2nd round draft picks, and $8 million in cash to the Raiders for Gruden.
The Raiders accepted and the following season, Oakland and Tampa Bay met in Super Bowl XXXVII. The Bucs got there on their impressive defense while the Raiders arrived due to their impressive offense. Yet Gruden still knew the Raiders’ plays from his time there, allowing him to prepare his defense for them. The Bucs would pick off Oakland 5 times that night & they had 3 defensive TDs. This led to a 48-21 victory for Tampa.
It’s pretty common to see stars in New York, and there is no team in sports history who would spend as much to get the best players. In 2004, the Yankees saw this pretty impressive player down in Texas named Alex Rodriguez who had been hitting home runs like a mad man. In fact, he led the league in RBIs in 2002 & led the AL in HRs from 2001-2003. This led the Yankees to trade the impressive shortstop Alfonso Soriano to the Texas Rangers in exchange for A-Rod.
A lot was expected of Rodriguez from the start. With the Yankees, he’d become a 2-time AL HR leader, 3-time Silver Slugger Award winner, and 2-time AL MVP award winner. This is on top of several All-Star appearances. Yet New York fans want titles so none of those awards and impressive stats mattered. However, in 2009 he’d assist the Yankees in winning the World Series.
20. Julius Erving Traded To The Philadelphia 76ers
Most people associate Julius Erving with being a 76er, yet he was not always known for this. In fact, he began his career in the ABA. He actually led the New York Nets to 2 ABA Championships in his time there. Yet in 1976, the owner of the Nets decided to sell Irving to the Philadelphia 76ers for a massive $3 million. This fee was actually used to help the Nets pay their expansion fee to enter the NBA from the ABA.
To his credit, Dr. J became one of the greatest players in NBA history. He became the 1981 NBA MVP, was put on 5 All-NBA First Teams and was an 11-time All-Star. Irving also took the 76ers to 4 NBA Finals appearances and helped them win an NBA championship in 1983. This became one of the NBA’s greatest offseason trades in history as a result.
Remember how we mentioned that coaches could be and have been traded in sports? The same can be said for baseball. One of the biggest happens to be Chuck Tanner. Tanner had been the Manager of the Chicago White Sox from 1970 to 1975 and eventually moved on to the Oakland Athletics in 1976. However, when they decided to relieve him of his Manager role, Chicago still owed him $60,000 for the remaining 3 years on his contract.
The A’s were not in the best position in 1976, and the Tanner contractual issues were still problematic. Ownership wanted to secure him for another 3 years but at a much lower fee. Eventually, the White Sox had to pay most of the $60,000 to Tanner and the A’s didn’t want the contractual headache. This led to them trading Tanner to the Pittsburgh Pirates in November of 1976 where Tanner helped the team become major contenders. Tanner eventually led the team to a World Series in 1979.
Laimbeer was drafted by the Cleveland Cavaliers in the 1979 NBA Draft. Weirdly, he decided to play professionally in Italy for the Basket Brescia Leonessa team for another year. He’d then return to the Cavs in 1980. However, Laimbeer was traded to the Detroit Pistons in 1982 and remained with the team until his retirement. With the Pistons, he became a 4-time NBA All-Star and helped the Pistons win 2 NBA Championships. He even led the league in rebounds in 1986.
Known for his toughness and hard fouls, Laimbeer made the Pistons a feared team in the 1980s. He was immensely popular among Pistons fans but hated by every player that went against the team. This trade turned out to be one of the greatest offseason trades in NBA history due to all Laimbeer did for the team.
The impressive German star known as Dirk Nowitzki was part of one of the greatest off-season trades in the NBA looking back on what occurred. The Milwaukee Bucks actually selected Nowitzki 9th overall in the 1998 NBA Draft. However, they decided to trade him to the Dallas Mavericks. The Mavs would draft Robert Traylor and trade him in a deal that allowed Nowitzki to come to Dallas.
Nowitzki remained with the Mavs his entire career. The reason this is one of the greatest offseason trades ever is due to what Nowitzki did for the team. While Nowitzki was the 2007 NBA MVP and became a 14-time NBA All-Star during his illustrious career, his real claim to fame is helping Dallas win the 2011 NBA Championship. He was even the Finals MVP!
For years, Boldin played alongside Larry Fitsgerald as an impressive tandem for the Arizona Cardinals. He was even a 3-time Pro Bowl selection during his career there. Boldin had an impressive 2009-2010 season, catching 84 passes for a little over 1,000 yards and 4 TDs. However, feeling they could benefit from a trade, Arizona agreed to a deal with the Baltimore Ravens in March of 2010.
The trade would send Boldin to Baltimore in exchange for the Ravens’ 3rd & 4th Round Draft Picks in the 2010 NFL Draft. This led to Boldin signing a 3-year deal with the Ravens as part of the trade. Funny enough, the trade worked out well for Boldin. His numbers were not huge in Baltimore. However, he would be a huge asset to the Ravens winning at Super Bowl XLVII. Boldin caught 6 passes for 104 yards receiving and even scored a touchdown.
Draper was drafted by the Winnipeg Jets in 1989 but did not see much action with the team his entire stint there. This led to the Jets deciding to trade Draper to the Detroit Red Wings. Did they do so for a big sum or for a quality player? Oh no, they traded Draper to the Red Wings for just $1. Dubbed the “One-Dollar Man” as a result, Draper wanted to make the Jets regret the trade.
Draper went on to play with the Red Wings for 17 years. He played over 1,000 games with the team. Considered an “enforcer” in today’s game, Draper was known as an impressive defender. Draper would even win the Frank J. Selke Trophy for his defense in the 2003-2004 season. Draper became a key asset for the Red Wings and assisted them in winning 4 Stanley Cup Championships.
Back in 1979, the Cleveland Cavaliers decided to trade their first-round draft pick in 1982 to the Los Angeles Lakers for a player named Don Ford. Since draft picks are determined by record and then a lottery system, the Cavs ended up having a bad year in the 1981-1982 season leading to a Top 3 pick. They would end up getting the #1 overall pick in the 1982 NBA Draft.
However, since the Ford trade gave away the pick to Los Angeles, the Lakers now had the #1 pick overall in 1982. They decided to use the said pick on James Worthy. He helped the Los Angeles Lakers win 3 NBA Championships, even becoming the NBA Finals MVP in the 1988 title run.
Martinez had proven his value for years in the league by 1998. He was a multi-time All-Star and even won the 1997 Cy Young Award. Yet free agency was approaching in 1998 and Martinez was too valuable to just cut and not try to get anything out of. This led the Montreal Expos to trade him to the Boston Red Sox for Carl Pavano and Tony Armas, Jr. Pedro signed a 6-year deal worth $75 million as part of the deal with a 7th-year option for $17 million.
The deal was huge for Boston. Pedro went on to become a 4-time MLB ERA leader, 3-time AL Strikeout leader, 1999 MLB Wins leader and 2 more Cy Young Awards with Boston. While he’d also become an MLB All-Star many more times, his biggest accomplishment was helping Boston win the 2004 World Series Championship. It was the first World Series win for Boston since 1918!! Due to all he did for Boston, this has to be one of the greatest offseason trades in MLB history.
Back in 1995, the Chicago Bulls had a huge hole at power forward with the departure of Horace Grant. This meant they had to trade for someone or find a man in free agency. It just so happens, the San Antonio Spurs were willing to part with Dennis Rodman. Keep in mind, Rodman had previously been a 2-time Defensive Player of the Year and had been the reigning NBA Rebounds leader since 1992.
However, prior to the 1995-1996 season starting up, the Spurs traded away Rodman for Will Perdue and cash considerations. He would go on to help the Chicago Bulls win 3 straight NBA Championships. He landed on the All-NBA First Team once during this point but remained the NBA’s Rebound leader up through the 1997-1998 season.
11. Kevin Garnett & Ray Allen Traded To The Boston Celtics
The Boston Celtics got busy in the summer of 2007. They were able to pull off not one, but two of the greatest offseason trades in NBA history. On June 8, 2007, the Seattle Supersonics traded Ray Allen, Glen Davis & the 35th overall pick in the 2007 NBA draft to the Celtics for Delonte West, Wally Szczerbiak, and the eventual fifth overall pick, Jeff Green. Upon completing this, the big deal happened on July 31, 2007.
Kevin Garnett would be traded to Boston from Minnesota for Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff, cash considerations, Boston’s 2009 first-round pick, and the 2009 first-round pick that Minnesota had traded to Boston in the Ricky Davis/Wally Szczerbiak trade of 2006. The 7-for-1 deal was the most players traded for one player in NBA history. It all paid off as Boston was able to win the NBA Championship in 2008.
O’Neal is known as one of the greatest players in NBA history, not just one of the best big men. He was a stud in college and even led the Orlando Magic over the Jordan-led Bulls to make it to the NBA Finals one year. Eventually, he’d end up in Los Angeles where O’Neal helped deliver 3 NBA Championships to the Lakers alongside Kobe Bryant. However, a problem occurred. After losing in the NBA Finals in 2004, Bryant and O’Neal no longer wished to play with each other.
One had to go and with Bryant being younger, it only made sense to send O’Neal away. This led to a massive trade on July 14, 2004, that would send O’Neal to the Miami Heat for Lamar Odom, Brian Grant, Caron Butler, and a future first-round draft pick. O’Neal would dominate in Miami upon arrival and helped the Heat win their first NBA Championship alongside Dwyane Wade in 2006.
In one of the most stunning and greatest offseason trades in NFL history, Faulk was traded from the Indianapolis Colts to the St. Louis Rams in 1999. The reason for the trade was that Faulk had outplayed his current deal with the Colts and was up for more money soon. Unwilling to pay, the Colts sent Faulk to the Rams for second & fifth-round picks in the upcoming 1999 NFL Draft. This trade allowed the Rams to become the infamous “Greatest Show on Turf.”
Alongside Isaac Bruce, Torry Holt, and Kurt Warner, Faulk and the Rams dominated offensively for years. Faulk won the 2000 NFL MVP Award and also led the league in touchdowns the same year. If that was not enough, just a year following his trade from Indy, he helped the Rams win Super Bowl XXXIV. Oh, and Faulk did go on to win 2 total Offensive Player of Year Awards and was a multi-time Pro-Bowl selection with the Rams.
8. Robert Parish & Kevin McHale Traded To The Boston Celtics
This might have been one of the most lopsided trades ever. The Boston Celtics were already a good team and even had a legendary coach named Red Auerbach working with them. Boston took a chance in 1980 and decided to send the first overall & 13th to the Warriors for veteran center Robert Parish and the third pick overall in the draft the same year. To their credit, the Warriors took Joe Barry Carroll and Rickey Brown respectively with their picks.
Boston would use their pick on Kevin McHale, however. Alongside Parish and Larry Bird, McHale would help the Celtics dominate the 1980s. They took home a collective 28 All-Star selections and won 3 NBA Championships together. They were the original “Big 3” in the NBA. This is why, according to most, it was one of the greatest offseason trades ever. Although, it did take a bit of luck too.
7. Bill Belichick Traded To The New England Patriots (Technically)
The situation involving Belichick was quite odd. He was a defensive coordinator and assistant head coach for years before becoming the head coach in New England. In fact, he was working with the New York Jets in both roles from 1997 to 1999. Yet the Jets decided to make Belichick their Head Coach in 2000 when Bill Parcells decided to step down. Belichick accepted but changed his mind about it a day later. He’d then resign from the Jets role and soon after he’d be introduced as the New England head man.
The Jets argued that Belichick was under contract with them, so they were owed compensation by the Patriots for Belichick. The NFL Commissioner seemed to agree, resulting in the Pats sending three future draft picks (including a first-rounder) to New York for Belichick in what amounts to a trade. Of course, as we know, Belichick would go on to become the greatest football coach in history, not just the best in the NFL. In total, Belichick has coached New England to 9 AFC Championships and 6 Super Bowl wins.
Leonard wanted out of San Antonio in 2018 and the team had to do something. This put the Spurs in a bad position as Leonard was in his last year and many teams would be on the fence about taking him on for what amounts to a one-year rental. The Toronto Raptors were willing to take the chance and ended up agreeing to a surprising trade on July 18, 2018.
Toronto would get Leonard and Danny Green in the trade while the Spurs would receive DeMar DeRozan, Jakob Pöltl, and a protected 2019 first-round draft pick. The gamble paid off and Kawhi led the Raptors to the 2019 NBA Championship and was named the NBA Finals MVP. Leonard is likely gone from Toronto in free agency but this gamble led to a championship.
In 1996, Bryant was coming out High School straight to the NBA and wanted to end up in Los Angeles. Bryant even threatened to play in Italy if he was drafted by a bad team that he couldn’t win with. Both the Nets and Hornets had interest in Bryant, but this scared off the Nets who had the 8h overall pick that year. A ton of amazing players came out in the 1996 NBA Draft, but Bryant was coveted and Charlotte knew he could be trade bait, so they took him 13th overall.
Many today believe this was done because the Hornets knew they could entice the Lakers to trade for Bryant. Everyone knew Jerry West wanted him and Kobe especially wanted to be there. They were right as the Lakers agreed to send Vlade Divac (someone they wanted to send out anyway) to Charlotte. Due to what Brynt became for LA, it’s clear this is one of the greatest offseason trades in NBA history.
4. Jerome Bettis Traded To The Pittsburgh Steelers
It is always said that if something isn’t broken, why fix it? Apparently, former Rams head coach Rich Brooks did not understand this concept. Bettis had rushed for over 1,400 yards and 7 TDs his rookie year with another 1,000-yard Sophomore year. Yet Brooks wanted to turn him into a fullback and it just did not work. The numbers went down for Bettis and the Rams did not benefit. Meanwhile, the Pittsburgh Steelers needed a feature back desperately.
This led to the Rams trading away Jerome Bettis to the Steelers for a second-round pick on the day of the 1996 NFL Draft. That pick turned out to be Ernie Conwell, a quality tight end for the Rams. Yet Bettis turned into a Hall of Fame running back with the Steelers. He had 6 straight 1,000-yard rushing seasons with 4 Pro-Bowl selections on the Steelers. “The Bus” also became a huge help to the Steelers on their way to winning Super Bowl XL.
3. Kareem Abdul-Jabbar Traded To The Los Angeles Lakers
Abdul-Jabbar is not only a black man but also a Muslim. While Kareem won an NBA Championship for the Milwaukee Bucks in 1971 and even racked up a couple of NBA MVPs, he felt that the midwest did not suit his needs. He simply did not like living in the Midwest, and despite being a famous basketball star he knew people of his religion and skin color was not always treated well in the area. Abdul-Jabbar had one year remaining on his deal with the Bucks and requested a trade to a bigger market.
This led to the Bucks trading Abdul-Jabbar to Los Angeles in 1975. In exchange for the trade, the Bucks would get Elmore Smith, Brian Winters, and two rookies named Dave Meyers & Junior Bridgeman. The Lakers would win 5 NBA Championships with Abdul-Jabbar at center and the man himself took home 3 more NBA MVPs and became the NBA’s All-Time Leader in Points, which he still holds today. Due to what Abdul-Jabbar did for LA, this was one of the greatest offseason trades in NBA history.
You’d be forgiven for thinking Ruth was always a member of the New York Yankees. Funny enough, though, he actually started his career as a pitcher and even played for the rival Boston Red Sox. He assisted the Red Sox in winning 3 World Series Championships even. While Ruth had emerged as an amazing hitter in 1917 and moved to this permanently from pitching, it was not enough for the Red Sox to keep him. They ended up selling Ruth (a trade for the time) in 1919 to the New York Yankees.
The deal would be for a huge sum at the time of $100,000. This began what was known as the “Boston Curse” as the team did not win another World Series Title for 86 years. Meanwhile, Ruth helped the Yankees win 4 World Series Championships and hit a record 714 Home Runs, which would stand for decades. He still remains 3rd all-time on the career homers list. Ruth is now synonymous with Yankee legend, with most forgetting he even had a role at the Red Sox to begin with.
We know Russell today for his work in Boston. Yet he was actually going to be drafted #1 overall by Rochester Royals in the 1956 NBA Draft. The Boston Celtics had the #2 overall pick after making a trade with the St. Louis Hawks to acquire it. Red Auerbach and Walter Brown both wanted Russell in Boston but they knew the Royals would take him #1 overall. This was when Boston’s owner Brown made a call.
Funny enough, Brown was also the President of the Ice Capades. This is a traveling skating show still running today that was obviously huge then. This led to Brown calling Lee Harrison, the owner of the Royals. He told him that if they let Russell slide to #2, he’d send the Ice Capades to Rochester for a week. The Royals agreed and drafted Si Green #1 overall. Russell, of course, helped Boston win 11 NBA Championships. This is the greatest offseason trade ever.