These are the most significant and notorious in MLB history and contain some smart and some very stupid transactions involving baseball's superstars.
The Babe was shipped from the Red Sox to the Yankees for a mere $125,000. He went on to play 15 years for the Yanks and hit 659 home runs with the team.
Over the hill at age 30? The O's acquired Robinson for his age-30 season in a four-player deal, and he went on to have a career year and win the AL Triple Crown in 1966.
The Hall of Famer arrived in Cincinnati from Houston in his age 28 season. His patience at the plate was underappreciated, and he won two MVP Awards with the Reds in eight seasons.
Bonds joined the team of his father and Willie Mays after signing a record-breaking, six-year, $43.75 million contract. He eventually went on to become the single-season and all-time home run leader, albeit with controversy.
Pedro was traded from Montreal to Boston for Tony Armas Jr. and Carl Pavano fresh off his first Cy Young Award. He won two more Cy Youngs in seven seasons with the Red Sox and helped end the Curse of the Bambino.
The Big Unit was a risk going into his age 35 season on a four-year, $52.4 million contract with the D-backs. During his five years in Arizona, he won four Cy Young Awards in what was arguably the greatest four-year stretch by a pitcher in history. He also helped Arizona to a World Series win in 2001.
Anaheim spent big on the 31-year-old Vaughn in 1998 after his big years in Boston, signing him to a six-year, $80 million contract. While he was productive with the Angels, Vaughn's numbers dropped off considerably in his first two years, and he missed all of 2001. He was eventually traded to the Mets for Kevin Appier.
Santana was selected in the Rule 5 draft by the Marlins from Houston and promptly traded to Minnesota for Jared Camp. While the lefty had some growing pains with the Twins, he eventually won two Cy Young Awards.
The M's won the rights to Ichiro from the Orix Blue Wave and installed him as their starting right fielder and leadoff man. Ichiro drew comparisons to Johnny Damon at the time, but it was soon clear he was something much better. He won the Rookie of the Year and MVP in his first season, made 10 All-Star Games, won 10 Gold Gloves and two batting titles and led the league in hits seven times.
Colorado approached the offseason with the goal of outpitching Coors Field. Its first big signing was Neagle, who inked a five-year, $51 million contract with the Rockies even after posting a 4.52 ERA the previous season. The contract was an absolute disaster for the Rox, as Neagle posted a 5.57 ERA in three seasons and missed time late in the contract due to injury.
Hampton famously signed with the Rockies in 2000, citing the Denver school system as one reason. He signed an eight-year, $121 million contract that made Denny Neagle's contract look like pocket change. Of course, the lefty lasted only two seasons in Colorado and posted a 5.75 ERA over that time.
Hundley joined the team of his father on a four-year, $24 million contract. After hitting 24 homers in consecutive years for the Dodgers, he hit only .187 in his first season with the Cubs and .211 in his second year with a total of 28 homers over two years. His career ended after the 2003 season.
A-Rod signed the richest contract in sports history, shocking the world with a 10-year, $252 million deal to join Texas. The fact the Rangers spent so much on one player was shocking, and it handicapped the team's ability to compete before the organization traded him to the Yankees after three seasons.
One year after signing Alex Rodriguez, the Rangers decided they needed pitching. Their solution was to sign Park to a five-year, $65 million contract. The fly ball pitcher was one of the worst players in baseball during his time with the Rangers, with a 5.79 ERA over three-plus seasons.
The cost-conscious Twins released Ortiz after he hit 20 homers in 2002. He joined the Red Sox to finish top five in the AL MVP voting in each of his first five seasons with the team. He made 10 All-Star teams and led the organization to three World Series titles.
St. Louis shipped J.D. Drew to Atlanta in the final year of his contract, acquiring Jason Marquis, Ray King and a top pitching prospect named Adam Wainwright. Wainwright has been one of the team's most important players over the last 10 years, finishing top three in the Cy Young voting four times.
Schilling joined Pedro Martinez as the Red Sox's second ace in 2004 after Arizona traded him for four players. He finished second in the AL Cy Young voting to Johan Santana in 2004 and helped the Red Sox to a World Series title, creating his own legend with the bloody sock.
The oft-injured Pavano looked like he'd turned a corner after making at least 31 starts in consecutive seasons as he entered free agency. That convinced the Yankees to sign him to a four-year deal worth nearly $40 million. For the life of the deal, he made only 26 starts with a 5.00 ERA.
Paying for Matthews' career year in 2006, the Angels signed the outfielder to a five-year, $50 million deal. He lasted only three seasons in Anaheim, posting a sub-.700 OPS in two of them.
Coming off an All-Star season for the rival Giants, Schmidt signed a three-year, $47 million contract with the Dodgers. He made only 10 starts over the life of the deal, posting a 6.02 ERA before his contract ended.
San Francisco was able to win despite Zito, but that doesn't make the contract much easier to swallow. The former Cy Young winner signed a seven-year, $126 million contract with the Giants but posted a 4.62 ERA with the team.
The cost-cutting Marlins shipped Miggy and Dontrelle Willis to Detroit for a package of players who never panned out in Florida. Over his time in Detroit, Cabrera has won five Silver Sluggers and two MVP Awards.
Silva signed a four-year, $48 million contract with Seattle, which was curious at best just one year removed from posting a 5.94 ERA. He was horrendous with the Mariners, going 5-18 with a 6.81 ERA in two seasons before getting traded to the Cubs for Milton Bradley.
Hamilton showed major upside in his major league debut in 2007 after a host of off-field issues early in his pro career, and he was shipped to Texas for hot young starter Edinson Volquez. While Volquez was up and down for the Reds, Hamilton made five straight All-Star Games and won the 2010 AL MVP.
The trade of Lee after the 2009 season still makes no sense. Philadelphia sent him to Seattle for three prospects who never panned out, even when the Phils had a team that looked primed for another playoff run in 2010. The team fell short in the 2010 NLCS before bringing Lee back as a free agent in 2011.
The Cardinals apparently didn't want to spend the money it would require to keep Pujols after 11 spectacular seasons, but the Angels were ready to make a splash. They signed the first baseman to a 10-year, $240 million deal. Pujols' play immediately dropped off, and he has just a .764 OPS in eight seasons with the Angels.
Angels owner "Arte" Moreno just couldn't keep his wallet shut, signing Hamilton to a five-year deal worth $125 million. Hamilton struggled with injuries in his first two years with the Angels and was traded to the Rangers along with $63 million after the slugger had a drug relapse.
Scherzer was coming off two All-Star seasons, including a Cy Young Award win in 2013, when he signed a seven-year, $210 million contract with the Nats. The contract brought obvious risk, but it's paid huge dividends for Washington. Over the first five seasons, Scherzer has been arguably MLB's best pitcher with two Cy Young Awards, four top three finishes and an All-Star appearance in each season. He also helped lead the Nationals to their first-ever World Series title in 2019.
Chicago stole Heyward from the rival Cardinals on an eight-year, $184 million contract. He's been an excellent defensive outfielder for the Cubs, winning two Gold Gloves, but Heyward's bat has crashed. He has just a .711 OPS in four seasons as the team's primary right fielder, averaging .252-12-57 during that time.
It didn't take long for Milwaukee's acquisition of Yelich from the Marlins to pay off. The right fielder went from a very good player to a great one, winning the NL MVP in his first season with the Brewers and finishing second in the voting in his second year. He also led the NL in batting average and OPS in both seasons. The Brewers traded four prospects to the Marlins in the deal, but only one of them (Jordan Yamamoto) has made a significant MLB contribution so far.
Seth Trachtman is a fantasy sports expert and diehard Kansas City Chiefs fan. He doesn't often Tweet, but when he does, you can find him on Twitter @sethroto.
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