MLB History: Ten Most Lopsided Trades of All Time

Feb 22, 2016; Mesa, AZ, USA; Chicago Cubs manager Joe Maddon (70) talks to president of baseball operations Theo Epstein during spring training camp at Sloan Park. Mandatory Credit: Rick Scuteri-USA TODAY Sports
Feb 22, 2016; Mesa, AZ, USA; Chicago Cubs manager Joe Maddon (70) talks to president of baseball operations Theo Epstein during spring training camp at Sloan Park. Mandatory Credit: Rick Scuteri-USA TODAY Sports
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Mandatory Credit: Jim Brown-USA TODAY Sports
Mandatory Credit: Jim Brown-USA TODAY Sports /

Whenever a team makes a trade, the hope is that the new players will end up helping to propel their team over the top. But sometimes, those trades end up setting a franchise back for the long term. These are the worst trades in the history of the MLB.

Ideally, when making a trade, the deal will help both sides. Even if it is a prospect for a veteran player, the short term potential to improve versus the longer term approach can make sense, depending on where the team finds itself. Even a rental for two or three months, if it brings in a championship, can be worth the price of that top prospect that goes on to stardom. After all, flags fly forever.

Yet, there are some trades that, even if they result in short term success, turn out to be tremendously horrendous. Seemingly every year, there is one trade in the MLB that, in retrospect, proved to be completely lopsided. These trades can set a franchise back for years, and even decades, depending on the success of those players who departed.

With the MLB Trade Deadline approaching, excitement is running high for the fans of those teams who are looking to make that final push for the postseason. Yet, even those trades, which seem to help at the time, can be a recipe for disaster. Just take a look at some of these moves that were made at the deadline.

And so, let us take a look back through history, and reflect on the ten most lopsided deals ever to be made in the MLB.

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10. Seattle Mariners send Jason Varitek and Derek Lowe to the Boston Red Sox for Heathcliff Slocumb – July 31, 1997.

In 1997, the Seattle Mariners were on their way towards the postseason. They lead the American League in runs and home runs that year, with their powerful offense built around Ken Griffey Jr, Alex Rodrigues and Edgar Martinez. Yet, they struggled in the bullpen, as closer Norm Charlton had an ERA of 7.85 and had just blown his eighth save of the year. They were desperate for an upgrade.

With that being the case, the Mariners acquired Heathcliff Slocumb from the Boston Red Sox, sending over Derek Lowe and minor league catcher Jason Varitek. Slocumb had been mediocre with the Red Sox, posting a 5.79 ERA and a 1.971 WHiP, but he had been an All Star closer two years ago. Plus, despite his struggles in Boston, he was still an upgrade over Charlton, showing how bad the closer situation was in Seattle.

He performed better with the Mariners, with a 4.13 ERA, 1.447 WHiP and ten saves, but that would not be enough as the Mariners were ousted in the ALDS. Meanwhile the Red Sox got Lowe, who would be an All Star as both a closer and the starter, a solid middle of the rotation starter who had moments where he carried the team on his right arm.

Varitek, despite being 25 at the time of the trade, became a star in Boston. A solid offensive threat, he solidified the position throughout the 2000’s, providing solid power at the bottom of the Red Sox lineup. He was also a marvel with the glove and when it came to calling a game, catching four no hitters and winning a Gold Glove award.

Yes, the Mariners needed relief help, and at the time, neither Lowe nor Varitek appeared destined for future stardom. Still, Dan Duquette, as he was wont to do, turned a mediocre asset into two pieces that would be key pieces in the Red Sox renaissance, and help lead Boston to a World Series title in 2004.

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9. Detroit Tigers trade John Smoltz to the Atlanta Braves for Doyle Alexander – August 12, 1987

In 1987, the Detroit Tigers were looking to make a push towards the postseason, as they sought their second World Series title of the decade. Their starting rotation was solid, with Jack Morris and Frank Tanana helping to lead the way, but the back end of their staff had struggled. Dan Petry and Jeff Robinson were getting battered on a regular basis, hindering the Tigers push to the postseason.

With that being the case, they acquired Doyle Alexander, a pitcher best known for his surly attitude, from the Atlanta Braves. Alexander had struggled in Atlanta, with a 5-10 record and a 4.15 ERA, but he was a revelation for Detroit. He dominated down the stretch, posting a 9-0 record with a 1.53 ERA and a 1.008 WHiP, numbers that led to a fourth place finish in the AL Cy Young award vote and a 13th place finish on the MVP ballot, despite pitching in the league for less than two months.

In exchange, the Braves received a minor league pitcher who post a cumulative 5.73 ERA and a 1.644 WHiP in 1987. That pitcher – John Smoltz. The following year, Smoltz would harness his stuff, dominating AAA before making his Major League debut at age 21.

While Alexander would remain in Detroit until his retirement after the 1989 season, Smoltz was a mainstay in Atlanta. An All Star in his second season in 1989, Smoltz would make nine All Star Games in total, including two as a closer. He won the Cy Young award in 1996, and became one of the few pitchers in Major League history to lead the league in wins and saves at some point in his career. His stellar performances, both as a starter and reliever, led to his induction in Cooperstown in 2015.

Not a bad haul for a player that the Braves had signed as a free agent only three months before.

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8. Cincinnati Reds trade Frank Robinson to the Baltimore Orioles for Milt Pappas, Jack Baldschun, and Dick Simpson – December 9, 1965

Frank Robinson was coming off an All Star season for the CIncinnati Reds in 1965. It was his sixth such selection, and the former MVP had a solid year with 33 home runs and a .296/.386/.540 batting line. But, as Robinson was aging, and the Reds thought that he was “an old 30,” they decided to trade their star slugger to the Orioles, with Milt Pappas as the key piece in return.

The trade, and the statements from the Reds about how he was washed up, angered Robinson. He responded with a season for the ages, punishing the American League as he won the Triple Crown. He posted a .316/.410/.637 batting line, leading the AL in all three categories, with 49 home runs, 122 RBI and 122 runs scored. The AL MVP, he also won the World Series MVP that year as the Orioles swept the Los Angeles Dodgers to capture their first championship.

Robinson would be a mainstay for the Orioles through 1971, making four more All Star teams and finishing third in the MVP vote twice. Pappas was a decent pitcher for the Reds, and won 30 games over two and a half years before being sent to Atlanta, but he was absolutely not on the same level as Robinson.

As for the other pieces involved, Baldschun was a mediocre reliever during his time in Cincinnati. He appeared in 51 games, but had a 5.52 ERA and a 1.706 WHiP. He did strike out 56 batters in 70.1 innings, but also walked 34 batters. Simpson served as a fourth outfielder, posting a .246/.335/.391 batting line in 136 games over two years.

Suffice to say, this is one trade the Reds would love to have back.

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7. Los Angeles Dodgers trade Pedro Martinez to the Montreal Expos for Delino Deshields – November 19, 1993

When Pedro Martinez first came to the Majors, there was no question as to his talent. With a tremendous fastball and the belief that he would defeat anyone he faced, Martinez certainly had the ability. However, at 5’11” and perhaps 160 pounds, the slight pitcher seemed destined to a relief role, if he could even hold up.

That was the mindset when the Dodgers sent Martinez to Montreal for second baseman Delino Deshields. At the time, the move was decried in Montreal, with even Expos manager Felipe Alou speaking out about his displeasure at losing the fan favorite. However, this trade would prove to be a steal for Montreal.

With his confidence and willingness to take the ball at any point in time to help the team, he rapidly earned the appreciation of Expos fans. He quickly blossomed into a star as a starter, making the 1996 All Star Game before having one of his best seasons in 1997. That year, he won the Cy Young award, posting a 17-8 record with a 1.74 ERA and 284 strikeouts against 32 walks in 217 innings. He would be sent to the Red Sox following that year, but he certainly left his mark in Montreal.

Deshields, meanwhile, never approached the same level of production in Los Angeles. He struggled with injuries and a batting slump during his time with the Dodgers, producing a .241/.326/.327 batting line with 114 stolen bases over his three seasons. Instead of continuing his ascension to stardom, Deshields regressed horribly.

Sometimes, fans are not the best judge of a trade. That was definitely the case here, as Martinez became a star while the former fan favorite was never the same.

Next: What could have been in New York

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6. New York Mets trade Nolan Ryan, Frank Estrada, Don Rose and Leroy Stanton to Los Angeles Angeles for Jim Fregosi – December 10, 1971

Jim Fregosi was one of the stars of the Los Angeles Angels during their first decade in existence. A shortstop with some power, Fregosi made six All Star teams and won a Gold Glove that decade, he began to slip in 1971 following foot surgery. Traded to the New York Mets, he continued to struggle, spending a season and a half there before being sent to the Rangers, having been a disappointment in Queens.

Compounding the failure of Fregosi in New York was the players they sent away. While Estrada never played in California, and Rose had one mediocre season as a swingman, Stanton became the Angels starting right fielder, hitting with some power and flashing enough speed to steal double digit bases twice. But the real star of the trade would be Nolan Ryan.

An enigmatic pitcher with an amazing fastball but erratic command, Ryan immediately became a star. He made his first All Star team in 1972, and in 1973, cemented his place as one of the best pitchers in baseball. Ryan threw his first two no hitters that year, while setting a single season record with 383 strikeouts, finishing second in the Cy Young voting. He continued to star for the Angles throughout the 1970’s before departing via free agency following the 1979 season.

This trade was made even worse by the state of the Mets pitching later in the decade. While Tom Seaver was an unquestioned ace, he was sent to Cincinnati following the 1976 season. Even then, Jon Matlack and Jerry Koosman were solid pitchers, but not the type that could help carry a team. Ryan, meanwhile, was an ace, someone that could have teamed with Seaver to make the Mets a formidable opponent during the rest of the decade.

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5. Philadelphia Athletics trade Shoeless Joe Jackson and Morrie Rath to the Cleveland Indians for Bris Lord – July 23, 1910

With the Philadelphia Athletics in the midst of their first Golden Era, manager Connie Mack was looking for players he could trust during the stretch run. One of those was former A’s outfielder, and owner of one of the greatest nicknames in MLB history, Bris Lord. Brought back to Philadelphia, Lord hit well, helping the team to World Series titles in 1910 and 1911.

However, the cost for those championships would prove to be a high one. In exchange for Lord, Mack sent infielder Morrie Rath and a player to be named later to Cleveland. Rath would play in 23 games with the Indians, posting a .194/.299/.2239 batting line before heading back to the minors, and eventually, out of the Indians system.

It was tha tplayer to be named later that made the trade. A week later, the A’s sent the rights to young outfielder Shoeless Joe Jackson to Cleveland, who immediately brought the youngster to the Majors. He produced a .387/.446/.587 batting line in 20 games, then became a true star the following year.

That year, Jackson would set the stage for a career that would leave him as one of the great hitters in baseball history. He produced a .408/.468/.590 batting line, notching 233 hits, 45 doubles, 19 triples and 41 stolen bases. While he never hit above .400 again in his career, Jackson was a superstar for the rest of the 1910’s, one of the best all around hitters the league had seen.

We all know how his career ended, as he was banned for life due to his involvement in the 1919 White Sox throwing the World Series. Yet, that does not take away from the type of player he was. While the A’s did win those two titles with Lord, they certainly could have used a hitter like Soeless Joe in their lineup.

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4. Seattle Mariners send Mark Langston and Mike Campbell to the Montreal Expos for Randy Johnson, Gene Harris and Brian Holman – May 25, 1989

Mark Langston had been an ace with the Seattle Mariners, leading the American League in strikeouts three times, winning two Gold Glove awards and making an All Star team. In his free agent season in 1989, Langston was the type of pitcher that would net a large return from a team that had an eye towards contention.

That was what happened when he was sent to the Montreal Expos. While he pitched well in Montreal, going 12-9 with a 2.39 ERA and 175 strikeouts in 176.2 innings, he bolted for the Angels that offseason. Meanwhile, the Expos sent three pitchers to the Mariners, all of whom could have been useful. Gene Harris was a league average middle reliever, and Brian Holman was a solid starter before arm issues ended his career.

However, the jewel of the trade was Randy Johnson. Much like Langston, he was a lefty strikeout pitcher, although he struggled with his command. After consulting with Rangers pitching coach Tom House, and all time great Nolan Ryan, he improved his control, becoming one of the greatest left handed pitchers in baseball history.

His accomplishments were remarkable. He fired two no hitters, including a perfect game. Johnson won five Cy Young awards, including four consecutive from 1999 through 2002. With over 300 victories and the second most strikeouts in MLB history, he was a legend, not just with the Mariners, but in the annuls of baseball.

Montreal got four good months out of Mark Langston. Meanwhile, the Mariners received one of the greatest pitchers of all time.

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3. Boston Red Sox trade Jeff Bagwell to the Houston Astros for Larry Andersen – August 30, 1990

Larry Andersen was a solid middle reliever, toiling in the Majors for 17 years. He only recorded 49 saves, and only made one start in his career, but he was a solid piece in the bullpen. Ultimately, he would have been remembered more for the various pranks he pulled than his time as a pitcher, except for his trade to the Red Sox.

With Boston in need of pitching help at the end of the 1990 season, they acquired Andersen for the final month of the year. He pitched well, posting a 1.23 ERA while striking out 25 batters in 22 innings before leaving via free agency, but the Astros received one of the greatest first basemen in history with Jeff Bagwell.

One of the rare five tool talents at first, Bagwell made an immediate impact in Houston. He won the Rookie of the Year award in 1991, and three years later, was the National League MVP. A power hitting first baseman, Bagwell even stole 30 or more bases in a season twice, becoming a two time member of the 30/30 club.

A four time All Star, three time Silver Slugger and a Gold Glove winner, Bagwell finished his career with over 400 home runs and 200 stolen bases, making him the only first baseman to reach that mark. He is likely to make the Hall of Fame, perhaps as early as 2017, a high price to pay for a middle reliever.

As the trade deadline looms, teams send top prospects away in hopes that the one middling bullpen arm can make a difference. The tale of Jeff Bagwell being traded for Larry Andersen should be a warning against such a move.

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2. Chicago Cubs trade Lou Brock, Jack Spring and Paul Toth to the St. Louis Cardinals for Ernie Broglio, Doug Clemens and Bobby Shantz – June 15, 1964

At the time, this trade appeared to be relatively fair. Ernie Broglio had been a solid pitcher, and was coming off a season where he went 18-8 with a 2.99 ERA and a 1.168 WHiP. He had struggled a bit during the early going of the 1964 season, but at 28 years old, was still considered to be in the prime of his career.

Lou Brock, meanwhile, had not hit well for the Chicago Cubs. Yes, he had blazing speed, but if he was unable to make contact, that did not matter. At the time of the trade, Brock had a .251/.300/.340 batting line, worth an OPS+ of 77. With only ten stolen bases, he just was not producing enough to remain in the lineup.

In retrospect, this trade was a steal for the Cardinals. Broglio was just about done at that point, and would have a 7-19 record with a 5.40 ERA and a 1.678 WHiP for the Cubs, being out of the Majors by the end of the 1964 season. Brock, meanwhile, would go on to be a star in St. Louis, as he finally tapped into his immense potential.

En route to becoming the all time stolen base leader before Rickey Henderson broke his record, Brock paid even more immediate dividends. At the time of the trade, the Cardinals were 3.5 games behind the Cubs in the National League. Not only would they overtake their divisional foe, but they would go on to win the World Series that year, while the Cubs still look back fondly at 1908.

Lou Brock blossomed into a Hall of Fame player in St. Louis. Perhaps he would have done the same in Chicago, but we will never know.

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1. Cincinnati Reds trade Christy Mathewson to the New York Giants for Amos Rusie – December 15, 1900

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During his heyday, Amos Rusie was one of the more dominant pitchers in baseball. An ace throughout the 1890’s, Rusie was a five time strikeout champion and won 20 or more games eight times. However, after a contract dispute with the Giants, he sat out for two years before his trade to the Reds.

While the Reds thought they were getting an ace in Rusie, he was no longer the same pitcher, going 0-1 with an 8.59 ERA and a 2.091 WHiP before being released. The player they traded, Christy Mathewson, turned into that ace with the Giants.

In his time in New York, Mathewson would 372 games, posting a 2.12 ERA and a 1.058 WHiP, striking out 2504 batters. He led the National League in ERA and strikeouts five times each, and won the pitching Triple Crown twice. He won 20 or more games in 13 of his 15 Major League seasons, proving to be a remarkably consistent workhorse.

Mathewson would eventually head back to CIncinnati, traded away as part of a five player deal. Despite allowing eight runs on 15 hits and a walk, he did earn the victory in his only outing in a Reds uniform.

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The Cincinnati Reds were looking for an ace to front their rotation. Little did they know they had one in place already.

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