For Major League Baseball teams, the pain of a trade gone wrong can last for years.

Allow us to illustrate.

We've highlighted a handful of trades—officially 13, but with one two-for-one special and one three-for-one special—from recent years that have already turned disastrous for one of the teams involved and broken down which will continue to haunt them in 2021 and likely future seasons, as well.

We considered only trades that have at least two seasons of returns by which to judge them. We also made sure to assess deals under their original terms, particularly regarding how many years of club control teams were exchanging at the time. We wanted to avoid harping on trades for which the book is technically closed.

We'll begin with some dishonorable mentions and then go through the list in chronological order.

Dishonorable Mentions

San Diego Padres: The Justin Upton Trade (Dec. 19, 2014)

The Padres got a solid season out of Upton in 2015, but it was for naught as they missed the playoffs. The trade for him notably cost them Max Fried, who broke out as a Cy Young Award contender for Atlanta in 2020. Even as stacked as their rotation is for 2021, the Padres might still wish Fried was on their side.

Los Angeles Dodgers: The Yordan Alvarez Trade (Aug. 1, 2016)

It must have stung the Dodgers to watch Alvarez win American League Rookie of the Year with the Houston Astros in 2019. Yet his absence didn't keep the Dodgers from winning the World Series in 2020, and there's now some uncertainty around him after he had surgery on both knees in 2020.

Houston Astros: The Ramon Laureano Trade (Nov. 20, 2017)

As much as the Astros might want to have their 2015 trade for Mike Fiers and Carlos Gomez back, their trade of Laureano to the Oakland Athletics could really start to hurt in 2021. Though they did fine without him between 2018 and 2020, he would sure fit well in their George Springer-less outfield now.

St. Louis Cardinals: The Randy Arozarena Trade (Jan. 9, 2020)

Only one season has passed since the Cardinals dealt Randy Arozarena to the Tampa Bay Rays, so it's one for the "Too Soon to Tell" file. Yet it's not trending well for St. Louis as Arozarena is coming off a record-breaking postseason performance and still under team control through 2026.

Boston Red Sox: The Mookie Betts Trade (Feb. 10, 2020)

It hasn't even been a year since the Red Sox sent Betts and David Price to the Los Angeles Dodgers, and it's important to note the former's free agency was looming at the time. But if nothing else, the sheer optics of this trade only look worse now than they did last February.

Arizona Diamondbacks: The Shelby Miller Trade

The Deal (Dec. 9, 2015): Arizona Diamondbacks get RHP Shelby Miller (minus-1.1 WAR) and LHP Gabe Speier (0); Atlanta gets SS Dansby Swanson (7.5), OF Ender Inciarte (10.0) and RHP Aaron Blair (minus-1.9)

The Arizona Diamondbacks didn't have the worst idea when they targeted Shelby Miller as a co-ace for the newly signed Zack Greinke in December 2015.

Though Miller had lost 17 games for Atlanta in the prior season, he did so with a well-above-average 127 ERA+ over 205.1 innings. He was also just 25 years old and under team control for three more seasons.

Even at the time, however, the consensus was that the D-backs paid too steep a price for Miller. Ender Inciarte was a young center fielder on the rise, while Dansby Swanson had been the team's No. 1 pick just a few months prior.

Inciarte, whose original club control ran through 2020, went on to become an All-Star and three-time Gold Glover in Atlanta. Swanson, meanwhile, has developed into a steady everyday shortstop who finally found an offensive groove as he racked up a 110 OPS+ in 2020. He's 26 and controlled through 2022.

As they watch Inciarte and Swanson from afar, the Diamondbacks don't have many fond memories of Miller to keep them comfortable. He made only 29 appearances and pitched to an ugly 71 ERA+ in Arizona.

Tampa Bay Rays: The Corey Dickerson Trade

The Deal (Jan. 28, 2016): Tampa Bay Rays get OF Corey Dickerson (4.4 WAR) and 3B Kevin Padlo (0); Colorado Rockies get RHP German Marquez (13.0) and LHP Jake McGee (1.7)

Perhaps it's a stretch to imply the Tampa Bay Rays' 2016 trade for Corey Dickerson was a disaster.

Dickerson enjoyed a couple of solid seasons in Tampa Bay, blasting 24 home runs in 2016 and making the American League All-Star team en route to 27 homers and a 118 OPS+ in 2017. Yet the latter proved to be the end of the line as the Rays designated him for assignment the following spring.

Because he had a track record of dominance and two remaining years of club control, Jake McGee was the original centerpiece of the Dickerson deal for the Colorado Rockies. With a good-not-great season at High-A in his wake, German Marquez seemed like more of a throw-in.

But then Marquez started his ascent, making his MLB debut in 2016 and positioning himself as a top-100 prospect for 2017. He's lived up to the hype since then, compiling a 119 ERA+ over 613.2 innings.

If the Rays had held on to Marquez, they would have had yet another top-shelf arm with which to attack the Los Angeles Dodgers in last year's doomed World Series run. What's more, the 25-year-old would still be under their control through 2022.

Chicago White Sox: The James Shields Trade

The Deal (June 4, 2016): Chicago White Sox get RHP James Shields (0.1 WAR); San Diego Padres get SS Fernando Tatis Jr. (7.0) and RHP Erik Johnson (minus-0.6)

In fairness to the Chicago White Sox, their 2016 trade for James Shields didn't keep them from contending in 2020. Likewise, it almost certainly won't keep them from contending in 2021.

It's still, however, on track to be one of the great misfires in MLB history.

The White Sox weren't especially good even when they acquired Shields from the San Diego Padres, and the man himself was clearly past his prime. It was no great surprise, then, that he pitched to a 79 ERA+ in service of losing teams through the end of his contract in 2018. 

The Padres have since developed Fernando Tatis Jr. into arguably the best shortstop in MLB as he's posted a 154 OPS+, 39 home runs and 27 stolen bases in 143 games since his debut in 2019. He's still only 22 and under club control through 2024.

Had the White Sox held on to Tatis, they would now have an all-timer of an infield in him, Tim Anderson, Yoan Moncada and reigning American League MVP Jose Abreu.

Miami Marlins: The Dan Straily Trade

The Deal (Jan. 19, 2017): Miami Marlins get RHP Dan Straily (1.8 WAR); Cincinnati Reds get RHPs Luis Castillo (9.6) and Austin Brice (0) and OF Zeek White (0)

After sinking to 100 losses in 2013, the Miami Marlins made progress with 77 wins in 2014 and then 79 wins in 2016. So on the eve of the 2017 campaign, a playoff spot was hypothetically within their reach.

At least in theory, their January 2017 trade for Dan Straily only bolstered their chances. He was coming off a 113 ERA+ over 191.1 innings for the Cincinnati Reds and was thus precisely the innings-eater Miami needed.

Yet for various reasons, the leap forward the Marlins were hoping for in 2017 never materialized. By the end of the year, they were in the hands of new owners and ticketed for a rebuild after Jeffrey Loria sold the team to Bruce Sherman and Derek Jeter.

Meanwhile in Cincinnati, it was in the latter half of 2017 that Luis Castillo arrived and started producing ace-like results. Through 90 major league starts, he now owns a 124 ERA+, 578 strikeouts and an All-Star nod.

If the Marlins had kept Castillo, he would now be part of an exciting young rotation alongside Sandy Alcantara, Sixto Sanchez and Pablo Lopez. To boot, the 28-year-old would be under Miami's control through 2023.

Chicago Cubs: The Jose Quintana Trade

The Deal (July 13, 2017): Chicago Cubs get LHP Jose Quintana (4.5 WAR); Chicago White Sox get OF Eloy Jimenez (2.8), RHP Dylan Cease (0.1) and INFs Matt Rose (0) and Bryant Flete (0)

The Chicago Cubs finally did it in 2016, winning the World Series for the first time in 108 years.

Understandably, they sought to keep their foot on the gas in 2017. When it became clear that their rotation needed another reliable arm, they got arguably the best starter on the market when they acquired Jose Quintana from the cross-town White Sox in July.

But while Quintana was an All-Star pitcher with a team-friendly contract that ran as far as 2020, he only had a 96 ERA+ through his first 18 starts of the '17 season. And to get him, the Cubs sacrificed the No. 8 (Eloy Jimenez) and No. 63 (Dylan Cease) prospects on MLB.com's top 100.

Sure enough, Quintana never got it together as he pitched to a 101 ERA+ on the North Side. The Cubs are now rebuilding, while their neighbors to the south are a rising contender, in part thanks to Jimenez and Cease.

The former has been an elite hitter since September 2019, and the latter is coming off a 111 ERA+ in 2020. Both are slated to remain with the White Sox through at least 2024.

Detroit Tigers: The Justin Verlander, Justin Upton and J.D. Martinez Trades

The J.D. Martinez Deal (July 18, 2017): Arizona Diamondbacks get OF J.D. Martinez (2.4 WAR); Detroit Tigers get INFs Dawel Lugo (minus-0.5), Sergio Alcantara (minus-0.3) and Jose King (0) 

The Justin Upton Deal (Aug. 31, 2017): Los Angeles Angels get OF Justin Upton (3.0); Tigers get RHPs Grayson Long (0) and Elvin Rodriguez (0)

The Justin Verlander Deal (Aug. 31, 2017): Houston Astros get RHP Justin Verlander (16.2) and OF Juan Ramirez (0); Tigers get OF Daz Cameron (minus-0.5), C Jake Rogers (minus-0.5) and RHP Franklin Perez (0)

After reigning as the kings of the AL Central between 2011 and 2014, the Detroit Tigers began slipping in 2015 and had little choice but to rebuild come 2017.

Thus did sluggers J.D. Martinez and Justin Upton and Cy Young Award winner Justin Verlander eventually depart via separate deals with the Arizona Diamondbacks (here), Los Angeles Angels (here) and Houston Astros (here), respectively.

Beyond clearing easily over $100 million in salaries from Detroit's books, these three trades also flooded the club's farm system with much-needed talent. Accordingly, Jim Callis of MLB.com eventually honored it as one of the most improved farm systems of 2017.

Four years later, though, it's shocking how little fruit the trades of Martinez, Upton and Verlander have actually borne for the Tigers.

It's not just that the eight players acquired in those deals are in the red (minus-1.8) with their total WAR in the majors. By our judgment and that of MLB.com, none of them is even a top-100 prospect right now. Though not the reason, all this is a significant reason the Tigers' rebuild is progressing so slowly.

Cincinnati Reds: The Brad Keller Trade

The Deal (Dec. 14, 2017): Cincinnati Reds get PTBNL or cash; Kansas City Royals get RHP Brad Keller (8.3 WAR)

Sans National League Cy Young Award winner Trevor Bauer, who's a free agent, the Reds have already traded ace closer Raisel Iglesias. Ace starters Sonny Gray and Luis Castillo could be next. 

One senses that the Reds don't see an easy road back to the playoffs after snapping a six-year drought in 2020. Likewise, one wonders what would be different if they still had Brad Keller.

To be sure, the Reds never truly had Keller in their possession. They selected him from the Diamondbacks in the Rule 5 draft in December 2017, only to immediately flip him to the Kansas City Royals.

Following a season in which he'd posted a 4.68 ERA at Double-A, Keller didn't seem to be much of a prospect at the time. Yet he's quietly developed into one of baseball's top pitchers—and nastiest slider artists—since the Royals called him up in 2018, compiling a 131 ERA+ over 360.1 innings.

Those are marks only 11 other pitchers have hit over the last three seasons. The 25-year-old Keller is the youngest of the bunch, and he won't reach free agency until after 2023.

Pittsburgh Pirates: The Gerrit Cole and Chris Archer Trades

The Gerrit Cole Deal (Jan. 13, 2018): Houston Astros get RHP Gerrit Cole (12.3 WAR); Pittsburgh Pirates get RHPs Joe Musgrove (3.6) and Michael Feliz (minus-0.5), 3B Colin Moran (0.1) and OF Jason Martin (minus-0.5)

The Chris Archer Deal (July 31, 2018): Pirates get RHP Chris Archer (1.3); Tampa Bay Rays get RHP Tyler Glasnow (3.9), OF Austin Meadows (4.1) and RHP Shane Baz (0)

Why did the Pittsburgh Pirates fire general manager Neal Huntington and, well, basically everyone with a leadership role after the 2019 season?

Well, put it this way: When the same team makes two of the worst trades in recent memory within months of each other, heads simply must roll.

When the Pirates traded Gerrit Cole to the Astros in January 2018, they thought they were getting four players who could step right in and prop open the club's contention window. Even though said window was barely open by July, they nonetheless went all-in to get Chris Archer from the Rays.

Ultimately, both trades had a hand in pushing the Pirates into the long-haul rebuild they're now in under general manager Ben Cherington.

Whereas Houston turned Cole into an ace worthy of a $324 million contract, none of the four players who came back to Pittsburgh have panned out as stars. Archer pitched to an 85 ERA+ in just 33 starts for the Pirates, while Tyler Glasnow and Austin Meadows—both of whom are under club control for at least three more seasons—have become cornerstone stars in Tampa Bay.

Miami Marlins: The Christian Yelich Trade

The Deal (Jan. 25, 2018): Milwaukee Brewers get OF Christian Yelich (14.8 WAR); Miami Marlins get OFs Lewis Brinson (minus-2.8) and Monte Harrison (minus-0.2), 2B Isan Diaz (minus-1.0) and RHP Jordan Yamamoto (minus-0.2)

Of all the reasons to be outraged by the Christian Yelich trade in retrospect, one of the more underrated ones is that the Marlins didn't have to do it.

Whereas it made some sense for Sherman and Jeter to move Giancarlo Stanton and the remainder of his $325 million contract after the 2017 season, Yelich wasn't too expensive or anywhere near the end of his prime.

He was only coming off his age-25 season, and he was also just three years into a team-friendly deal that would pay him a modest $43.3 million through 2021. There might have been a way for the Marlins to keep him and build around him.

Instead, there Yelich went to the Milwaukee Brewers in January 2018 for a four-player package headlined by top prospect Lewis Brinson. Ultimately, neither he nor any of the other three players had much to do with Miami's playoff run in 2020. For that matter, none of the four looms large in the club's plans for 2021.

Meanwhile in Milwaukee, Yelich collected an NL MVP in 2018 and made a run at another in 2019. Even after his step back in 2020, he'll enter 2021 as a candidate to join the NL MVP race once again.

Baltimore Orioles: The Mike Yastrzemski Trade

The Deal (March 23, 2019): Baltimore Orioles get RHP Tyler Herb (0 WAR); San Francisco Giants get OF Mike Yastrzemski (5.5)

Particularly with regard to their trade of Manny Machado, it became clear during the 2018 season that the Baltimore Orioles were going to be rebuilding for a while.

That might have been Mike Yastrzemski's avenue to finally break in with the club that had drafted him back in 2013. But as he said last March, that's not the vibe he got: "I felt like they didn't view me like that, even if I did."

At the time, Yastrzemski had never been a top-100 prospect, and he had never truly broken out in the minors. In other words, he didn't have much going for him apart from his Hall of Fame bloodlines.

Yet the San Francisco Giants endeavored to give him the chance Baltimore wouldn't, trading for him in March 2019 and calling him up in May. He's since established himself as one of baseball's top outfielders by way of a 137 OPS+ and 31 home runs in 161 games.

Though Yastrzemski is already 30 years old, his club control runs all the way through 2025. With the end of their rebuild nearly in sight, the Orioles must be wishing they could have him back.

Stats courtesy of Baseball Reference and FanGraphs.