The most painful thing anyone can experience, save for maybe a paper cut, is the bite of a Major League Baseball trade gone wrong.

Need examples? We got 'em.

We've recalled 15 trades—some of which we've lumped together for [waves hands] reasons—from recent years that have turned disastrous for one team and which will likely be just as bad, if not worse, in 2023. These concern the surrendering of players who were unproven or even on a downswing at the time but who have since realized or reclaimed stardom.

Expecting to read about the trades of Manny Machado from 2018 or of Mookie Betts from 2020? Well, don't. Both may be notorious flops, but the club control that the Baltimore Orioles and Boston Red Sox were trading at the time has long since run out. It's therefore disingenuous to wonder what things would be like if they still had Machado and Betts today.

We'll start with some dishonorable mentions before hitting on some multiple-for-one specials, and then we'll check others off one at a time in chronological order.

Dishonorable Mentions

Chicago White Sox: The James Shields-Fernando Tatís Jr. Trade

The Deal (June 4, 2016): Chicago White Sox get RHP James Shields (minus-0.3 WAR); San Diego Padres get SS Fernando Tatís Jr. (13.6), RHP Erik Johnson (minus-0.6)

This looked like an all-time blunder for the White Sox as Tatís was going off for a 160 OPS+, 81 home runs and 52 stolen bases between 2019 and 2021. But following his suspension and multiple surgeries in 2022, one now has to wonder if the worst has past for the Pale Hose.

Miami Marlins: The Dan Straily-Luis Castillo Trade

The Deal (Jan. 19, 2017): Miami Marlins get RHP Dan Straily (1.9 WAR); Cincinnati Reds get RHP Luis Catillo (18.3), RHP Austin Brice (minus-0.5), OF Zeek White (0)

Former Marlins president David Samson says he would do this one again, for whatever that's worth. For our part, we sided against giving it the full-bash treatment because today's Marlins have so much pitching that they were able to sacrifice Pablo López for Luis Arráez just last week.

Seattle Mariners: The David Phelps-Pablo López Trade

The Deal (July 20, 2017): Seattle Mariners get RHP David Phelps (0.2); Miami Marlins get RHP Pablo López (8.5), RHP Lukas Schiraldi (0), RHP Brandon Miller (0), OF Brayan Hernandez (0)

López was indeed traded for a middling pitcher in his own right, as Phelps was a good-not-great relievers at the time, and he ultimately made just 10 appearances for Seattle. The Mariners are nonetheless in the same boat as the Marlins in having too much pitching to really fret about it.

Los Angeles Dodgers: The Tony Watson-Oneil Cruz Trade

The Deal (July 31, 2017): Los Angeles Dodgers get LHP Tony Watson (0.4 WAR); Pittsburgh Pirates get SS Oneil Cruz (2.4), RHP Angel German (0)

This, of course, depends on how Cruz continues to develop. But if he starts getting bat to ball more frequently, his other eye-popping tools may well turn him into the kind of star that the Dodgers would probably prefer to have at shortstop instead of Miguel Rojas.

Houston Astros: The Martín Maldonado-Patrick Sandoval Trade

The Deal (July 26, 2018): Houston Astros get C Martín Maldonado (0.1 WAR); Los Angeles Angels get LHP Patrick Sandoval (5.9), international bonus money

Sandoval should probably be a bigger star after pitching to a 2.91 ERA last season. And even though the Astros have a good rotation lined up for 2023, they may find themselves missing the lefty if the guys they have struggle to paper over the absence of reigning American League Cy Young Award winner Justin Verlander.

Pittsburgh Pirates: The Chris Archer-Tyler Glasnow-Austin Meadows Trade

The Deal (July 31, 2018): Pittsburgh Pirates get RHP Chris Archer (1.2 WAR); Tampa Bay Rays get RHP Tyler Glasnow (6.5), OF Austin Meadows (6.2), RHP Shane Baz (0.5)

The reality of this trade isn't as bad as its reputation at this point. Meadows and Glasnow barely played in 2022 because of injuries, while Baz is going to miss all of 2023 recovering from Tommy John surgery. Like with the Shields-Tatís trade, the worst may be over for the Bucs.

Multiple Closer Giveaways

We've lumped these trades together because, beyond the fact that each involved the exchange of a present or future closer, a little bit of retrospective grace is warranted. Evaluating the present value of relief pitchers is a notoriously fickle process, after all.

The Rangers' Trade of Emmanuel Clase (Dec. 15, 2019): Texas Rangers get RHP Corey Kluber (0.1 WAR); Cleveland Guardians get RHP Emmanuel Clase (5.7), CF Delino Deshields (0), cash

It's funny to think that this trade was seen as an easy win for the Rangers at the time it was made. There was clearly a mass underestimation of Clase, who's since leaned on his triple-digit cutter to rack up a 306 ERA+ and 66 saves across the past two seasons. A pitcher like that would be mighty useful in a Texas bullpen that doesn't really have a set closer.

The Pirates' Trade of Clay Holmes (July 26, 2021): Pittsburgh Pirates get INF Diego Castillo (minus-0.3 WAR), INF Hoy Park (minus-0.5); New York Yankees get RHP Clay Holmes (2.6)

Holmes did have his devastating sinker when he was with the Pirates, but they just didn't do much to help him use it properly. Kudos to the Yankees for cracking that code and turning Holmes into an All-Star closer who might otherwise be part of a nasty late-relief duo alongside David Bednar in Pittsburgh right now.

The Brewers' Trade of Josh Hader (Aug. 1, 2022): Milwaukee Brewers get LHP Taylor Rogers (minus-0.5 WAR), RHP Dinelson Lamet (0), OF Esteury Ruiz (minus-0.2), LHP Robert Gasser (0); San Diego Padres get LHP Josh Hader (minus-1.0)

On the field, this trade initially looked like a flop for both teams. It was clearly more of a loss for Milwaukee off the field, however, and then the whole on-field script flipped when Hader allowed just one hit and struck out 10 of the 18 men he faced for San Diego in the playoffs. The Brewers will miss having him in tandem with Devin Williams in 2023.

The Angels' Trade of Raisel Iglesias (Aug. 2, 2022): Los Angeles Angels get RHP Jesse Chavez (minus-0.5 WAR), LHP Tucker Davidson (minus-0.6); Atlanta gets RHP Raisel Iglesias (1.4)

Iglesias was pitching in such a way that the Angels perhaps weren't unjustified in dumping the remainder of his $58 million contract on Atlanta. The problem was that his peripherals were really good, so go figure that he returned to form and allowed just one earned run in 26.1 innings the rest of the way. The Angels sure could use him back in their bullpen.

Tampa Bay Rays: The Jake Cronenworth, Blake Snell and Nate Lowe Trades

There's a sort of underground meme that the Rays don't make bad trades, but that feels more true than it actually is. Every team does, and these deals prove that applies to even the Rays.

The Jake Cronenworth Deal (Dec. 6, 2019): Tampa Bay Rays get RF Hunter Renfroe (0 WAR), 2B Esteban Quiroz (0.4), INF Xavier Edwards (0); San Diego Padres get 2B Jake Cronenworth (10.5), OF Tommy Pham (1.3)

This, notably, was the one that drew the ire of then-Rays ace Blake Snell, who really didn't like the Pham and Edwards element of it. In hindsight, though, he should have been more upset about losing Cronenworth.

He was coming off a big minor-league season at the time, having posted a .949 OPS over 94 games at the Triple-A level. He's had little trouble translating that momentum to the majors in San Diego, notably making the National League All-Star team in each of the past two years.

The Nathaniel Lowe Deal (Dec. 10, 2020): Rays get OF Heriberto Hernandez (0 WAR), INF Osleivis Basabe (0), 1B Alexander Ovalles (0), OF Carl Chester (0); Texas Rangers get 1B Nate Lowe (5.7), 1B Jake Guenther (0)

The Rays might have thought they were keeping the best of the two Lowe brothers when they traded Nathaniel to the Rangers. Still in the organization was Josh, who had been the 13th overall pick in the 2016 draft and was on his way to becoming a top-100 prospect.

Well, now Nathaniel is fresh off winning a Silver Slugger and Josh is in a state of roster limbo after his 52-game debut with the Rays saw him hit just .221 while striking out 33.3 percent of the time. "Oops" seems a fair conclusion to draw.

The Snell Deal (Dec. 29, 2020): Tampa Bay Rays get RHP Luis Patiño (minus-0.6 WAR), C Francisco Mejía (2.3), RHP Cole Wilcox (0), C Blake Hunt (0); San Diego Padres get LHP Blake Snell (3.4)

Unbeknownst to him back in Dec. 2019, Snell would eventually be reunited with Pham. The sailing hasn't all been smooth for the 2018 AL Cy Young Award winner in San Diego, but he has momentum going into 2023 after finishing last season with a 2.19 ERA over his last 14 starts.

Meanwhile in Tampa, Patiño was supposed to be the big get for the Rays. But he likewise finds himself in roster limbo, as he missed much of 2022 with an oblique strain and has otherwise pitched to a 5.09 ERA when he has suited up for the Rays.

San Diego Padres: The Justin Upton-Max Fried Trade

The Deal (Dec. 19, 2014): San Diego Padres get LF Justin Upton (4.2 WAR), RHP Aaron Northcraft (0.2); Atlanta gets LHP Max Fried (17.1), OF Mallex Smith (1.0), INF Jace Peterson (0.9), OF Dustin Peterson (0)

Atlanta and San Diego were two teams headed in completely opposite directions when they hooked up for this trade, with the former quickly dismantling a recent contender and the latter trying to build one overnight.

Indeed, Upton was arguably the biggest prize of an offseason haul that ultimately saw the Padres also add his Atlanta teammate, Craig Kimbrel, as well as Matt Kemp, Wil Myers and James Shields. He was coming off a 29-homer season for which he earned a Silver Slugger and even some MVP votes.

Alas, the contender that the Padres thought they were building never materialized amid an 88-loss season in 2015. Upton subsequently left as a free agent, and it ultimately wasn't until 2020 that San Diego general manager A.J. Preller finally got his contender.

All Atlanta got out of this trade is one of the most well-rounded pitchers in baseball today. Fried has won three straight Gold Gloves while pitching to a superb 159 ERA+ since 2020. The Padres can only wish they had him in a rotation in which the talent drops off sharply after the front three of Yu Darvish, Joe Musgrove and Blake Snell.

Los Angeles Dodgers: The Josh Fields-for-Yordan Álvarez Trade

The Deal (Aug. 1, 2016): Los Angeles Dodgers get RHP Josh Fields (minus-0.3 WAR); Houston Astros get DH/LF Yordan Álvarez (13.6 WAR)

You knew this one was coming, and it only happened in the first place because Dodgers president of baseball operations Andrew Friedman didn't really know what he had after he signed Álvarez out of Cuba in June 2016:

"We signed him the day before the [international signing] period ended, and it was more because we were about to be cut out of big-ticket signings. Ironically, the big question in the industry at that time was about the power. Which, I'm not sure how that was the question."

To be fair to Fields for a moment, it's not as if he had a bad time with the Dodgers. He appeared in 124 games across three seasons and accumulated a 2.61 ERA in the process. Mostly in low-leverage situations, mind you, but those outs still count.

Álvarez, though, is one of the best young hitters to come around in a long time. His 368 regular-season games with the Astros have produced a 163 OPS+ and 98 home runs, and they likely wouldn't have won last year's World Series without him.

To have lost a guy like that hurts under any circumstances. Under circumstances that now see the Dodgers suddenly missing Turners Trea and Justin, Cody Bellinger and Joey Gallo from their offense, it hurts that much more.

Chicago Cubs: The José Quintana-Dylan Cease-Eloy Jiménez Trade

The Deal (July 13, 2017): Chicago Cubs get LHP José Quintana (3.6 WAR); Chicago White Sox get RHP Dylan Cease (9.2), LF/DH Eloy Jiménez (5.3), 1B Matt Rose (0), INF Bryan Flete (0)

In the moment, the Cubs' trade for Quintana was hardly outrageous. They were the reigning World Series champions, after all, and it was clear by mid-July of 2017 that their title defense needed another starter.

Now that this acknowledgement is out of the way, we can also acknowledge that it was always a risky trade. Quintana wasn't living up to his All-Star effort in 2016 at the time, so the Cubs seemingly paid an above-market price in handing over their two best prospects for him.

The passing of time hasn't exactly made said price look like a bargain. Jiménez has been an impact hitter (i.e., a 123 OPS+) for the White Sox when he's been healthy. Cease possesses perhaps baseball's best pitch and is now coming off a big-time breakout that saw him finish second to Justin Verlander in the AL Cy Young Award race.

We're on the side of thinking the new-look Cubs could actually be pretty good in 2023, but they'd look better if they had more power and at least one swing-and-miss hurler in their starting rotation. With Jiménez and Cease, in other words.

St. Louis Cardinals: The Marcell Ozuna-Sandy Alcántara Trade

The Deal (Dec. 14, 2017): St. Louis Cardinals get LF Marcell Ozuna (4.6 WAR); Miami Marlins get RHP Sandy Alcántara (16.8), RHP Zac Gallen (1.3), LHP Daniel Castano (1.0), OF Magneuris Sierra (minus-1.0)

It wasn't long after the Marlins were sold in 2017 that the new owners planted a "For Sale" sign on the club's roster. Reigning National League MVP Giancarlo Stanton was the main attraction, clearly, but Marcell Ozuna was one heck of a consolation prize.

He had gone off that year, demolishing previous career highs by batting .312 and smashing 37 home runs and even winning a Gold Glove. Further, he was only 27 and not slated to become a free agent for two more years.

As they were then coming off an 83-win season in which they were squarely in the middle of the pack in runs scored, even now it's hard to blame the Cardinals for wanting Ozuna badly enough to give up three of their 14 best prospects. And Ozuna was ultimately solid in St. Louis, hitting to a 107 OPS+ and 52 home runs in two seasons.

It's therefore saying something that this trade resembles an all-time "oof," and more so now while the Cardinals are heading into 2023 with a flimsy-looking rotation. If it had Alcántara and Gallen, who finished first and fifth in the NL Cy Young Award voting last year, suffice it to say it would look a tad more solid.

San Francisco Giants: The Andrew McCutchen-Bryan Reynolds Trade

The Deal (Jan. 15, 2018): San Francisco Giants get RF Andrew McCutchen (1.6 WAR), cash; Pittsburgh Pirates get CF Bryan Reynolds (13.6), RHP Kyle Crick (1.0), international bonus money

It's obviously easy for us to say now, but what the Giants should have done after a 98-loss season in 2017 was look to rebuild. Or, at least, they could have pivoted to a slightly different philosophy.

What they did instead was effectively double-down on pursuing success with a roster full of aging stars. The trade for McCutchen was but one of two notable deals they made for the sake of this pursuit during the 2017-18 offseason, with the other being a swap that brought back Evan Longoria from the Rays.

Neither really paid huge dividends, though the Giants surely got less out of the McCutchen trade. He posted a good-not-great 115 OPS+ for a club that predictably went nowhere, resulting in him getting flipped to the New York Yankees at the end of August.

The Pirates, meanwhile, have seen Reynolds become a full-blown star who's put up a 136 OPS+ and 51 home runs over the past two seasons. He understandably wants out of Pittsburgh, but the odds of the Giants reacquiring him via trade don't seem especially high. Which is too bad, because they could use a better center fielder than Mike Yastrzemski.

St. Louis Cardinals: The Randy Arozarena Trade

The Deal (Jan. 9, 2020): St. Louis Cardinals get LHP Matthew Liberatore (minus-0.5 WAR), C Edgardo Rodriguez (0), supplemental draft pick; Tampa Bay Rays get LF Randy Arozarena (7.8), DH José Martínez (0.2), supplemental draft pick

This one is not as bad as the Ozuna trade, but it's nonetheless further proof that Cardinals president of baseball operations John Mozeliak doesn't have a spotless record even though the team has yet to have a losing season under his watch.

Heck, Mozeliak himself even issued a mea culpa less than a year after he sent Arozarena to the Rays:

Not that Arozarena gave him much choice, of course. This was when he was in full "Playoff Randy" mode for the Rays in the 2020 postseason, eventually setting all-time records with 29 hits and 10 home runs. He subsequently won the AL Rookie of the Year in 2021 and followed with a 20-homer, 32-steal season in 2022.

There are nonetheless silver linings for the Cardinals with regard to this trade. Their outfield mix is fine even without Arozarena, and they used the supplemental pick on Tink Hence, who's now their second-best prospect after slugging outfielder Jordan Walker.

San Diego Padres: The Austin Nola-Ty France-Andrés Muñoz Trade

The Deal (Aug. 31, 2020): San Diego Padres get C Austin Nola (3.2 WAR), RHP Dan Altavilla (0.1), RHP Austin Adams (0.3); Seattle Mariners get 1B Ty France (7.9), RHP Andrés Muñoz (1.5), C Luis Torrens (1.0), OF Taylor Trammell (0)

On account of him being one of the best prospects in baseball, this one was seen as "The Taylor Trammell Trade" at the time. But in retrospect, there should have been more skepticism based on his down season in 2019 and the lack of a minor-league season in 2020.

What we know for sure now is that the Padres didn't really know what they had in either France or Muñoz. The former was already something of a revelation when the Friars traded him to Seattle, and he's since racked up a 127 OPS+ and 40 home runs in 315 games in the Pacific Northwest.

Muñoz, meanwhile, finished last season on a tear that saw him permit only six earned runs while striking out 71 batters over 44.2 innings. His stuff is GIF-able, to say the least.

The Padres simply bought too high on Nola, who was hitting well but was already past the age-30 threshold. He's a decent guy to have behind the plate, to be sure, but their roster would look better with France at first base and Muñoz alongside Josh Hader in the pen.

Colorado Rockies: The Nolan Arenado Trade

The Deal (Feb. 1, 2021): Colorado Rockies get LHP Austin Gomber (0.9 WAR), 3B Elehurus Montero (0.1), INF Mateo Gil (0), RHP Tony Locey (0); St. Louis Cardinals get 3B Nolan Arenado (12.0)

At the time the Rockies made this trade, Arenado was only one year into a seven-year, $234 million extension and well entrenched among the best players in the franchise's history.

To trade a guy like that is a sin in its own right. To also agree to pay as much as $51 million of his remaining contract and only take back a finesse left-hander and none of the Cardinals' seven best prospects, and then turn around and sign a diminished Kris Bryant for $187 million barely more than a year later? That's ninth-circle stuff.

About the only thing to say in the Rockies' defense is that they didn't have any guarantees Arenado was going to serve out the remainder of his deal. He wasn't keeping his discontent with the franchise—then coming off consecutive fourth-place finishes in the National League West—a secret, so the prospect of him opting out after 2021 was very real.

What Arenado's back-to-back opt-ins with the Cardinals suggest, however, is that he might have stuck around if the Rockies were running a more competent ship. That obviously wasn't the case then, and things are now just as bad but in a more baffling way. The Rockies are set to rank in the top half of MLB for payroll in 2023, yet they project to be the league's worst team.

Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.