There are typically more than two hundred trades every calendar year in Major League Baseball, and, occasionally, they hurt for years after the fact.

Which swaps from at least a year ago are most painful to this day?

All of these haunting trades happened between Jan. 1, 2017 and Dec. 31, 2023, and at least one of the players the team wishes it hadn't traded away still could have been under team control for the 2025 season.

A few examples of what doesn't count: Baltimore trading away Manny Machado in 2018 a few months before he became a free agent; Boston trading away Mookie Betts in 2020 prior to his final year of arbitration eligibility; Miami trading away Christian Yelich in 2018, whose contract would have expired at the end of 2022.

They may well still regret making those moves, but the teams would've lost those players (or had to pay a whole lot more to keep them) by now anyway.

But the Cubs sending Dylan Cease to the White Sox in 2017 and St. Louis trading Adolis García for cash considerations in 2019? Neither of those players has reached free agency yet, so they definitely count.

In each case, what the team actually got in return for the player(s) in question is crucial information, too. For instance, Arizona trading Jazz Chisholm Jr. to Miami for Zac Gallen in 2019 was hardly a regrettable move for either side.

Though, there's a different Gallen swap that still stings.

Trades are presented in chronological order.

Dylan Cease to the White Sox

The Trade: Chicago Cubs send Dylan Cease, Eloy Jiménez, Bryant Flete and Matt Rose to Chicago White Sox for Jose Quintana (July 13, 2017)

In Jose Quintana, the Chicago Cubs thought they were getting 3.5 years of an ace at a pretty reasonable price.

He had signed a five-year, $26.5M extension with the Chicago White Sox before the 2014 season began, which would have him earning nearly $9M in 2018 before $10.5M club options for each of 2019 and 2020.

And from 2012-16, FanGraphs rated Quintana as the 11th-most valuable pitcher in baseball, tied with Stephen Strasburg.

Even back then before contracts really started going bonkers, he likely would've been able to get close to $20M per year in free agency, so the Cubs leapt at the opportunity, giving up their top two prospects (Dylan Cease and Eloy Jiménez) and two others who never made it to the majors (Bryant Flete and Matt Rose) to get him.

Unfortunately for the Cubs, Quintana did not deliver the goods. They did exercise those club options for 2019 and 2020, but he maxed out at 1.5 bWAR in 2018, pitching much more like a No. 3 or No. 4 starter than the ace they were anticipating. (In fact, he was their Game 3 starter in the NLDS in 2017 and didn't pitch for them in their brief 2018 and 2020 postseason appearances.)

Even more unfortunately for the Cubs, Cease did deliver for the White Sox, nearly winning the AL Cy Young in 2022 and amounting to 16.0 bWAR from 2021-24 with one year remaining before he reaches free agency.

Jiménez initially provided good value when healthy, too, finishing fourth in the 2019 AL Rookie of the Year vote, and earning a Silver Slugger in 2020. The Cubs very much could have used his bat in both of those years.

Zac Gallen and Sandy Alcántara to the Marlins

The Trade: St. Louis Cardinals send Sandy Alcántara, Zac Gallen, Daniel Castano and Magneuris Sierra to Miami Marlins for Marcell Ozuna (Dec. 14, 2017)

In 2017, Giancarlo Stanton and Marcell Ozuna combined to give the Miami Marlins 96 home runs and 256 runs batted in. And yet, they finished eight games below .500 and couldn't justify continuing to pay Stanton's ballooning contract while going nowhere fast.

Thus, they traded the 2017 NL MVP to the New York Yankees on Dec. 11. And three days later, they sent Ozuna's final two years of arbitration eligibility to the Cardinals for three pitching prospects and a rookie outfielder.

The outfielder (Magneuris Sierra) and one of the pitchers (Daniel Castano) didn't amount to much of anything.

But Sandy Alcántara and Zac Gallen sure did pan out well. Even with Alcántara missing the entire 2024 season to Tommy John surgery, they've both been top-20 pitchers in baseball since the beginning of 2019, per FanGraphs.

To his credit, Ozuna at least gave the Cardinals two respectable seasons. Nothing compared to the .924 OPS he posted in his final year with Miami, but hard to argue with a combined 52 home runs and 177 RBI, with multiple WAR in each season.

But could you imagine if they had just held onto Gallen and Alcántara?

In 2022, the Cardinals already had the NL MVP (Paul Goldschmidt) and the third-place finisher in that vote (Nolan Arenado), but they could've also had the Cy Young winner (Alcántara) and the fifth-place finisher in that vote (Gallen).

Not only would that team have been all sorts of special, but they might have been able to avoid the rebuilding situation they find themselves in at the moment, as Gallen is just now entering his final year before hitting free agency for the first time. Could have at least avoided needing to just hope for the best from both Lance Lynn and Kyle Gibson in 2024.

Tampa Bay Hits Jackpot for Chris Archer

The Trade: Tampa Bay Rays send Chris Archer to Pittsburgh Pirates for Tyler Glasnow, Austin Meadows and a player to be named later (Shane Baz) (July 31, 2018)

Because Shane Baz is still several years away from reaching free agency, this trade is the gift that keeps on giving to this annual article.

Chris Archer was the rare instance of Pittsburgh going all-in as a buyer at the trade deadline. The Pirates gave up their 2017 first-round pick (Baz), a top prospect (Austin Meadows) and a young pitcher who had a 5.79 ERA through 56 uninspiring appearances (Tyler Glasnow).

Baz has been limited by injury, but has been worth 2.7 bWAR thus far to Tampa Bay. Glasnow was worth 8.6 bWAR before they traded him to the Dodgers last winter. Meadows gave them a 6.0 bWAR, received AL MVP votes in both 2019 and 2021 and was flipped to Detroit for Isaac Paredes, who gave them another 9.0 bWAR in the span of 2.5 years.

All told, what a return for the Rays, who were just doing their typical salary dump thing.

They had signed Archer to a six-year, $25.5M extension in 2014, but he was getting more expensive, up to $6.25M for the 2018 season, slated for $7.5M in 2019 before a $9M club option for 2020 and an $11M club option for 2021.

So they unloaded him on Pittsburgh, which was still trying to figure out its rotation after trading away Gerrit Cole six months prior. And between the 2018 and 2019 campaigns, he made 33 starts with a 4.92 ERA.

Not great.

Worse yet, the Pirates decided that was good enough to bring him back, exercising that $9M option for 2020—only to find out in June that he would miss the entire truncated season after undergoing surgery for thoracic outlet syndrome. (They went ahead and declined the 2021 option.)

Rangers Purchase Adolis García

The Trade: St. Louis Cardinals send Adolis García to Texas Rangers for cash considerations (Dec. 21, 2019)

Trading a player straight up for "cash considerations" happens all the time, but almost always for guys that neither team expects to amount to much of anything.

In the 2024 calendar year alone, Spotrac lists 90 such transactions.

Of the several hundred that went down from 2017-23, though, only one stands out as particularly regrettable—and still painful years after the fact.

When the St. Louis Cardinals signed Kwang Hyun Kim in mid-December 2019, they needed to make room for him on the 40-man roster, opting to designate Adolis García for assignment, trading him four days later to the Texas Rangers for ye olde cash considerations.

Then 26 years old, García hit 32 home runs that year at Triple-A Memphis, but they didn't view him as a big part of their future outfield plans. (Same goes for Randy Arozarena, by the way, who they traded to Tampa Bay a few weeks later. Though, they did at least get back Matthew Liberatore in that one.)

In the five years since, right field has been a revolving door of mediocrity for the Cardinals, with 10 different players appearing in at least 17 games there, led primarily by Lars Nootbaar, Dylan Carlson and Jordan Walker.

Meanwhile, in Texas, García has been a two-time All-Star, a Gold Glove winner, the 2023 ALCS MVP and a World Series champion.

At least Kim gave the Cardinals two years with a sub-3.00 ERA?

The Nolan Arenado Fleecing Heard 'Round the World

The Trade: Colorado Rockies send Nolan Arenado and $51 million to St. Louis Cardinals for LHP Austin Gomber, 3B Elehuris Montero, RHP Tony Locey, RHP Jake Sommers and IF Mateo Gil (Feb. 2, 2021)

Had the Rockies not made this embarrassment of a trade, it is extremely likely that Nolan Arenado would have exercised one of his opt-out clauses to get the heck out of Colorado and enter free agency after either the 2021 or 2022 season.

From that perspective, you could argue this one doesn't belong on the list. And at least they got something for a superstar who they fully expected would leave them high and dry as soon as he could.

However, those five somethings have collectively amounted to basically nothing, three of them yet to make their MLB debuts, while Elehuris Montero had a minus-1.7 bWAR over the past three seasons before Colorado released him in November. The only one to provide any ROI is Austin Gomber, but certainly not much with a 5.08 ERA over the past four years.

The kicker, of course, is the cash.

Colorado retained nearly one-third of the money still owed on Arenado's eight-year, $260M contract, effectively paying the Cardinals $51M to take a Platinum Glove third baseman and five-time All-Star off their hands.

Some lot of good that gift actually did for the Cardinals. They made the playoffs in both 2021 and 2022 but didn't win a game in either October and now they're also trying to trade Arenado away.

Still, one of the most lopsided, what-in-the-world trades in any sport in the past decade.

PCA to CHC

The Trade: New York Mets send Pete Crow-Armstrong to Chicago Cubs for Javier Báez and Trevor Williams (July 30, 2021)

The New York Mets took Pete Crow-Armstrong 19th overall in the 2020 draft. But there was no minor league baseball that year, and he only appeared in six Single-A games in 2021 before undergoing season-ending shoulder surgery.

So when the trade deadline rolled around that summer and they were looking to bolster a team that had a four-game lead in the NL East, they were willing to part with PCA before ever getting much of a look at what he could do for them.

Both players they added ended up being great pickups. Javier Báez had an .886 OPS for his two months in Queens. Trevor Williams had an 3.06 ERA in 32.1 innings of work down the stretch. (He pitched well for them the following season, too.)

Nevertheless, the 2021 Mets relentlessly crashed and burned, losing 38 of their final 60 games and missing the postseason by an 11.5-game margin.

They gained nothing by giving up Crow-Armstrong.

Fast-forward a year and a half, and PCA had blossomed into one of the top prospects in all of baseball in the Cubs farm system. Though his initial foray into the majors in September 2023 was a hitless mess, he was one of the best defensive centerfielders in the majors in 2024 and may well become a real star in 2025.

And for all the money the Mets have been willing to spend to build what they hope will be a champion, center field is a pretty major question mark for them heading into the upcoming season. If they had Crow-Armstrong out there along with Brandon Nimmo and Juan Soto, that'd probably be the best outfield in baseball.

3 Prospects for 9 Tyler Mahle Appearances

The Trade: Minnesota Twins acquire Tyler Mahle from Cincinnati Reds for Spencer Steer, Christian Encarnacion-Strand and Steve Hajjar (Aug. 2, 2022)

At the time, this one felt like a win for Minnesota.

Three days after Seattle gave up a ton of prospect capital to get 1.5 years of Luis Castillo, the Twins were able to acquire 1.5 years of Tyler Mahle without giving up a single top-100 prospect.

And there were high hopes for "no longer pitching home games at Great American Ball Park" Mahle, who in 2021 had a 5.63 ERA at home compared to 2.30 on the road, and who was red hot in the six weeks leading up to the trade deadline, posting a sub-3.00 ERA over his final nine starts with Cincinnati.

It wasn't outlandish to think he'd be as valuable as Castillo, if not even more so. And they got him for what comparatively seemed like peanuts.

However, in his third appearance with Minnesota, Mahle left after eight batters because of a shoulder injury. And by the end of the following April, he was done for that year, needing Tommy John surgery.

He ended up pitching just 42 innings for the Twins before leaving in free agency.

Meanwhile, Spencer Steer was a fantastic acquisition for Cincinnati, already hitting 45 big league homers and playing in darn near every game over the past two seasons. And though this past season was brutal for Christian Encarnacion-Strand, the expectation is that he'll be a near-everyday player between 1B and DH in 2025.

Angels Go All-In on Final Year with Shohei Ohtani

The Trade: Los Angeles Angels send Ky Bush and Edgar Quero to Chicago White Sox for Lucas Giolito and Reynaldo López (July 26, 2023)

The motivation behind this trade (and the subsequent acquisitions of C.J. Cron, Randal Grichuk and Dominic Leone) was obvious: the Angels were desperate to finally get to the postseason in what the entire world pretty well knew was going to be Shohei Ohtani's last season with them.

They were going to need to leapfrog several teams in order to get there, but they were only 3.5 games back, and with the hope that Mike Trout would be able to return from his broken hamate bone at some point in mid-August to help them finish the fight.

So they shipped two of their best prospects to the White Sox in exchange for the best two-month-rental pitcher on the board (Lucas Giolito) and a rental reliever who they hoped would help spruce up the bullpen.

Unfortunately, it went disastrously.

López pitched well enough for his 13 innings of work, even tallying two saves. But Giolito made six starts with a 6.89 ERA before the Angels put both pitchers on waivers, each claimed by the Guardians 36 days after they were traded to the Angels—during which time, Los Angeles went 12-21, dropping hopelessly out of contention.

When Trout returned for one game on August 22 before landing back on the IL, that was the final straw.

They knew it was a gamble, of course, but they sure do regret it now.

Ky Bush tore through the minors last season and had a cup of coffee in the majors. He should be in the mix for a spot in the rotation in 2025. And Edgar Quero remains one of the top 100 overall prospects, likely headed for his MLB debut in what will be his age-22 season.

Seattle's Salary Dump Mistake

The Trade: Seattle Mariners send Eugenio Suárez to Arizona Diamondbacks for Seby Zavala and Carlos Vargas (Nov. 22, 2023)

Seattle was exceptionally busy on the trade front last offseason, adding (in addition to this trade), Luke Raley, Luis Urías, Jackson Kowar, Cole Phillips, Jorge Polanco, Mitch Haniger and Gregory Santos while unloading Robbie Ray, Jose Caballero, Justin Topa, Jarred Kelenic, Marco Gonzales and quite a bit more across their nine trades.

For the most part, the trades were...fine. The Mariners certainly didn't get what they were hoping to get out of Polanco, Haniger and Santos, but they didn't get retrospectively fleeced in the majority of those deals.

Parting with Suárez in a salary dump that didn't even save them all that much money, though, was a major regret.

Suárez was due $11M for 2024, plus a $15M club option with a $2M buyout for 2025. But what they used at third base in his stead was a platoon of Luis Urías ($5M), Josh Rojas ($3.1M) and Dylan Moore ($3.1M) which cost them a combined $11.2M.

So, did they actually save any money?

Moore played more than just third base, but they could have just not traded for Urías and traded away Rojas instead of Suárez and basically broken even on the balance sheet—and definitely been better off on offense.

While Suárez hit 30 home runs and led Arizona's MLB-best offense with 101 RBI, Seattle's "as 3B" batting split was a .213 batting average with 12 home runs and 49 RBI, buried at either eighth or ninth in the batting order in just about every game for a team that couldn't score worth a darn for the first five months of the season.

Making matters worse here, Seby Zavala was below replacement level before the Mariners cut him loose, and Carlos Vargas spent the entire season at Triple-A Tacoma. Maybe he'll make some impact in their bullpen moving forward, but too little too late to salvage anything for the 2024 team that squandered a championship-caliber starting rotation.

Red Sox Give Up on Chris Sale

The Trade: Boston Red Sox send Chris Sale and $17M to Atlanta Braves for Vaughn Grissom (Dec. 30, 2023)

For the hour or so between when this trade was announced and when we knew about the cash involved in the deal, it initially made a lot of sense for both teams.

Chris Sale (who had a $20M club option for 2025 before Atlanta signed him to an extension) had made just 31 appearances over the previous four seasons combined for the Red Sox, and it looked like they were finally dumping his bloated, $27.5M salary in exchange for a promising middle infielder with a .287 batting average in 64 games played. And on the Atlanta side of the equation, it was a high-upside gamble to help out a rotation that got questionable in a hurry after Spencer Strider, Max Fried and Charlie Morton.

But when we learned that Boston was sending Atlanta more than 60 percent of Sale's 2024 salary in the deal, the move became more of a head-scratcher.

And knowing now how the 2024 season played out—Sale winning the NL Cy Young for Atlanta; Grissom doing absolutely nothing for the Red Sox while an underachieving starting rotation 'led' them to a third consecutive year of mediocrity—this looks, in retrospect, like an all-timer of a disastrous deal for Boston.

There's a chance Grissom could come back this season, play a big role for Boston and somewhat balance the scales here. However, that's rather unlikely, if only because two of the top prospects in this farm system are middle infielders (Marcelo Mayer and Kristian Campbell) who ought to be ready for the big leagues this season, if not by Opening Day.

Because of that, it's plausible Grissom never plays again for the Red Sox, which would cement this swap as one of the most lopsided deals in decades.