The MLB offseason is a transformative time with free-agency signings and trades helping to reshape the landscape of the sport for the upcoming year.

However, those headline-grabbing moves don't always work out as hoped.

Whether it's a big-money free-agent signing that doesn't pan out, a blockbuster trade that turns into a lopsided deal in hindsight or a premature decision to non-tender or release a late-blooming star, every club has at least a few moves they wish they could take back.

Scanning back over the past decade of transactions, we've selected each MLB team's biggest offseason regret since the 2012-13 offseason.

Buckle up for a rocky trip down memory lane.

Arizona Diamondbacks

Date: December 9, 2014

Transaction: OF Yasmany Tomás signed a six-year, $68.5 million deal in free agency.

The Arizona Diamondbacks were hoping they had found the next Yoenis Cespedes or José Abreu when they signed fellow Cuban defector Yasmany Tomas to a massive six-year deal.

Instead, they got a one-dimensional slugger whose defensive shortcomings overshadowed anything he did in the batter's box. His most productive season came in 2016 when he launched 31 home runs, but he was still a negative-WAR player that year and logged minus-2.5 WAR in 309 games over the life of the contract.

That's bad enough for it to get the nod by a narrow margin over the blockbuster deal that involved sending Dansby Swanson to the Atlanta Braves for Shelby Miller in 2015.

Atlanta Braves

Date: November 29, 2012

Transaction: OF B.J. Upton signed a five-year, $75.25 million deal in free agency.

The Atlanta Braves would probably love to shed the contracts of Marcell Ozuna and Eddie Rosario from their current payroll, but neither deal holds a candle to the B.J. Upton signing in terms of most regrettable.

Even in a contract year when he tallied 28 home runs and nabbed 31 steals, Upton still had a middling .298 on-base percentage and a pedestrian 108 OPS+. However, his ability to play center field and the fact that he was coming off his age-27 season convinced the Braves to ignore those red flags and spend big.

He went on to hit .198/.279/.314 with minus-1.7 WAR in 267 games before Atlanta cut its losses and packaged him along with All-Star closer Craig Kimbrel in a deal with the San Diego Padres prior to the 2015 season.

Baltimore Orioles

Date: January 21, 2016

Transaction: 1B Chris Davis signed a seven-year, $161 million deal in free agency.

Slugger Chris Davis led the AL with 47 home runs in 2015, but his free-agent market was not as robust as expected, and in the end it seemed like the Baltimore Orioles were bidding against themselves to bring him back.

After another productive season in 2016, he quickly devolved into one of the least productive players in baseball, struggling to a .185 average and 37.4 percent strikeout rate while logging an unsightly minus-5.8 WAR over the next four years.

Injuries cost him all of the 2021 season and he retired prior to 2022 while still receiving his final year's salary. With deferred money, the O's will pay him $2.8 million annually through the 2037 season.

Boston Red Sox

Date: November 25, 2014

Transaction: 3B Pablo Sandoval signed a five-year, $95 million deal in free agency.

The Boston Red Sox spent big during the 2014-15 offseason, adding Pablo Sandoval and Hanley Ramirez (four years, $88 million) on a pair of ill-fated free-agency deals.

Sandoval struggled to stay in shape and on the field from the start, and he ended up hitting .237/.286/.360 for a 71 OPS+ and minus-1.6 WAR in 161 games before he was released midway through his third season with the team.

The fact that he would then return to the San Francisco Giants and provide some solid production in a part-time role while the Red Sox were still paying him was just salt in the wound.

Chicago Cubs

Date: December 15, 2015

Transaction: OF Jason Heyward signed an eight-year, $184 million deal in free agency.

How much is an inspiring speech during a rain delay in Game 7 of the World Series worth?

For the Chicago Cubs, the answer to that question is roughly $184 million, as his fabled pep talk after the skies opened up in Cleveland is about the only positive from Jason Heyward's tenure with the team.

He did win Gold Gloves in his first two seasons with the club, but he hit just .245/.323/.377 for an 86 OPS+ and 8.9 WAR in 744 games before he was released this offseason ahead of the final year of his contract.

The 33-year-old will try to win a roster spot with the Los Angeles Dodgers this spring after inking a minor league deal.

Chicago White Sox

Date: December 9, 2014

Transaction: RHP Jeff Samardzija, RHP Michael Ynoa acquired from Oakland Athletics in exchange for SS Marcus Semien, RHP Chris Bassitt, C Josh Phegley, 1B Rangel Ravelo.

The Oakland Athletics went all-in at the 2014 trade deadline, acquiring Jon Lester and Jeff Samardzija in separate trades to bolster the starting rotation, but it was back to cutting costs that offseason.

That meant Samardzija hit the trade block ahead of his final year of club control, and the Chicago White Sox parted with a package of four prospects to acquire him. He went 11-13 with a 4.96 ERA in 214 innings for a White Sox team that finished 10 games below .500, and then he left in free agency.

Meanwhile, Marcus Semien and Chris Bassitt both developed into impact players, tallying a combined 30.2 WAR during their time in Oakland.

Cincinnati Reds

Date: February 19, 2014

Transaction: RHP Homer Bailey signed a six-year, $105 million extension.

Homer Bailey logged a 3.49 ERA, 1.12 WHIP and 199 strikeouts in 209 innings during the 2013 season, and the Cincinnati Reds rewarded him with a nine-figure extension during the offseason.

Injuries cut short his 2014 campaign and he was never the same, struggling to a 6.25 ERA and 1.68 WHIP while allowing opposing hitters to bat an absurd .316/.377/.511 against him during the middle four years of the extension. He offered up this gem when asked about a potential move to the bullpen:

Prior to the final season of his contract, he was traded to the Los Angeles Dodgers along with prospects Josiah Gray and Jeter Downs for Yasiel Puig, Alex Wood, Matt Kemp and Kyle Farmer in a shuffling of bad contracts. The Dodgers released him the day after that deal was completed.

Cleveland Guardians

Date: January 3, 2013

Transaction: OF Nick Swisher signed a four-year, $56 million deal in free agency.

The generally tight-fisted Cleveland front office was busy during the 2012-13 offseason, signing outfielders Nick Swisher and Michael Bourn (four years, $48 million) in an effort to bolster a roster that had fallen down the standings with a 68-94 record the previous year.

Swisher had a 115 OPS+ with 22 home runs and 3.7 WAR during his first season in Cleveland, but his production fell off a cliff the following year. Midway through the 2015 season he was traded to the Atlanta Braves along with Bourn and cash for another bad contract in third baseman Chris Johnson.

The three-team deal that sent Yandy Díaz to the Tampa Bay Rays prior to the 2019 season is worth a mention, though they did get a solid year out of Carlos Santana while also unloading Edwin Encarnación in that trade.

Colorado Rockies

Date: February 1, 2021

Transaction: Acquired RHP Austin Gomber, 3B Elehuris Montero, RHP Jake Sommers, RHP Tony Locey, SS Mateo Gil from the Colorado Rockies for Nolan Arenado, $51 million

How?! How is this all the Colorado Rockies managed to get for Nolan Arenado?

The true regret originates long before the trade was made, with the bone-headed decision by the front office to shop the face of the franchise just two years after he signed a huge long-term deal.

"There's a lot of disrespect from people there that I don't want to be a part of," Arenado told reporters in response to the Colorado front office admitting it was listening to offers.

With that, it became a very public rift between the player and team, which undercut the Rockies' bargaining power. It became clear that a split was inevitable, and they were left to take the best offer before the start of the new season.

But again, how in the world was that the best offer?!

Detroit Tigers

Date: March 28, 2014

Transaction: 1B Miguel Cabrera signed an eight-year, $242 million extension.

Miguel Cabrera still had two years left on his contract when he signed this massive extension, which meant the eight-year deal didn't start until his age-33 season in 2016.

It's hard to argue with the numbers he produced in the three years leading up to that extension, with three straight AL batting titles, a Triple Crown and a pair of AL MVP wins, but betting on a player to produce like that into his late 30s is almost always a losing one.

He continued to produce at an MVP-caliber level through the 2016 season, but things fell off a cliff from there. Over the past six years, he has hit .262/.330/.385 for a 96 OPS+ with minus-2.1 WAR in 603 games, and he is still owed another $32 million in 2023 in the final year of that extension.

If nothing else, the deal allowed Cabrera to record his 3,000th hit and 500th home run while wearing a Tigers uniform.

Houston Astros

Date: March 22, 2014

Transaction: OF J.D. Martinez released.

The Houston Astros were coming off a 111-loss season and were still in the early stages of a full-scale rebuild when they released J.D. Martinez just before Opening Day in 2014.

The 25-year-old had hit .250/.272/.378 for a 79 OPS+ with seven home runs and a 26.5 percent strikeout rate in 310 plate appearances the previous season, but the Astros didn't see enough to keep him around.

The Tigers scooped him up two days after he was cut loose, helped him retool his swing, and the rest is history.

He hit .315/.358/.553 with 30 doubles and 23 home runs in 2014 and quickly developed into one of the most feared sluggers in baseball.

Kansas City Royals

Date: December 16, 2013

Transaction: 2B Omar Infante signed a four-year, $30 million deal in free agency.

This is a prime example of why it's never wise to pay for a career year.

Omar Infante was a useful utility player with a career .275/.315/.397 line and 90 OPS+ in 11 seasons before he hit .318/.345/.450 with 10 home runs, 51 RBI and 2.6 WAR in 2013, just in time to test the free-agency waters.

He hit .238 with a .269 on-base percentage and minus-0.6 WAR before he was released midway through the third year of his contract, and his lack of production led the Royals to part with top prospect Sean Manaea to acquire Ben Zobrist at the 2015 deadline ahead of their run to a World Series title.

The Ian Kennedy signing also deserves a mention, but he was able to rebuild some value with a move to the bullpen and a resurgence in the closer's role.

Los Angeles Angels

Date: December 15, 2012

Transaction: OF Josh Hamilton signed a five-year, $125 million deal in free agency.

The Albert Pujols deal didn't turn out as hoped for the Los Angeles Angels and the Anthony Rendon signing is well on its way to being a massive bust, but the pick here still has to be the Josh Hamilton contract.

Coming off a season when he finished fifth in the AL MVP voting by posting a 141 OPS+ with 43 home runs and 128 RBI, Hamilton was one of the top players on the market, and the free-spending Angels gave him a five-year deal in hopes of slotting him alongside Pujols in the middle of a new-look lineup.

His production fell off dramatically in his Angels debut; he was limited to 89 games the following year; and then he underwent shoulder surgery during spring training prior to his third season.

While recovering, he suffered a relapse of drug and alcohol use, and the Angels traded him back to the Rangers, eating the bulk of the $80 million he was still owed in the process.

Los Angeles Dodgers

Date: December 30, 2015

Transaction: LHP Scott Kazmir signed to a three-year, $48 million contract in free agency.

After the oft-injured Scott Kazmir strung together healthy seasons in 2014 (190.1 IP, 3.55 ERA) and 2015 (183.0 IP, 3.10 ERA), the Los Angeles Dodgers signed him to a three-year deal in free agency hoping that trend could continue.

The left-hander went 10-6 with a 4.56 ERA, 1.36 WHIP and 134 strikeouts in 136.1 innings during his first season with the team, but he didn't throw another pitch in a Dodgers uniform after that debut.

Injuries kept him on the sidelines for the entirety of the 2017 season, and he was traded to the Atlanta Braves along with Adrián González, Brandon McCarthy and Charlie Culberson in a bad salary swap that brought Matt Kemp back to Los Angeles.

Miami Marlins

Date: January 19, 2016

Transaction: LHP Wei-Yin Chen signed a five-year, $80 million deal in free agency.

The cutoff for this article was the 2012-13 offseason. Otherwise, the 2011-12 offseason when the Miami Marlins signed José Reyes, Mark Buehrle and Heath Bell in hopes of ushering in their new stadium with a bang would have offered plenty of viable options for inclusion.

Instead, the pick is the five-year deal given to Wei-Yin Chen, a pitcher who had a 3.72 ERA and 4.14 FIP in 706.2 innings with the Baltimore Orioles before he was inexplicably paid like a front-line starter.

The left-hander posted a 4.75 ERA in 289.2 innings during his first three seasons in Miami, and then he moved into the bullpen in 2019 where he struggled to a 6.59 ERA in 45 appearances. The Marlins released him ahead of the final year of his deal, eating $22 million due to the back-loaded nature of the contract.

Milwaukee Brewers

Date: March 6, 2020

Transaction: OF Christian Yelich signed a seven-year, $188.5 million extension.

The Milwaukee Brewers had every reason to believe Christian Yelich was going to be a franchise cornerstone and perennial MVP candidate when they signed him to the largest deal in franchise history.

Things just haven't worked out that way.

He won NL MVP honors in 2018 and followed that up with a 179 OPS+, 44 home runs, 30 steals and 7.0 WAR in 2019 before signing the long-term extension.

Since then, he has hit .243/.358/.388 for a 107 OPS+ with 35 home runs in 1,393 plate appearances, and his $23.9 million luxury-tax figure in 2022 accounted for nearly 17 percent of the small-market team's payroll.

Minnesota Twins

Date: December 3, 2013

Transaction: RHP Ricky Nolasco signed to a four-year, $49 million deal in free agency.

A four-year, $49 million deal might not seem like much in today's market, but it was the third-largest contract given to a starting pitcher during the 2013-14 offseason and the largest free-agency deal in Minnesota Twins history at the time.

The right-hander had the best season of his career in 2013, going 13-11 with a 3.70 ERA, 1.21 WHIP and 165 strikeouts in 199.1 innings, closing the season on a high note with the Los Angeles Dodgers after he was traded at the deadline.

His time in Minnesota was decidedly less productive. He struggled to a 5.44 ERA in 321 innings over the first two-and-a-half years of his contract before he was traded to the Los Angeles Angels along with top prospect Alex Meyer for Hector Santiago and Alan Busenitz.

New York Mets

Date: December 2, 2013

Transaction: IF Justin Turner non-tendered.

It was just a quick transaction note on Twitter, accompanied by a handful of other names.

Turner hit .280 with a 100 OPS+ in 214 plate appearances with the New York Mets in 2013, but his limited defensive value made him an expendable bench piece.

He caught on with the Los Angeles Dodgers and promptly hit .340/.404/.493 over 322 plate appearances as a utility player before taking over as the team's everyday third baseman. All told, he racked up 34.0 WAR and a pair of All-Star appearances in nine seasons with the Dodgers before departing in free agency this offseason.

New York Yankees

Date: December 7, 2013

Transaction: OF Jacoby Ellsbury signed a seven-year, $153 million deal in free agency.

It took a seven-year, $153 million deal for the Yankees to pry Jacoby Ellsbury away from the rival Boston Red Sox, and while he was a 3.6-WAR player his first season in New York, things quickly unraveled.

The speedy outfielder had an 89 OPS+ and 6.3 WAR total over the next three years before he spent the entire 2018 and 2019 seasons watching from the sidelines because of a variety of injuries.

Things then ended on bad terms when he was released and the Yankees tried to withhold his final year's salary for receiving outside medical treatment. The MLBPA filed a grievance that was settled outside of a hearing.

Oakland Athletics

Date: March 31, 2017

Transaction: 1B Max Muncy released.

The deal that sent Josh Donaldson to the Toronto Blue Jays is a strong contender here, but that was more of a necessary evil given the fact that the penny-pinching Oakland organization was never going to be able to keep him long term.

Instead, it's the decision to release Max Muncy that stands as the team's most regrettable decision of the past decade.

After hitting just .195 in 245 plate appearances in Oakland, Muncy was released, and a month later he caught on with the Los Angeles Dodgers on a minor league deal. He spent the entire 2017 season at Triple-A, hitting .309/.414/.491 in 110 games.

The following year he returned to the majors as a new player, logging a 161 OPS+ and 35 home runs. He has been worth 17.7 WAR over the past five seasons while making a pair of All-Star appearances.

Philadelphia Phillies

Date: March 12, 2018

Transaction: RHP Jake Arrieta signed a three-year, $75 million deal in free agency.

The Philadelphia Phillies have not been shy about handing out massive deals in free agency in recent years, but when they signed Jake Arrieta prior to the 2018 season, he immediately became the highest-paid player on the roster by a wide margin.

The 2015 NL Cy Young winner logged a 3.96 ERA in 172.2 innings during his first season with the team, but he struggled with injuries and ineffectiveness over the final two years of the deal to post a 4.75 ERA in 33 starts.

The under-the-radar prospect swap that sent infielder Curtis Mead to the Tampa Bay Rays in exchange for left-hander Cristopher Sanchez in 2019 could soon make its way onto this list. Mead hit .298/.390/.532 in the upper levels of the minors last year and checked in at No. 29 in B/R's recent Top 100 prospect list update.

Pittsburgh Pirates

Date: January 13, 2018

Transaction: RHP Joe Musgrove, RHP Michael Feliz, OF Jason Martin, 1B Colin Moran acquired from the Houston Astros for RHP Gerrit Cole.

After Gerrit Cole went 19-8 with a 2.60 ERA and 202 strikeouts in 208 innings during a breakout season in 2015 when he earned a $531,000 salary and a $10,000 bonus for making the All-Star team, the Pittsburgh Pirates offered him a salary of $538,000 for the 2016 season.

Cole told reporters:

"When you perform at a level that draws the praise of management, teammates, coaches and fans, you expect appropriate compensation. I understand the business of this game, but it is hard to accept that a year of performance success does not warrant an increase in pay. They even threatened a salary reduction to the league minimum if I did not agree."

The sides ultimately settled on a $541,000 salary, matching his earnings from the previous season, but the damage was done and it was abundantly clear Cole was gone the second he hit free agency.

With two years of control left in 2018, the Pirates decided to sell high, and while Joe Musgrove has since developed into a front-line starter in San Diego, the Pirates have little to show for this trade.

San Diego Padres

Date: December 19, 2014

Transaction: OF Justin Upton, RHP Aaron Northcutt acquired from San Diego Padres for LHP Max Fried, OF Mallex Smith, IF Jace Peterson, OF Dustin Peterson.

There are a lot of options here.

Signing Eric Hosmer. Trading a young Anthony Rizzo to the Chicago Cubs. Trading Trea Turner in a three-team deal for Wil Myers. Trading for Matt Kemp during a busy 2014-15 offseason that showed winning the offseason rarely matters.

However, we've landed on the deal that sent Max Fried to the Atlanta Braves as the team's most regrettable move, as he could have the greatest impact on the current club if he were still around.

The No. 7 pick in the 2012 draft, Fried was recovering from Tommy John surgery at the time of the trade, but he quickly developed into a top prospect upon returning and is now a bona fide ace atop the Atlanta rotation.

San Francisco Giants

Date: January 15, 2018

Transaction: OF Andrew McCutchen, cash acquired from the Pittsburgh Pirates for OF Bryan Reynolds, RHP Kyle Crick, international bonus pool money

Unwilling to admit that their window of contention had closed following a 98-loss season, the San Francisco Giants swung a pair of deals during the 2017-18 offseason to acquire Evan Longoria from the Tampa Bay Rays and Andrew McCutchen from the Pittsburgh Pirates.

They improved in the win-loss column, but only incrementally to 73-89 as they still finished a distant fourth in the NL West.

McCutchen was traded again during that season to the New York Yankees for a pair of prospects who have yet to make an impact, but the Giants are still feeling the sting of giving up All-Star outfielder Bryan Reynolds before he ever reached the majors.

Seattle Mariners

Date: December 9, 2015

Transaction: 1B Adam Lind acquired from the Seattle Mariners for RHP Freddy Peralta, RHP Carlos Herrera, RHP Daniel Missaki

For all the wheeling and dealing that Jerry Dipoto has done since taking the reins in the Seattle front office in 2015, it's surprising there are not more deals worth considering.

Freddy Peralta was a 19-year-old who had yet to pitch above rookie ball and the No. 15 prospect in the Seattle farm system at the time of this trade, but he has since developed into an electric young starter with a 3.08 ERA and 281 strikeouts in 222.1 innings the past two seasons.

First baseman Adam Lind hit .239/.286/.431 for a 94 OPS+ with 20 home runs and minus-0.3 WAR in his only season in Seattle.

St. Louis Cardinals

Date: December 14, 2017

Transaction: OF Marcell Ozuna acquired from the Miami Marlins in exchange for RHP Sandy Alcantara, RHP Zac Gallen, OF Magneuris Sierra, LHP Daniel Castano

This has a chance to go down as one of the worst trades in baseball history.

Marcell Ozuna hit .312/.376/.548 with 30 doubles, 37 home runs, 124 RBI and 5.6 WAR during his final season with the Miami Marlins in 2017, and he went to the Cardinals with two years of club control remaining.

However, he never came close to matching that level of production in St. Louis, posting a 107 OPS+ while averaging 26 home runs, 88 RBI and 2.3 WAR in two seasons before departing in free agency.

Sandy Alcantara just won NL Cy Young honors with the Marlins and Zac Gallen finished fifth in the balloting as the ace of the Arizona Diamondbacks after he was traded again in a one-for-one swap for Jazz Chisholm Jr. Pencil those two into the St. Louis rotation and they might be World Series favorites.

Tampa Bay Rays

Date: December 10, 2020

Transaction: OF Heriberto Hernandez, SS Osleivis Basabe, 1B/OF Alexander Ovalles acquired from the Texas Rangers for 1B Nathaniel Lowe, OF Carl Chester, 1B/OF Jake Guenther

Despite Nathaniel Lowe's gaudy numbers in the minors, the Rays never really gave him an extended look in the majors before he was traded to the Texas Rangers in a prospect-heavy, six-player deal prior to the 2021 season.

He immediately took over as the Rangers' starting first baseman and posted a 112 OPS+ with 18 home runs and 72 RBI and then took his game to another level this past season when he logged a 141 OPS+ with 27 home runs and won AL Silver Slugger honors on the strength of a red-hot second half.

Honorable mention to the five-player deal that sent Jake Cronenworth to the San Diego Padres with Tommy Pham for Hunter Renfroe, Xavier Edwards and Esteban Quiroz, all of whom are no longer with the Tampa Bay organization.

Texas Rangers

Date: December 15, 2019

Transaction: RHP Corey Kluber acquired from Cleveland Guardians for RHP Emmanuel Clase, OF Delino DeShields.

The Texas Rangers rolled the dice on two-time AL Cy Young winner Corey Kluber's ability to return to form after a fractured forearm sidelined him during the 2019 season.

He would pitch exactly one inning before a torn muscle in his right shoulder sidelined him once again, and that turned out to be his only appearance in a Rangers uniform as he walked in free agency that offseason.

Hard-throwing Emmanuel Clase had an equally inauspicious 2020 season when he was slapped with an 80-game suspension after he tested positive for performance-enhancing drugs, but over the past two years he has quickly developed into one of baseball's elite relievers.

The 24-year-old has a 1.33 ERA, 0.84 WHIP and 9.5 K/9 in 148 appearances in Cleveland, nailing down 66 of 75 save chances and earning an All-Star selection and AL Reliever of the Year honors in 2022.

Toronto Blue Jays

Date: November 20, 2015

Transaction: RHP Jesse Chavez acquired from the Oakland Athletics for RHP Liam Hendriks.

Liam Hendriks posted strong numbers in 2015 with the Toronto Blue Jays after the team reacquired him in a trade with the Royals, posting a 2.92 ERA, 1.08 WHIP and 9.9 K/9 in 58 appearances.

The following offseason he was flipped to Oakland for fellow reliever Jesse Chavez, and it was with the Athletics that Hendriks would develop into one of baseball's elite closers.

Meanwhile, Chavez had a 4.57 ERA in 39 appearances with the Blue Jays before he was traded again, this time to the Los Angeles Dodgers for right-hander Mike Bolsinger, who pitched to a 6.31 ERA in 41.1 innings in Toronto.

Washington Nationals

Date: December 9, 2019

Transaction: RHP Stephen Strasburg signed a seven-year, $245 million deal in free agency.

The Washington Nationals should have just accepted a clean break after their World Series title in 2019.

Third baseman Anthony Rendon and World Series MVP Stephen Strasburg were both free agents, and they both ended up signing seven-year, $245 million deals, with Rendon joining the Los Angeles Angels and Strasburg returning to the Nationals.

Since signing that contract, Strasburg has pitched just 31.1 innings in three seasons while earning $105 million. He is still owed another $140 million over the next four years, but with $80 million in total deferrals, the Nationals will still be paying him in 2029.

At least Patrick Corbin helped the team win that World Series in his first season with the team in 2019. Strasburg hasn't done anything since signing his new deal.

All stats courtesy of Baseball Reference and FanGraphs.