Should've, would've and could've are three of the most painful words for a fan of a Major League Baseball franchise, but let's look back on the 2023-24 offseason to identify the one move (or non-move) where each team would like to have a mulligan.

For some teams, it was a challenge to even pinpoint a clear misstep. Both New York teams and both Chicago teams did pretty well in hindsight—even though one of the Windy City teams is a lost cause in 2024.

For a lot of teams, though, the challenge was choosing from the several mulligans they'd love to have, based on how things have played out this season.

Teams are broken up by division and listed in alphabetical order within each division. Unless otherwise noted, statistics are current through the start of play Monday.

American League East

Baltimore Orioles: Signing Craig Kimbrel

The O's only made two noteworthy moves this offseason, trading for Corbin Burnes and signing Craig Kimbrel for $13 million.

The former has been great. The latter has been a problem.

Kimbrel started the season well, allowing just one earned run in his first 11 games. However, after a combined line of 2.1 IP, 6 H, 6 ER, 7 BB over his next five appearances, he was removed from the closer role. He did effortlessly convert a "low-leverage save" Sunday, staked to a three-run lead while Yennier Cano was unavailable after pitching the previous two days. Maybe that's the start of a comeback.

Boston Red Sox: Trading Chris Sale for Lucas Giolito

Technically, the Red Sox traded Sale to Atlanta for Vaughn Grissom and signed Giolito as a free agent. But the moves happened on consecutive days, with the Sale trade going down almost as a means of justifying signing Giolito. (It wasn't even a good salary dump, either, as Boston retained $17 million of the $27.5 million Sale was owed for 2024.)

But while Sale has been putting up Cy Young-caliber numbers in Atlanta, the Red Sox lost Giolito to a season-ending UCL surgery in mid-March.

(Granted, the starting rotation has held up incredibly well even without both Sale and Giolito. That doesn't mean they don't wish they could have that pair of moves back, though.)

New York Yankees: Trading Ben Rortvedt for Jon Berti

Perhaps "not offering more for Yoshinobu Yamamoto" is actually New York's biggest offseason regret, but the two big moves the Yankees made—trading for Juan Soto and signing Marcus Stroman—have panned out well thus far.

However, the last-day-of-the-offseason trade of C Ben Rortvedt and minor league OF John Cruz for IF Jon Berti looks a bit rough in hindsight.

Berti did finally get his first extra-base hit of the season Sunday in the form of a three-run homer, but Rortvedt has become one of Tampa Bay's most valuable players while Austin Wells has struggled as half of New York's catcher tandem.

Tampa Bay Rays: Signing Phil Maton

The Tyler Glasnow trade has actually worked out nicely for Tampa Bay.

Yes, Glasnow is shoving for the Dodgers, but Ryan Pepiot was pitching well before landing on the IL after taking a comebacker off his leg, and Jonny DeLuca was batting .300 as recently as Sunday morning. They can keep both of those guys through at least 2028, and they saved around $30 million in 2024 salary. Hard to complain about that one.

Making Maton the fifth-highest paid player on the roster, however, hasn't looked as wise. Through 21 appearances, he has a 5.09 ERA. To be fair, most of that came in one five-run implosion. Still, he has already blown two saves, matching his total from each of the previous two seasons in Houston.

Toronto Blue Jays: Whiffing on Shohei Ohtani

There are 29 teams who wish they had been able to sign the sensation who might be on his way to winning a triple crown this year, but Toronto is the one that almost pulled it off.

Without Ohtani, the Blue Jays offense has been abysmal, scoring fewer runs than every team except for the woebegone White Sox.

When Justin Turner had a nearly 1.000 OPS as the primary designated hitter 20 games into the season, that was at least a nice consolation prize for Toronto. In 21 games since then, though, he has a .424 OPS and almost as many GIDPs (4) as RBI (5).

American League Central

Chicago White Sox: Signing John Brebbia

For as bad as the team presently is, the White Sox had a solid offseason, getting quite the haul of prospects/controllable assets in the Dylan Cease, Aaron Bummer and Gregory Santos trades. And, for the most part, they didn't unnecessarily throw money at free agents in advance of what was always going to be a lost season.

They did give $4 million to Brebbia, though. Plus a $6 million mutual option with a $1.5 million buyout for next season. There are also incentives in the contract that would net him another million bucks if he makes 60 appearances this season—which he's roughly on pace to do, despite a 5.93 ERA.

That's just a bizarre investment in a 33-year-old reliever who isn't going to be part of their long-term plans.

Cleveland Guardians: Designating Cal Quantrill for assignment

Not many offseason moves to choose from here, as Cleveland had probably the most uneventful winter of any club.

There was a nice big head-scratcher, though, as the Guardians designated Quantrill for assignment with two years of team control remaining, traded him to Colorado for a low-level prospect (Kody Huff) and later replaced him in the rotation with a Carlos Carrasco reunion.

Quantrill has pitched (by Rockies standards) exceptionally well, while Carrasco has struggled to the tune of a 5.16 ERA.

(In Cleveland's defense, Carrasco wasn't Plan A. They signed him to a minor league deal and gave him a roster spot because of the elbow inflammation from which Gavin Williams is still recovering. Nevertheless, cutting Quantrill to save a few million dollars was befuddling.)

Detroit Tigers: Letting Spencer Turnbull go

There were some extenuating circumstances with this divorce, but the Tigers could have brought back Turnbull for next to nothing. He made $2.15 million in 2023 and ended up signing a one-year, $2 million deal with the Phillies after the Tigers non-tendered him.

In Philadelphia, the 31-year-old has flourished. He had a 1.53 ERA in his first 35.1 innings pitched and could be an intriguing trade chip if he continues pitching well in what is currently a middle-relief role.

Meanwhile, Detroit signed Kenta Maeda to a two-year, $24 million deal in free agency, and he had a 6.75 ERA in seven starts before hitting the IL with a viral illness.

Kansas City Royals: Spending $5 million on Will Smith

On the one hand, Smith pitched for each of the past three World Series champions. Getting that type of success into a clubhouse that languished through 106 losses last season was a reasonably sound idea.

On the other hand, he had a 4.40 ERA last season and pitched his way out of a closer gig, and the Royals offered him more than triple what he made in 2023 ($1.5 million) to serve as their closer.

It took all of six team games for him to lose the closer job again, though he has at least pitched much better over the past month, starting to work his way back into higher-leverage situations.

Minnesota Twins: Trading for Manuel Margot

Amid the Bally Sports/Diamond Group RSN chaos, Minnesota didn't really know what it could afford to spend this offseason. So, it didn't spend much of anything outside of taking a discounted flyer on Margot.

Of Margot's $10 million salary in 2024, the Dodgers are paying $4 million and the Rays are paying $2 million—as well as the $2 million buyout of his $12 million mutual option if it isn't exercised.

So, the Twins are only on the hook for $4 million here. Even at that price, though, they haven't even remotely gotten their money's worth, with Margot currently sporting a .513 OPS and the worst bWAR on the Minnesota roster.

American League West

Houston Astros: Not addressing the injured rotation

Houston knew long ago that it wouldn't have Luis Garcia or Lance McCullers Jr. until several months into the season, and found out during spring training that neither Justin Verlander nor Jose Urquidy would be ready for Opening Day.

Rather than make a last-minute move to do something about the depleted rotation, they just decided to let it ride with "sophomores" Hunter Brown and J.P. France, rookie Spencer Arrighetti and journeyman Ronel Blanco getting regular turns through the rotation.

The Astros trusted they could tread water with those arms until the other ones got healthier.

Aside from Blanco, though, they all struggled. And even his incredible start has been marred by a 10-game suspension for sticky stuff.

Los Angeles Angels: Signing Robert Stephenson

When the Angels gave Stephenson a three-year, $33 million contract in January, they had no way of knowing his arm was a ticking time bomb.

The 31-year-old missed spring training with shoulder soreness and faced just one batter during a rehab assignment before suffering a season-ending UCL injury. That Tommy John surgery in late April will likely keep him out for at least half of the 2025 campaign, too.

Even if Stephenson was healthy, though, the move never made much sense. The Halos already had an All-Star closer in Carlos Estévez and weren't good enough to justify spending eight figures per year on a setup guy.

That's a "final piece of a World Series contender" move, not a "we just lost Shohei Ohtani and will probably be terrible this season" move.

Oakland A's: Signing Alex Wood and trading for Ross Stripling

Speaking of moves that never made sense, what was the possible motivation behind Oakland spending $9.25 million for one year of 34-year-old Stripling and $8.5 million for one year of 33-year-old Wood?

Both middle-aged arms had an ERA north of 4.40 over the previous four seasons and were never going to be part of this club's long-term, rebuilding plans. Yet, the A's made them the two highest-paid players on the roster—only to watch both of them cobble together an ERA north of 5.00.

Seattle Mariners: Making Mitch Garver one of their highest-paid players

After trading away Jarred Kelenic and knowing that re-signing Teoscar Hernández wasn't in the budget, the Mariners had to do something to address their lack of corner outfielders and DH options.

So they gave Garver—who made $3.9 million in 2023 and who has struggled to stay healthy throughout his career—a two-year, $24 million contract to become their primary DH.

Thus far, he has remained healthy, but he has just a .607 OPS compared to a mark of .826 over the previous three seasons. He's not the only reason this offense has struggled, but Seattle definitely hasn't gotten what it paid for with Garver.

Texas Rangers: Signing another injured starter

In the long run, perhaps signing Tyler Mahle to a two-year, $22 million deal will end up being a great move for the Rangers.

However, when they signed him, they already knew he was recovering from Tommy John surgery and wouldn't be back until at least the second half of the season. They also already knew Jacob deGrom was in the same boat and Max Scherzer was headed for back surgery and likely out for the first half of the year.

They were basically banking on no other pitchers getting injured before the All-Star Break, at which point the rotation would start to become awesome.

However, that gamble aged poorly, with Nathan Eovaldi, Dane Dunning and Cory Bradford all on the IL, forcing the Rangers to sign Michael Lorenzen late in spring training while also letting both José Ureña and Jack Leiter make occasional spot starts.

National League East

Atlanta Braves: Letting Kirby Yates go

Yates missed most of 2020, all of 2021 and most of 2022 with an elbow injury, but he had an impressive comeback year in 2023, tossing 60.1 innings with a 3.28 ERA and 11.9 K/9 at the age of 36.

Atlanta had a club option on the 2019 All-Star and could have brought him back for $5.75 million, but instead paid a $1.25 million buyout to let him become a free agent. He signed with the Rangers for $4.5 million and has re-emerged as one of the best closers in the game, boasting a 0.98 ERA with three wins, seven saves and no blown saves.

Atlanta's bullpen has been mostly solid without Yates, but what stings is it traded away five guys and spent $5.5 million to replace Yates with Aaron Bummer, who hasn't pitched all that well.

Miami Marlins: Signing Tim Anderson

You could argue Miami's biggest offseason mistake was not trading away Jesús Luzardo when he might have been the most coveted starting pitcher on the block. But the Marlins should still be able to get great value for him this summer, if they decide to move him.

What they won't get any value for is Anderson, who has somehow been even worse than last year. He's currently on the IL with a back injury, and his .456 OPS ranks dead-last among the 234 players with at least 110 plate appearances in 2024.

Tough sledding for the seventh-highest paid player on the payroll.

New York Mets: Trading for Adrian Houser

Most of New York's offseason moves have panned out nicely. Both Luis Severino and Sean Manaea have sub-3.50 ERAs. J.D. Martinez is batting .315, and Harrison Bader has been respectable as the primary centerfielder.

However, trading for Houser (and Tyrone Taylor) certainly could have gone better.

Granted, they gave up next to nothing in the trade. It was a salary dump for the Brewers, who only asked for Coleman Crow in return—a minor league pitcher who will miss the entirety of 2024 while recovering from Tommy John surgery.

Nevertheless, Houser has a 7.44 ERA with more walks (23) than strikeouts (17) and has already pitched his way out of the starting rotation.

Philadelphia Phillies: Signing Whit Merrifield

Kind of hard to find fault in anything the Phillies did this offseason, given how well they have played through their first 48 games.

That $8 million pickup of Merrifield hasn't been what they hoped it would be, though.

His versatility on defense is nice, as the Phillies have used him at second base, third base and left field somewhat regularly. But the 35-year-old utilityman has lost his way at the plate, saddled with a .552 OPS compared to a .750 mark across his previous eight seasons.

Washington Nationals: Signing Joey Gallo

The Nationals made a bunch of intriguing, inexpensive one-year acquisitions this offseason, which will make for quite the trade deadline yard sale if they continue to play sub-.500 baseball.

Dylan Floro ($2.25 million) has allowed one run in 22.2 innings of work. Nick Senzel ($2 million), Eddie Rosario ($2 million) and Jesse Winker ($1.5 million) aren't hitting for average, but they've each clubbed at least five home runs and could be valuable additions to a contender's depth.

And then there's Gallo, making $5 million for a .129 batting average and a strikeout rate of darn near 50 percent. Maybe he heats up over the summer, but it's hard to imagine they'll be able to flip him for a prospect or two as they did with Jeimer Candelario last year.

National League Central

Chicago Cubs: Not adding another starting pitcher

Hard to argue with any of the moves the Cubs made this offseason. Shōta Imanaga has been a sensation. Hector Neris has pitched well enough to assume the closer role. Bringing back Cody Bellinger was clutch. And acquiring Michael Busch and Yency Almonte for a pair of single-A minor leaguers could go down as an all-time fleecing.

They probably should have signed one more starting pitcher, though, right?

They had no way of knowing that all of Justin Steele, Jameson Taillon, Jordan Wicks and Kyle Hendricks would spend time on the IL before the end of April, but it left them needing to spot start Ben Brown and Hayden Wesneski on occasion. They also used Luke Little as an opener at one point.

Cincinnati Reds: Signing Jeimer Candelario

When the Reds inked Candelario to a three-year, $45 million deal, it seemed like a wildly unnecessary move for a team that already had a surplus of infielders. But between losing Matt McLain possibly for the year (shoulder injury), Noelvi Marte for half the season (PEDs) and Christian Encarnacion-Strand for the foreseeable future (broken wrist), they ended up needing an infielder after all.

That said, for being the highest-paid player on the roster, Candelario hasn't come anywhere close to delivering on his salary. Baseball Reference puts his year-to-date value at below replacement level.

The Reds would have been better off simply not non-tendering Nick Senzel and spending that $45 million elsewhere.

Milwaukee Brewers: Trading away Corbin Burnes

The Brewers were stuck between a rock and a hard place with Burnes. They weren't going to be able to re-sign him before he hits free agency this coming winter, and it didn't seem like they had a roster capable of contending for a World Series.

Trading him away for a pair of players (DL Hall and Joey Ortiz) who won't hit free agency until after 2029 was an understandable decision.

But now they're surprisingly in first place in the NL Central and figure to be on the hunt for starting pitching at the trade deadline, in part because Hall (7.71 ERA in four starts before landing on the IL) wasn't ready to be a regular in the rotation.

Pittsburgh Pirates: Signing Aroldis Chapman

Pittsburgh signed six players to one-year deals with a price tag of $2.5 million or more, none of whom has particularly panned out.

At least most of them were reasonable investments/gambles.

Making Chapman the highest-salaried player on the roster at $10.5 million when they already had an established closer in David Bednar was mind-boggling.

And for their trouble, Chapman has given the Pirates by far the worst WHIP of his career (1.66), walking batters left and right.

St. Louis Cardinals: Trading away Tyler O'Neill

O'Neill is in his final season before hitting free agency, and the Cardinals had a logjam of what appeared to be serviceable outfielders. Trading him to Boston for a pair of pitching prospects made sense.

Unfortunately, while O'Neill has clubbed 11 home runs for the Red Sox, the quartet of Jordan Walker, Victor Scott II, Michael Siani and Dylan Carlson has been a disaster for St. Louis, combining for zero home runs in 247 trips to the plate.

This has contributed significantly to a Cardinals offense that ranks dead-last in the National League in total runs scored and a record six games below .500.

National League West

Arizona Diamondbacks: Neglecting the bullpen

After Kevin Ginkel turned in an incredible run through the postseason (11.2 IP, 0 R), the Diamondbacks evidently forgot that an unreliable bullpen is what almost caused them to miss the playoffs in the first place, opting not to add a single relief pitcher this offseason via trade or free agency.

That decision has not aged well, as Ginkel has come back to earth while closer Paul Sewald opened the season on the IL and is just now getting back into the swings of things in the ninth inning.

The Diamondbacks entered Monday tied for the MLB "lead" with 10 blown saves, which is equal to the number of save chances they've actually converted.

Colorado Rockies: Signing Dakota Hudson

Similar to the White Sox, the Rockies are a dumpster fire, even though they had a decent offseason.

They signed young star Ezequiel Tovar to a seven-year extension. The flyer they took on Cal Quantrill has panned out thus far. Same goes for signing Jacob Stallings to be their back-up catcher. And they didn't unnecessarily bury themselves under another big contract to a free agent. All good stuff.

The only minor complaint is that signing Hudson seems to have been a waste of $1.5 million. The former St. Louis Cardinal has a 5.89 ERA and entered Monday with more walks (27) and more losses (seven) than any other NL pitcher.

Los Angeles Dodgers: Trading away Michael Busch

Hard to argue with any of the five big acquisitions the Dodgers made. Shohei Ohtani, Yoshinobu Yamamoto, Tyler Glasnow, Teoscar Hernández and James Paxton have all played big roles in staking them to what is already starting to look like an insurmountable lead in the NL West.

How much do they regret trading away Busch, though?

They didn't really have any room for him on the big league roster with Freddie Freeman and Max Muncy locking down the corner infield spots and Ohtani cemented at DH. However, when he homered in five consecutive mid-April games for the Cubs, it sure looked like Los Angeles made a short-sighted move in shipping him out for a couple of low-level minor leaguers.

San Diego Padres: Letting Seth Lugo go

Lugo declined a $7.5 million player option for 2024 before signing a three-year, $45 million deal with Kansas City, so it's not like San Diego kicked him to the curb.

It could have made more of an effort to re-sign him, though.

While Lugo is putting up Cy Young-caliber numbers for the Royals (1.79 ERA, 0.98 WHIP through 10 starts), the back end of the Padres rotation has been rough. Matt Waldron is hit or miss. Same goes for Michael King—though at least when he's on, you can see why they were willing to give up Juan Soto to get him. Randy Vásquez has been mostly miss.

That constant question mark at the No. 4 and No. 5 spots in the rotation may well cost San Diego a spot in the postseason.

San Francisco Giants: Signing Blake Snell

There's time for Snell to turn things around, as he is expected to come off the IL to start Wednesday against the Pirates. And at 23-25, the Giants are only a game back in the "Dude. It's May. Why are you even looking at this already?" wild-card standings.

Through 30 percent of the season, though, the 31-year-old has made three starts for the Giants with an 11.57 ERA.

Not exactly what they had in mind when they gave the two-time Cy Young winner a two-year, $62 million deal.