Every MLB Team's Big Offseason Regret That's Being Exposed in 2019

As the 2019 Major League Baseball season nears its halfway mark, what teams did right during the previous offseason is coming into focus.

So is what they did wrong.

That's where our focus was as we sought to highlight the biggest regrets teams should have about how they approached the most recent hot-stove season. In some cases, those involved specific players who were or weren't added in trades or free agency. In other cases, they involved more general blunders.

We'll proceed in alphabetical order by city.

Stats accurate through Tuesday.

Record: 38-37, T-3rd in NL West

Coming into the year, the Arizona Diamondbacks' offseason losses—i.e., Paul Goldschmidt, Patrick Corbin and A.J. Pollock—loomed a lot larger than their offseason gains.

Yet Carson Kelly and Luke Weaver have thus far constituted the better end of the Goldschmidt trade. The D-backs have also scored with their low-risk signings of Greg Holland, Adam Jones and Merrill Kelly.

Perhaps the only thing to tsk-tsk the Snakes for is their relative inaction with their bullpen. It didn't get any new additions apart from Holland, and that's being exposed amid the regressions of Archie Bradley and Yoshihisa Hirano. Arizona's pen has just a 4.40 ERA and a pitifully low strikeout rate.

Of course, the Diamondbacks are in the National League wild-card race anyway. But with a better bullpen, they would probably be more in the race.

Record: 44-31, 1st in NL East

The Atlanta Braves are already in first place, and it won't be long before their signing of 2015 American League Cy Young Award winner Dallas Keuchel starts bearing fruit.

In the meantime, the Braves have already benefited from adding veteran sluggers Josh Donaldson and Brian McCann to their lineup. They're therefore in a position to have no regrets.

Save for not reuniting with old friend Craig Kimbrel. The Braves were often linked to the seven-time All-Star closer while he was still afloat on the free-agent waters, yet MLB.com's Mark Bowman speculated that they wouldn't pounce unless Kimbrel lowered his ask to a three-year deal.

Well, Kimbrel signed with the Chicago Cubs for a reasonable $43 million over three years. With that, the Braves missed out on a guy who might have been a boon for a shaky bullpen that's done more harm than good to their win probability.

Record: 21-53, 5th in AL East

After losing 115 games in 2018, the Baltimore Orioles never stood a chance of turning themselves back into a contender in a single offseason. They could merely take steps toward that goal.

To that end, it's looking like they should have traded Mychal Givens.

Though he was coming off a relatively disappointing 3.99 ERA, the 29-year-old right-hander still had considerable trade value during the offseason. He did boast a career 3.12 ERA and 10.4 strikeouts per nine innings, after all, and he had three years of club control remaining.

Yet the O's held on to Givens, and that decision is backfiring. In putting up a 5.28 ERA and allowing eight home runs in only 29 innings, he's transformed from a valuable trade chip into a mere change-of-scenery candidate.

Record: 41-35, 3rd in AL East

Not surprisingly, the Boston Red Sox mostly kept the band together after they won 108 games and the World Series in 2018.

They let Craig Kimbrel go, but they re-signed World Series MVP Steve Pearce and fellow World Series hero Nathan Eovaldi. The former got a one-year, $6.3 million deal. The latter, a four-year, $68 million whopper.

Nearly halfway through 2019, however, the Red Sox have gotten nary a thing from either player. Pearce's season has been wrecked by injuries and ineffectiveness. The injury bug has also bitten Eovaldi, who underwent elbow surgery after only four starts in April.

It's a credit to the Red Sox that they're in contention anyway. But in hindsight, they would have been better off saving some or all of the Pearce/Eovaldi money for Kimbrel or to make other upgrades to a bullpen with a blown save problem.

Record: 40-33, 1st in NL Central

The Cubs looked like a fit for Craig Kimbrel as soon as he entered free agency last fall. They finally got him earlier in June when he agreed to a three-year, $43 million contract.

Because he signed after the draft, the Cubs avoided having to surrender a draft pick for Kimbrel. They also probably saved a few million bucks by waiting him out.

Yet it's fair to wonder what the Cubs lost by waiting so long to add Kimbrel to the bullpen. Said pen has thus far struggled with a 4.20 ERA and a negative win probability. It's entirely reasonable to think that things wouldn't be so bad if Kimbrel had been involved from day one.

Likewise, it's entirely reasonable to presume that the Cubs would have the NL Central lead firmly in their hands.

Record: 35-37, 3rd in AL Central

The 195 losses that the Chicago White Sox accrued in 2017 and 2018 were collateral damage amid a rebuild that now looks to be nearly over. They've made the leap from bad to respectable.

Perhaps the White Sox would be outright good this season if they'd been a little more bold during the offseason.

According to Jon Paul Morosi of MLB.com, the White Sox had interest in both Bryce Harper and Manny Machado. Per Robert Murray of The Athletic, they were also linked to slugging catcher Yasmani Grandal. Still other big-name players were named with the South Siders here and there throughout the offseason.

Yet despite the constant rumors, the White Sox didn't add any big-name players. It's possible their interest in said players was overblown. It's also possible they simply whiffed and that their offseason was one big missed opportunity.

Record: 34-38, 4th in NL Central

Between Sonny Gray, Tanner Roark and Derek Dietrich, the Cincinnati Reds made some of the better additions of any team during the offseason. Their deal for Yasiel Puig, however, is a different story.

To be fair, the Reds also got Alex Wood, Matt Kemp and Kyle Farmer from the Los Angeles Dodgers in a December blockbuster. Yet Puig was the main draw and therefore primarily responsible for ensuring the Reds wouldn't miss the two prospects they sent away.

Alas, Puig has gone "thud" with a .682 OPS and zero wins above replacement. Farmer has also been a dud. Wood has yet to pitch this season because of a bad back. Kemp was released in early May.

Adding insult to injury is the fact that the two prospects who left Cincinnati—right-hander Josiah Gray and infielder Jeter Downs—are having strong seasons in the Dodgers system.

Record: 39-34, 2nd in AL Central

Because the Cleveland Indians are in contention for the AL's second wild-card spot, perhaps their biggest offseason regret should be over cutting their payroll.

Yet there have certainly been more negative developments than positive ones for the Indians this season. Notably, their pitching staff has been wrecked by health woes, and their offense has been a disaster.

A rebuild seems so inevitable right now that it's fair to second-guess if the Indians should have preemptively entered into one while they were shedding payroll. They definitely toyed with the idea, as two-time AL Cy Young Award winner Corey Kluber otherwise wouldn't have been available in trade talks.

Not trading him is looking like a misfire now. Kluber, 33, had oodles of value during the offseason, but it's all gone now after his early regression and broken arm. And given his age, his value may be gone for good.

Record: 39-34, 2nd in NL West

Though the 2018 Colorado Rockies won 91 games and made the playoffs, they were undone by an offense that simply didn't have enough depth.

DJ LeMahieu wasn't part of the problem, as he put up a solid .749 OPS and hit a career-best 15 home runs. Yet the Rockies let him go anyway, as they effectively chose to spend on Daniel Murphy instead.

Murphy has been better lately, yet the 34-year-old is thus far living up to Colorado's two-year, $24 million investment with a modest .777 OPS and five homers. For exactly the same deal, LeMahieu has given the New York Yankees an .814 OPS and eight homers. And that's sans help from Coors Field.

In hindsight, the Rockies might have spent their $24 million on LeMahieu. Even better, they might have simply splurged to keep him and add Murphy.

Record: 26-44, 4th in AL Central

There might not have been a more obvious offseason trade candidate than Nicholas Castellanos.

The Detroit Tigers began the offseason firmly entrenched in a rebuild, and Castellanos was ticketed for his final season under their control. He indeed wanted to be traded, and the career-best .854 OPS and 74 extra-base hits he'd racked up in 2018 figured to help the Tigers find a taker.

They never did, however. According to general manager Al Avila, that was because there was "no interest" on the trade market.

Regardless, whatever hope the Tigers had of selling high on Castellanos is gone now. His OPS has dropped to .764, and he's not even pretending like a contract extension might be headed his way. Amid these circumstances, the Tigers may have to practically give him away.

Record: 48-27, 1st in AL West

The Houston Astros boast one of the best records in MLB as well as one of the best run differentials at plus-100. Speaking generally, they're a well-oiled machine that's invulnerable even to nit-picking.

Still, they arguably should have re-signed Dallas Keuchel.

According to Ken Rosenthal of Fox Sports, the Astros made one- and two-year offers to the veteran left-hander. Keuchel turned those down, but he never escaped Houston's comfort zone en route to signing a one-year deal with the Braves.

Perhaps Keuchel was simply done with the Astros at that point, regardless of what they might have been offering. But in any case, the Houston starting rotation would be five strong if it had Keuchel right now.

Record: 25-49, 5th in AL Central

The Kansas City Royals never had a serious chance of contending in 2019, so they did the right thing by filling out their roster with low-risk additions over the offseason. Holding on to Whit Merrifield could have backfired, but his trade value is only trending upward.

Yet if there is one thing the Royals might have done differently, it's take the advice that former general manager Steve Phillips offered via MLB Network Radio in November: "Trade Salvador Perez."

The veteran catcher was fresh off a second straight season of 27 homers, and his contract had three reasonably priced seasons left on it. But as they did with Eric Hosmer, Mike Moustakas and Lorenzo Cain, the Royals sided with sentimentality and kept Perez, only to watch him undergo Tommy John surgery in March.

This wasn't necessarily an egregious miscalculation, but it does count as an "oops."

Record: 38-37, 4th in AL West

The Los Angeles Angels entered the offseason in need of starting pitchers and a closer. Their solution was to spend nearly $30 million worth of one-year contracts on Matt Harvey, Trevor Cahill and Cody Allen.

In the immortal words of Happy Gilmore: "Talk about your all-time backfires."

Harvey (back) and Cahill (elbow) are on the injured list. When they have been able to pitch, they've struggled mightily to the tune of a 7.32 ERA over 22 combined appearances. Allen, meanwhile, was designated for assignment Saturday after flopping with a 6.26 ERA over 25 appearances.

Even at the time, it was easy to wonder if the Angels should have put their money into one or two decidedly good pitchers rather than three risky ones. It's even easier to wonder that now.

Record: 50-25, 1st in NL West

The Dodgers are having an impressive season. What makes it look even more impressive is the fact that their biggest offseason move has also been their least fruitful one.

In the wake of the trade that sent Yasiel Puig and Matt Kemp to the Reds, the Dodgers' solution to their sudden outfielder shortage was to sign A.J. Pollock to a four-year, $55 million deal.

Pollock's injury history and post-prime production meant the Dodgers were taking on some risk with his deal. Sure enough, Pollock was a dud out of the gate before going under the knife to correct an issue relating to an elbow injury that initially sidelined him in 2016.

Pollock hasn't played since April 28. Meanwhile, the Dodgers outfield's MLB-best WAR is raising questions about how big a role he should play upon his return.

Record: 26-46, 5th in NL East

A trade of star catcher J.T. Realmuto was the Miami Marlins' top priority for the offseason. They got that done in February, and for a good return, to boot.

It's a shame the Marlins didn't do as well for relievers Kyle Barraclough, Drew Steckenrider and Adam Conley.

They had put a high price on each ahead of the 2018 trade deadline, yet they only got international bonus money for Barraclough in an October deal with the Washington Nationals. Steckenrider and Conley, meanwhile, stay put.

Their trade value has since evaporated. Steckenrider by way of a 6.28 ERA and an elbow injury. Conley simply by a 7.86 ERA over 30 appearances. Neither figures to be worth anything in a trade any time soon.

Record: 40-34, 2nd in NL Central

The Milwaukee Brewers went into the offseason on a high after winning 96 games and advancing to Game 7 of the National League Championship Series. Yet they clearly needed starting pitching.

They didn't get any. The Brewers instead left their starting pitching alone while they added elsewhere, notably by signing Yasmani Grandal and re-signing Mike Moustakas.

Those moves have worked out perfectly, as Grandal and Moustakas are on track to be named to next month's All-Star Game. If only the same could be said of Milwaukee's decision to leave good enough alone with its starting pitching. Brewers starters have gone from a solid 3.92 ERA in 2018 to an ugly 4.76 mark this year.

The Brewers are contending anyway, but they might be in first place if they'd addressed their starting pitching need.

Record: 48-25, 1st in AL Central

The Minnesota Twins have the best record and best run differential (plus-115) in the AL, yet they would look even better if they had Craig Kimbrel.

The Twins were often linked to the veteran closer throughout the offseason, and they "pushed hard" for him right up until he signed with the Cubs, according to Dan Hayes of The Athletic. Now that he's gone, they'll have to make do with other options in the ninth inning.

Right now, their defaults are lefty Taylor Rogers and righty Blake Parker. The former is nigh untouchable. The latter, on the other hand, has a 4.26 ERA and fewer strikeouts (20) than innings pitched (25.1).

In other words, Parker is no Kimbrel.

Record: 35-39, 4th in NL East

After enduring a second straight losing season in 2018, the New York Mets arguably needed to spend the offseason rebuilding. Instead, they did the opposite under agent-turned-GM Brodie Van Wagenen.

Through a series of trades and free-agent signings, the Mets brought aboard Robinson Cano, Edwin Diaz, Wilson Ramos, Jed Lowrie, Jeurys Familia, J.D. Davis and Keon Broxton. Combined with what they already had, the Mets seemed to have enough firepower to lead the way back to contention.

That hasn't happened in large part because the offseason haul has been a near total flop. And the worst may still be yet to come, as all of the new additions (save Broxton, who was traded) are due to stick around beyond 2019.

Entering a full-on rebuild may be the only way out of this mess. The irony is that the Mets may be staring at a longer rebuild now than they were at the outset of the offseason.

Record: 46-27, 1st in AL East

As of the start of spring training, the Yankees seemed to have it all. But then the injury bug put a hex on their roster, starting with a bout of shoulder inflammation for staff ace Luis Severino.

Pretty much as soon as Severino went down, speculation began that the Yankees would bring in Dallas Keuchel as a ringer. That speculation continued right up until early June, and the Yankees even offered the southpaw a prorated deal worth $11-12 million, according to MLB Network's Jon Heyman.

That obviously wasn't good enough, as Keuchel signed with the Braves for $13 million.

For now, the Yankees can take solace in the fact that they're in first place anyway. The Tampa Bay Rays and Red Sox are chasing them, however. And with a 4.98 ERA in June, Yankees starters aren't exactly holding the line.

Record: 39-36, 3rd in AL West

It's to the Oakland Athletics' credit that they didn't rest on their laurels after winning 97 games in 2018, yet they made a curious move when they signed Joakim Soria to a two-year, $15 million deal.

Soria was solid overall last season, but he was fresh off a weak turn with the Brewers in the stretch run. If nothing else, it was a reminder that the 35-year-old's prime was squarely in his past.

What's more, the A's didn't need Soria. Whereas their bullpen was one of baseball's best in 2018, their rotation was lucky to escape with even a 4.17 ERA. Evidently, that was where the A's needed to focus their offseason efforts.

Fast-forward to now, and Soria has disappointed with a 5.35 ERA. The $15 million would have been better spent on a rotation that's barely improved in going from a 4.17 ERA to a 4.09 ERA.

Record: 39-34, 2nd in NL East

It was a given that the Philadelphia Phillies would sign either Bryce Harper or Manny Machado this offseason. The only real question was which one it would be.

Per Todd Zolecki of MLB.com, the Phillies may have preferred Machado early in the offseason. He would have filled a major need at third base. Beyond that, he was simply a better overall player than Harper.

But Machado went to the San Diego Padres for $300 million, and the Phillies landed Harper for $330 million. Neither player has gotten off to an especially good start with his new club, yet the trend of Machado (1.9 WAR) being better than Harper (0.5 WAR) is nonetheless holding true.

The Phillies may yet get their money's worth out of Harper throughout the 13-year life of his deal. For now, though, they have every reason to be feeling buyer's remorse.

Record: 33-40, 5th in NL Central

Even though they were only a fringe contender, the Pittsburgh Pirates went for glory with blockbuster deals for Chris Archer and Keone Kela at last year's trade deadline.

After that didn't lead to a postseason berth, the next logical step should have been to double-down and make more trades and/or spend on free agents. Certainly, the Pirates should have taken this step as the rest of the NL Central grew stronger around them in the offseason.

They never did. Jung Ho Kang's $3 million deal marked Pittsburgh's biggest free-agent signing of the offseason, and Erik Gonzalez was the team's biggest trade acquisition.

The Pirates' quiet offseason begat a razor-thin margin for error in 2019. Lo and behold, they've crashed and burned so badly that it's only fair to question whether a rebuild should be their next step.

Record: 38-37, T-3rd in NL West

Well before the Padres signed Manny Machado to play third base and promoted Fernando Tatis Jr. to play shortstop, they actually had a dire need for infielders around first baseman Eric Hosmer.

Hence their signing of Ian Kinsler in December. But while he filled an obvious hole at second base for only $8 million, it was odd that the Padres wanted him on a two-year deal.

This was, after all, a 36-year-old coming off the worst season of his career. There was also a question of whether the Padres really wanted him standing in the way of top prospect Luis Urias, who figured to slot in next to Tatis at shortstop sooner rather than later.

Several months later, the signing of Kinsler isn't looking any better. He hasn't recovered from last year's fall from grace. Meanwhile, Urias is stuck hitting .332/.422/.654 for Triple-A El Paso.

Record: 31-41, 5th in NL West

Yeah, that's right. Nothing.

Indeed, "nothing" is pretty much what the San Francisco Giants did during the offseason. There was some buzz about their signing Bryce Harper, but it obviously didn't lead to anything. There was also buzz about their trading away core veterans, but they kept all of them.

Frankly, the Harper overtures never made sense in light of the 187 losses the Giants racked up in 2017 and 2018. As for the trade rumors, the Giants really only could have sold high on lefty reliever Will Smith.

Several months into 2019, Smith is having an even better season than he did in 2018. Likewise, Madison Bumgarner, Jeff Samardzija, Tony Watson, Brandon Belt and Pablo Sandoval have either maintained or improved their trade value. Assuming the Giants can cash in, their quiet offseason will have paid off.

Record: 32-46, 5th in AL West

The Seattle Mariners spent the offseason transforming their roster into a weird collection of old (Jay Bruce and Edwin Encarnacion) and young (Domingo Santana and J.P. Crawford) reclamation projects.

This initially seemed like a stroke of genius, as the Mariners jetted out to 13-2 start. But they're just 18-45 since then, and recent trades of Bruce and Encarnacion marked their transition into trade deadline sellers.

The bright side amid all this is that the farm system has sneakily become one of the five best in all of baseball. It should only get better as they cash in more trade chips.

Yet the big question is where it would be right now if GM Jerry Dipoto had simply committed to a rebuild rather than try to have it both ways in the offseason. If he had, the Mariners might already have baseball's No. 1 farm system and an accordingly bright future.

Record: 38-35, 3rd in NL Central

After winning 88 games in 2018, the St. Louis Cardinals put themselves in position to win more in 2019 by adding Paul Goldschmidt, Andrew Miller and Matt Wieters.

But those hypothetical wins would only come if their starting rotation held together. Rather than safeguard against that, the Cardinals opted to trust that Carlos Martinez, Adam Wainwright and Michael Wacha would be more durable and effective than they had been in 2018.

None of them has been, and Miles Mikolas' regression from last season's ace-like form has only increased the hardship of the club's rotation. It has a 4.36 ERA, and it's almost certainly performed even worse than that.

Had the Cardinals brought in at least one reliable pitcher (e.g., Dallas Keuchel), they might not be looking up at the Brewers and Cubs right now.

Record: 43-31, 2nd in AL East

It's apparent Edwin Encarnacion was on the Rays' radar for a good long while.

The Rays were involved in the three-team deal that sent him from the Indians to the Mariners in December. According to Jon Paul Morosi, they then promptly wanted Encarnacion for themselves.

Per Joel Sherman of the New York Post, the Rays were still chasing after the veteran slugger when he was traded Saturday. But they either couldn't or didn't want to pay down as much of Encarnacion's salary as the Yankees were willing to, so to the Bronx he went.

With that, the Rays finally missed out on the AL's leading home run hitter. If they had only acted sooner, they could have taken on opponents with a more powerful offense in addition to their extraordinary run prevention. That might have put the AL East lead firmly in their grip.

Record: 39-35, 2nd in AL West

The Texas Rangers are arguably the biggest surprise of the season. And this is despite how they handled their starting rotation in the offseason.

To be fair, signing Lance Lynn to a three-year, $30 million contract has paid dividends. He's pitched better than his 4.16 ERA indicates, and he's eaten nearly as many innings (93.0) as staff ace Mike Minor (95.2).

Drew Smyly, Shelby Miller and Edinson Volquez were supposed to fill out the rest of the rotation. All three were several years removed from being relevant and recovering from Tommy John surgery, to boot. Not surprisingly, all three have flopped.

With better pitchers around Minor and Lynn, the Rangers rotation would surely be doing better than a 5.05 ERA. As a result, the team might be AL West contenders rather than simply AL wild-card contenders.

Record: 26-48, 4th in AL East

The Toronto Blue Jays didn't have much to do in the offseason besides make low-risk additions and potentially trade some veterans. To the latter end, their decision to hold on to Marcus Stroman for a potential sell-high situation at the deadline is working perfectly.

As such, it's time to transition into nit-pick mode and ask: What was with the Randal Grichuk extension?

Grichuk was coming off a solid .803 OPS and 25 homers when he signed his five-year, $52 million deal. But that was over just 124 games, and his career has been mostly defined by injuries and long stretches of ineffectiveness.

If the Blue Jays simply wanted to show their fans a sign of good faith, well, that's admirable. But with Grichuk now struggling with a .690 OPS and 0.2 WAR, they might like to have that one back.

Record: 34-38, 3rd in NL East

Once they officially lost Bryce Harper to the Phillies, the Nationals turned their attention to making sure they wouldn't also lose Anthony Rendon the next offseason.

According to Todd Dybas of NBC Sports Washington, the Nationals approached Rendon with an extension offer shortly after the Rockies extended fellow third baseman Nolan Arenado for $260 million. But Washington's offer wasn't good enough for Rendon, who turned it down.

Rendon effectively chose to bet on himself in doing so. To say he's winning that bet would be an understatement. Albeit in just 57 games, his walk year thus far features a career-best 1.075 OPS.

Exactly what it would have taken to get Rendon to sign in February is unknown. Yet it was almost certainly less than what it'll require to sign him as a free agent this offseason.

Stats courtesy of Baseball Reference and FanGraphs.