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Each MLB Team's Big Offseason Regret Being Exposed So Far

Zachary D. RymerJun 6, 2021

Now that June is here, it's a little late to say "It's still early..." about anything happening in the 2021 Major League Baseball season. Teams have an idea of what is and isn't working.

Regarding the latter, every team has at least one offseason decision that's backfiring on them now.

So, we picked out one winter maneuver for which each team might like a do-over if given the chance. These mostly cover deals that were or weren't made, though there's also one controversial hiring decision that sticks out like a proverbial sore thumb.

We'll go division by division, starting in the American League East and ending in the National League West.

American League East

1 of 6
DJ LeMahieu
DJ LeMahieu

Baltimore Orioles: Fruitless Minor League Deals

The Orioles went into the 2020-21 offseason looking to advance their rebuild, and they did so by cashing in shortstop Jose Iglesias and right-hander Alex Cobb on the trade market. Otherwise, the only practical expectation anyone could have had for the team was that it would dig up some diamonds in the rough.

The O's tried to do this by signing eight players to minor league deals, but not one of those is panning out. Only hurlers Matt Harvey and Wade LeBlanc have actually played for Baltimore, and they have a 6.94 ERA between them. Meanwhile, other teams have had better luck (see here and here) with MiLB deals.

Boston Red Sox: The Andrew Benintendi-Franchy Cordero Trade

The Red Sox have beaten expectations so far in 2021, and that's partially thanks to some of the low-risk maneuvers they made during the winter. For instance, starter Garrett Richards, reliever Adam Ottavino and outfielders Hunter Renfroe and Enrique Hernandez have all done their bit.

However, the trade that sent Andrew Benintendi to the Kansas City Royals in February hasn't worked out for Boston. He's hitting a solid .295, whereas Franchy Cordero hit just .179 before he was optioned. It thus could be up to minor league righty Josh Winckowski to dignify the deal in the long run.

New York Yankees: Putting It All on DJ LeMahieu

Instead of going all-out on upgrades from outside the organization, the Yankees' big move over the winter was to re-sign reigning batting champion DJ LeMahieu to a six-year, $90 million pact. That's too many years for a 32-year-old, but the length helped lower his average annual value for luxury-tax purposes.

Yet even despite that, the Yankees still carried out the rest of their offseason shopping in the bargain bin and even traded Ottavino to Boston for tax reasons. That frugality has been a factor in their slow start to 2021, and LeMahieu isn't picking up the slack by hitting just .259 with nine extra-base hits.

Tampa Bay Rays: The Nate Lowe Trade

At 37-23, the Rays have the best record in the American League. While that's not entirely because their offseason additions are paying huge dividends, they're at least getting good stuff out of catcher Mike Zunino and veteran left-hander Rich Hill.

But if there's a nit to pick here, it's that the Rays didn't have to trade first baseman Nate Lowe to the Texas Rangers in December. And it now looks like they shouldn't have, as he has a solid .729 OPS while the Rays are getting just a .703 OPS out of their first basemen.

Toronto Blue Jays: Letting Taijuan Walker Get Away

The Blue Jays were one of the more active teams on last winter's free-agent market, ultimately dishing out nearly $190 million worth of contracts to center fielder George Springer, infielder Marcus Semien, and pitchers Robbie Ray, Kirby Yates, Tyler Chatwood and David Phelps.

Yet we can't help but wonder how Taijuan Walker wasn't caught in Toronto's spending net. He might have re-signed if the team had so much as matched the two-year, $20 million offer he accepted from the New York Mets. If so, the 2.17 ERA he has right now would have been a major boost for Toronto's thin rotation.

American League Central

2 of 6
Tony La Russa
Tony La Russa

Chicago White Sox: Hiring Tony La Russa

Immediately following the end of their 2020 season, the White Sox courted controversy by firing Rick Renteria even though he had led the team to the playoffs. They then attracted even more controversy with a reportedly ownership-driven decision to hire Tony La Russa, who had last managed in 2011.

Granted, La Russa hasn't kept the White Sox from rising to first place. The team has nonetheless underachieved under his watch, and he's found himself in the spotlight for all the wrong reasons. It's doubtful that he'll be fired, but he clearly never should have been hired.

Cleveland: Non-Tendering Tyler Naquin

Though Cleveland isn't quite on Chicago's level, it's keeping things close even though its offseason was marked by a payroll crunch that resulted in the departures of shortstop Francisco Lindor, first baseman Carlos Santana and pitchers Carlos Carrasco and Brad Hand. 

But if it could go back, Cleveland probably wouldn't non-tender outfielder Tyler Naquin in lieu of paying him a modest $2 million salary. The 11 home runs he has for the Cincinnati Reds this year would have been a boon to a Cleveland outfield that has only 20 homers as a whole.

Detroit Tigers: A General Lack of Creativity

There was likely never any scenario in which the Tigers could have "won" the 2020-21 offseason, so it's perhaps forgivable that they didn't even try. If anything, it was a welcome sight that they spent so much as $25.4 million on free agents.

Still, the Tigers might have attempted to jump-start their rebuild by making some trades, scooping up some undervalued players on minor league deals or by extending in-house players. But they did nothing of the sort, and that's at least one contributing factor to the club's ongoing futility.

Kansas City Royals: Hunter Dozier's Contract Extension

Like the Tigers, the Royals entered last winter with their eyes more so on the long-term future than on 2021. Unlike the Tigers, however, they not only signed free agents (e.g., Santana) but also made trades (e.g., Benintendi) and even did extensions for catcher Salvador Perez and third baseman Hunter Dozier.

But even if it was only for $25 million over four years, Dozier's deal was puzzling at the time because he was already 29 and coming off a mediocre 2020 season. With minus-1.4 rWAR to his name, he's now one of MLB's worst everyday players in 2021.

Minnesota Twins: Not Closing on Charlie Morton

There isn't a singular explanation for why the Twins have sunk to last place in the AL Central after winning the division in 2019 and 2020. It's a combination of injuries, disappointing performances and even a little bad luck to boot.

Yet it's also hard to forget that the Twins nearly signed starter Charlie Morton before he took a one-year, $15 million offer from Atlanta. The Twins ultimately pivoted to a $10 million gamble on J.A. Happ and Matt Shoemaker, who both have ERAs well north of 5.00 while Morton has fared much better with a 4.21 ERA.

American League West

3 of 6
Elvis Andrus
Elvis Andrus

Houston Astros: Not Making a Splash on a Reliever

Once George Springer left as a free agent, the Astros arguably should have been more proactive about filling his shoes in center field. They instead handed the position to Myles Straw, who's barely been a replacement-level performer thus far in 2021.

However, Houston's offense has been just fine in spite of Shaw. Particularly given that standouts like Liam Hendriks and Brad Hand were on the club's radar, it's harder to forgive the lack of major additions to a bullpen that's at the bottom of the AL in win probability added

Los Angeles Angels: Not Going Bigger with Rotation Upgrades

Mike Trout's calf injury obviously isn't helping, but the general story of the Angels' latest disappointing season is a familiar one: enough hitting, not nearly enough pitching. Specifically, the club's rotation has had major issues in the process of racking up a 5.11 ERA.

Those issues might have been avoided if the Angels had been more aggressive in chasing, say, Trevor Bauer in free agency or Joe Musgrove, Yu Darvish or Lance Lynn on the trade market. They instead went for quantity over quality by adding Alex Cobb and Jose Quintana, who've combined for a 5.59 ERA.

Oakland Athletics: Believing Elvis Andrus Was a Shortstop Solution

The Athletics endured some significant losses to free agency over the winter, including Hendriks from their bullpen and Marcus Semien from their lineup. But whereas the pen has been chugging along just fine without the former, the club's lineup is sorely missing the latter.

With Semien gone, Oakland's solution was to acquire veteran Elvis Andrus in a bad-contract swap with the Rangers. The A's were surely hoping that the 32-year-old had something left in the tank, but that hasn't been the case as he's managed just a .516 OPS and minus-0.7 rWAR.

Seattle Mariners: Neglecting Their Offense

Because they're only two games below .500, this season might look like another step forward for the Mariners after they had a better-than-expected campaign in 2020. But in the context of their minus-58 run differential, they're almost certainly playing above their heads.

It's no big secret that the Mariners are specifically having trouble on offense. They've already been no-hit twice and they're batting an MLB-low .206 as a team. So in retrospect, it's hard not to wonder if they should have added at least one hitter as they otherwise focused their offseason shopping on the mound.

Texas Rangers: Rolling the Dice on David Dahl

Because they finished in last place in 2020, it shouldn't be a big surprise that the Rangers are once again in last place this season. It nonetheless feels like a waste after the team made all sorts of moves throughout the winter.

None of those have been outrageously disappointing, yet the signing of David Dahl comes the closest. He may have only cost $2.7 million, but he was coming off a minus-1.0 rWAR season. Rather than revert to his All-Star form of 2019, he's stayed below replacement-level with minus-0.7 rWAR in 2021.

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National League East

4 of 6
Francisco Lindor
Francisco Lindor

Atlanta: Bringing Back Marcell Ozuna

In the wake of three straight NL East titles, Atlanta has been a major letdown as it's racked up a 27-29 record. It hasn't helped that some of the club's offseason moves have backfired, up to and especially including the re-signing Marcell Ozuna to a four-year, $64 million deal.

Atlanta was banking on Ozuna replicating his superb 2020 season even though it was a clear outlier. Sure enough, he had just a .645 OPS before breaking two fingers. Following his arrest on assault and battery charges, there's now a question of when or even if he'll suit up for Atlanta again even if the team can't void his deal.

Miami Marlins: Not Landing Willson Contreras

After snapping a 17-year playoff drought in 2020, the Marlins have seemingly come back to earth with a 24-33 record in 2021. But they've only allowed five more runs than they've scored, so there is something to the notion that they ought to be just a game under .500.

Not bad for a team that, per its minus-0.8 rWAR at the position, has the worst catching in the National League. That could have the Marlins kicking themselves for not going harder after Chicago Cubs backstop Willson Contreras, who was indeed on the club's radar at one point.

New York Mets: Going All-In on Francisco Lindor

The Mets were perhaps the most active team on the 2020-21 market, and now they're in first place even despite their myriad injuries. Any team in that position doesn't have a whole lot to complain about.

Still, new owner Steve Cohen can't be thrilled about the early returns of the big Lindor/Carlos Carrasco trade with Cleveland in January. Carrasco has yet to take the hill because of a torn hamstring, while Lindor has just a .659 OPS and five homers. What's more, the latter's $341 million deal doesn't even start until next year.

Philadelphia Phillies: Going for Quantity Over Quality in the Bullpen

Of all the reasons the Phillies finished under .500 in 2020, none was as obvious or as demoralizing as the team's bullpen. It finished the year with a 7.06 ERA and easily the worst win probability added in the majors.

In fairness, the Phillies did spring into action and add guys like right-hander Sam Coonrod and left-hander Jose Alvarado over the winter. Yet they did so in lieu of much bigger possible upgrades—including Liam Hendriks and Brad Hand—so they can't claim to be blindsided by the ongoing issues their bullpen is having in 2021.

Washington Nationals: Skimping on Rotation Depth

After winning the World Series in 2019, the Nationals took an immediate step back with a 24-36 showing in 2020. One of their bigger problems was a rotation that got only two starts out of Stephen Strasburg in the process of finishing with a 5.38 ERA.

But over the winter, the Nats limited their rotation additions to a post-prime Jon Lester. He's been OK, but not nearly good enough to account for Strasburg's continuing injury issues and the struggles of Patrick Corbin and Joe Ross. All told, Nats starters not named Max Scherzer have a 5.01 ERA.

National League Central

5 of 6
Eugenio Suarez
Eugenio Suarez

Chicago Cubs: If Only They Had Yu Darvish Right Now

Back in April, the Cubs were a losing team that was seemingly on its way to a trade-deadline sell-off that would see Kris Bryant and Javier Baez leave town after franchise mainstays like Jon Lester, Kyle Schwarber and front-office leader Theo Epstein had done so over the winter.

Well, now they're a red-hot team that's more so in a position to buy at the deadline. And since their rotation is one area they may look to upgrade, they might be feeling sheepish about trading ace righty Yu Darvish in December. They didn't need to do that, and they'd be even better off now if they hadn't.

Cincinnati Reds: An Actual Shortstop Would Have Been Nice

As they've gotten just a 4.38 ERA out of their starters, the Reds are surely wishing they still had Trevor Bauer atop their rotation. But since bringing him back was never a realistic possibility, it's hard to hold his departure against the Reds.

Yet the Reds could have and indeed wanted to upgrade at shortstop. They just never did, ultimately forcing them to try out an experiment with Eugenio Suarez at short. He's now back at third base while shortstop has produced a minus-0.7 rWAR, so it's fair to say that Cincinnati's inaction at short has backfired.

Milwaukee Brewers: Missing Out on Justin Turner and Marcus Semien

With aces Brandon Woodruff and Corbin Burnes at the forefront, the Brewers have one heck of a pitching staff. They're only three games over .500, however, because they just can't hit. Per their 83 OPS+, they have the second-worst offense in all of MLB.

If only the Brewers had been able to land Semien or Turner. Both players (see here and here) were in consideration for Milwaukee before signing with Toronto and the Los Angeles Dodgers, respectively. Alas, the Brewers can only watch from afar as both are now having terrific seasons.

Pittsburgh Pirates: No Buried Treasure Among Their MiLB Deals

Compared to a relatively restrained 2019-20 offseason, the Pirates dove headlong into a rebuild this past winter. They notably traded Joe Musgrove, Josh Bell and Jameson Taillon, and it's as hard to criticize those deals now as it was at the time they were made.

But like the Orioles and Tigers, the Pirates have failed to find any hidden gems with their minor league signings. Of the eight they made, the only one who has been even remotely rewarding is the resurrection of Chasen Shreve as a left-handed specialist out of the bullpen.

St. Louis Cardinals: Skimping on Pitching Depth

The Cardinals initially laid low as the 2020-21 offseason unfolded but then sprang to action in late January and early February. They re-signed longtime battery mates Yadier Molina and Adam Wainwright and, even better, landed superstar third baseman Nolan Arenado from the Rockies.

But apart from the Wainwright deal, the Cardinals did little to shore up a pitching staff that clearly needed more depth. They're paying the price for that now, as said staff has a modest 4.20 ERA and is headed for trying times with Jack Flaherty now on the injured list with a strained oblique.

National League West

6 of 6
Trevor Story
Trevor Story

Arizona Diamondbacks: Maybe They Should Have Blown It Up

While they were on their way to a 25-35 record in 2020, the Diamondbacks paused to trade center fielder Starling Marte and pitchers Robbie Ray and Archie Bradley ahead of the August 31 deadline. After that, further trades might have followed as the team plunged deeper into a rebuild over the winter.

Instead, Arizona did...well, really not a whole lot. If the idea was to bank on a bounce-back season led by incumbents, that isn't happening as the team has sunk to last place once again. What's more, trade chips like outfielders Kole Calhoun and David Peralta haven't exactly appreciated in value.

Colorado Rockies: Not Trading Trevor Story

While the D-backs effectively stood pat throughout the 2020-21 offseason, the Rockies more or less did the same right up until they dealt Nolan Arenado to the Cardinals. That one move annihilated the club's already slim playoff hopes, so further rebuilding measures figured to follow.

Yet against all logic, the Rockies opted to hold on to star shortstop Trevor Story. Since he was a valuable chip on the cusp of free agency, that never did make much sense. And because he was mired in a down year even before he developed elbow inflammation, it looks even more boneheaded now.

Los Angeles Dodgers: Going Low-Risk with Pen Additions

After winning their first World Series title in three decades, the Dodgers kept the pedal to the medal by inking Trevor Bauer and re-signing Justin Turner. And while they're only in third place right now, it's hard to call them a bust while they're also 10 games over .500 with a plus-85 run differential.

Part of the reason the Dodgers are playing under expectations, however, is because their bullpen has been just OK at boosting the team's win probability. In a somewhat related story, the Dodgers merely made low-risk additions to said pen rather than follow through on their interest in big fish like Liam Hendriks.

San Diego Padres: Maybe They Would Take Back the Ha-Seong Kim Deal

By way of a series of headline moves that included trades for Joe Musgrove, Yu Darvish and Blake Snell, the Padres arguably won the 2020-21 offseason. And not one of those three big deals has truly come back to bite the Padres amid their 36-24 start. Snell has a 4.83 ERA, sure, but he's only made two bad starts.

Rather, it's the four-year, $28 million deal they did with Korean star Ha-Seong Kim that the Padres might like to have back. The Padres didn't have an obvious role for him even before they re-signed utility man Jurickson Profar. Fast-forward to now, and Kim is hitting just .200 in a not-quite-everyday role.

San Francisco Giants: Skimping on Bullpen Depth

First place in the NL West was supposed to belong to the Dodgers or Padres, but the Giants have held it for 27 days this season. Of the many explanations for this surprise, some notable ones include their offseason deals with pitchers Kevin Gausman, Anthony DeSclafani and Alex Wood.

However, the Giants haven't really scored on any of the low-risk additions (e.g., Jake McGee) that they made to their bullpen. That's been a factor in driving their win probability added into the red, so this is yet another situation where a deal with a brand-name reliever (e.g., Hendriks) would have helped.

Chapman's Game-Saving Play 😱

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