Predicting Each MLB Team's Most Crushing Offseason Regret
Even the most successful MLB offseason rarely goes off without a hitch.
The Houston Astros probably don't win the World Series last year if they don't roll the dice on signing Charlie Morton. The Josh Reddick signing also looks like a great move a year later.
The Brian McCann trade is another story.
While the veteran backstop had a solid season, he cost the Astros two pitching prospects—Albert Abreu and Jorge Guzman—who now rank among Baseball America's Top 100 prospects.
There will always be regrets in hindsight.
With that in mind, we've predicted each team's biggest regret of this offseason.
AL East
1 of 6
Baltimore Orioles: Not trading Manny Machado
The Orioles are not going to contend in 2018, and by the time they're willing to accept that fact, Machado is going to be a two-month rental with an obvious ceiling on his trade value.
If they had accepted their fate and shopped him right when the offseason began, teams could have adjusted their offseason plans accordingly and the O's would have been able to maximize the value of their star free-agent-to-be.
Boston Red Sox: Playing hardball with J.D. Martinez
There's still a very good chance Martinez winds up in Boston.
However, the Red Sox's unwillingness to move from their initial five-year offer—which is for somewhere between $100 million and $125 million but closer to the former, per Alex Speier of the Boston Globe—had resulted in a standstill.
If the two sides remain in a stalemate until after the season starts, Martinez could find himself playing catch-up as opposed to building off a career year.
New York Yankees: Failing to sign an insurance policy on the infield
Prospects Gleyber Torres and Miguel Andujar are the best in-house candidates to fill the vacancies at second and third base.
However, there are inevitable growing pains when it comes to first-year players, and assuming their transition will be a smooth one is asking a lot.
With guys like Ronald Torreyes, Danny Espinosa, Tyler Wade and Jace Peterson as the top alternatives on the roster, signing a versatile veteran like Eduardo Nunez would be a great fit.
There's been no indication something like that is in the team's plans, though.
Tampa Bay Rays: Not trading Alex Colome
On the surface, Colome had a terrific 2017 season en route to leading the AL with 47 saves.
However, his ERA (1.91 to 3.24), WHIP (1.02 to 1.20), H/9 (6.8 to 7.7), BB/9 (2.4 to 3.1), K/9 (11.3 to 7.8) and opponents' batting average (.206 to .232) all moved in the wrong direction.
The Rays will regret not selling high.
Toronto Blue Jays: Trading Dominic Leone
Assuming Roberto Osuna rebounds from a rocky season that included 10 blown saves, the Blue Jays will still need someone in the setup role.
Leone—who was traded to St. Louis in the Randal Grichuk deal—was quietly terrific last season with a 2.56 ERA, 1.05 WHIP and 10.4 K/9, as well as 11 holds in 65 appearances.
When the bullpen is shaky and Grichuk fails to break out with the change of scenery, the Blue Jays will be rethinking that move.
AL Central
2 of 6
Chicago White Sox: Not signing another veteran starting pitcher
As it stands, the White Sox will open the season with Reynaldo Lopez, Lucas Giolito and Carson Fulmer rounding out the starting rotation behind Miguel Gonzalez and James Shields.
All three of those young pitchers have a chance to be significant pieces of the long-term puzzle on the South Side, but they need to be careful not to overextend them in what will be a rebuilding year.
The Atlanta Braves had the right idea last offseason when they added R.A. Dickey, Bartolo Colon and Jaime Garcia, despite having a number of young arms who could have filled rotation spots.
Cleveland Indians: Signing Yonder Alonso
Why not Logan Morrison? Heck, even Lucas Duda might have been a better option.
While the overall numbers looked good for Alonso last season, it's hard to ignore his second-half swoon as he hit just .254/.354/.420 with eight home runs after the All-Star break.
His on-base skills are likely what attracted the Indians as they tried to replace on-base machine Carlos Santana, but they might be disappointed to find out his first-half explosion last year was a fluke.
Detroit Tigers: Not selling high on Shane Greene
There are not many movable parts left on the Tigers roster, but reliever Shane Greene is one player they should have shopped more aggressively.
The former starter settled in nicely to a full-time bullpen role, posting a 2.66 ERA with nine saves and 14 holds in 71 appearances.
However, a 3.84 FIP and a 4.5 walk rate are good indications he was pitching over his head, and the Tigers should have made every effort to market his three remaining years of control and sell high.
Kansas City Royals: Not shopping Whit Merrifield
What does a rebuilding team do with a 29-year-old late-bloomer who posts a 3.9 WAR in his first full season in the majors?
Trade him! Trade him yesterday!
Merrifield is a great story and a fan favorite, but he's not going to be part of the next contending Royals team given his age and his value will never be higher.
Minnesota Twins: Not going all-in on Yu Darvish
The Twins were in the mix for Darvish all offseason, and they made it no secret he was their No. 1 priority.
In the end, he ended up signing with the Cubs.
On their end, the Twins needed to realize they couldn't just match the offers that other teams were making; they needed to blow them away to convince the top pitcher on the market to spurn proven contenders to come to Minneapolis.
In the end, they didn't go all-in, and now they're left to settle for Plan B or Plan C.
AL West
3 of 6
Houston Astros: Trusting Ken Giles with the closer's role
The Astros added Joe Smith and Hector Rondon to the relief corps and also have Brad Peacock and Collin McHugh pitching in relief thanks to their abundance of starting pitching options.
However, they're still entrusting Giles with the closer job.
The 27-year-old is a strikeout machine and he had a terrific regular season. But manager A.J. Hinch completely lost faith in him during the playoffs, and there's no telling how he responds.
For a team with legitimate hopes of repeating, upgrading in the ninth inning might have been wise.
Los Angeles Angels: Not acquiring a proven closer
The Angels figure to be one of the most improved teams in baseball with a full season of Justin Upton, the additions of Zack Cozart and Ian Kinsler and a starting rotation that is finally healthy.
But who's going to close games?
Blake Parker, Cam Bedrosian and Keynan Middleton are currently penciled into the closer and setup roles on Roster Resource. That trio has a combined 20 career saves.
Jim Johnson is the most proven option on the roster, but he was just 22-of-31 on save chances with a 5.56 ERA for the Braves last season.
Oakland Athletics: Trading Heath Fillmyer
It was tricky to find a move the A's might regret.
Selling high on Ryon Healy with his lack of on-base ability or defensive position was a smart move, the Stephen Piscotty trade could be an absolute steal and the Yusmeiro Petit signing looks like money well spent.
Keep an eye on right-hander Heath Fillmyer, who was sent to Kansas City in the same deal that brought Brandon Moss and controllable reliever Ryan Buchter to Oakland.
The 23-year-old had a solid season in Double-A and has middle-of-the-rotation upside if he can improve his overall command.
Seattle Mariners: Not addressing the starting rotation
Marco Gonzalez should not be relied on as the No. 5 starter on a team with playoff aspirations.
Behind the unproven left-hander, the Mariners have a stable of uninspiring depth options, including Andrew Moore, Rob Whalen, Chase De Jong, Ariel Miranda and Hisashi Iwakuma if he can get healthy.
Beyond that, Felix Hernandez is not the pitcher he once was in the No. 2 starter spot, and both Mike Leake and Erasmo Ramirez look better at the back of a rotation than in the middle.
I'm not sure they've done enough to keep pace in the AL West.
Texas Rangers: Relying on Delino DeShields Jr. as an everyday player
The Rangers have tried this once before.
After Deshields' impressive rookie season as a Rule 5 pick in 2015, the Rangers handed him a starting job the following season.
He responded by hitting .209 with a 55 OPS+ and ended up spending a good chunk of the season in the minors.
As a result, the 25-year-old began last season on the outside looking in, but he eventually played his way into a starting job and now is really the only viable option to play center field on the roster.
Risky.
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NL East
4 of 6
Atlanta Braves: Not signing Todd Frazier
Not only should he have no trouble outperforming the two-year, $17 million deal he landed from the New York Mets, but Frazier would have been a great addition to a young Atlanta clubhouse.
As it stands, the Braves will have some combination of Johan Camargo and Rio Ruiz keep the hot corner warm until top prospect Austin Riley is ready to take over.
The 20-year-old has just 48 games above the High-A level to his credit, so midway through the 2019 season seems like a reasonable ETA. That would have coincided perfectly with Frazier's contract.
Miami Marlins: Keeping J.T. Realmuto
He doesn't want to be there, and he'd bring a huge prospect in return.
Not wanting to trade him in-division to the Washington Nationals without getting either Victor Robles or Juan Soto is understandable.
However, there's still time to get a deal done with the Astros with Kyle Tucker as the centerpiece, according to Craig Mish of SiriusXM.
They need to make it happen for the good of everyone involved.
New York Mets: Not adding starting pitching depth
One pitcher topped 120 innings for the Mets last season.
One.
So what have they done to address the precarious nature of their oft-injured starting staff this offseason as they look to chase down the Nationals?
Nothing.
Philadelphia Phillies: Not spending on one of the top starting pitchers
Aaron Nola took a big step forward last season, quietly emerging as one of the better starters in the NL by going 12-11 with a 3.54 ERA, 1.21 WHIP and 184 strikeouts in 168 innings.
Now the Phillies need to find him some support.
Jerad Eickhoff and Vince Velasquez have both shown flashes in the past, and there are plenty of other potential rotation pieces on the roster.
Adding a proven veteran by signing one of the top starters on the market would have been a good allocation of their significant available funds. Instead, they opted to spend on Carlos Santana.
Washington Nationals: Failing to add a No. 5 starter
Joe Ross will likely be sidelined the duration of the 2018 season after undergoing Tommy John surgery last July.
That leaves the Nationals with a spot to fill at the back of the rotation, and there's no clear-cut, in-house solution currently on the roster.
Prospect Erick Fedde was shelled in his first taste of MLB action last season, and expecting non-roster invitees Edwin Jackson and Tommy Milone to be the answer is wishful thinking.
For a team that's all-in on the 2018 season, the back of the rotation can't be a revolving door.
NL Central
5 of 6
Chicago Cubs: Not extending a core piece
We're getting nit-picky here after the Cubs signed Yu Darvish and Tyler Chatwood to fill out the starting rotation and also bolstered the relief corps.
Still, it would have been nice to see at least one long-term piece locked up.
Willson Contreras, Javier Baez and Kyle Hendricks appear to be the most likely candidates for an early extension. Kris Bryant will almost certainly wait at least until next offseason when Bryce Harper and Manny Machado set a new earnings bar.
Cincinnati Reds: Letting Zack Cozart walk
There's something to be said for backing a young pitching staff with stellar infield defense.
In that sense, the Reds might miss Cozart's glove even more than they miss his bat on the heels of a breakout offensive season.
Jose Peraza—his likely replacement—did not grade out well defensively at shortstop last season (422.1 INN, -6 DRS, -8.7 UZR/150), and those shortcomings will only be magnified at one of the most important positions on the diamond.
Milwaukee Brewers: Not upgrading the starting rotation
Adding Christian Yelich and Lorenzo Cain immediately makes the Brewers better and should give them one of the most potent offenses.
Is a rotation fronted by Chase Anderson, Zach Davies and eventually Jimmy Nelson (once he returns from shoulder surgery) good enough to consider them legitimate World Series contenders?
Even if they don't break the bank to sign Jake Arrieta, adding someone like Lance Lynn or Alex Cobb would provide some needed length and veteran stability to the starting staff.
For now, they seem content with the moves they've made.
Pittsburgh Pirates: Selling low on Gerrit Cole
No disrespect to Colin Moran, Joe Musgrove, Michael Feliz and Jason Martin, but it's hard to believe the Pirates were not able to get more for Gerrit Cole.
Moran could be the starting third baseman, Musgrove will get a shot at the rotation, Feliz can turn into a late-inning reliever and Martin is at least a top-20 prospect in the organization.
There's no impact talent in that group, though.
After Cole pitched to a modest 4.26 ERA and 1.25 WHIP in 203 innings last season, one can't help but wonder if the Pirates would have been better served to wait until July and hope he regained his frontline form.
St. Louis Cardinals: Trusting Luke Gregerson with the closer's role
The past two seasons the Cardinals have gotten a taste of what it's like to not have a trustworthy closer.
Heck, they were using waiver claim Juan Nicasio to close out games in the heat of a playoff chase last September.
And yet, they still seem confident entrusting the closer's role to Gregerson.
The 33-year-old had a less-than-stellar 4.57 ERA and 1.34 WHIP in a setup role for the Astros last season, and he has just one season (2015) with more than 15 saves to his credit.
NL West
6 of 6
Arizona Diamondbacks: Not taking advantage of the J.D. Martinez situation
"Sources suggest that the D-backs have broached 'creative' ways to keep Martinez," wrote Jon Heyman of FanRag Sports.
They need to make it happen.
Everyone expected the Red Sox to swoop in, meet his asking price and be done with it when the offseason began.
Instead, the D-backs find themselves with an unexpected opportunity to bring Martinez back, and they need to do whatever it takes with legitimate title contention within reach.
Colorado Rockies: Signing Chris Iannetta instead of Jonathan Lucroy
Let's start by recognizing that Iannetta was really good in 2017.
A 114 OPS+ with 17 home runs in 316 plate appearances kind of good.
He should have no problem living up to his two-year, $8.5 million deal and knows how to handle a pitching staff.
Still, Lucroy and the Rockies were a great fit over the final two months. If he bounces back, he could wind up being the biggest bargain of the offseason, and the Rockies could be kicking themselves.
Los Angeles Dodgers: Not adequately replacing Brandon Morrow
It was abundantly clear last October how much Morrow meant to the Dodgers bullpen when he appeared in 13 of the team's 14 games—including all seven World Series games.
Letting someone else pick up the bill after he made good on a minor league deal is fine.
Signing Tom Koehler to replace him might not be good enough, though.
If Pedro Baez doesn't rebound and Koehler fails to duplicate his late-season success in Toronto, the Dodgers could be scrambling for a right-handed setup man they trust.
San Diego Padres: Trading Enyel De Los Santos
It's still unclear what the Padres were thinking with the Freddy Galvis deal.
They traded a quality pitching prospect for a 1.3 WAR player who posted an 83 OPS+ last year, is owed $6.825 million this year and is headed for free agency at season's end.
If they wanted to plug the hole at shortstop with a short-term, glove-first player, they could have signed Alcides Escobar for half the price and kept the prospect.
If De Los Santos—who posted a 3.78 ERA and 1.19 WHIP with 138 strikeouts in 150 innings at Double-A last year—makes any sort of MLB impact in 2018 or beyond, this move will be a bust.
San Francisco Giants: Buying instead of selling
Evan Longoria and Andrew McCutchen will make the Giants better.
Whether they're good enough now to go from a 64-win team to a playoff contender is another story entirely.
On top of that, a team in desperate need of young, controllable talent looking to the future mortgaged two of their most promising young assets—Christian Arroyo and Bryan Reynolds—to get those deals done.
When they fall out of the playoff race by midseason, they'll regret not accepting the inevitable and starting to rebuild.
All stats courtesy of Baseball Reference and FanGraphs, unless otherwise noted.
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