Major League Baseball teams are always active in trying to make improvements to their team’s roster, whether it is for the current season or for the future. Just because front offices are active does not necessarily mean that all these moves are equal.
Sometimes in making a big push to become a playoff contender, teams will make bold moves that end up being pretty bad for the team. These types of deals often result in the team having large contracts to veteran players the team often regrets acquiring, or giving up a couple solid prospects for a player who ends up underperforming.
In fairness, for every bad move a team makes there has been a move that has turned out to be very smart. Extensive player scouting and player assessment strategies have helped teams discover players who will make their team. It is these scouting strategies that help make potentially bad moves turn out to be very smart moves.
For the purposes of this article, we will be looking back at recent transactions that have happened since the start of the past offseason since there haven’t been very many significant roster moves made so far this season. This article will discuss ten recent roster moves that MLB teams are already regretting, and another ten moves that have looked fairly smart.
20 Regret: Rockies Extending Charlie Blackmon
Timing is of the essence in baseball. Not only is that true for hitters and pitchers on the field, but also for front offices. In the offseason, the Colorado Rockies knew they had to figure out what to do with star outfielder Charlie Blackmon. He is an elite outfielder who was scheduled to hit free agency after this season. In a move that looked smart at the time, the Rockies gave Blackmon a 6-year/$108 million extension in April 2018.
After having a terrific 2017 season, Blackmon has been merely average offensively and defensively so far in 2018.
With the benefit of hindsight, the Rockies probably could have signed Blackmon for cheaper had they waited.
19 Smart: Astros Acquiring Gerrit Cole
The Houston Astros have their sights set on defending their World Series Championship. One of their big moves in the offseason was trading for starting pitcher Gerrit Cole. The Astros had a talented rotation already with Keuchel, Verlander, Morton, and McCullers. However, the addition of Cole improves their rotation considerably.
Cole has pitched like a true ace of the rotation and has been everything the Astros could have hoped for, and then some. The 2018 All-Star also has been pitching some of the best baseball so far in his career, further providing another top level starter to an already talented Astros rotation.
18 Regret: Cubs Signing Yu Darvish
The Chicago Cubs had a perfectly solid 2017 season, although they fell short of making it to the World Series again. One of the main items on their off-season to do list was to land a top of the rotation starting pitcher. It made perfect sense that they would strongly pursue the top free agent pitcher available, Yu Darvish.
The Cubs eventually won the Darvish sweepstakes, signing the 31-year-old to a lucrative six year/$126 million contract. So far, this contract has not looked good for the Cubs front office. Darvish has struggled throughout the first half of 2018, allowing more runs than he usually has throughout his career.
17 Smart: Dodgers Acquiring Max Muncy
The Los Angeles Dodgers get a lot of attention for their high team payroll and high-profile signings and trades they have made in recent seasons. However, there have been a couple of under the radar moves the Dodgers have made that have paid big dividends for the team. One notable move is when the Dodgers signed infielder Max Muncy to a minor league deal back in April 2017. The move was barely mentioned at the time.
A year later, the 27-year-old is having a breakout season. He is showing off some impressive power and a strong ability to get on base.
In addition, Muncy was also a participant in the 2018 Home Run Derby.
16 Regret: Blue Jays Not Trading Josh Donaldson
Over the past offseason, the Toronto Blue Jays were reportedly considering trading their star third baseman Josh Donaldson. The St. Louis Cardinals were one of the most prominent teams actively engaging the Blue Jays in trade discussions, as they badly needed a power hitter in the middle of their lineup.
The Blue Jays decided to hold on to Donaldson in hopes of contending or trading him at the deadline. Now a clear seller, the Jays will be unable to move Donaldson because he has been injured for much of the first half of the season. The Jays missed their chance to trade Donaldson for a couple of solid prospects.
15 Smart: Angels Signing Shohei Ohtani
Shohei Ohtani’s MLB free agency after coming over from Japan was heavily publicized over the offseason. After much speculation, Ohtani finally announced he was signing with the Los Angeles Angels. They have finally managed to find a quality middle of the order bat who can help Mike Trout, while also being a quality starting pitcher.
Ohtani has had his share of ups and downs to start his MLB career, but has been a very solid hitter. Players of Ohtani’s calibre often do not come cheaply so, even if it takes him a bit to finally find his groove consistently, the Angels know they have him locked up on a very affordable contract.
14 Regret: Cardinals Acquiring Marcell Ozuna
The St. Louis Cardinals thought they were getting a legitimate middle of the order power bat with a strong ability to get on base when they traded for Miami Marlins outfielder Marcell Ozuna.
To do so, they gave up a couple of very talented prospects in Sandy Alcantara, Magneuris Sierra, Zac Gallen, and Daniel Castano.
In exchange for giving up that talent, Ozuna has not been as effective as the Cardinals had hoped. While he is hitting below his career average, he is still getting on base at a respectable rate. The problem is that nearly all of his hits have been singles. Not exactly the most useful for a player who had previously shown an ability to hit homers and extra-base hits.
13 Smart: Red Sox Releasing Hanley Ramirez
The Boston Red Sox signed Hanley Ramirez to a 4-year/$88 million deal back in 2014. That contract turned out to be a disaster for the Red Sox, as Ramirez had mostly been relegated to the bench. After struggling immensely in May this year, the Red Sox decided to release the 34-year-old. They felt it was better for the team to not have him occupying a spot on the active roster.
Nearly two months later, the move appears to have been a smart one. The Red Sox have since acquired Steve Pearce from the Blue Jays, who will serve a similar role as Ramirez but at only a fraction of the cost. Meanwhile, Ramirez has not been signed by another MLB team yet.
12 Regret: Rockies Signing Wade Davis
The Colorado Rockies know that they will always have a tough time enticing free agent starting pitchers to sign with them because of how notoriously hitter-friendly Coors Field is. This is partly why they instead chose to load up on quality bullpen arms, headlined by closer Wade Davis.
While it is a good idea in theory, it has backfired badly for the Rockies thus far. Davis is signed to one of the largest ever contracts for a reliever, and he is on the wrong side of 30. Unfortunately for the Rockies, Davis has not been anywhere near as dominant as he was with the Royals and Cubs in recent years.
11 Smart: Yankees Acquiring Giancarlo Stanton
The New York Yankees trading for Giancarlo Stanton and his massive contract could eventually turn out to be a burden. However, the early returns that the Yankees have been seeing from Stanton qualifies this as a smart move at this point. Stanton has pretty much done everything the Yankees had hoped for.
He has made good use of the short outfield walls at Yankee Stadium, and has been hitting home run after home run.
The Yankees offense has been formidable for the most part, likely in large part due to the presence of Stanton in the middle of the lineup. His presence makes pitchers less likely to pitch around fellow slugger Aaron Judge.
10 Regret: Braves Releasing Jose Bautista
Jose Bautista is not the superstar outfielder he once was during his prime years with the Toronto Blue Jays. After waiting through free agency, he eventually signed on with the Atlanta Braves on a minor league contract. The Braves eventually promoted him to the major league team, where he appeared in only a handful of games.
The Braves released him, and he quickly signed with division rival New York Mets. Since then, Bautista has actually been a pretty decent baseball player. He has hit a couple of home runs, played decent defense, and has apparently generated trade interest from rival clubs.
9 Smart: Red Sox Signing JD Martinez
The Boston Red Sox entered the offseason knowing that they needed to go out and acquire a power bat, preferably a left handed bat who could handle the Designated Hitter (DH) duties. The Red Sox had needed to fill that void that occurred when David Ortiz retired two years ago. Finally, this past offseason, the Red Sox found the solution in JD Martinez.
After extensive back and forth negotiations and uncertainty over whether a deal would come to fruition, Martinez eventually signed with the Red Sox. He has been well worth the contract, having been a consistent source of home runs and extra-base hits so far.
8 Regret: Braves Trading Matt Kemp
Most Atlanta Braves fans would criticize their front office for trading the onerous contract owed to the veteran outfielder Matt Kemp. The trade essentially amounted to a salary switch, since the Braves took on the big contracts of Brandon McCarthy and Adrian Gonzalez (since released).
The L.A. Dodgers have certainly reaped the benefits of an apparent resurgent year from Kemp – something probably nobody saw coming entering the season.
At the halfway point in the season, Kemp is hitting over .300 and shown some good power at the plate en route to making the All-Star team this year. The Braves probably hope they still had him on their roster!
7 Smart: Mariners Acquiring Dee Gordon
Over the offseason, the Seattle Mariners traded for second baseman Dee Gordon from the Miami Marlins. At the time it happened, it was seen as a head scratcher since they already had Robinson Cano entrenched at second. Even more eyebrows were raised with skepticism when Seattle’s plans were to shift Gordon to center field.
It turns out the Mariners knew what they were doing! Gordon has been something of a sparkplug for the team atop the batting lineup. The addition of Gordon has also paid dividends since Cano was surprisingly suspended earlier this year, meaning the Mariners could easily shift Gordon to second base right away.
6 Regret: Giants Acquiring Evan Longoria
During the offseason, the San Francisco Giants decided to double down on pushing for a playoff spot in 2018 rather than tearing apart an aging veteran roster.
They sought to acquire veteran hitters and one of the notable acquisitions they made was trading for veteran third baseman Evan Longoria, from the Tampa Bay Rays.
However, Longoria has not been the big middle of the order power bat the Giants were seeking. While he has not necessarily been a bad player, Longoria has been merely league average – and will miss much of 2018 due to injury.
5 Smart: Phillies Signing Jake Arrieta
The Chicago Cubs decided to pursue the top starting pitcher on the market in Yu Darvish rather than re-signing Jake Arrieta. The Cubs felt Darvish was better suited to helping them return to the World Series. While that could eventually prove to be the case at some point in Darvish’s contract, the Phillies have reaped the rewards here.
Late in the offseason, Jake Arrieta signed a multi-year deal with the Philadelphia Phillies. The Phillies have turned into surprising playoff contenders, aided by their solid pitching. Arrieta has helped out the Phillies’ cause, and has actually outpitched and outperformed Darvish thus far – and on a cheaper contract.
4 Regret: Padres Acquiring Chase Headley And Bryan Mitchell
For some reason, the San Diego Padres decided to trade a decent prospect in Jabari Blash to the New York Yankees for third baseman Chase Headley and reliever Bryan Mitchell. Even at the time it happened, this trade made very little sense for the Padres. After all, the Padres were loaded with infielders, so they decided to trade for… another infielder in Headley.
At the halfway point in the season, this trade has looked even worse for the Padres. They took on Headley’s oversized contract largely because they expected big things from Mitchell. Unfortunately, Mitchell has struggled considerably since joining the Padres. As for Headley, he was designated for assignment by the Padres in May.
3 Smart: Blue Jays Acquiring Yangervis Solarte
For many Toronto Blue Jay fans at the time, their acquisition of infielder Yangervis Solarte was seen as more of a depth move. After all, the Blue Jays had already traded for infielder Aledmys Diaz a month prior.
While there wasn’t much doubt that Solarte and Diaz would combine to much more effective than Ryan Goins and Darwin Barney, not many fans would have foreseen the type of season Solarte has been having.
The charismatic Solarte has been a very solid and consistent performer for the Blue Jays so far this season. He has been one of the rare bright spots on a Jays team that has not had very many.
2 Regret: Red Sox Not Demoting Rafael Devers
The Boston Red Sox are one of MLB’s top teams largely because they boast one of the league’s most dominant offenses. A number of players on their roster came up through the Red Sox’ farm system including Mookie Betts, Xander Bogaerts, and Andrew Benintendi. At the start of the season, the Red Sox named young prospect Rafael Devers as their starting third baseman. He spent much of the first half of the season at third base, even though he struggled considerably and looked overmatched. In addition, he has piled up error after error at third base.
In a season where the Red Sox want to contend, it is not best for Devers or the team to have him still trying to figure things out in the major leagues. It could stunt his development and confidence, and possibly cost the team wins.
1 Smart: Padres Being Patient In Trading Brad Hand
There was a lot of speculation with San Diego Padres would trade closer Brad Hand at the trade deadline last summer, but it never happened. Similar trade rumors happened over the offseason, but it never happened then either. Hand had a breakout season last year and his value was incredibly high. There was a risk the Padres wait too long to trade him, and risk Hand losing value. This did not happen with Brad Hand and the Padres. Hand replicated his success so far in 2018 yet again, meaning his trade value (if they trade him) grew better than it was last year, hence the terrific return the Padres got when they traded him to Cleveland this summer (Francisco Mejia).