The Boston Red Sox have one of the most storied histories in the entire MLB and due to this clear fact, they are extremely popular amongst baseball fans. Although they had an 86-year period where they failed to win a World Series, they were still beloved by their fans because of their constant efforts and pushes of optimism. When the team finally would end up winning back in 2004, it sparked them to now be one of the most successful franchises since then. The team has been making some truly wonderful moves since then that has helped them win another two championships as well. However, the constant pursuit of winning has also led to some truly abysmal additions that have hurt them for quite some time as well.
With all that has been stated thus far, we will be looking at ten recent moves made by the Red Sox that they got right and ten more that will forever haunt them. There is no question that the Red Sox have had amazing management over the years, but that does not mean that were not able to make massive mistakes as well. In fact, even during these past few years of immense success, the team has made so many major mistakes that have set them back a lot when it comes to their finances. At the end of the day, the Red Sox are one of the most intriguing teams to follow in the league recently because of how hard they constantly are looking to make the big moves to win.
Nonetheless, let’s look at the ten recent moves that the Red Sox got right and ten that haunt them!
20 Got Right: Trading For Ian Kinsler
The Red Sox made a pretty smart move at the deadline this season by bringing in Ian Kinsler from the Angels. With Dustin Pedroia’s future questionable and him most likely done for the season, the Sox decided to bring Kinsler in as his replacement for the postseason.
Kinsler had been struggling a bit during this season and saw his numbers drop, but since coming to the Sox, he has been a very reliable player. In fact, he has been a great addition both offensively and defensively. At the end of the day, this looks like the perfect rental addition.
19 Haunts Them: Trading Jon Lester
With the Red Sox out of postseason contention in 2014 and with his contract expiring, the Red Sox decided to move Jon Lester to the Oakland A’s for Yoenis Cespedes. This looked like a wise move because Cespedes was hitting his prime at that point and they could have used him long-term.
However, the Red Sox would end up trading Cespedes to the Tigers during the off-season. The Sox thought that they would have been able to bring Lester back via free agency, yet the Cubs ended up winning the bidding war. At the end of the day, they essentially would lose their ace for nothing.
18 Got Right: Trading For Steve Pearce
The Red Sox made a pretty small move before the trade deadline when they brought in Steve Pearce from the Blue Jays. They made this move to add some depth to their roster and to bring in a utility player. However, Pearce has truly exceeded expectations and has been fantastic.
Pearce’s legacy with the Red Sox was formed when he hit three home runs against the Yankees in one game. Now he is already a fan favorite and appears to be the perfect depth piece for their postseason run. Overall, this was an amazing move for them and one that was a true surprise.
17 Haunts Them: Signing Hanley Ramirez
Hanley Ramirez was a fan favorite with the Red Sox, so when the team released him at the beginning stages of the season, there was understandably some sadness. However, when you look at his contract and the way he produced, it honestly makes a lot of sense at the end of the day.
Ramirez was making elite level money, while playing at the league average. With the Red Sox needing to re-sign many of their younger player to their big contracts, it makes a lot of sense that they decided to move him out before he was set to make his $22 million bonus next season.
16 Got Right: Letting Jacoby Ellsbury Leave
After their 2013 World Series win, the Red Sox had a very tough decision when it came to Jacoby Ellsbury. There was no question that they wanted to re-sign because of his importance to the team, but once he hit the open market, it became clear that they truly could not.
The Yankees would end up winning his services by giving him a massive seven-year, $153 million deal. Since Ellsbury joined the Yankees, he completely has lost his step and now his career appears to be in jeopardy because of his injuries. At the end of the day, the Sox dodged a real bullet.
15 Haunts Them: Extending Adrian Gonzalez
After the Red Sox finally traded for Adrian Gonzalez, they quickly gave him a seven-year, $154 million deal. At the time of the signing, this looked like a steal because of the fact that Gonzalez was one of the most complete players in the league. The Sox finally got their star first baseman.
However, although Gonzalez would go on to have a solid first season with the team, it became clear that he did not like playing under the immense pressure in Boston. So after just one and a half seasons with the team, he ended up being traded to the Dodgers, where his career would then fall off.
14 Got Right: Trading For Rick Porcello
The Red Sox would end up getting Rick Porcello in the deal that sent Yoenis Cespedes to the Tigers. This was a very wise move for the team because the Red Sox needed pitching and Porcello had an abundance of potential as well. However, he struggled a lot in his first season.
Yet, he would bounce back the following year and put up a solid 22-4 record and won the AL Cy Young Award. Although his numbers have dropped off a little bit since this year, he now is one of the most effective starters on the team and is closing in on another potential 20 win season.
13 Haunts Them: Signing John Lackey
When the Red Sox signed John Lackey, they believed that they were getting a new ace to lead to the charge. However, this would actually not be the case because of the fact that Lackey struggled immensely with his team. From the very start, there were major issues.
However, Lackey’s 2011 season would end up being the year that truly made this massive signing a mistake. He would put up an absolutely poor 6.41 ERA, which would be one of the worst seasons of the modern era. However, he did turn it around a little during the 2013 Postseason, but still, this was a bad signing.
12 Got Right: Trading Clay Buchholz
Clay Buchholz entered the MLB with a major bang when he pitched a no-hitter in just his second career start. This would make the team see him as a legitimate future star for them and he would end up being solid. During his prime years, Buchholz would be a two-time all-star and solid second starter.
However, during the ending stages of his tenure with the team, Buchholz really began to drop off and that can be blamed on his many injuries. The Sox ended up trading him to the Phillies after this and it was the right move due to the money saved. Today, he has turned it around however and is pitching well with the Diamondbacks.
11 Haunts Them: Failing To Trade For A Reliever (2018)
This year’s Red Sox team is easily one of the best ones that we have seen in a long time and they are destined for greatness. However, even the best of teams have a weakness and this year’s for the Sox is their bullpen. However, they did not add an arm before the deadline.
This could very well end up being the biggest mistake for them this season because they have one of the worst bullpens in the league. When the postseason comes around, it is hard to believe that their bullpen will be able to hold the fort nicely, so this could be a decision that haunts them immensely.
10 Got Right: Signing J.D. Martinez
The Red Sox made the signing of the year when they brought in J.D. Martinez to a five-year, $110 million deal this off-season. Martinez had come off a career year with the Tigers and Diamondbacks that saw him hit 46 home runs. The Sox expected him to be able to do that.
However, Martinez has already exceeded expectations this season by putting up an MVP caliber year. He is easily one of the best players in the entire league at this present time and has truly been the player that has carried them over the rest of the competition in the league.
9 Haunts Them: Trading Travis Shaw
After two very solid seasons with the Red Sox, the team decided to trade Travis Shaw to the Brewers for reliever Tyler Thornburg. This move made it clear that the team was moving toward using Pablo Sandoval as their permanent starting third baseman, even though he had been struggling a lot.
This trade now is viewed as one of the worst ones of recent memory because Shaw has developed into a great power hitter for the Brewers, while Thornburg has barely pitched for the Sox and has been awful when he has. At the end of the day, this was a clear mistake from the team.
8 Got Right: Signing David Price
There is absolutely no question that there has been a lot of criticism over the David Price signing. This is largely because of the fact that Price has been openly agitated with the media and even has caused scenes within the dressing room because of it. However, things have changed.
Price is easily one of the best pitchers on the team and is a huge reason as to why the Sox are at the top of the league. Although he has had some injury troubles, he is now pitching at the level that was expected of him. At the end of the day, this is a move that they got right for the overall skill of the team.
7 Haunts Them: Trading Anthony Rizzo
Anthony Rizzo was the big prospect that the Red Sox traded in the deal for Adrian Gonzalez. Although Rizzo would never develop into anything for the Padres, he became a star when he was dealt to the Cubs. Now it is clear that the team wishes that they held onto him.
Rizzo is one of the best all-around players in the game and is a huge reason as to why the team would end up winning the World Series back in 2016. If the Sox had Rizzo at this time, they would be absolutely unstoppable, so it is clear that this trade will haunt them forever.
6 Got Right: Trading For Craig Kimbrel
The Red Sox made a pretty huge move when they shockingly traded for Craig Kimbrel from the San Diego Padres. Kimbrel is obviously one of the best closers in all of baseball and is on the verge of ending up being near the top of the all-time saves list in the MLB.
Since being traded to the Sox, Kimbrel has seen his skill level progress even more and he is a huge reason as to why the team is so strong at the moment. This was an amazing decision by management and if they can extend him after this season, they could be set as contenders for a long period of time.
5 Haunts Them: Signing Carl Crawford
The Red Sox had always been interested in picking up Carl Crawford because of the fact that he was the star player of the Rays, a team in their division. Before signing with the Sox, Crawford was one of the best players in the entire league and an all-around star.
However, as soon as he came to the Red Sox, Crawford’s skill dropped off dramatically and it showed that he was a horrible fit for a bigger market. He simply was not worth the seven-year, $142 million deal and they luckily were able to send him to the Dodgers before his salary hurt them too dramatically.
4 Got Right: Signing Mitch Moreland
The Red Sox made a minor move when they signed Mitch Moreland to a one-year deal back in 2017. However, since they made this move, Moreland has progressed as a player and is now a very important piece of the roster. In fact, he even made the all-star team this season.
At the end of the day, Moreland is a player that the team lucked out with immensely and now appears to be a part of their long-term future. With his ability to provide some spectacular defensive work and solid power, this is a player who ended up being a complete steal for them.
3 Haunts Them: Signing Pablo Sandoval
Pablo Sandoval is easily the worst signing in the history of the Red Sox and this is evidenced by the fact that he simply appeared to not care once he got his huge deal. Sandoval, who once was a star with the Giants and led them to three championships, just appeared to stop trying with the Sox.
When seeing how Sandoval ended up getting a massive four-year, $58 million deal and he produced nothing for the team, this can go down as one of the worst moves of all-time. In fact, the team paid $95 million to him just to be able to buy him out. When seeing how poorly he played, it makes a lot of sense.
2 Got Right: Trading For Chris Sale
The Red Sox completely formed themselves as contenders again when they made the massive trade to bring in Chris Sale from the White Sox. Sale is easily one of the best pitchers in all of baseball and has been completely lights out for the team since he has arrived with them.
At the end of the day, it is quite apparent that pitching wins championships and they truly have that opportunity with Sale as their ace. Although he has been struggling with ongoing injuries this season, he is easily the best trade of their recent history and is due for a massive extension in the near future.
1 Haunts Them: Signing Rusney Castillo
The Red Sox thought that they had landed their next star when they signed international free agent Rusney Castillo to a seven-year, $72.5 million contract back in 2014. However, since signing this deal, Castillo struggled with the team immensely and has not played an MLB game since 2016.
When seeing how astronomically awful he ended up playing for the Sox, it is quite apparent that this is a signing that will haunt them until the deal is finally over. However, with this contract not set to expire until the end of the 2020 season, this is going to take quite some time to get completely done with.