In 2018, the Boston Red Sox “did damage” by winning 108 games during the regular season, on route to winning the World Series in convincing fashion, by defeating two 100-win teams (Yankees & Astros) in the process.

In 2019, however, the only damage the Sox are inflicting is on themselves.

Despite pulling themselves back in the race for a potential wild card spot, it seems unlikely that the defending world champs will be able to fend off both the Tampa Bay Rays, who have been a pleasant surprise in the American League, or the offensive juggernaut that is the New York Yankees, who picked up their 50th win of the season last night.

Boston currently sits at 44-38 overall, third in the AL East, and currently hold a .500 record in games played at Fenway Park this season, making a recipe for mediocrity down the stretch.

As the defending World Series champions set to

Though players, such as Xander Boagarts and Rafael Devers, have contributed mightily this season, Mookie Betts, who is currently the reigning AL MVP, has had a lackluster campaign thus far posting a .266 batting average with just 13 homeruns and 36 runs batted in, and although his batting average is up, J.D. Martinez has also suffered a setback to last season’s campaign, where he slashed a .330/.402/.629 with 43 long balls and 130 runs batted in.

Martinez is currently hitting .285/.364/.516 with 16 long balls and just 42 runs batted in and leads the American League All-Star voting for designated hitters. Both Martinez and Betts, despite their lackluster play, will be starters in the American League in this year’s All-Star Game on July 9th at Progressive Field in Cleveland, Ohio.

As the defending World Series champions set to cross the pond and play their arch-nemesis New York Yankees in London, England this weekend, Dave Dombrowski and company have some decisions to make, and it’s all dependent on how Boston fairs in the next four weeks. With their poor performance thus far in 2019, there are multiple factors that the front office may want to take into consideration.

Big Player Contracts

Trade Mookie

Not only has Boston underperformed after last season’s’ historic win total, they will also have some key names coming off the books in only a short matter of time, as Mookie Betts and JD Martinez could be on their way out of “bean town” in the near future, if not, at the trading deadline on August 1st.

Betts, ranked the No. 1 right fielder in today’s game at the start of the 2019 season, will see his current contract come to an end after the 2020 season and has incited that he will not be signing any extensions with Boston within the next two seasons.

When being approached about his current contract situation and possible extension with the club back in Spring Training, Betts insisted that he plans on becoming an unrestricted free-agent following the 2020 season.

“That’s exactly what I expect. I don’t expect anything to happen till I’m a free agent,” when speaking to The Boston Globe’s Alex Speier.

Alongside Mookie Betts, is arguably the best hitter in the Red Sox starting lineup right now, in JD Martinez. Martinez was signed to a five-year contract, worth $110 million in February of 2018, which includes a player opt-out clause after this season, along with opt-outs at the end of 2020 and 2021, giving Martinez that option to become an unrestricted free-agent for just the second time in three seasons.

Martinez is owed $23,750,000 at the end of the 2019 season, the same amount he made in last season’s championship season. The Red Sox’ slugger is set to make the same amount in 2020, with his salary taking a dip in 2021 and 2022 at $19,350,000. With Martinez still in his prime, and many teams looking for a middle of the order bat, JD may look to take a chance on himself, following the 2019 season and opt-out of his current deal.

Red Sox Current Farm System

Trade Mookie

Once upon a time, Boston’s farm system produced the likes of Mookie Betts, Andrew Benintendi, Rafael Devers, Xander Bogaerts and Jackie Bradley Jr., as this core was a direct result of multiple AL East titles (2016, 2017, 2018), as well as one World Series championship (2018).

However, in 2019, the system ranks #30 in Major League Baseball, with Michael Chavis, being the only Sox prospect ranked in the Top 100 among MLB Prospects this season.

Given Boston’s lack of farm system depth, and the Red Sox big-league season struggles continuing, Dave Dombrowski, Boston’s President of Baseball Operations, may have to swallow a tough pill when it comes to his current roster.

Trade Mookie

After Boston’s 6-13 start in April, David Price took it upon himself to share his thoughts on how poorly the team had played, and even turned a possible rumor into a potential reality.

“If we don’t start playing better, J.D. Martinez, Mookie Betts, maybe myself, we could get traded. We’re, what, 30th in minor league systems?” Price told the Boston Globe’s Alex Speier. “We’re dead last. We don’t play better, Mookie Betts will be traded, J.D. Martinez will be traded. It will be tough for a while here.”

The Cold Truth

Trade Mookie

At the end of the day, all good things must come to an end.

Given the fact that Dave Dombrowski took it upon himself to sign Xander Bogaerts and Chris Sale to long-term extensions during spring training this season, Red Sox management now finds themselves in a hole, where they may not be able to reel Mookie Betts back in come the end of the 2020 season.

Dave Dombroski spoke very candidly about the Red Sox restrictions to maintain their entire roster down the line, on a podcast episode of “Section 10” back in January at Boston’s “Winter Weekend” event, saying that he knows, in all likelyhood, that Boston will not have the funds to re-sign all of their top talent.

Given the extensions handed out to Sale and Bogaerts this season, what Mookie Betts is likely to command come 2020, and JD Martinez’s current opt-out clause, it seems as if this long-lasted fairytale could be coming to an end, sooner rather than later as Boston will look to get something out of Betts and Martinez if they feel that they won’t have the money to keep them.

If the Red Sox catch fire in the coming weeks and maintain a solid record headed into October, maybe this is all talk. However, if Boston continues to fall short of anything less then in raw playoff picture, look for 2019’s MLB Trade Deadline to be bigger than ever, with Dave Dombrowski making moves he didn’t think he’d have to make three months ago.

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Jack O’Hara

Host of Belly Up Sports' 50/50 BOOKING Podcast available on Apple Podcasts & Spotify Host of The O'SHOW Podcast available on Spotify & Podbean

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