Coming off a World Series Championship, everyone has eyes on the 2019 Boston Red Sox. However, there are an abundance of existing questions.

As Red Sox fans, we should have our eyes on the impending free agents. We have already endured a roller coaster of emotions with Craig Kimbrel (with no end in sight), can you imagine next offseason when names like Xander Bogaerts, Chris Sale, Brock Holt, Rick Porcello, Mitch Moreland, Eduardo Nunez, Steve Pearce, and Tyler Thornburg are free agents?

Now, in reality, the decision for some of those names will already be made before the offseason begins, either through trades or extensions. Blame it on recency bias or not, but most of those names I would actually like to see back in 2020: Bogaerts, Sale, Holt, and Moreland. These are givens based on skill and what they can bring to the team when healthy. If Porcello has an average or slightly below average, I do not believe he is worth the money, especially when there are so many other options to use it on. Pearce needs to prove he can bring consistency to the lineup and not just show up in big moments and I would be more than fine letting Nunez walk.

Trouble with Bogaerts?

The name that really sticks out for me is Xander Bogaerts. I believe the Red Sox will sign Sale and Holt no problem, but Bogaerts, I am not so sure. It pains me to think about Bogaerts not being on this team, especially after all the trouble and tribulation the team went through to finally get a consistent, elite (Yeah, I said it) shortstop. What pains me EVEN more is I can see a likely scenario where Bogaerts isn’t even on the team at the end of the year. Yes, I mean traded. That jerk Manny Machado is probably going be the reason too. No way can the Red Sox pay Xander what Machado is going get in these next couple of days. Even if they could pay him around the same amount of money, do we really want that to happen? That means most likely no Mookie, JBJ, and/or Sale at the least.

I’ll admit I am a JBJ stan, but out of those 4 guys, I honestly think Bogaerts is at the bottom of the list. On an additional note, can you imagine if J.D. Martinez opts out in 2019 too? All financial hell would break loose.

Built to Win Now

We can’t leave out the news of Mookie’s one-year, 20M deal. I am honestly happy with this. I felt like a second year of going to arbitration could have damaged the relationship and Mookie is just one of those guys. He is one of those guys where you just have to pay him what he wants because he can bring the MVP caliber year almost every season. He is special and would be a downright shame if he were to put on any other jersey throughout his career.

No matter what happens this 2019 season, the Red Sox are going have a ton of tough decisions to make by the start of the 2020 season. Which then they will have to go through it all again with different players. I can guarantee there is going to be some heartbreak with some of these players. We can’t possible expect all of them to take hometown discounts.

Whatever Dealin’ Dave decides… I just hope it brings another parade of Duckboats.