Prioritizing the contract extensions for Boston’s upcoming free agents

Baseball sucks. In terms of free agency, baseball seems to make it worse on the fans than any other professional sport. You get to watch these guys play for what feels like forever. You start to feel a weird attachment to them because you’ve heard about them since they were 18 years old, playing in the Gulf Coast League. And then they all get to the big leagues around the same time and thrive together, winning pennants and championships, MVP awards and Cy Youngs. And then it seems you have to pick two of them to sign long-term. It sucks.

The Red Sox are unfortunately heading toward Decision Day and I am already depressed about it. I love Mookie Betts, Xander Bogaerts, Jackie Bradley Jr. and Chris Sale. I don’t want to choose between those guys. I want all four of them in a Red Sox uniform for life. The reality is that that’s just not going to happen. Here’s how I would prioritize contracts for Boston’s upcoming free agents:

5. It feels like letting Rick Porcello go after this year is a foregone conclusion. It’s hard to imagine the Red Sox putting together an offer in free agency that’s better than what a less fortunate team could offer. Porcello is the fourth or fifth best pitcher in the rotation with Nathan Eovaldi returning to Boston next season. Porcello is the 13th highest paid starting pitcher in baseball right now but there’s simply no way he commands that kind of money next year going into his age 31 season. I could see him signing a two or three-year deal with a team starving for an innings eater. With more pressing contract extensions approaching, Boston is likely going to shy away from tying up more money on starting pitchers than it needs to. The Red Sox also have prospects like Tanner Houck and Jay Groome making their way through the minor league system, which they hope reduces the need for long-term options in the rotation going forward.

4. I really do love Xander Bogaerts and it truly pains me to put him in the No. 4 spot on this list, but I don’t see anyway around it. Bogaerts, who is a free agent after this coming season, has made all the right strides since his first full season in Boston in 2014. There has been a visible increase in power and a noticeable improvement on defense. Unfortunately, he is a client of Scott Boras and may command more on the open market than Boston will be willing to pay.

In regards to average salary, Spotrac has shortstops making the second lowest of all positions in the league. Elvis Andrus signed an eight-year, $120 million contract with Texas in 2015, making him the highest paid shortstop in the game. Over the last three seasons, Baseball Reference has Bogaerts’ WAR at 9.8, while Andrus is at 10.2. You know what else Bogaerts and Andrus have in common? They are both Boras clients. You know Boras is going into that contract meeting with Boston armed with memories of the deal Andrus signed with Texas. And, remember, that deal was four years ago and didn’t come on the open market. Either way, a decision on Bogey is going to set the stage for what the Sox do with their other free agents.

3. Prioritizing Jackie Bradley Jr. ahead of Bogaerts may be an unpopular decision — but I think it’s the right one. I am publically in the camp that thinks his defensive genius overshadows his inconsistent offense and no one is going to convince me otherwise. This camp is also riding high after Bradley’s postseason heroics (with a bat as opposed to the glove, no less). JBJ is a generational talent in centerfield and I don’t want to see him doing what he does in any other uniform when he becomes a free agent in 2021. Unlike at shortstop, the Red Sox do have plenty of organizational depth in the outfield, which is one thing that may prevent the team from extending Bradley if the price is too high.

It’s not easy to find a contract comparable to what JBJ deserves because there’s really not many guys out there like him. Even with offensive prowess lower than some of the highest paid outfielders in the league, Bradley is also a client of Boras and that alone should net him an annual salary between $15 million and $20 million with the way the market is right now. Money wise, that would put him in line with the likes of Jason Heyward, Justin Upton, Lorenzo Cain, Ian Desmond and Dexter Fowler. I think it’s a small price to pay to have Bradley trolling the outfield in Boston for the foreseeable future.

2. Boston’s inability to lock up Jon Lester long term years ago might play into Chris Sale’s favor when he becomes a free agent in 2020. Sure, it’s a different GM at the helm now. And one who has proven his willingness to spend the money needed to get the guy he wants in recent years. But the backlash from not signing Lester long-term is certainly not forgotten even almost four years later. Sale has also publicly stated that he’s willing to be underpaid his whole career as long as he’s having fun on the mound. That’s obviously great news for the Sox if it ends up proving true. Surely, Sale had fun closing out the World Series on the mound last season.

The 29-year-old’s recent shoulder trouble is definitely cause for concern. The way I look at it is that Sale is not going to be able to do what he does now for the rest of his career. Much like David Price did this season, Sale will have to go through a period of re-defining how he gets outs at some point. I have no doubt in my mind that Sale can do that with ease and it certainly helps to have Price in the same clubhouse while he goes through that process. I have no problem with the Sox breaking the bank to bring Sale back for another five years.

1. Boston absolutely needs to cut the biggest check it’s ever written with Mookie Betts’ name on it in the very near future — and preferably before he hits the open market in 2021. I think signing the 2018 MVP to an early extension becomes a little easier once Manny Machado and Bryce Harper have signed deals as Betts has publicly stated that he’s paying very close attention to what those guys do. I absolutely do not care how big the contract is and I’d go as far as to say that Betts should be making Mike Trout money. It would be a monumental, colossal, mammoth failure on the front office to ever let Mookie Betts play baseball in another uniform. That being said, Betts has to be willing to sit down and talk shop before he hits free agency. Reports say he hasn’t been in the past but who knows what Boston was offering at that point. Whatever it was, double it and try again until he says yes.