Following Mike Trout’s Mega Deal, All Eyes Shift to Mookie Betts

When the news broke that Los Angeles Angels’ superstar Mike Trout signed his monstrous 12-year, $430 million extension, the baseball world shared one collective thought: “Wow.”

On the other hand, around the still snow-covered streets of Boston, fans and baseball diehards alike had another thought: “Uh-oh, how much is Mookie going to want now?”

The reason for the “Uh-oh” preceding that thought is the fact that, to this point, Mookie Betts and the Boston Red Sox have come nowhere close to a contract extension in their recent discussions with each other. Betts did nothing to put minds at ease when he spoke to the media on Wednesday.

The roadmap for Betts is becoming clear. He intends to take himself to the free agent market and see what teams are willing to bid for him. It is also becoming more and more clear how rich a contract Betts will be looking for. He will likely seek a deal larger than Bryce Harper‘s $330 million deal with the Philadelphia Phillies, but probably just south of Trout’s historic 12-year, $430 million deal. Betts will also likely command an average annual salary around $32 million, similar to that of Nolan Arenado of the Colorado Rockies — who agreed to an eight-year, $260 million extension with the Rockies three weeks ago.

The good news for the Red Sox and their faithful fans is that the team has until the 2020 offseason to negotiate a contract extension with Betts. Betts has one more year of arbitration left after 2019, so the Red Sox still have time to work with him on a contract and potentially lock him into a long-term deal the way the Angels did with Trout, or the Rockies did with Arenado.

The Angels went through a similar process with Trout, who gave little indication that he was eager to sign an extension with the team as his free agency loomed ever-nearer. However, as we all know now, once Trout was presented with the contract he wanted, he wasted no time putting pen to paper and committing himself to the Angels organization. The same could be the case for Betts and the Red Sox. The last two contract offers from the Sox have reportedly been in the $100-200 million range, respectively, which seems like a blatant lowball offer at this point. Should the Red Sox decide to pony up and offer Betts something closer to a $400 million contract, there is likely a strong chance he would take it.

That, unfortunately, is where the problem lies for the Red Sox. Is the team willing to fork over $400 million to one player, albeit a superstar player, when they have several other looming roster issues to address over the next few years?

One of those roster issues concerns their ace and the man who nailed down the final out in the team’s 2018 World Series victory, Chris Sale. The dominant left-hander is a free agent after this season, and the Red Sox have already expressed interest in signing him to an extension. Sale is not the only player whom the Red Sox are interested in keeping around long-term, as the team has also been engaged in negotiations with All-Star shortstop Xander Bogaerts, as reported by Jason Mastrodonato of the Boston Herald earlier this Spring.

“Conversations have been had, but I don’t really want to get into any further details, aside from, as I said, these are great players,” Werner said. “In a perfect world, we’d love to them to be with us for the rest of their careers.”

Neither Bogaerts or Sale will come cheap, but the Red Sox appear motivated to dole out the money necessary to keep those two players around as part of the team’s core. Tack those two pending contracts on top of whatever astronomical deal Betts will receive and the picture starts to look slightly grim and, frankly, unrealistic for Boston.

Unrealistic does not mean impossible, however, and the Red Sox certainly possess the payroll and capital needed to make a roster like that work. It is not as if this is the Tampa Bay Rays who struggle to make money and keep star players due to a lack of resources. The Red Sox ownership group insists that they learned their lesson from horribly mismanaging the Jon Lester situation many years ago. Back then they lowballed Lester so badly that they alienated and spurned a talented player who actually wanted to play in Boston. They cannot afford to make that same mistake with Betts if they truly want him in Boston on a long-term basis.

It would behoove the Red Sox to bust open their checkbook and make a significant, fair offer to Betts and hope to re-sign him before he hits the free agent market in 2020. Ultimately, the decision belongs to Betts, and he may decide to test the market no matter what kind of offer the Red Sox present him with. Nevertheless, the Red Sox must not ignore the fact that they have a superstar talent on their roster who fueled them to a World Series championship while winning the AL Most Valuable Player Award, and that is definitely a talent worth spending the money on.

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