When J.D. Martinez decided not to opt out of the remainder of his contract with the Boston Red Sox on Monday, you could hear the groans coming from the South Side of Chicago.
"Here we go again."
It wasn't quite like the Manny Machado saga from a year ago, which dragged on for months before a conclusion that still has White Sox fans stewing with anger. But it was another case of wishing, hoping and — perhaps most notably — hearing about speculation. Martinez made all the sense in the world as a potential White Sox target this winter, just as there was so much upside to chasing an elite talent like Machado last winter. But the result was the same: no superstar on the South Side.
Of course, this offseason is just beginning, and the White Sox certainly plan to be aggressive once more in pursuing big names. One of the goals of Rick Hahn's rebuilding effort is to bring in an impact talent from outside the organization. With all that Machado money still able to be allocated, the possibility exists that this winter, with its Coles and its Rendons and its Bumgarners, could be the time to deploy those dollars.
There's been a heavy focus on free agency not just because of the big names out there, but because of the perception of the White Sox ability to make trades. Past Luis Robert, Nick Madrigal and Michael Kopech — all firmly part of the White Sox long-term plans — the next tier of guys in the minor leagues was plagued by injuries and under-performance. And as a result, it seems, from the outside, it would be rather difficult for Hahn to construct a package of prospects alluring enough to pry away one of the game's great talents. Just look back to the deals Hahn pulled off that sent Chris Sale, Adam Eaton and Jose Quintana away. The White Sox don't have prospects the caliber of Kopech, Yoan Moncada, Lucas Giolito, Reynaldo Lopez, Eloy Jimenez and Dylan Cease to construct those kinds of packages.
But the White Sox, when dealing away Sale, Eaton and Quintana, weren't exactly desperate. The Red Sox might be.
Up in Boston, there's a well publicized effort to trim salary, chiefly with the goal of getting under the luxury tax. The Red Sox had one of the three highest payrolls in baseball last season, and Dave Dombrowski lost his job for inking pricey long-term deals that now sit like albatrosses around the necks of the Beantown-based ancient mariners. Sale got one of them. David Price got another. Nathan Eovaldi got one, too. And with Martinez opting to stick with the remaining $62.5 million on his contract — for now, anyway; he can opt out again next winter if he so pleases — the Red Sox are going to have to shed salary via trade. Because those three pitchers are so pricey and not exactly the guys they were when they signed those deals in the first place, that leaves Boston with the very real necessity to trade away either Martinez or Mookie Betts.
Those are two players who would qualify as the kind of big splash the White Sox are looking to make. Could a deal with the Red Sox be the route the White Sox take to get there?
Martinez still seems like a perfect fit, and you can't blame him for sticking with the $23.75 million he's set to make this season and three potential years of job security rather than testing a free-agent market that might have been limited to a small handful of American League teams. But maybe there is still a chance he ends up on the South Side. The Athletic's Chad Jennings had this to say about a potential union between the two differently colored pairs of Sox:
"The White Sox do have quite a few young starting pitchers who either underperformed or were hurt in 2019. Among them was 25-year-old Reynaldo Lopez, who became a source of frustration. Perhaps the Red Sox could find a way to get one of those pitchers involved to fill an immediate need. If not, the Red Sox could be satisfied with a lesser prospect or two, which would still be more return than they would have gotten if Martinez had opted out."
Now certainly Lopez or a "lesser prospect or two" sounds like a reasonable return for up to three years of Martinez. Of course, therein lies the rub with any deal for Martinez: He can opt out of his deal at this time next year, meaning any team that were to deal for him would be doing so for potentially just one season. The same is true in any deal for Betts, who like Martinez is one of the game's elite hitters. Yes, perhaps the return package would be uniquely lessened with Boston wanting to get rid of salary — Betts is projected to receive a whopping $27.7 million through arbitration — but Betts is supposedly dedicated to reaching his own free agency next winter, making him a mere a one-year rental.
If Hahn's front office wants to stick to their focus on the long term, shopping for one-year rentals might not make a lot of sense. But there are other ways to help the Red Sox shed salary, ones that might line up better with the White Sox planned contention window.
That's where The Athletic's Ken Rosenthal comes in. He threw out a lot of possibilities when talking about the Red Sox situation Tuesday morning, and one seemed mighty intriguing from a White Sox standpoint.
"A better path might be to move left-hander David Price, who is owed $96 million over the next three years, or righty Nathan Eovaldi, who is owed $51 million over the next three. Impossible, you say? Well, what if the Red Sox included cash in a trade and also attached left fielder Andrew Benintendi, who remains cost-effective as he enters his first year of arbitration?"
Now that is interesting. Yes, it involves paying and dedicating a roster spot to Price or Eovaldi, who despite their heroics in the 2018 World Series, aren't very dreamy adds for a White Sox team looking to ramp up to perennial contention. Those guys' contracts are albatrosses in Boston. They wouldn't get much better in Chicago, even though the White Sox are in no danger of bumping up to the luxury tax. But both Price and Eovaldi could be usable pitchers for the White Sox in 2020 and beyond, even if they aren't performing at a level their contracts say they should be.
The real appealing element of that suggestion, though, is the upside of Benintendi. He has three affordable, arbitration-eligible seasons remaining until he hits free agency, making him a long-term piece. He's also very good, with a .277/.354/.442 slash line to go along with 51 homers in his 471-game big league career. Like much of what happened last season in Boston, 2019 was nowhere near as good as 2018 for Benintendi, who posted career highs in hits, runs scored, doubles, stolen bases, walks and on-base percentage during the Red Sox march to a world championship. In 2019, he slashed .266/.343/.431 with 13 homers, 40 doubles, 68 RBIs and 10 stolen bases in 138 games. He also struck out 34 more times in 10 fewer games.
Benintendi brings additional value as a left-handed hitter, something almost completely missing from the White Sox lineup. He is also a left fielder, a position the White Sox have filled with Jimenez. Neither player has ever played right field, and putting either there could be signing up for some unwanted defensive issues down the road. But Benintendi is a young, controllable, very good baseball player, and that seems like the kind of thing the White Sox, who have worked hard to achieve their much discussed financial flexibility, would be interested in.
Who knows if the White Sox are looking to make a move for any of these potentially acquirable Red Sox. But their supposed availability — at a price you rarely see for such talent — given the situation in Boston could make for interesting opportunities.
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