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Boston Red Sox might be aggressive in free agency this winter; here are 10 guys they could pursue | Chris Cotillo (MLB Notebook) logo 9/14/2021 Chris Cotillo,

CHICAGO — The Red Sox are in the thick of a postseason race, but that doesn’t mean it’s too early to start looking ahead to the winter. Boston is sure to be busy on both the free-agent and trade markets — though negotiations on a new collective bargaining agreement might cause some of the hot stove action to be delayed.

But that’s no fun, so instead, we’ll look ahead to some free agents the Red Sox pursue. Note that this is just pure speculation based on needs — and not an indication that the club has had discussions on any of these players.

1. Robbie Ray, SP, Blue Jays

Ray is going to get paid after a career year (11-5, 2.69 ERA in 170 ⅓ innings), and if the Red Sox want to pay up to get a veteran starter, he might be their guy. Assuming Chris Sale, Nathan Eovaldi and Tanner Houck are locked into rotation spots — and Nick Pivetta probably is, too — it will be interesting to see if the Red Sox commit to Garrett Whitlock as well. Still, it’s almost a certainty Boston will pursue starting help, especially if Eduardo Rodriguez signs elsewhere.

2. Max Scherzer, SP, Dodgers

Boston had interest in Scherzer at the trade deadline and could once again this winter, though the future Hall of Famer had a clear desire to go west when debating whether or not to waive his no-trade clause in July and that might be the case again this winter. If the Red Sox are trying to go all-in, signing the 37-year-old to a short-term (2 year?) deal would be the ultimate win-now move. It’s easy to dream of a Scherzer-Sale one-two punch at the top of a contending rotation.

3. Eduardo Rodriguez, SP, Red Sox

Put bluntly, Rodriguez — who owns a 5.15 ERA in 27 starts — has had a bad contract year, though the advanced numbers (3.54 FIP, 10.5 K/9) suggest he has been the victim of some bad luck. Considering what Rodriguez has meant to the Sox throughout his career, it’s almost certain the club will try to re-sign him at a certain price. One avenue could be issuing him the qualifying offer (effectively a one-year deal in the $20 million range), which he would surely accept. If anything, Rodriguez has proven he is healthy and durable after missing 2020 with myocarditis (heart inflammation).

4. Kevin Gausman, SP, Giants

Gausman has been stellar in San Francisco this season, as he owns a 2.65 ERA in 29 starts. He will — along with Ray and Scherzer — be one of the top free agent starters available this winter. The 30-year-old accepted the qualifying offer from the Giants last winter, so he won’t be eligible to receive one again. That means he won’t be tied to draft-pick compensation, which is surely a plus in the eyes of a forward-thinking executive like Chaim Bloom. Like Ray, Gausman will likely be handsomely paid. If the Sox play in the high-end starter market, he could be a name to watch.

5. Raisel Iglesias, RP, Angels

Iglesias has quietly been one of the best relievers in baseball for years and has not lost a beat in 2021. The former Red has a 2.71 ERA, 94 strikeouts and 31 saves in his first year for the Angels, who inexplicably did not trade him at the deadline. It’s unclear if the Red Sox — who extended Matt Barnes in July — will pursue a high-end closer this winter. Barnes’ second-half struggles may force them to do so. And if that’s the case, Iglesias is one of the best names available.

6. Starling Marte, OF, Athletics

The Sox had some discussions with the Marlins about acquiring Marte before the deadline but the A’s offered promising lefty Jesus Luzardo and were able to land him. A possible off-season pursuit of Marte (or any other outfielder) completely depends on what the Red Sox plan to do with Kiké Hernández. Originally, Hernández was signed to be the full-time second baseman, but the roster (Christian Arroyo’s performance, as well as Franchy Cordero’s, in a negative way) led to Hernández becoming the de facto full-time center-fielder. The Sox have the flexibility to start Hernández at either position and upgrade the other one. If they sign someone like Marte, Hernández could shift back to second.

7. Marcus Semien, 2B, Blue Jays

Conversely, the Sox could keep Hernández in center field and look to upgrade at second base. It’s clear Arroyo isn’t reliable enough to be a full-time player and that Jeter Downs (.570 OPS in Triple-A) won’t be ready in 2022. Semien, who has had an incredible year in Toronto, will be expensive but would shore up the club’s infield defense while giving the Red Sox another potent bat. Like many others, he could prove to be too rich for Bloom’s blood.

8. Kyle Schwarber, DH/OF, Red Sox

Schwarber has been excellent since joining the Red Sox, and though he’s not a clean fit positionally, Alex Cora has made it work. It will be interesting to see what kind of deal Schwarber commands after a career year, and the bidding could very well get too rich for Bloom’s blood. But if the deal is a reasonable one, Schwarber could return in the designated hitter/outfield/first base role he has played so far this season. His bat changes an entire lineup and he’s known as a great presence in the clubhouse.

9. Javier Báez, 2B/SS, Mets

Báez, like Semien, would be signed to play second base if the Red Sox keep Hernández in center field. The former Cub has previously gone on the record saying he would only be willing to play second base if Francisco Lindor is the shortstop, but his relationship with Cora could force him to bend his self-made rules a bit. Báez’s inconsistency, plus the fallout from his “thumbs-down” incident in New York, could lower his value, especially on a market that will include Carlos Correa, Trevor Story and Carlos Correa. Theoretically, the Red Sox could get a bargain here.

10. Collin McHugh, SP/RP, Rays

McHugh signed with the Red Sox before the 2020 season but never suited up for them, as he was rehabbing an injury and ended up opting out during summer camp. In 2021, he has been lights-out for the Rays, posting a 1.46 ERA and striking out 69 batters in 55 ⅓ innings as a swingman. The Red Sox prioritized long relief last winter when they signed Matt Andriese early in the winter. That move didn’t work out, but someone like McHugh would prove valuable to the pitching staff.

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