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Major League Baseball's offseason has been ongoing for close to two months now, but the trade market didn't heat up until Monday afternoon. That's when the Atlanta Braves, Milwaukee Brewers, and Oakland Athletics agreed to a three-team, nine-player blockbuster involving catchers Sean Murphy and William Contreras. (You can read CBS Sports' full analysis of that trade here.) 

Given how many teams had been involved in the Murphy talks, it stands to reason that a resolution on that front could create movement elsewhere on the market. Add in how the first half of the offseason has played out with respect to free agency, and we felt this was as good of a time as any to put forth some questions we'll be asking about the trade market over the coming weeks.

With that established, here are four questions we're pondering.

1. Will the Pirates honor Reynolds' request?

Earlier this month, outfielder Bryan Reynolds made a rare trade request. The Pirates are under no obligation to give in and trade Reynolds, who will remain under team control through the 2025 season, but they're certain to continue fielding calls to gauge his availability and Pittsburgh's asking price.

You can understand why other teams would have interest in Reynolds. He's a 27-year-old switch-hitter who has posted a 127 OPS+ in nearly 500 career big-league games while primarily playing center field. (He's likely to slide to a corner for his next employer.) Overall, Reynolds has amassed close to 14 Wins Above Replacement in parts of four seasons, or more than three per season (and that's without adjusting for the pandemic-shortened 2020 campaign).

So, will the Pirates move Reynolds this winter? Right now, the answer seems to be no. The Athletic's Ken Rosenthal quoted one executive recently who said the Pirates are seeking a "Soto-type package" in return for Reynolds. The Nationals, for those with short memories, fetched five young players (plus Luke Voit) in exchange for Juan Soto (and Josh Bell) at the trade deadline. The Pirates are unlikely to get a similar return for a number of reasons -- among them: Soto is a superior player, for one, and there's no Bell attached.

If and when the Pirates lower their ask, be it this offseason or next, expect Reynolds to resume his status as a walking trade rumor.

2. Can the Blue Jays capitalize on the catching market?

It's always hard to find a good catcher, and we're at the point in the winter where it's inching closer to impossible. Willson Contreras is a Cardinal; Murphy is a Brave; and Christian Vázquez is a Twin. That leaves few worthwhile backstops out there, be it on the free-agent or trade market.

Enter the Toronto Blue Jays, who are in an enviable position as a team with an abundance of catchers. They currently employ Danny Jansen, Alejandro Kirk, and Gabriel Moreno, each of whom could slot in as a starter for several other teams. Predictably, the Blue Jays have signaled a willingness to deal from their position of strength if they can find a trade that makes their roster better.

Jansen would seem like the most obvious candidate to go. He's the oldest of the group at 27 years old, and he's two seasons from free agency. He just had the finest effort of his career, too, as he hit for a 141 OPS+ in 72 games. Teams might question if Jansen can keep up his numbers if he's asked to shoulder a 120-plus-game workload, but let's face it: even if he can't, he's more likely to produce in some way than Austin Hedges and other lower-tier free agents.

The Chicago Cubs, Houston Astros, Tampa Bay Rays, and Boston Red Sox are among those who could be in the market for a new backstop. Whether any of them can or will make the Blue Jays a compelling offer is to be seen. One way or another, the Blue Jays seem certain to trade a catcher before the deadline.

3. Will the Red Sox avoid another Bogaerts-like mistake?

The Red Sox entered last spring knowing that longtime shortstop Xander Bogaerts would likely opt out of his contract at season's end. They didn't trade him when they had a chance, either prior to or during the season, when it was clear that they were not going to realistically compete for a playoff spot. Instead, they made him an unserious offer in the spring and then another in the winter, only to watch him sign a long-term deal with the San Diego Padres.

The Red Sox are now staring down the same situation with third baseman Rafael Devers, who will qualify for free agency at year's end. Will Chaim Bloom and company be able to prevent history from repeating itself? Maybe not. 

Team president Sam Kennedy was asked about the Devers situation on Tuesday. "We'll keep doing what I said we're going to do," he told reporters, including Chris Cotillo, "which is making the right decisions."

What, precisely, the "right decision" entails here is anyone's guess. Normally, you'd think that would mean reaching an extension with an important piece of the franchise, but Bogaerts (and Mookie Betts before him) proved the Red Sox won't bend just to satisfy their fan base. To wit, the Red Sox were reported as being "very far off" from meeting Devers' price back in April. It's unclear if anything has changed in that respect, but clearly no deal has been reached.

As such, it would probably behoove the Red Sox to listen to what the Los Angeles Dodgers, Cubs, San Francisco Giants, and others would be willing to part with in order to net a full season of Devers. That doesn't mean they will, of course -- they've indicated they intend to compete for a postseason spot next year -- but it would be nice to see them take a pragmatic approach in a team-building area outside of contract negotiations with their best players.

4. Should a team take advantage of the pitching market?

We'll end with a more philosophical question about whether a team will make a top starting pitcher available to offer an alternative to the free-agent market.  

So far this winter has been bereft of attractive trade options. The Cleveland Guardians don't appear to be moving Shane Bieber (though some of their other starters can be had), nor do the Milwaukee Brewers seem interested in parting with Corbin Burnes or Brandon Woodruff. The Miami Marlins were expected to move Pablo López, but nothing has happened on that front, either.

That would seem to set the stage for some team to step up and take advantage by landing a slew of prospects from a team who wants to upgrade their rotation without handing out a massive contract to a free-agent starter. Perhaps it's not that surprising, then, that's Jim Callis suggested on Tuesday that he's heard the Atlanta Braves are gauging interest in left-hander Max Fried. (Others have since rebuked Callis' report.) Even if the Braves aren't shopping Fried, he makes for a useful example of the point we're trying to make here, which is that it can pay off to be cognizant of any and all arbitrage possibilities.