The 2020 season is a season like no other and the trade deadline is not likely to be any different.
With 16 teams making the playoffs and a 60-game schedule, contention isn't quite what it normally is. While it looks like we may finish the season without a major health-related disaster snowballing out of control, teams have questions to wrestle with this year about just what a playoff spot actually means in 2020 and whether a team with a .450 record should be adding players.
For a team that decides it does want to be a buyer, there's always an opportunity out there somewhere. Here are some trade targets for top teams with a pressing need and teams on the bubble looking to address a weakness and get over the playoff line. I tried to pick players who are at least plausibly available, so as fun as it would be to imagineer a Mike Trout trade, that's not actually going to happen.
1. Houston Astros: Kevin Gausman

The Astros have survived the loss of Gerrit Cole to free agency and the loss of Justin Verlander to injury so far, but that doesn't mean it's an ideal situation, especially as they look up at the Oakland A's in the AL West standings. After Zack Greinke, and assuming Framber Valdez's improved control sticks, there's a lot of risk in the rest of the rotation and risk is something elite teams try to avoid.
The Giants tend to be a bit resistant toward being sellers, but with Gausman on a one-year deal and without any particular history in San Francisco the way someone like Brandon Belt or Brandon Crawford have, I'd be surprised if they weren't willing to move Gausman in a week. Gausman has a sterling 34:5 K/BB ratio and the Astros have had success in the past with pitchers who were just missing one last crucial element in their repertoire. In Gausman's case, it's the lack of a truly dependable breaking pitch.
2. Chicago Cubs: Mychal Givens

Baltimore is a surprise contender this season, but I'm of a firm belief that the O's consider 2020's surprise .500-ishness a fun diversion rather than any sign the team is actually a contender. The team's bullpen has been surprisingly deep and with Givens a free agent after 2021, they'd have to pay market value to keep him around for the years when the Orioles are truly a contender rather than just scrambling for the last playoff spot in a year in which more than half the teams play postseason baseball.
Craig Kimbrel has looked more like his typical self in his past few outings after his disastrous start to the season, but even if he's at least back to his Boston level instead of his Atlanta dominance, the Cubs could use more bullpen depth, something they didn't really address sufficiently in the offseason.
3. Washington Nationals: Jonathan Schoop

Starlin Castro was just placed on the injured list with a broken wrist that required surgery, and while he's hopeful he could return to the roster in the playoffs, the Nats have to actually get there first to make that even a possibility. Below .500, the Nats would be smart to treat the second-base problem with urgency.
Luis Garcia has held up well in a few games in the majors, but one has to consider that he's never played above Double-A before this, a level at which he hit .257/.280/.337. He's a good prospect, but the Nats need a bit more certainty, and shuffling Asdrubal Cabrera into the position, given his defensive challenges, is also less than ideal. Schoop's 2017 looks like a real outlier, but he's good enough to fill a hole and can function as a shortstop in a pinch.
4. Milwaukee Brewers: Kyle Seager

Seager showed a lot of positive signs in 2019, hitting .260/.339/.524 after a .203/.288/.371 first half that was shortened due to his hand injury from late 2018. That surge has continued this season with Seager's OPS hanging north of .900. The Mariners are going nowhere and when has Jerry Dipoto ever needed an excuse to make a trade?
I like Luis Urias and Eric Sogard on the Brewers, but Urias ought to be getting the lion's share of the playing time at shortstop and Sogard's best fit is probably more of a supersub role. Seager might just solve the third-base issue for the team for the next year and a half.
5. Cleveland Indians: Jackie Bradley Jr.

Another year, another lackluster offseason performance by the Indians in remedying their outfield issues. Oscar Mercado has already lost his job in center and the Indians have turned to Delino DeShields Jr., who is largely Billy Hamilton but slower and with less defense in center. Bradley isn't exactly having a good year for the Red Sox, but the Indians have shown the willingness to roll the dice before on a struggling outfielder if he comes cheaply (see Yasiel Puig, 2019). Bradley's a free agent after 2020 and it was an open question last year whether the team would even tender him a contract, so it's not as if the Sox are in a position to demand the world.
6. Atlanta Braves: Ryan McMahon

McMahon was a fine prospect at one point, but the Rockies spent 2018 and 2019 jerking him up and down from the minors and from position to position, the team placing its usual priority on the middling veterans they so often favor. I still think Austin Riley's going to be a fine offensive player in the long run despite a disappointing 2020 so far, but I'm less confident that the position will be third base, a position McMahon's comfortable with. It would be interesting to see what McMahon could do with consistent playing time and he has more upside than Johan Camargo does.
7. St. Louis Cardinals: Johnny Cueto

The Cardinals have an unusual challenge in having to make up 10-12 games that most of the rest of baseball has already played. That creates some testing times for the team's rotation depth, even if Carlos Martinez comes back gangbusters from his COVID-19 stint. Cueto's star days are probably behind him, but he at least appears to be healthy, and assuming the contract issues can be worked out -- I'm certainly not suggesting the Cards pick up the nearly $30 million still guaranteed to Cueto -- an extra innings-eater might be extremely helpful now, with Cueto essentially inheriting impending free-agent Adam Wainwright's role in 2021, should Wainwright not return.
8. Cincinnati Reds: Tony Watson

Cincinnati's rotation has been sterling in 2020, but one of the reasons the team is struggling to break .500 is a bullpen with an ERA hovering around 6.0. I don't expect them to do anything major, with Amir Garrett the only lefty in the bullpen they can really be sure about, but some added depth would be nice. Watson's problematic shoulder appears to be staying more or less together and, like Gausman, he has no history with the Giants that would cause upper management to feel the need to retain his services. A free agent after the 2020 season, Watson's unlikely to command a serious prospect.