The Trade Desk

Trades are the lifeblood of fantasy baseball home leagues. The conversations around them help keep us connected, engaged, and make our league more fun. Striking deals isn’t always easy. There are often hurt feelings around lopsided proposals, league-mates who value players differently, and that one guy who wants to veto everything. We can improve our fantasy squads with the waiver wire, but our collective hit rates are low. Quite often, those pickups backfire in the form of a hitter’s cold streak or a pitcher’s blowup, which inevitably leads to dropping the player. The one facet we have control of in home leagues is trading.

Managers are often emotionally tied to certain players – specifically, ones they’ve drafted or ones they targeted in drafts and missed. Also, we’re not all great at zooming out for a long-term view and not being stuck in the moment. Good analysis can be washed away by recency bias and small sample sizes. No one can force us to make a deal, so it’s the one element of the game we have some control over and can use proper value assessment and negotiation techniques to our advantage.

This column will recommend hitters and pitchers to attempt to sell-high or buy-low, and touch on trade strategies. No two leagues or two managers are the same. You know your league-mates best: what kind of deal they’ll scoff at, which player type they’re willing to deal or acquire, and how good their player and market valuation skills are. I’ll do my best to dig deep and present realistic opportunities. If there’s someone in your league who will swap their Josh Naylor (0-19 through five games) for a red-hot Joey Wiemer, it’s probably time to find a new manager for their spot, or a more competitive league. Early in the season is usually a great time to take advantage of a good deal, as we can potentially lean into targeting players who are off to slow starts. We can also use fandom to our advantage, specifically when we know a league-mate is a diehard fan of a specific Major League team and may be blinded by subjectivity.

Sell High

Owen Caissie (OF), Miami Marlins

Caissie may not be the most marketable fantasy asset because of his low draft cost, but he is off to a hot start, and there is enough buzz around him that it’s worth exploring a deal with your league-mates. This won’t work in shallow Yahoo leagues where he’s 17% rostered. It may on Fantrax (77% rostered), or in NL-only leagues, or deeper formats like Ottoneu (99.7% rostered).

The Marlins acquired the 23-year-old former Cubs prospect in the offseason. The left-handed Caissie plays right field and was left on the bench for one of the two lefties the Marlins faced this year (he hit 8th against the other). Through four games, he is slashing .385/.429/.769 with a home run, a stolen base, and four RBIs. The Marlins opened the season against two of the weaker pitching staffs (the Rockies and White Sox), and will have a tough stretch against much better pitching over the next few weeks – the Yankees, Reds, Tigers, Braves, and Brewers. Moreover, there will be an inordinately high number of lefties among starting pitchers the Marlins are projected to face in the next couple of weeks. For example, they are lined up to face Ryan Weathers and Max Fried this weekend, three Reds lefties and Tarik Skubal next week. Caissie may crack the lineup against one or two of those southpaws, but we can’t expect him to crack the lineup regularly in the short term.

Granted, it’s a long season. Caissie lovers are in it for the long haul and for his potential upside. Nevertheless, I feel confident that now is the time to strike a deal for a hitter who will play consistently and be a better source of fantasy production. My reasons for selling are threefold: 1) this is a sell-high window, 2) he is a platoon hitter, and 3) he is a WhiffsMonster. In a large Minor League sample, Caissie owned a 29% strikeout rate (28% in Triple-A) and a contact rate around 69-70%. The FanGraphs’ preseason projection models pegged him for a 31-32% strikeout rate and a batting average in the .230-.250 range. Caissie has power/speed upside and is certainly far from a finished product, but we must wonder why the Padres (2020 Yu Darvish deal) and Cubs (Edward Cabrera deal) were both so quick to part with him.

We aren’t likely to pull one over on our league-mates, but almost every league has a Cubs fan, and that Cubs fan might just have a special emotional attachment to Caissie we can use to our advantage. It wouldn’t be a bad idea to test out the waters by offering Caissie for a non-platooning, slow-starter with a 150+ preseason ADP like Brenton Doyle, Jordan Beck, or Reds leadoff man, TJ Friedl. We can also consider shooting for the stars a bit with a 1:1 offer for fellow strong-side platoon hitter, Kerry Carpenter.

In keeper or dynasty formats, I would still be open to shopping Caissie, but my ask would be higher. His value is higher in those leagues than in redraft, since 2026 is likely to include a steep learning curve for a guy with that much swing-and-miss. Given his low draft cost, he could be an easy low-cost keeper. But the hype is still high and you may still be able to get a better return by moving him than keeping him.

Don’t underestimate the current buzz around Caissie, and consider shipping him for an upgrade before the roller coaster starts its way downhill.

Any Mediocre Starting Pitcher with a Strong First Outing

We likely aren’t going to get much in return for Michael Soroka, Landen Roupp, or Michael McGreevy, but it’s worth exploring. One of them may have a breakout season, but “breakout” is a relative term if their ceiling isn’t Top-20 SP. Especially if you have a specific return in mind – a sub-$5 preseason value hitter or pitcher you have a strong long-term belief in. Mike Burrows comes to mind as a pitcher with a higher preseason draft cost who should outperform this trio and is worth targeting. You can casually mention that Burrows is pitching in Coors Field next week, or perhaps even wait until his Wednesday start against the Red Sox, in case he gets a little roughed up again and his stock declines further. If you weren’t a Burrows guy to begin with, then it doesn’t make sense. But this is the best way to do it: chip away on small deals you feel you have an edge on, instead of piecing together wild blockbusters with no clear advantage. Only make deals where you feel you have the clear advantage.

Buy Low

Taylor Ward (OF), Baltimore Orioles (+ shopping Chase DeLauter)

It is much more difficult to buy low on hyped, popular players who might be off to slow starts, like Bryce Harper, Roman Anthony, or Wyatt Langford. Most of your league-mates aren’t fools. They aren’t going to trade away a high draft capital guy based on a five-game sample. The best deals are often in the mid-round value weeds, which we can grind away one deal at a time.

The Orioles are off to a slow start, but they project as one of the best offenses in 2026. Batting atop that lineup is a guy who produced well last season (36 HR, 103 RBI), but wasn’t too pricey in drafts just a few weeks ago (150-170 ADP). He could slide down the lineup, but as of now, Ward leads off in front of Gunnar Henderson and Pete Alonso – it doesn’t get much better than that. Ward is a batting average liability (.228, .246 the last two seasons), but it’s part of the package for a guy with a 13.4% barrel rate since 2024, now playing half his games at Oriole Park. A league-mate might smell this “random” trade offer a mile away (or read this article) and reject it outright. Though, if it’s part of a 2-for-2 or 2-for-1 deal (where you’re offering the 1), it might be a little less obvious. Call me crazy, but this might be the opportunity to pull off a heist for Chase DeLauter, if you have him. If I posted a poll on rest-of-season value between Ward and DeLauter for the rest of the season, my instinct tells me DeLauter would win. As for their actual rest-of-season value, I’d still prefer Ward, but would have some trepidation about trading a heralded prospect with a great profile. This type of deal works if you boost the perception of DeLauter’s value by asking for a throw-in alongside Ward in a 2-for-1 deal — someone who provides you with bench depth, but still offers some upside and staying power on your roster. To shop DeLauter is to feel out your league-mates’ perception of player value on a buzzy prospect producing at a high level over a short period of time, or if we’re concerned about his poor health history.

Any Mid-Valued Starting Pitcher with a Poor First Outing

Consider seeing what it would take to acquire a pitcher like Tanner Bibee, Shota Imanaga or Shane Baz, all of who had rough first starts, not to mention, Bibee’s injury scare. Baz was a buzzy, helium pitcher in drafts just a few weeks ago, though perhaps the leaguemate who has him thinks “he just got paid, he won’t care” or “there he is! same old Baz”. If you missed him as one of your draft targets, then consider these next couple of days as your window to buy low. Emerson Hancock looked terrific on Sunday night, and perhaps 2026 is his true breakout, but I’d rather have Baz, and it’s not really close.

These proposals aren’t one-fits-all since every league and set of managers are different. What’s unfathomable in one home league might be easy to pull off on another. Just be mindful about tipping your hand on your true intent whenever possible, take advantage of league-mates’ personal tendencies or biases, and never send an offer you don’t feel confident that you’re getting the better end of the deal.