3 early-season trades Pirates must make

The Pittsburgh Pirates may not be at the top of the standings, but there is a new energy about the ballclub this May. The arrival of top pitching prospect Paul Skenes, punctuated by his six-inning, no-hit, 11-strikeout performance Friday in Chicago, has injected hope into a fan base that hasn’t seen postseason baseball in nearly a full decade.

With Skenes, Jared Jones and Mitch Keller atop the rotation for the foreseeable future, the puzzle is starting to come together for the Pirates’ path to contention. But it’s clear 2024 is still a bridge year, and the ladder to the top of Major League Baseball is brutally tough to climb. So for the remainder of this season, general manager Ben Cherington needs to turn his focus to setting the Pirates up to hit the ground running in 2025.

Which brings us to the task at hand: Making smart trades now to set the Pirates up for the not-so-distant future where they might have a chance to topple the throne of the NL Central. The top of the rotation is set, there are some solid lineup pieces to build around, but there are gaps waiting to be filled. With the right moves, Pittsburgh can become a powerhouse for years to come.

Trade CF Michael A. Taylor to Guardians

One of the biggest setbacks to the Pirates’ 2024 season so far is that the veterans they have on one-year contracts, classic trade fodder for any sub-.500 team, have been terrible. Rowdy Tellez is one of the least valuable players in the league, Martin Perez has struggled and Marco Gonzales is hurt. But teams are always looking for outfield defense and Michael A. Taylor is one of the very best in that regard.

The next logical step, then, is to look for a trade partner with subpar center field defense. The Cleveland Guardians stand out because they are playing converted infielder Tyler Freeman in center field just about every game. Freeman did make a great catch Friday night, but he’s still the second-worst qualified center fielder in outs above average (OAA) with -2. Taylor, meanwhile, has five OAA, tying him for first at the position.

Even if Taylor rarely gets at-bats, he can be hugely valuable for Cleveland as they try to fend off the Minnesota Twins and Kansas City Royals in the division. In fact, Minnesota would be another potential trade partner for Taylor if Byron Buxton remains on the IL, so there’s more incentive for them to get the deal done. And the Pirates could secure a high-upside piece like lefty starter Jackson Humphries, Cleveland’s No. 13 prospect, helping them balance their rotation of the future.

Trade RP Aroldis Chapman to Royals

What a full-circle moment this would be, huh? Aroldis Chapman looked finished at the end of 2022, went to the Kansas City Royals and sparked a resurgence, got traded to the eventual world champion Texas Rangers and signed a free agent contract in Pittsburgh. Now that he’s struggling in Pittsburgh, what better situation to find his groove again than Kansas City, the redux?

The Royals are 25th in fWAR from their bullpen this season at a round 0.0. Though Chapman hasn’t pitched well yet with a 1.77 WHIP in 2024, there’s value in experience and somehow, you just know he’ll be on the mound during one of the biggest white-knuckle moments of the baseball season. Kansas City has the requisite young core and veteran leadership to make a playoff push, but they need a lefty option in the bullpen down the stretch.

Since Chapman is a true rental on a $10.5 million deal, the Pirates are likely going to have to eat a significant chunk of salary to get the prospect return they want. But as the team with the 26th-highest payroll in the league, that’s exactly what Pittsburgh can afford to do. Royals No. 15 prospect Javier Vaz is the type of pure hitter Pittsburgh is lacking in their system and would be a versatile piece of their 2025 roster.

Acquire Orioles OF Heston Kjerstad

The Pirates had the right idea when acquiring former San Francisco Giants catcher Joey Bart. Take a former top prospect who was blocked at his position in his previous organization and give him a lane to succeed with a new franchise. But now, it’s time to take a bigger swing and go all-in on Heston Kjerstad, who remains one of the top prospects in all of baseball, but has nowhere to play on the loaded Baltimore Orioles roster.

The former second overall pick of the 2020 draft, Kjerstad is still stuck in AAA at the age of 25, putting up a 1.143 OPS with 11 homers in 25 games. It’s painfully obvious he’s big-league ready, but unless the Orioles are hit with a slough of injuries, there’s no place for him in the Baltimore outfield. The Pirates need to come over the top with a godfather offer to convince the Orioles to part ways with a potential future star.

In this hypothetical, Cherington sends No. 4 prospect Anthony Solometo and No. 10 prospect Mike Burrows to Baltimore for Kjerstad. The Orioles get two young pitchers nearly ready to make their big-league debuts and Pittsburgh gets the young bat it needs while keeping their own best pitching prospect behind Skenes, Bubba Chandler. It’s a bold play to trade two prospects for one, but it’s just the play the Pirates need to make to slingshot themselves to the top of the NL Central in 2025.