Scott Boras: Pirates’ Aggressive Free-Agent Strategy Is the Right Step

The Pittsburgh Pirates are sending a message this offseason: maybe they’re done sitting quietly on the sidelines in free agency. At baseball’s winter meetings, super-agent Scott Boras said general manager Ben Cherington has been chasing multiple Boras clients, hinting at a more ambitious—if still budget-conscious—approach in Pittsburgh.

Pirates Shift From Passive to Proactive in Free Agency

For years, Pirates fans watched other small-market teams outbid them for big bats and frontline pitching. This winter feels different.

Boras says the Pirates have been consistently engaged, actually asking about a wide range of players instead of just bargain hunting at the end of the market.

Boras even went out of his way to praise the team’s new attitude, calling Pittsburgh’s assertiveness a positive development for the franchise. Coming from a guy famous for pushing clubs to spend, that’s no small thing.

Why Scott Boras’ Praise Actually Matters

When Boras highlights a team’s activity, it usually means the front office is in the mix for mid- to upper-tier talent. For a franchise that’s often ignored in Boras negotiations, the Pirates’ presence in these talks feels like a real shift in how the league sees them.

Kazuma Okamoto: A High-Ceiling International Target

One of the more intriguing names linked to Pittsburgh is Kazuma Okamoto, a 29-year-old Japanese infielder. Okamoto brings the sort of upside the Pirates rarely chase in international free agency, mixing power and on-base skills in the middle of the infield.

Last season, Okamoto hit .327 with 15 home runs. That kind of production would instantly upgrade the Pirates’ lineup.

The elbow injury that cost him some time is a concern, but the bat is legit. His infield versatility would give Cherington some flexibility as other roster decisions unfold.

How Okamoto Fits the Pirates’ Roster Construction

The Pirates need impact hitters who can grow with their young core. Okamoto fits that need.

He could stabilize third or first base, lengthen the lineup around emerging stars, and provide a middle-order presence Pittsburgh hasn’t had since its last playoff run. For a team balancing risk and upside, he seems like a swing worth taking.

Kyle Schwarber: The Big Offer That Came Up Short

Maybe the clearest sign of the Pirates’ new urgency is their pursuit of Kyle Schwarber. Pittsburgh reportedly made a four-year offer to the Phillies slugger, but Schwarber returned to Philadelphia on a five-year, $150 million deal.

Even though they missed out, that bid says a lot. The Pirates were willing to commit serious money and years to a top power bat, something that would’ve been almost unthinkable for them in recent offseasons.

What the Schwarber Chase Tells Us About the Budget

Schwarber’s price point gives us a rough idea of where the Pirates are aiming. They’re not shopping at the very top of the market, but they seem ready to play just below it.

That opens the door for other impact bats whose price tags aren’t quite as high as Schwarber’s.

Pete Alonso and Other Big Names on the Radar

Two marquee Boras clients, Alex Bregman and Cody Bellinger, are probably out of Pittsburgh’s financial range. But Pete Alonso remains interesting.

Alonso’s profile—pure right-handed power at first base—doesn’t exactly match the Pirates’ needs, but his bat is so loud you can’t just ignore him.

He signed a two-year, $54 million deal with an opt-out last offseason and is expected to get a contract a bit below Schwarber’s. That’s a steep number, but since the Pirates chased Schwarber, Alonso’s market at least sparks some internal debate.

Why Alonso Is Complicated but Tempting

Alonso overlaps with some internal options at first base and adds another right-handed bat to a lineup that could use more lefty balance. Still, his ability to change a game with one swing—year after year—would give Pittsburgh a presence in the middle of the order that’s hard to find.

This is the kind of risk you take when you think your team’s competitive window is starting to open. It’s not a slam dunk, but it’s the sort of move that gets fans talking.

Pitching Targets and Trade Possibilities

On the pitching side, Boras clients like Ranger Suárez, Tatsuya Imai, and Zac Gallen have come up in market chatter. They don’t seem like great fits for what the Pirates want right now.

The trade market feels more interesting. Boras himself tossed out a few possible trade chips among his clients, including:

Bohm brings contact and size at third, Adell has loud tools that haven’t fully clicked, and Jung offers power with solid defense when healthy.

How Trades Could Complement Free-Agent Moves

For a mid-market team, the sweet spot is usually blending shorter-term free-agent deals with upside-heavy trades. If the Pirates can use their farm system without gutting it, adding a Bohm or Adell type alongside a free-agent bat like Okamoto could really change their offensive ceiling.

What This Offseason Means for the Pirates’ Future

Nothing’s guaranteed until contracts are signed. Still, you can’t ignore the pattern: the Pirates aren’t just watching the market unfold this time.

They’re tossing out multi-year offers to top power hitters. They’re poking around at international infielders, too.

The front office is eyeing both free agents and trade options, even from the top of Boras’ list. That’s not something we’ve seen often from this club.

Maybe they’ll land Okamoto. Maybe they chase a deal for Alonso, or swing a trade for Bohm or Jung.

But here’s the thing: the real story is philosophical. Pittsburgh’s acting like a team that wants to win soon, not someday.

Will they actually pull it off? That’s what’ll decide if this winter is a real turning point—or just another flirtation with something bigger.

 
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