The Juan Soto sweepstakes this winter was a heck of a follow up to the Shohei Ohtani madness of last year’s offseason.

Rumors about Soto swirled for weeks before coming to a head, when he eventually signed a record-breaking deal with the New York Mets for 15 years and $765 million.

Soto famously turned down a $430 million contract extension earlier in his career, back when he was with the Washington Nationals. The Nats tried several times to get Soto to commit to an extension, failing as Soto continued to gamble on himself.

That bet has clearly paid off, as Soto is now the richest player in the sport just a few short years removed from those discussions with Washington.

Soto’s experience isn’t unique. There are guys who have previously refused to sign an extension, like Mookie Betts in Boston, who were traded by their original teams prior to hitting free agency.

And in most cases like that, barring injury it works out in favor of the player.

That said, some guys do benefit from signing early. Bobby Witt Jr. has a monster contract in place that will likely keep him in Kansas City for the better part of his career.

And seeing as he was 5 years from free agency when that deal was signed, Witt is much richer today than he would have been otherwise.

The obvious parallel here is to current Orioles’ star shortstop Gunnar Henderson. Orioles fans have been wondering for over a year if Baltimore is going to be willing to pony up the type of cash to lock up Henderson on a long-term contract extension before he gets close to free agency.

But after the year Henderson just had, it’s almost difficult seeing how the two sides will come to a deal.

Juan Soto’s contract might screw the Orioles when it comes to Gunnar Henderson

Henderson was near the top of the list for pre-arbitration bonus pool payouts in 2024, and will receive about $3 million in total payroll earnings for his efforts this year.

Coming off an 8 fWAR season, that makes him one of the most underpaid players in the sport. To this point, there’s no real sign that the Orioles are pursuing extension talks, or whether Henderson would be open to them in the first place.

During this year’s Winter Meetings, there was some buzz going around about whether Henderson, who is due to be a free agent in four years’ time, could be the first $1 billion player.

It seems a bit crazy but four years of inflation, coupled with the opportunity for Henderson to go out and prove he’s one of the best, could lead to an historic contract for the star Oriole.

During those same meetings, agent Scott Boras was asked about potential contract extensions and he mentioned Henderson in particular as the type of guy who could benefit from waiting for free agency. That’s great news for Henderson, but it’s rough to head as an Orioles’ fan.

We’d love to see the O’s get the opportunity to lock up Henderson for the next decade, plus. But whether Henderson is amenable to the idea remains to be seen.

If it’s up to Scott Boras, there’s no chance the two sides will work out an extension but we’ll have to wait and see how it plays out.