Brewers just gave Orioles a new reason to believe in a Gunnar Henderson extension

Most Baltimore Orioles fans have been screaming for the organization to sign Gunnar Henderson to a long-term deal for the past several seasons. He won the AL Rookie of the Year Award in 2023, went to his first All-Star Game in 2024, and even in down-year, posted a 121 OPS+ and 5.3 bWAR in 2025. Henderson is a bona fide star and is arguably the best shortstop in the league, not named Bobby Witt Jr.

Witt is signed to a mega-deal with the Kansas City Royals. But he signed that 11-year, $288.7 million contract two years ago, meaning that the price tag for an MVP-caliber shortstop has gone up since then. Witt's deal can top out at over $370 million, and that's likely the starting price if Henderson and O's start talking about a long-term contract.

But the numbers are only part of the equation. Even if Baltimore was willing to match the unimaginable salary requirements to ink Henderson to a long-term pact, they've got to negotiate with Scott Boras.

Henderson is represented by the Boras Corporation, and most baseball fans know that MLB's super agent prefers to take his top-tier clients all the way through their arbitration window and onto the open market. It's a frustrating strategy for fans, but it's doubtful that Boras' clients despise his game plan.

Brewers-Cooper Pratt deal offers Orioles glimmer of hope for Gunnar Henderson extension

Boras, however, recently negotiated a long-term extension for another one of his clients — Milwaukee Brewers prospect Cooper Pratt. The young shortstop is a highly regarded player in the Brewers' organization, and he just signed an eight-year, $50.75 million deal with Milwaukee even though he hasn't even swung a bat during a Major League game. Pratt's deal also includes two club options worth $15 million each.

Pratt becomes the latest of a short list of Boras clients to agree to a long-term extension before hitting free agency. Others who are on that list include Xander Bogaerts (six-year, $120 million deal with the Boston Red Sox), Jose Altuve (five-year, $151 million deal with the Houston Astros), and Stephen Strasburg (seven-year, $175 million deal with the Washington Nationals).

The O's are past the point of offering Henderson the type of bargain that Pratt just signed. If Baltimore isn't willing to go near the high-end of Witt's extension with the Royals, they needn't even bother. But if the Orioles are willing to fork over true market value for Henderson's services, Pratt's deal with the Brewers serves as a reminder that Boras isn't always inflexible.