Gunnar Henderson is the best shortstop in baseball and a clear extension candidate for the Baltimore Orioles, so what is the holdup? Baltimore has one of the most promising young cores in the league but has yet to lock down any of its young stars. Shortstop Gunnar Henderson is one of the young stars Orioles fans would like to see extended to a long-term deal.
Extending Orioles Star Shortstop: Why It Matters and What’s Holding Up Progress
A second-round draft pick in 2019, the same draft that made Adley Rutschman an Oriole, Henderson quickly established himself as a franchise cornerstone. Like Rutschman, the 2023 AL Rookie of the Year is under club control for the foreseeable future but should be extended sooner rather than later. Henderson made his MLB debut towards the end of the 2022 season, before his breakout rookie campaign the following year. The then-22-year-old slashed .255/.325/.489 with 28 homers and 82 RBI over 150 games winning his first Silver Slugger. Henderson had a stellar sophomore showing as Baltimore’s everyday shortstop batting .281/.364/.529 with 37 homers, 92 RBI, and 21 steals. He started his first All-Star game, and after finishing eighth in AL MVP voting as a rookie, he finished fourth in 2024.
Henderson has been in near lockstep with Royals shortstop Bobby Witt Jr., the second-overall pick in 2019, since his debut. Witt, the only shortstop in MLB history to have achieved two 30–30 seasons, signed an 11-year, $288.7 million contract extension with the Royals last season. So, why has Baltimore not signed Henderson, the top shortstop right now according to MLB Network, to a long-term extension? The answer could simply be his representation.
Could Scott Boras Be Holding Gunnar Henderson Back from a Long-Term Extension?
Unlike Witt, Scott Boras represents Henderson, who generally prefers taking his clients to free agency over long-term extensions. Henderson could sign one of the most expensive contracts in MLB history one day, and his value is only increasing. After turning 23 this past June, Baltimore’s country boy would hit the open market going into his age-28 season. While the Orioles have plenty of time to make a long-term offer, could extending him now be the better plan?
Going into his age-24 season, Henderson owns a career .268/.346 /.504 slash line and a 16.2 WAR through 343 games. The 23-year-old shortstop ranked in the top 10% of major league hitters in nearly every offensive category last season. He recorded career-highs in home runs, steals, and value while posting a career-low 22.1% strikeout rate in 2024. As Henderson enters his third full season in the majors, he is arguably the best player in Baltimore right now.
One thing Boras does is he gets his players paid. While he prefers testing free agency over long-term extensions, Baltimore could make Henderson an offer he simply cannot refuse. Henderson will make an estimated $800,000 this upcoming season in his final season before becoming arbitration eligible in 2026. Baltimore has little money locked up beyond 2026, which could be because of the many young stars due for extensions.
Shortstops are often among the highest-paid position players in the majors, just look at Witt and Mets’ shortstop Francisco Lindor. Tampa Bay signed Wander Franco, three years younger than Henderson, to an 11-year, $182 million extension in 2021. Boras could easily make a case for a lucrative long-term extension to keep Henderson in Baltimore for years to come, but time will tell if that happens. However, the longer that the Orioles wait to open the extension conversation, the more expensive Henderson will likely become.
Main Photo Credits: Kim Klement Neitzel-Imagn Images
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