Just three weeks after the Orioles’ 2023 campaign came to a close, the Texas Rangers took down the Arizona Diamondbacks to complete the postseason and send major league baseball into what should be a fascinating offseason. From crafting contract extensions to making free agent and trade acquisitions, Mike Elias and his crew will have their hands full as they traverse the long and baseball-less winter.
Just a year removed from his infamous “lift-off” comment, which drew criticism after the team was relatively inactive at last year’s winter meetings, Elias will have plenty of questions asked of him if he fails to deliver once again. Expectations are high among the Baltimore faithful and while the level of play on the field has risen to the task, the commitment from the front office and ownership has yet to do so.
Over the next few weeks, I will discuss my hopes and dreams for what the Orioles can do to change that narrative during what should be a thrilling few months of rumblings, rumors, and (hopefully) roster moves. So, without further ado, let’s dive into the most pressing matter on the Orioles’ agenda: contract extensions.
Now that the Orioles have established a winning culture, the next step is to ensure that culture remains in Baltimore for the long haul. The easiest way to do that is to extend the talent already present within the organization, whether that be the veterans who have contracts that are soon to run out or the young stars who will only see their price tag rise over the next few years.
Teams like the Braves have found tremendous success by extending their best players within the first two years of their rookie contracts. Not only does this help to avoid contract disputes and the deterioration of relationships that frequently arise during arbitration, but it also gives the team a chance to lock up future superstars before they have reached their full potential. There is, of course, an element of risk that ownership must be willing to take when crafting these sorts of deals, but the potential returns are exponential.
Unfortunately, even if John Angelos was willing to take a leap of faith and offer an eight-plus year contract to one of the Orioles’ young superstars, it might already be too late. Adley Rutschman has established himself as a consensus top-three catcher in baseball, Gunnar Henderson is about to be named the AL Rookie of the Year, and Kyle Bradish will almost certainly receive AL Cy Young votes. Still, Rutschman, Henderson, Bradish, and the rest of the young core still have multiple years of relatively low salaries remaining on their rookie contracts, so offering them more money up front and a few extra years of stability could be enticing.
Rutschman is the most important name on the list given his role in the team’s success. Not only has he been a consistent force at the top of the batting lineup over the past two years, but he has also been one of the best defenders at the most difficult position in baseball and has established an excellent rapport with the pitching staff.
Our former BSL colleague Stephen Loftus took a look at what it might take to extend Rutschman back in 2021, but given that the Orioles have miraculously gone 158 and 109 since his arrival, it’s safe to say that his impact has been greater than anyone could have imagined and he therefore will cost more than what Orioles fans originally hoped. That being said, letting Rutschman walk out the door after the 2027 season is simply not an option so the front office will need to find a way to get a deal done this winter regardless of what it takes.
Looking around the league, Sean Murphy’s 6-year, $73 million deal that he signed with the Braves last December seems like a good starting point for negotiations. While Rutschman will likely require a greater yearly salary, Murphy signed his extension with three years remaining on his rookie contract (Rutschman has four) so the numbers may not end up being as far apart as they might initially seem. Seven years and $100 million-$120 million would be a fair price for both sides.
Henderson is an even trickier situation for a number of reasons. First off, he’s just 22 years old and will therefore reach free agency when he is 27. Most players don’t hit free agency until a few years after that, so he could afford to sign an eight or nine year deal with the Orioles and still reach the open market with plenty of time left in his career.
Alternatively, Henderson is a Scott Boras client which means he will likely go wherever the biggest paycheck lies. The Orioles still have the upper-hand in negotiations given that the young shortstop has two years left before arbitration, but the longer they wait to strike a deal, the smaller that advantage will become.
There’s also the Jackson Holliday situation which could cause problems in negotiations. If Holliday lives up to expectations, he will be one of the best middle infielders in baseball within the next few years. While having two superstars next to each other will be great in the short term, the reality of the situation is that both of them are going to want to be paid shortstop money and only one of them (or none of them if Angelos refuses to open up his pocketbook) will be able to. The Orioles may be hesitant to pay Henderson until they see what they have in Holliday, but waiting any longer to lock down Henderson may eliminate the chance of it happening altogether.
Still, it’s important to remember that Henderson is coming off of one of the best rookie seasons in franchise history. Not only did he slash .255/.325/.489 while posting a 6.3 bWAR during the regular season, but he was also one of the only players to show up and impress in the postseason. Henderson is a generational talent and Baltimore fans should be able to enjoy he and Rutschman well beyond their rookie contracts. A nine-year deal worth somewhere between $150 and $200 million should get the job done.
Moving over to the pitchers, Bradish and Grayson Rodriguez are probably more likely to accept long-term contracts. However, the same reasons they would want to lock up their futures now are likely deterrents for the front office, who have shown themselves to be extremely risk averse.
Not only are pitchers much more subject to injuries than position players, but pitching is significantly more volatile than hitting. There have been plenty of cases of pitchers who have impressed over a one or two year span, received a large payday, and regressed significantly shortly after. Because of this, pitchers rarely receive contracts that last longer than five or six years so given that Bradish and Rodriguez still have plenty of time remaining on their rookie deals, there’s very little incentive for the front office to extend either of them until at least 2025.
It should also be noted that there are plenty of veterans on the roster who are also worthy of consideration for a contract extension. Cedric Mullins, Austin Hays, Anthony Santander, Ryan Mountcastle, and John Means all are set to become free agents within the next three years, and while keeping all of them around seems unlikely, locking down a couple of them to serve as veteran presences would make a lot of sense.
Mullins seems like the most likely candidate of the bunch given his well-rounded skill set and track record of good health, but the Orioles’ selection of Enrique Bradfield Jr. in the first round of last summer’s MLB Draft leads me to believe the front office doesn’t see him as their long-term center fielder. While a move to one of the corner spots would make sense, Hays might be better suited to stick around in that role given his comfort in left field and the fact that the Orioles have a plethora of young left-handed bats.
Santander and Mountcastle are also likely fighting for just one spot given their defensive limitations. Santander has been the more consistent of the two, but he will need to develop into a serviceable first baseman if he is going to stay in Baltimore for the long haul. Given that Rutschman is set to start at DH for 35-40 over the next few years, the Orioles cannot afford to pay out big money to someone whose sole contributions come from their bat.
As for Means, his future will largely depend on how he performs over the next twelve months. He has established a deep connection with the city of Baltimore and seems like a perfect fit to serve as a mentor to the young arms in the system, but he will need to build upon his strong finish to 2023 while staying healthy before earning a new contract.
Anyone who stepped into Camden Yards in September or October could feel excitement around this team, and given their lack of experience and the influx of talent still present in the minor leagues, the best is likely yet to come. The worst possible thing that the front office could do is let the players who brought baseball back to Baltimore leave at the end of their six-year rookie contracts, and the longer they wait to strike a deal, the more likely that outcome becomes. Extensions need to happen and they need to happen sooner than later if the Orioles are going to take the next step towards winning a World Series title.
Luke Rollfinke is a student at Vanderbilt where he is pursuing a career in sports journalism. A recent graduate from the Friends School of Baltimore, Luke has spent his entire childhood in Charm City and is a devoted Orioles fan. In the past, he has written for SB Nation and has worked closely with Ravens columnist John Eisenberg. From nights at Camden Yards to Sunday afternoons watching NFL Redzone, Luke eats, sleeps, and breathes sports. He is excited to bring his perspective to BSL.