Extensions in MLB are the only thing keeping torpedo bats off the front page or talk radio every day. Around Opening Day, contract extensions were awarded to a talented array of players:
Blue Jays 1B Vladimir Guerrero Jr.: Fourteen years, $500 million
Red Sox LHP Garrett Crochet: Six years, $170 million with an opt-out after 2030
Padres OF Jackson Merrill: Nine years, $135 million with a club option
Diamondbacks 2B Ketel Marte: Six years, $116.5 million with a player option
Mariners C Cal Raleigh: Six years, $105 million
Red Sox 2B Kristian Campbell: Eight years, $60 million with two club options
Blue Jays C Alejandro Kirk: Five years, $58 million
Guardians RHP Tanner Bibee: Five years, $48 million with a club option
Diamondbacks RHP Brandon Pfaadt: Four years, $45 million with a club option
The reasons both a team and player would be interested in an extension are fairly simple. They provide the protection of early guaranteed money as a hedge against injury but also a failure to live up to expectations. Ask Jon Singleton and Scott Kingery if they are glad they took $10 million and $28 million, respectively, before they ever played in big league games.
Owners’ reasons for targeting extensions have changed throughout the years. When the Orioles extended Jim Palmer and Scott McGregor back in the ’70s and early ’80s, it was merely to keep the player away from free agency. Today, buying out arbitration years is a huge part of the game and played a part in most of these extensions this spring.
Also playing a part in this spate of extensions appears to be the labor outlook of the sport. Many of the prominent folks involved in the labor discussions, such as MLBPA executive director Tony Clark, are expecting a lockout after the 2026 season when the current collective bargaining agreement expires. Some agents may be simply advising certain players to grab as much guaranteed money as possible to have it in hand.
I cited nine players having signed extensions around Opening Day. Last season, only Ceddanne Rafaela’s eight-year, $50 million extension was signed in the same time period. That could bode well for an ongoing number of clubs and players to hop on the bandwagon.
Needless to say, in Baltimore, there has been a growing outcry about when the O’s will get in the game and lock down a couple of their own.
That seems like a reasonable question, and it brings back bad memories of how the Orioles handled Manny Machado. After getting attached to Machado and then knowing the club missed its moment to sign him, the late Peter Angelos doubled down on his mistake by holding on to Machado in the second half of 2017 when his value would have been at its highest with a year and half of control left.
Ultimately, the only player of any value obtained by then-executive vice president of baseball operations Dan Duquette from the Dodgers for 2.5 months of Machado was right-hander Dean Kremer. If dealt the year before the O’s could have obtained two, maybe three top-tier prospects for a season and a half of Machado.
And while nobody in Baltimore — the fans or management — wants to lose Gunnar Henderson, Jackson Holliday, Adley Rutschman or Jordan Westburg, modern baseball requires teams to sign notable players or move on from them in time to truly make up for the loss.
Angelos held some, shall we say, inconsistent ways of making personnel decisions during his tenure of nearly 30 years at the helm. John Angelos had the temperament and wisdom to allow his baseball people run the baseball side, but he didn’t have access to the capital to contemplate signing guys like Rutschman early on.
That brings us to David Rubenstein and his group. They didn’t accrue the wherewithal to purchase the Orioles and MASN for $1.725 billion without being smart long-range planners. My bet is on the Rubenstein group and GM Mike Elias navigating these tricky waters much more expertly than the previous ownership group.
But remember, it takes two to tango on extensions. Henderson, Holliday and Westburg are represented by Scott Boras, who is notorious for not really engaging in the buyout game. Boras is perfectly fine with taking his players all the way up to free agency.
That leaves Rutschman and perhaps Cedric Mullins and Cade Povich as reasonable targets to extend. While it’s not impossible to somehow extend Henderson, the combination of Boras and just how good and expensive the shortstop is getting makes me think Henderson will be a painful test for the Rubenstein group. Westburg might be the most signable of the Boras trio.
In the modern game, if the Orioles were to lose a player of the magnitude of any of these guys, they have to end up with value on the other side.
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