Jordan Montgomery sends message to Scott Boras after horrible free agency showing

World Series - Texas Rangers v Arizona Diamondbacks - Game Five
World Series - Texas Rangers v Arizona Diamondbacks - Game Five / Christian Petersen/GettyImages

The name of the game this offseason was pitching. The free agent crowd was jam-packed with some of the best pitchers around but light position players, so fans sort of expected a mad dash from teams to make up for their deficits. Instead, what we got was one of the most agonizingly slow free agent periods in recent memory.

Largely to blame for the stalling was high-powered agent Scott Boras, who maintans a packed list of notable MLB clients. Five of them hit free agency at the end of last season — Blake Snell, Cody Bellinger, Jordan Montgomery, Matt Chapman, and JD Martinez — all of whom were expecting massive payouts and probably figured they had the man for the job. Boras is known for his hardheadedness and ability to milk huge amounts of money out of teams for his clients.

That hardheadedness was still very present, but the latter trait not so much. All five had to settle for what basically come down to one-year deals (with player options galore) and lower salaries than anyone was projecting because Boras was playing chicken with teams. Montgomery was the last domino to fall, signing with the Diamondbacks a day into the regular season.

It was easy to imagine that all five were probably displeased with their outcomes, and Montgomery turned his displeasure into action. He reportedly dropped Boras as his agent, instead turning to Wasserman agents Joel Wolfe and Nick Chanock.

Jordan Montgomery fires Scott Boras after MLB free agency debacle

After his World Series-winning run with the Rangers, during which time he threw 31 innings for a 2.90 ERA, predictions for his next contract generally ranged between five years and around $100 million to six years and $150 million. What he got instead was one guaranteed year and $25 million for it, with a player option for a second year and escalating pay based on the number of starts he makes in 2024.

The problem with Boras' strategy is clear: he thought teams would cave faster than he would. Based on all of the Boras Five's deals, he was wrong.

Wolfe's clients include Nolan Arenado, Yu Darvish, Trevor Story, Giancarlo Stanton, and Yoshinobu Yamamoto, who received the highest value contract for a pitcher this year. His career earnings on behalf of players is a staggering $1.2 billion, so it seems like Montgomery will be in better hands as Boras may be losing his touch.