Absurd Alex Bregman contract demand would suggest Scott Boras hasn't learned a thing

All eyes are on Juan Soto and where he's going to sign, but he isn't the only star position player that super-agent Scott Boras is representing. Alex Bregman is another Boras client who has hit the open market and is going to look for a massive contract in free agency.

During his nine seasons with the Houston Astros, Bregman has consistently been one of the best third basemen in the game. He's a two-time All-Star, a Silver Slugger winner, a Gold Glove winner, and a two-time World Series champion. Not only is his regular season resume impressive, but he has 99 career postseason games under his belt. That's over half of a regular season.

Given all Bregman has accomplished at age 30, he's going to receive tons of interest. The Athletic's Tim Britton (subscription required) believes he'll eventually ink a seven-year deal worth $189 million, paying him $27 million annually.

While that's a pretty penny, it doesn't feel too far-fetched. Bregman is very good, and free agents often get more money than fans expect them to. Ken Rosenthal of The Athletic believes that the $189 million Britton has Bregman making isn't close to the demands Bregman and Boras will have. He believes that Bregman and Boras will be seeking something similar to the 11-year, $350 million extension that Manny Machado signed with the San Diego Padres ahead of the 2023 campaign. That's going from a lot of money to an astronomical amount of money.

"The Athletic’s Tim Britton projects a seven-year, $189 million contract for free-agent third baseman Alex Bregman. I suspect that Bregman and his agent, Scott Boras, are aiming higher — specifically, at a deal closer to the 11-year, $350 million extensionManny Machado signed with the San Diego Padres in February 2023," Rosenthal wrote.

If true, these demands would prove to be costly for Bregman and would prove Boras hasn't learned a thing from last offseason.

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Astronomical contract demands would prove Scott Boras hasn't learned a thing

When Machado signed his mega-extension, he was not only an established superstar, but he was coming off a season in which he finished as the NL MVP runner-up and helped lead the Padres to an unlikely NLCS berth. Those factors, combined with the Padres doing whatever they could to ensure Machado did not opt out of the initial deal he signed and some desperation from late owner Peter Seidler to field a winning team forced the front office's hand. Bregman has none of these things going for him.

While he's still a good player, Bregman's .768 OPS this past season was a career low. His OPS has steadily declined from .820 to .768 over the last three seasons, and he hasn't come close to replicating his MVP-level season in 2019. He hit 41 home runs, drove in 112 runs, drew 119 walks, and had a 1.015 OPS that season. He has not hit more than 30 home runs, driven in 100 runs, drawn 100 walks, or had an OPS over .820 since then. He is still good, but good players don't get anything close to $350 million. Bregman is not 2022 Machado, especially after the season he just had.

With that in mind, no owner is going to come close to shelling out $350 million for Bregman - nor should they. It'd be surprising if a team offered him $200 million based on the platform season he just had.

If Boras holds firm at these insane demands, Bregman will be in for a long offseason. It sounds as if he could be in for the same kind of offseason that Boras clients such as Jordan Montgomery, Blake Snell, Cody Bellinger, and Matt Chapman had last offseason.

All four of those players were projected to receive long-term deals but settled for short-term high-AAV deals. If Boras is stuck at the $350 million figure or anything close to it, Bregman will be waiting a long time for a deal that inevitably will never come. The longer he waits, the more likely it is that he'd inevitably have to settle for a similar kind of short-term deal once teams find their Bregman alternatives.

While the short-term deal proved to be fine for Chapman thanks to his mid-season extension, the other three who waited are still searching for their long-term deals. It went so poorly for the Boras Four to the point where MLB fans were calling him "washed." Bregman could take a risk by taking a short-term deal hoping to build his value up further, but that also raises the chance of him never even getting the $189 million Britton projects.

As of now, it's unclear what kind of contract Boras is seeking for Bregman. If it's anything close to the $350 million that Rosenthal throws out, though, that could prove to be costly for his client and would prove that he didn't learn a thing from last offseason.