BANK ON BREGGY

How an unconventional approach could keep Alex Bregman in an Astros uniform

How an unconventional approach could keep Alex Bregman in an Astros uniform
Can the Astros afford to let Alex Bregman hit free agency.?Composite image by Brandon Strange.

Astros owner Jim Crane may want to check under his sofa cushions for loose change, start clipping coupons, take a hammer to his piggy bank, and consider playing golf after 1 p.m. and eating dinner before 5 p.m. for the early bird special. Because the price of signing star third baseman Alex Bregman to a contract extension – which the Astros have said is on their to-do list – just went through the Minute Maid Park roof.

Breggy may want to send Manny Machado a thank you note and a free case of salsa.

The San Diego Padres signed their All-Star third sacker Machado to an 11-year contract worth $350 million this week. If Machado got $350 million, what will Bregman be worth if the Astros allow him to hit the free agent market after the 2024 season?

Let's compare and contrast. Actually there isn't much to contrast. Machado and Bregman have put up remarkably comparable numbers during their careers.

Career batting average: Machado (.282), Bregman (.277).

On-base percentage: Machado (.341), Bregman (.375).

OPS: Machado (.833), Bregman (.872).

Slugging: Machado (.493), Bregman (.497).

Both are slick fielders and fan favorites in their home cities. Machado was the third player taken in the 2010 draft. Bregman went No. 2 in 2015. Bregman has the edge in postseason statistics, a higher batting average and, of course, two World Series rings to Machado's zero. Of course, it helps that Bregman has played his entire 7-year career with the Astros while Machado has bounced from Baltimore to Los Angeles to San Diego during his 12 years in the big leagues.

Getting back to … if Machado is worth $350 million now without having to go through free agency, what might Bregman command on the open market if he stays healthy and productive through the 2024 season? The number could be staggering.

Bregman's agent is Scott Boras, who isn't exactly known for playing footsie with team owners and offering hometown discounts. You see Machado's $350 million? His agent is Boras. While we can only guess what baseball's economy will be like in 2024 heading into the 2025 season, what goes up doesn't always come down.

The stars and dollar signs are lining up for Bregman. The New York Yankees might be lurking for a third baseman. The current Yankee third baseman is Josh Donaldson. If you're real quiet, you can hear the echo of Yankees fans booing him last season when Donaldson hit a career low .222, He's also 37 years old. The Yankees played a split-squad game this week. Donaldson was with the B-team. While Donaldson is still the starter, consider that a message delivered.

Machado is 30 years old. That's how old Bregman will be at the end of 2024.

Bregman has a lot of intangibles in his favor. He is a baseball fanatic, obsessed with the game. He is involved with the city, offering his time to charities. He was born to do post-game interviews. He is a marketing dream. He has his own line of condiments.

Unlike the Astros, the Yankees aren't averse to offering long-term contracts, which Bregman surely could command in free agency. Sure, Bregman is saying all the right things down in spring training. He loves the Astros, he loves Houston, he loves his teammates. The Astros certainly would love to have Bregman play his entire career in Houston. His agent loves money and long-term deals, though.

Let's not minimize this, especially if he hits free agency and the Yankees are desperate for a third baseman. Bregman is Jewish. He would be a dream acquisition for New York. There are 1.6 million Jews in New York City. That's more than Tel Aviv and Jerusalem combined. Endorsement deals? Fugeddabbout it. Bregman's wife Reagan is a regular guest on Channel 2's Houston Life show. She would be hosting Coffee Talk on cable in New York.

Bregman, to his credit, isn't shy about saying he's open to suggestions of what might be available to him. Beloved as Bregman is in Houston, the Astros have said goodbye to popular players rather than offer long-term contracts. What the Astros could do is this - tear up his current contract and offer Bregman insane money, whatever it takes, over five years. That would keep Bregman here at least for the short haul, and Bregman would be only 33, still in his prime, when he's up for a new contract. Done deal.

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Gerrit Cole and Hunter Brown share the same agent now. Composite Getty Image.

There's no denying that this year's World Series champs (LA Dodgers) have some serious firepower on their roster. And one of the ways they were able to assemble such a talented team involved players like Shohei Ohtani being willing to differ their money.

Just this week, there was some speculation that the Yankees could do something similar when restructuring Gerrit Cole's contract, that would allow them more flexibility in the present.

The Yankees ended up calling Cole's bluff about opting out, and no adjustment was made to the contract.

But this situation got us thinking, would the Astros consider a tactic like this to maximize the roster? At this point, it doesn't seem all that likely. Just last year, the team handed out a $95 million contract to Josh Hader, without any differed money.

The other factor that also has to come into play is the tax threshold. The organization would have to give the okay to go over it again in order to make a splash signing this offseason. Which unfortunately does not sound like the plan right now when listening to GM Dana Brown at the Winter Meetings.

Astros pitcher hires a new agent

Now that MLB free agency is in full swing, most of the attention moving forward will be focused on players like Alex Bregman, Pete Alonso, and Juan Soto.

But for Astros fans, there might be someone else to keep an eye on this offseason and next. Starting pitcher Hunter Brown quietly hired super agent Scott Boras recently.

With Brown still another season away from his first year of arbitration, he should be with the Astros for the foreseeable future.

However, the hiring of Boras does raise some interesting questions. Why make the move now? Certainly, Brown could use some more cash, as he's set to make less than a million in 2025.

Perhaps Brown wants to land some HEB commercials to fatten his wallet. And if Bregman does leave the team in free agency, a spot will open up for another player, in theory. And three of the players in the HEB ads are represented by Boras (Jose Altuve, Lance McCullers Jr. and Bregman).

Jeremy Pena has been stacking cash from Taquerias Arandas for several years now, maybe Brown would like an opportunity to do an endorsement similar to that.

I say all this half kidding, but Brown does look like the future ace of this staff, and I'm sure there are plenty of advertisers that would have interest in Hunter.

There is another element that could have initiated the hiring of Boras. Would Brown be willing to sign an extension early with the Astros similar to the deal the team made with Cristian Javier?

Their situations are actually pretty comparable, except Javier was one year further into his career (3 years of MLB service time) and eligible for arbitration before agreeing to the extension.

If Brown was heading into arbitration this offseason, it wouldn't be surprising at all for the Astros to be considering a long-term deal with him that buys up all his arbitration years. The 'Stros love these types of contract extensions. We've seen them do it with Bregman, the aforementioned Javier, and others.

One of the main differences though between Brown and Javier is their rookie year numbers. Brown only pitched 20.1 innings in his first season (2022). While Javier pitched 54.1 innings his rookie year. However, his rookie season was in 2020, so Javier completed a full year of service time despite the shortened season. Whereas Brown didn't get called up until September 2022.

Another difference is performance. Javier never posted an ERA over 3.55 in his first three seasons. As opposed to Brown, who had a disastrous year in 2023. He made 29 starts, recording an ERA over 5.

It wasn't until May of 2024 that Brown started using his two-seam fastball with great success and becoming one of the most dominant pitchers in the American League.

The Astros had a bigger sample size to judge Javier. However, if Brown has another quality season in 2025, Houston and Brown should definitely be having conversations about an extension. Especially with Framber Valdez being in the final year of his contract in 2025. Hunter could be the unquestioned ace one year from now.

Still, though, there are some concerns with handing out these early extensions. For example, if the Astros had it to do over again, would they still extend Javier?

After receiving his extension before the 2023 season, he went on to post the highest ERA of his career (4.56), and then blew out his elbow in May 2024.

And if we're going by Luis Garcia's recovery timeline from Tommy John surgery, we may not see Javier pitch at all in 2025.

So even with a sample size of three terrific seasons, the Javier extension looks like a miss with the benefit of hindsight. It will be interesting to see if that deal impacts Dana Brown's decision-making going forward.

Especially since Javier was Dana's first big contract extension as the Astros GM.

Be sure to watch the video as we discuss how the Astros can get the most out of their roster, the pros and cons of signing Hunter Brown early, and much more!

*Catch our weekly Stone Cold ‘Stros podcasts. Brandon Strange, Josh Jordan, and Charlie Pallilo discuss varied Astros topics. The post for the week generally goes up Monday afternoon. Find all via The SportsMap HOU YouTube channel or listen to episodes in their entirety at Apple, Spotify or wherever you get your podcasts.

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