When Alex Bregman entered free agency, he was absolutely clear about what he wanted. Harboring “no desire to accept a short-term contract,” the player patiently waited for the exact moment for the light to go off. However, that’s easier said than done as the clock ticked by with no contracts in sight. At one point, Bregman was reported to be conversing with multiple teams, but a problem presented itself.

Despite being a two-time All-Star and World Series champion, as well as a Gold Glove and Silver Slugger Award recipient, hitting for a 132 OPS+ for his career, and being tied for the 12th most Wins Above Replacement since 2016, the conundrum was so much so that Bregman’s free agency status trickled down to February, despite his status as the best player available in the open market.

The Houston Astros had reportedly made a six-year, $156 million offer to the 30-year-old in November last year, which the latter had gracefully declined in hopes of a seven-year, $189 million contract. The problem now? Teams were finding it pretty difficult to keep up. As per CBS Sports’ RJ Anderson, “Blame it on the local television contract quagmire; blame it on the greed of the owners; blame it on whatever other factors you want. The bottom line is that it’s difficult to gin up a market for a top free agent when there are so few teams willing to enter a bid.” 

However, like they say, all’s well that ends well. Last week, raising several eyebrows (the reason for which we’ll tell you later), the third baseman signed a three-year, $120 million contract with the Boston Red Sox. Notably, Boston had drafted the two-time All Star the 29th round out of high school in 2012, but eventually didn’t sign him. The catch? As per ESPN’s Buster Olney, the player’s deal also includes an opt out after 2025 and ’26, and several deferrals—used to put off owed money into the future and lessen the burden in the present—that reportedly reduces the contract’s present day value to around $90 million. A rather gloomy prospect, isn’t it?

Well, Bregman’s surely not sad about it. In an introductory news conference on Sunday, the player had confidently stated, “I’m a winning player. This is a winning organization. Those players are winning players. We have winning coaches here. I plan on winning here after talking with some of the guys over the last two days. I can see that there’s something special here.” But wait till you what the other offer was, and you’re surely going to be confused.

The veteran was reportedly offered a six-year, $171.5 million with an opt-out clause after the 2026 season, which he surprisingly resigned. Was it all about the money, then? Yes, and no. Apart from the Astros and the Tigers deals, Bregman reportedly also had an offer from the Cubs for four years and $120 million with opt outs after ’26 and ’27, but ultimately chose the one where he’d get the highest average annual deal, as Boston made a last-minute push to bump their newest player’s salary to $40 million per year. However, ask the player himself, and he’s surely not going to mention that.

And that’s exactly what happened during the press conference when a media personnel asked, “What questions did you have for…[the] guys throughout the organization when you were trying to make the decision [on] if you want to come here or not?”

To this, Bregman responded, “When Scott [Boras] and I started out and started talking about places we may want to go, winning was the most important. So, when they showed their vision on how this organization was going to win now and in the future, that was pretty cool.”

Having said that, looks like the Tigers ultimately failed to get their hands on a player they absolutely needed…

What did Detroit lack in their offer? 

The Tigers threw down $28.58 million per year for six seasons, while the Red Sox sweetened the deal with $40 million per season for just three years. Reflecting on the most appropriate choice for Bregman, Boston indeed looks like the part. Heavy bucks pour in with the option to hit the free market after a single season. For the Red Sox, it’s a huge win securing the New Mexico native.

The road ahead, however, is very different for the Tigers.

They will now count on Matt Vierling and Jace Jung to help pick things up at third. Vierling, 28, has seen 443 games in his career and is, by and large, a right-handed hitter. Jung, the 24-year-old prospect, has a lot of offensive potential but needs to sharpen his defense. It’s a bit of a gamble, but hey, sometimes that’s how you find hidden gems.

With spring training breathing down the neck and Bregman heading to Boston with a fat contract and a clear path to more riches, the Tigers are left to hope Vierling and Jung can fill some pretty big shoes.

Do you think they will be able to? Comment your thoughts here!