Where Does Alex Bregman Fit Among Cubs' Largest Contracts Ever?

Chicago is home to five Big Four teams, the fourth-most in the country. The city offers everything a professional athlete could ever dream of in a home base. Full disclosure: I am a lifelong Red Sox fan. In most areas of my life, I strive to be progressive and forward-thinking. But when it comes to baseball, I reject modernity and embrace tradition. That’s part of why I hold a soft spot for the Cubs. Like the Red Sox, they echo this sentiment with the second-oldest ballpark in baseball and a passionate, cross-generational fanbase.

In light of the Alex Bregman signing, I’ll admit — if given the choice between living in Chicago and Boston, I’d choose the former. Chicago boasts an affordable cost of living compared to other major domestic markets. The Art Institute of Chicago has one of the best art collections in the world. Given its location, there’s an endless array of outdoor activities along Lake Michigan and the Chicago River. Its food scene is as good as it gets. (For me, a city automatically gets bonus points for having a Nobu and a Starbucks Reserve Roastery.) Movies set or filmed in Chicago are stronger than those from Boston, no matter how many times Ben Affleck tries to prove otherwise.

While Chicago’s appeal gets athletes to pick up the phone, money ultimately closes the deal. The Cubs’ free-agent history might be modest by MLB’s current standards, but the signing of Alex Bregman signals a shift in Jed Hoyer’s approach to acquiring talent. So, let’s dive into how the Cubs got here.

1. Jason Heyward: 8 years, $184 million

In his walk season, Jason Heyward put together one of the strongest performances of his career with the St. Louis Cardinals. Unfortunately, his offensive production never matched the Cubs’ largest contract in franchise history, as he posted a .245 AVG, .700 OPS, 88 wRC+, and 7.2 fWAR. His defense, however, was top-notch. After winning his third Gold Glove in 2016, Heyward became the first position player to win the award in three consecutive years with three different teams. Teammates raved about his clubhouse presence, and he was regarded as a strong leader. With one remaining season left on his contract, the Cubs ended up releasing Heyward in November 2022.

2. Dansby Swanson: 7 years, $177 million

Three seasons into his Cubs tenure, Dansby Swanson has recorded a .243 AVG, .721 OPS, 101 wRC+, and 12.4 fWAR. While his bat is average ( @RandallPnkFloyd noted he has a ton of swing and miss stuff in his profile), Swanson’s defense is elite. Since 2023, he ranks third among qualified shortstops with 20 Outs Above Average and a Fielding Run Value of 31.

Swanson has four remaining years left on his contract, so it’s a little premature to evaluate it fully. As much as I love statistics, I’m also a strong supporter of intangibles and makeup. Much of Swanson’s value is reflected in his clubhouse presence and leadership role. As a long-term fixture in the clubhouse, he serves as a mentor for younger players like Pete Crow-Armstrong and Matt Shaw.

3. Alex Bregman: 5 years, $175 million

North Side Baseball has posted several quality articles about the Alex Bregman signing. To avoid repeating what’s already covered, you can read more here:

• Anatomy of an At-Bat: What Alex Bregman Brings to the Table by Jason Ross

• Should We Be Worried About Alex Bregman Hitting for Power at Wrigley Field? by Randy Holt

• Like Dansby Swanson, Alex Bregman Was Always Cubs' Top Target by Matt Ostrowski

• Alex Bregman's Swing is Exactly What Cubs Lineup Was Missing by Matthew Trueblood

• How Cubs Lineup Could Look with Alex Bregman in Fold by Matthew Trueblood

4. Jon Lester: 6 years, $155 million

Like Alex Bregman, Jon Lester opted to sign with the Cubs over the Red Sox. Lester was a dependable workhorse who embodied a bygone pitcher archetype just as pitch-tracking and velocity/movement started to dominate baseball. Metrics/statistics don’t truly capture his value, and on paper, they’re average. Between 2015 and 2016, his four-seamer only averaged at 92.9 mph. And yet, Lester posted a 3.64 ERA, 3.86 FIP, 15.5% K-BB%, and 16.8 fWAR in 1,002.2 innings in Chicago. On his best days, he’d throw seven to eight solid innings — sometimes a complete game — and provide the bullpen with some rest. Lester left an enduring legacy as a reliable ace, clubhouse leader, and key component in breaking the Cubs’ 108-year World Series title drought. 

5. Alfonso Soriano: 8 years, $136 million

For a full breakdown of Alfonso Soriano’s career, check out his bio from North Side Baseball’s Players Project. In the preceding season before Soriano signed with the Cubs, he rejected a couple of extension offers from the Nationals. During his Cubs’ tenure, he led the team in fWAR (18.1) and posted a .264 AVG, .812 OPS, and 109 wRC+. He slugged a total of 181 home runs and never hit fewer than 20 in a single season. As Soriano aged, his defense regressed heavily. Between 2007 and 2013, his minus-13 Defensive Runs Saved ranked 47th among outfielders. However, in his first season with the Cubs, he graded out at 17 (3rd). Two years later, it plummeted to minus-11 (56th). Soriano’s teammates regarded him as a veteran role model who carried himself with professionalism. 

A few days before the 2013 trade deadline, Soriano was sent to the Yankees in exchange for pitching prospect Corey Black. He had a little over one year remaining on his contract.

How will Bregman’s contract age? Only time will tell.

Long-term free agent deals rarely age well, but the Cubs can afford to take the risk. They consistently generate one of the highest revenues in the league — $585 million in 2024, ranking third — so they can afford to absorb the back end of Bregman’s deal. The Cubs have consistently prioritized clubhouse presence in their long-term contracts. Bregman fits that mold perfectly, along with a proven track record of winning.