With billions of dollars being thrown around on Major League Baseball’s free-agent market, it’s a good time to reminisce about the biggest contracts in each team’s history.

So, that’s what we’ve done—with a twist!

We could have sifted through all 30 teams’ free-agent signing histories—records of which dating as far back as 1991 are well-kept by Cot’s Baseball Contracts—in search of the highest guarantees, but that would have A) been boring and B) required making a faulty assumption that dollars from years past are worth the same as dollars in 2022.

Since that’s not the case, we dared to adjust for inflation.

We opted for the simple path of using the consumer price index and a standard adjustment calculation to gauge how much the value of deals has inflated since the season in which they began. For obvious reasons, we left pacts signed this winter alone. Here are the full results.

We didn’t limit ourselves to one selection for each club if the results were close. We otherwise carried out our analysis by asking two simple questions about each signing:

Was it a good idea?

Did it work out?

We’ll hand out honorable mentions in cases where a team’s highest unmanipulated guarantee is different from its highest inflation-adjusted guarantee.

Arizona Diamondbacks: Zack Greinke

Signing Year: 2015

The Terms: 6 Years, $206.5 Million

In 2022 Dollars: $253.3 Million

Was It a Good Idea?

This wasn’t so much a bad idea as the wrong team taking too big of a risk.

As he won the American League Cy Young Award in 2009 and was fresh off posting a Maddux-ian 1.66 ERA in 2015, Zack Greinke headed the desert with ace bona fides. But the Diamondbacks could only spend so much to flesh out the rest of their roster, hence how he accounted for 35 percent of their payroll in 2016.

Did It Work Out?

Not to the degree that the Diamondbacks hoped.

Greinke was mostly very good in pitching to a 131 ERA+ in the three-plus seasons he spent with the Snakes. But apart from a lone playoff run in 2017, the team struggled to make the most of his presence before it cut its losses and traded him to the Houston Astros in 2019.

Atlanta: B.J. Upton

Signing Year: 2012

The Terms: 5 Years, $75.25 Million

In 2022 Dollars: $95.1 Million

Was It a Good Idea?

Heavens, no.

B.J. Upton had his moments with the Tampa Bay Rays—never more so than during his legendary eight-game run during the 2008 playoffs—but his production got increasingly volatile toward the end of it. He posted just a .316 OBP from 2009 to 2012, culminating in an ugly .298 OBP in ’12 that should have scared Atlanta more than it did.

Did It Work Out?

Once again: Heavens, no.

Rather than revert to what he had been in his best days with the Rays, Upton didn’t do much of anything as he posted a 66 OPS+ and minus-1.7 rWAR across 2013 and 2014. After that, Atlanta’s only way out was to package him with Craig Kimbrel in a trade to the San Diego Padres that quickened an ongoing rebuild.