4 times the Cardinals went after some of the best players in free agency

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One of the biggest complaints among St. Louis Cardinals fans and those who cover the team is that the club is unwilling to get uncomfortable with free-agent contracts and raise their payroll significantly.

It's true that the Cardinals find themselves outside of the top-10 payrolls in baseball by a significant margin. There is no website out there that can give you the actual payroll numbers that teams are working with, but they give you about as close of an estimate as we can get. Spotrac has the Cardinals with the 17th-highest payroll in baseball ($152 million) and is $53 million behind the 10th-place Atlanta Braves. FanGraphs has the Cardinals with the 14th-highest payroll ($172 million) and has them $23 million behind the 10th-place Astros.

While there are significant differences in those estimates, the point is the Cardinals are likely somewhere between $23 million and $53 million short of having a top-10 payroll in all of baseball, and that's with the current salaries they have in 2023. Shedding Adam Wainwright, Jack Flaherty, Jordan Montgomery, Jordan Hicks, Paul DeJong, Drew VerHagen, and Chris Stratton from their books all increase that number significantly.

John Mozeliak has been very candid that the Cardinals need to make changes to the way they approach team building, and has already identified the need to bring in, in his words, three starting pitchers via free agency or trade this offseason. All of this indicates to me that there will be a renewed level of aggressiveness shown this offseason by the front office.

Renewed? I'm sure some would say they've never had the level of aggressiveness needed to compete with the biggest markets in the offseason. While the Cardinals are not constantly in the mix for top-end free agents, they have indeed shown a willingness to dive into those markets in the past. They need to do so again this offseason.

Here are four times the Cardinals went after some of the best available free agents

Matt Holliday

Following the 2009 season, the Cardinals had a massive decision to make regarding free agent Matt Holliday. They acquired Holliday at the trade deadline as a rental, and he played like one of the best players in baseball down the stretch for St. Louis. Teams like the Yankees, Red Sox, Mets, and others were lurking, and St. Louis also had the looming free agency of Albert Pujols just two years away.

Holliday did not sign an extension with St. Louis before hitting free agency like many of their biggest signings have. He was on the open market, able to get competitive offers from other clubs, forcing St. Louis to have to outbid the market if they wanted to retain their star. Holliday was easily the best free agent available that winter.

And the Cardinals proceeded to hand out the largest free agent contract by any team that winter to Holliday, inking a seven-year, $120 million deal with the outfielder. Holliday was a Scott Boras client as well, adding even more to the list of things that would shock fans if it happened today.

While there are plenty of massive free-agent contracts that do not work out, Holliday was a huge part of the club's 2011 World Series victory and helped the club contend for National League pennants throughout the mid-2010s. Some may say "Well, $120 million is not that much money", but back in 2010, that was one of the largest contracts in baseball.

It's safe to say the Cardinals do not regret handing out that kind of money to Holliday, and it shows that not only were they willing to give out a large sum of money, but they also were willing to be the biggest spenders in free agency that year.

David Price

The Cardinals needed starting pitching in December 2015, and both David Price and the team believed that they had a deal in place before the left-handed played a round of golf that day.

Then the Red Sox came in and upped the offer by about $30 million, and Price inked a seven-year, $217 million deal with Boston that day. St. Louis was willing to go up to almost $200 million to sign one of the best-starting pitchers on the open market and was outbid at the very last second in a Hail Mary move by the Red Sox.

While we can all agree that the Cardinals dodged a massive bullet by missing out on Price, it's telling to me that they had the full intention of paying a starting pitcher that kind of money. Assuming Price's contract was the same amount of years in the $180 million range, that means St. Louis was looking to pay Price around $26 million a year annually to be a starter for them.

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Do you know who else will be looking for money like that in the near future? Aaron Nola, Blake Snell, and Yoshinobu Yamamoto. If the Cardinals are serious about improving their starting pitching this offseason, they'll get into a similar sweepstakes once again.

Sure, they did not go up to the $217 million number that Boston came in with last second, but that would have been $31 million a year over seven years for a starting pitcher. To put that into context, excluding extensions signed before free agency, Price's deal is the seventh largest free agent contract signed in the last decade, and second only to Gerrit Cole's massive nine-year, $324 million deal with the Yankees. Price's deal is the third-largest contract to a pitcher in MLB history when you include Strasburg's extension with the Nationals.

I don't blame the Cardinals for balking at that asking price. But I think we would all be fair to criticize them if they do not go back into the high-end pitching market to find a new starter this offseason.

Willson Contreras

Here's an example that actually gives me a lot of confidence that the Cardinals will back up their words when it comes to acquiring starting pitching talent.

Going into the 2022 offseason, Mozeliak and the Cardinals' front office made it abundantly clear to all of baseball that they needed to get a new starting catcher that offseason. They didn't even try to suggest that Andrew Knizner or Ivan Herrea could be the solution for them. Honestly, it may have made things harder for them since every agent and front office knew the Cardinals were backed up into a corner.

While the Cardinals balked at the asking price of the Oakland Athletics for Sean Murphy, to their credit, they pivoted to the best possible free agent available in Contreras and gave him a five-year, $87.5 million deal to become their new catcher. It's not a massive deal when compared to the kinds of deals that are handed out to top free agents today, but that much money over five years to a catcher is certainly a risk.

The Cardinals did not show up after the offseason saying they tried their best but the market was too high, and instead went bargain shopping or turned to players they viewed as "lesser options" internally. No, they went out and got one of the best players available to fill the need they had.

Jason Heyward

After trading for Jason Heyward to fill their right-field void for the 2015 season, the Cardinals were aggressive in their attempts to re-sign him, reportedly offering over $200 million to the outfielder. Instead, Heyward turned down offers of over $200 million from the Cardinals, Angels, and Nationals to sign a eight-year, $184 million deal with the Chicago Cubs.

Heyward helped the Cubs go on to win the World Series in 2016, but his contract ended up being a terrible one overall for the club. Again, like David Price, the Cardinals avoided a major mistake by not getting Heyward.

This once again showed the willingness St. Louis had to go out and offer one of the best deals possible to one of the best free agents on the market. Heyward has other motives though that led him to become a Cub instead.

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I'm not going to tell you that this guarantees the Cardinals will be making a massive signing this offseason. I won't even try to say that you should not be skeptical of them doing so. But what I do think these four examples show is that St. Louis has gone after top-end talents when they felt like they needed to. Do I find it frustrating that there are really only four examples in the last decade? Of course. But I think it does show that there is precedent for this kind of move, and I really do believe the Cardinals are ready to be aggressive in the starting pitching market.

Check out my weekly podcast "Redbird Rundown" on YouTube, Spotify, or Apple Podcasts as well as follow me on Twitter @joshjacoMLB for more Cardinals content

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