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

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.