MLB insider Robert Murray wrote about Max Scherzer and the Cardinals' mutual interest in one another last off-season before he ended up signing with the New York Mets. The Cardinals passed on handing him the lucrative deal that the Mets gave Scherzer, but it's also not the first time the Cardinals passed on the future Hall of Famer.
Two other times during Scherzer's career, the Cardinals had the inside track to bring the right-hander into their organization. Being from the St. Louis area, he was drafted by the Cardinals in the 43rd round back in 2003. Scherzer grew up a Cardinals fan, but with the desire to attend college, St. Louis was going to have to, in his words, "buy me out of my commitment". The Cardinals decided not to.
The second time the Cardinals passed on Scherzer was during the 2014-2015 off-season, which saw them get outbid by the Red Sox for the services of David Price. The Cardinals and Scherzer reportedly had mutual interest once again, but for whatever reason, the Cardinals did not compete with the Nationals' offer.
Although one can say the Cardinals just do not hand out contracts like that to pitchers, it's obvious they were willing to go to that kind of number with Price during the process. The Cardinals aren't afraid to spend big money on quality players, their worry, like all of baseball, is that the player will not perform to the dollar value of the contract. In the case of Scherzer, he is one of the few pitchers who had pitched above the value of not just one, but two mega deals that he got in free agency.
The Cardinals will once again have an opportunity to pursue Scherzer in free agency this next off-season, but at the end of the day, this club's World Series chances would be drastically different had they gone for him at any of these inflection points of his career.