15 free agent and trade near-misses that would've changed Cardinals history

15 near-misses in free agency and trade market that could've changed Cardinals' history

Almost every single season, we all wonder what the St. Louis Cardinals will do to improve their roster. Rumors often swirl around the league about what they could be up to, most of the time having very little substance to them.

But sometimes, those rumors were founded, and there are moves that came so close to being true but just weren't in the "cards". See what I did there?

Some of these "near-misses" end up being bullets dodged for the club. Whether it was deciding to hold onto a prospect who would later be a major contributor, or refusing to give out a large contract to a player who would end up being a bust, those missed deals or trades feel very good looking back on them.

Other times, the club had an opportunity to change their trajectory for the better and instead chose to pass on that free agent signing who would have been the perfect fit or decide not to trade for a player who would have proven to be an excellent trade. Sometimes you can feel the "miss" at the moment, but there are also misses that you don't realize how big of a deal it would've been until years later.

The Cardinals, because of their rich history, have a number of these situations that you can look back on. Because of how good industry insiders have gotten at leaking information in recent years, even a team as tight-lipped as the Cardinals has begun to have their thinking leaked to the general public.

Let's look at 15 near misses, in no particular order, that could have changed Cardinals history.

David Price, 2015

Here is the first line from Bob Nightengale's story in December 2015.

"David Price teed off Tuesday morning at a charity golf tournament in Las Vegas believing he would be spending the next seven years pitching for the St. Louis Cardinals. By the time he left the event hosted by former major leaguer Wally Joyner, Price had agreed to become a member of the Boston Red Sox with a deal that will make him the richest pitcher in history."

Price was signed to a seven-year, $217 million contract by the Red Sox, which was reportedly at least $30 million more than what the Cardinals had offered him.

At the moment, the deal made a ton of sense for Price. He was coming off his age 29 season where he went 18-5 with a 2.45 ERA for the Detroit Tigers and the Toronto Blue Jays and was second in Cy Young voting that year. But most people would agree that the deal went poorly though.

Although he helped the Red Sox win a World Series, he went 53-26 with a 3.78 ERA in 700 innings of work. He wasn't a bad pitcher the first three years of the deal, but overall, he wasn't the kind of pitcher you give a record deal to.

That kind of contract is an issue on your books, even for a team like the Red Sox or Dodgers, but imagine if the Cardinals had that deal, even at $30 million total less than what he got in his deal. That would have hamstrung their pocketbooks for years and would have been a huge disaster.

Fernando Tatis Jr., 2015

Former Cardinal Fernando Tatis Sr. opened the can of worms back in 2020 when he said in an interview that the Cardinals had scouted his son, Fernando Tatis Jr., and were close to signing him.

The Cardinals offered him a contract in international free agency, but the Chicago White Sox had outbid them for his services. Here's the real kicker though. They outbid the Cardinals by $100,000. Yeah, that's right, just $100,000.

Tatis Jr. was later traded to the San Diego Padres by the White Sox in the James Shields trade, and made his MLB debut in 2019 at age 20, finishing 3rd in Rookie of the Year voting while playing just 84 games. Tatis Jr. finished fourth in MVP voting in 2020 and 3rd in 2021 and has emerged as one of the best young players in the sport.

Obviously, his PED suspension is a huge black mark on his career, but I'm not sure many Cardinals fans would be against the idea of him as their shortstop or a corner outfielder right now. He has a career .955 OPS and is just 24 years old. Inserting him into the Cardinals lineup would take it to a whole other level.

Terry Francona, 2011

After the 2011 World Series win, Tony La Russa retired from being the Cardinals' manager, creating perhaps the hottest job in years for managers to interview for.

Being a manager for the Cardinals, especially when you get to inherit a team ready to win more World Series, should be any manager's dream. That is exactly why Terry Francona interviewed for the job, but the Cardinals decided to hire Mike Matheny instead.

Francona had already won two World Series as the manager of the Red Sox, proving to be the kind of manager that could replace La Russa. Matheny had no managing experience. Matheny would go on to manage the Cardinals for seven years with a 591-474 record, one World Series appearance, and losing in the NLCS twice. He was fired midway through the 2018 season when the Cardinals had a 47-46 record and missed the playoffs the two seasons prior.

Francona, on the other hand, became the Cleveland manager in 2013, posting a winning season every year except 2021 despite having top players like Francisco Lindor traded away from his team. He led them to Game 7 of the World Series in 2016 against the Chicago Cubs.

Francona is universally viewed as one of the game's best managers, and not only may he have helped the club win more World Series from 2012-2016, but he also may have helped this current Cardinals team scrap more wins until the front office fixes their rotation.

Jason Heyward, 2015

The Cardinals dodged two major bullets in the 2015 offseason. They were first outbid by the Red Sox for Price, but then they were also turned down by their free agent outfielder Jason Heyward, who took less money to sign with the Chicago Cubs that offseason.

To anyone who says the Cardinals don't make big offers, this offseason alone they made $200 million contract offers to both Price and Heyward. Heyward instead chose to sign with the Cubs, saying they were a younger team who were more ready to compete long-term than the Cardinals.

Heyward played a key role during the 2016 World Series, helping motivate the team to come back and win Game 7 against the Cleveland Indians. From 2016-2022 though, he slashed just .245/.323/.377 with 62 HR and 289 RBI, eventually being released by the Cubs after the 2022 season.

For as much as it hurt in the moment to see Heyward go to their rival, Cardinals fans are pretty excited that he left their money on the table.

Relocating to Detroit, 1935

I decided to sprinkle in a few more moves that weren't free-agent or trade related that could have drastically changed the history of the Cardinals. A move to a whole different city qualifies for sure.

In 1934, the Gashouse Gang beat the Detroit Tigers in the World Series. The Cardinals owner at the time, Sam Breadon, was open to moving the Cardinals to a different city, as they were not drawing the same amount of fans as other cities, and had another team, the Browns, in St. Louis already.

Back then, Detroit was a booming sports town and was ready to add another team if given the opportunity. But the Tigers' ownership would have never allowed for it, and the lack of other clear options ended up putting to bed the idea for the Cardinals' owner and they have remained in St. Louis ever since.

Giancarlo Stanton, 2017

Technically, the Cardinals traded for Giancarlo Stanton during the 2017 offseason. He just refused to waive his no-trade clause for them. And that decision had so many ripple effects for both clubs.

Stanton did not want to go to St. Louis or San Francisco and was later dealt to the New York Yankees instead, who took on about $270 million of the remaining $295 million on his deal. While Stanton is a fun player, his contract would have been a huge burden for the Cardinals.

From 2018-2023, Stanton has slashed .255/.339/.501 with 115 HR and 310 RBI. When he's healthy, he's still a mammoth bat in the lineup, but his health is almost never there. He's averaged about 100 games played each season for the Yankees and is pretty much a DH only for them. Although the Cardinals have the DH now, 2018-2021 would have been rough.

The Cardinals would then turn around and send the same package they offered for Stanton to the Marlins for Marcell Ozuna, who was one of the best hitters in baseball the year prior. The deal included future aces, Sandy Alcantara and Zac Gallen. At least they didn't trade them for a massive contract like Stanton, I guess.

Max Scherzer, 2003, 2014, and 2021

Yup. The Cardinals passed on Max Scherzer three times, the first instance being when they drafted him.

Scherzer was a local prospect who was coming out of high school, but the Cardinals did not offer him enough money as a 43rd-round pick to make it worth skipping college. He was later drafted 11th overall in the 2006 draft by the Diamondbacks.

After an incredible beginning to his career and winning his first career Cy Young in 2013, Scherzer was a free agent in the 2014 offseason, but the Cardinals did not seriously bid on him and he went to the Nationals on a seven-year, $210 million deal. Scherzer won two Cy Youngs during that contract, finished second one, and third twice while going 99-47 with a 2.75 ERA over the course of it.

Then after the 2021 offseason, Scherzer was once again a free agent, looking for a short-term deal with a record AAV. The Mets decided to grant him his wish, signing him to a three-year, $130 million deal. While this season has not gone well for Scherzer, he did go 11-5 with a 2.29 ERA in 145.1 innings last year.

Not signing him in 2021 is slightly defensible, but passing on him in 2003 and 2014 were huge mistakes. They did not sign their local high school product which could have been a huge asset in the early 2010s (he won Cy Young in 2013, the year they lost the World Series). And then they said no thanks in 2014 when the very next offseason they pursued Price with a similar kind of deal.

Oscar Taveras passing away, 2014

I remember the week the baseball world found out about the passing of Oscar Taveras. He has just put himself on the national scene during the NLCS loss to the San Francisco Giants but then passed away in a car accident in the Dominican Republic during the duration of the World Series.

The most important part of this point is that we lost a life in 2014, something that we can all agree we wished never would have happened and is a terrible tragedy.

While that's the most important thing to remember, we did also lose out on a potential superstar outfielder in the making. Taveras was the best Cardinals' prospect since Albert Pujols, boasting one of the best left-handed swings you'll see from a guy that young.

The Cardinals spent the next few years trying to find ways to replace what they thought he would become, trading for Ozuna, signing Dexter Fowler, and other moves that set the club back significantly.

No one knows how Taveras' career would have panned out, but it is crazy to think he would be turning 31 years old in June.

Bryce Harper, 2018

While the Cardinals did not make a play for Bryce Harper while he was in free agency, this to me remains one of the biggest mistakes they have ever made.

Harper had just finished up his age-25 season when he hit free agency and had a career .900 OPS in his age-19-25 seasons while making six All-Star teams and having one of the best seasons in MLB history in 2015 when he won the MVP.

Harper sat in free agency most of the winter, eventually receiving a 13-year, $330 million deal from the Philadelphia Phillies. While this deal seems massive, you need to remember three things. First, Harper was going to turn 26 during the first year of the deal, so he was only signed through his age-38 season. Second, the deal was so long that he's only making $26 million a year, which makes him only the 19th highest-paid player in baseball this year. Third, Harper was so good, that he deserved every dollar he wanted.

What has Harper done since he signed that deal? He's arguably been better. He's had a .939 OPS since 2019, won another MVP, and was clutch for the Phillies on their way to the World Series in 2022. The Cardinals should not have sat on the sideline and let Harper end up becoming underpaid by another team.

And since he is not making an insane AAV like many of the biggest deals in today's game, the club could have afforded him, Paul Goldschmidt, and Nolan Arenado.

Marcus Stroman, 2021

When free agency started in 2021, Marcus Stroman felt like the perfect signing for the Cardinals. They instead decided to pay Steven Matz, locking them into another underperforming back-of-the-rotation starter instead of grabbing a guy who could have led their rotation this year.

The three-year, $71 million deal that Stroman got from the Cubs is a lot more money than the four-year, $44 million that Matz got, but you get what you pay for. Stroman put up a 3.50 ERA in 138.2 innings last year, and so far in 2023, has a 2.28 ERA in 47.1 innings of work.

The Cardinals have invested way too many dollars in middle-of-the-rotation arms in recent years, burning them time and time again.

Stroman, on the other hand, is killing it for the Cubs and would have helped stabilize the Cardinals' rotation in a huge way. Not only would the Cardinals be in a much better spot right now, but then they could go into the deadline and get one more ace and have a strong playoff rotation of that new ace, Stroman, Montgomery, and Mikolas or Flaherty.

Josh Donaldson, 2018

Right before the beginning of the 2018 season, the Cardinals reportedly offered then-prospect Jack Flaherty to the Toronto Blue Jays for a one-year rental of Josh Donaldson.

The Blue Jays said no, which turned out to be a very good thing for the Cardinals. Donaldson played in just 52 games in 2018, posting a .801 OPS, while Flaherty was a stud for the St. Louis rotation in 2018-2019.

Where things could have really gone south for the Cardinals is that they likely would have tried to extend him if they were giving up that kind of asset to get him. So not only would they have dealt Flaherty, but they may have been stuck with Donaldson long-term, instead of grabbing Nolan Arenado from the Rockies.

Alex Reyes, Carlos Martinez, and Jack Flaherty staying healthy

While we can talk over and over again about the Cardinals trading away or not signing certain starting pitchers, it would not be as glaring of an issue if Alex Reyes, Carlos Martinez, or Jack Flaherty had stayed healthy for the club.

Alex Reyes was one of the top prospects in all of baseball and showed during his debut season in 2016 that he had all of the makings of an ace. Unfortunately, he began to battle numerous injuries after that, relegating him to becoming a bullpen arm but still struggling with injuries today.

Jack Flaherty was one of the top starters in baseball from 2018-2021, finishing 4th in Cy Young voting in 2019 and 13th in MVP voting. He has battled numerous injuries since then as well and has lost a lot of his velocity now as well.

I think people forget how good Carlos Martinez was for the Cardinals for most of his career. From 2015-2018, Martinez went 50-33 with a 3.22 ERA and 8.9 SO/9 while being named to two All-Star teams.

Honestly, it's shocking that the club could have three talents like that in their rotation recently and all three would let injuries derail their career. Pair that with losing guys like Sandy Alcantara and Zac Gallen, and it's crazy to think they now have such a bleak rotation.

Zack Wheeler, 2019

Approaching the trade deadline in 2019, the St. Louis Cardinals had the opportunity to add a very good starter in the form of Zack Wheeler, but the Mets were asking for one of Harrison Bader or Tyler O'Neill, and the club decided to pass on the move.

Wheeler ended up not being dealt, but was elite down the stretch, posting a 2.83 ERA during the second half, netting him a big contract from the Phillies in the offseason.

There's no guarantee the Cardinals could have brought him back in free agency, but the club does have a good track record of retaining guys when they trade for them. Since signing his new deal, he has gone 33-21 with a 2.91 ERA in 482.1 innings, finishing second in Cy Young voting in 2021.

I know Bader was a fan favorite, but it sounds like he could have easily brought an ace to St. Louis, so I'm shocked they passed on that.

Sean Murphy, 2022

Last but not least, the Sean Murphy sweepstakes will be linked to the Cardinals for years to come.

Contreras has been an awesome Cardinal so far, so this is not necessarily a bad thing that the Cardinals went in that direction instead. Had the Cardinals traded for Murphy, they likely would not have two of the following players anymore: Nolan Gorman, Lars Nootbaar, Brendan Donovan, or Gordon Graceffo.

Now, the Cardinals would instead have the best catcher in baseball, who may be a net positive on the pitching staff and could have signed or acquired guys like Cody Bellinger, Dansby Swanson, Nathan Eovaldi, or Pablo Lopez instead of spending money on Contreras.

We won't know the true repercussions of this deal until years from now, but outside of the chaos the Cardinals have created by removing Contreras from catching duties, it looks like the Cardinals were able to avoid giving up emerging stars in Gorman and Nootbaar, and very valuable pieces in Donovan or Graceffo.