
The St. Louis Cardinals continue to remain relevant in the postseason discussion thanks to a solid month-plus of play since the All-Star break. After struggling out of the break, the team has been one of the best in the National League since the calendar turned to August. They have done so with starting pitching that has kept the team in games and the continued offensive breakouts from Alec Burleson and Jordan Walker.
It does not show up in the box score, but another reason for the August success has been the consistent spectacular work the Cardinals have done with the glove. With a pitching staff that allows plenty of contact, the defense around the field gives the arms confidence to fill up the strike zone and let the fielders do the work. As the fourth-best defensive team in the majors this season, the glove work behind the staff has been nothing short of spectacular.
If you have been on social media in the past couple of months, there is a continuous debate about how much defense should be valued, especially when looking at the NL Rookie of the Year race. Unpopular side bar take: Give me a 30 homer, 100 RBI guy that knows the strike zone in the lineup. Sorry JJ.
For this iteration of the roster in St. Louis, however, the defense has been valuable for the pitch-to-contact staff. Wetherholt is one of the best defenders in baseball, regardless of position, and Alec Burleson has finally gotten the respect he deserves for his stellar work at the first base bag. Those two surprises and passable performance at the hot corner has taken some attention away from one of the best shortstops in the game in Masyn Winn. Currently, Winn and Wetherholt make up the best defensive middle infield in all of baseball and we have seen plenty of times where Winn’s arm (sorry Justin Turner) has gotten outs no other player in the game would be able to get.
Cardinals should lock up Masyn Winn before his bat makes him too expensive
The glove and arm have never been a question for Winn, who is in his fourth big league season. Where people still need convincing is with the bat, especially after the former top prospect put together a successful minor league career together on offense. It has not completely translated to the majors just yet, but there have been signs that he is on the verge of reaching another level in the box.
His current hand/wrist injury notwithstanding, Winn has looked more comfortable as a hitter with a noticeable change in his approach. Known offensive threat Pedro Pages suggested a slight change for the shortstop between games in a doubleheader, and the adjustment paid immediate dividends for Winn. In five games since, Winn has three extra-base hits and two walks, but he has still struck out eight times in that span. That level of offense, if sustainable, when matched with his otherworldly defense, to me makes Masyn Winn an easy choice for an extension.
As we all know, VEB has the smartest fanbase in baseball and the majority of you agreed with me in June when Doc ran a poll asking if Winn should be extended. 63% of you agree that now is the time to get it done, and I am pushing it a little further and saying they should get this hammered out before the end of the season.
My annual prediction of Masyn Winn being a 20 homer, 20 stolen base threat looks worse and worse every year, but expect me to beat that drum once again heading into the 2027 campaign. Since his solid rookie season, his overall offensive numbers have been going the wrong direction but there has always been a reason (or excuse) for why he has not yet reached the same level of production as he did in the minor leagues with his bat or his legs. Maybe all he needed was a little more Pedro Pages in his life to put everything together.
Winn debuted in 2023 as a 21-year-old coming off a strong season in Memphis and has been with the major league team ever since, mostly because of his nightly highlight reel plays. Because of the early debut, Winn will be arbitration eligible for the first time this offseason and will become a free agent after the 2029 season. At that point, the shortstop will be just 27-years-old and hopefully blossoming into the hitter we all want him to be.
That is why I have some concerns with the Cardinals playing the waiting game around Winn and his contract when talking extension. There has not been much reporting, if any, about either sides desire to work out a longer term contract, but that does not necessarily mean there is bad blood from anyone. To me, it signals that both player and team are hoping for more production from Winn and want to see additional improvement before sitting down at the negotiation table. If I were Chaim Bloom, which thankfully I am not, I would take these next few weeks to get a price and start talking numbers… just in case the bat does finally take off.
“Take off” for me means a .270 hitter that shows gap-to-gap ability and can pop double digit (I’ll drop my number to 15) homers and steal as many or more bases. Take that offensive skillset and put it on one of the best defensive shortstop in all of baseball and you now have one of the more complete players in the National League. C.J. Abrams is currently the only NL shortstop to surpass all of those numbers while Willy Adames and Elly De La Cruz have the power but not the average. Otto Lopez has the average and stolen bases while Konnor Griffin would have likely surpassed those numbers if not for injury.
In Abrams’ case, the Nationals are also planning to move him off of shortstop so if Winn could truly end up being that player we would be looking at a top shortstop in the league. Unfair expectations, sure, but he is still just 24 and will hopefully be in a lineup that will give him more opportunity to succeed in the future. Right now, Winn is relied upon to be a run-producer and also a table setter in the middle-third of the order but his skillset would be better used at the bottom of the lineup. With the Cardinals top four (or five) boasting above-average offensive potential, a couple free agent additions or other minor league options could push Winn to be the perfect 8/9-hole hitter in a competitive lineup.
So why is the time now if there are still so many questions about his bat? I want him locked up now because an investment into Winn for another six years is a safe option. While he has missed regular season time with minor injuries in his career, he has not looked hampered by the knee issues in a big way in the field. His arm will continue to play for another decade even if his lateral movement does drop a bit in the next few seasons. I am normally against paying for defense, but in Winn’s case, he has proven time and again to be a valuable piece up the middle and a major league-average bat would only raise his price.
If Bloom is able to get Winn to the table before the postseason, a six-year deal could end up being a discount if the Pages adjustment sticks. I am also a believer that he is a hard worker who wants to spend his best years in St. Louis, so rewarding him with confidence (and money) could continue to push him to be the hitter I still believe he can be.
I am pretty bad at comps and extension estimates, so anyone who is on board with a Masyn Winn extension should drop their thoughts below. I would like to say 6/$100 million would be a fair point for both player and team, but it’s also not my money.
Thanks as always!




















