{"id":556820,"date":"2026-02-05T23:10:18","date_gmt":"2026-02-05T23:10:18","guid":{"rendered":"https:\/\/www.rawchili.com\/mlb\/556820\/"},"modified":"2026-02-05T23:10:18","modified_gmt":"2026-02-05T23:10:18","slug":"should-the-st-louis-cardinals-extend-masyn-winn-now-later-or-never-2","status":"publish","type":"post","link":"https:\/\/www.rawchili.com\/mlb\/556820\/","title":{"rendered":"Should the St. Louis Cardinals Extend Masyn Winn Now, Later or Never?"},"content":{"rendered":"

I think it\u2019s safe to say that most St. Louis Cardinals fans are anxious to identify the next St. Louis Cardinals core group of players you rebuild around. Once identified, you would hope to lock those players into long-term extensions. If you were St. Louis Cardinals President of Baseball Operations Chaim Bloom, would you work to extend shortstop Masyn Winn? Would your answer be now, later or never?<\/p>\n

The St. Louis Cardinals still have four years of team control as he\u2019s currently on a trajectory to reach free agency after the 2029 season, but he\u2019s eligible for arbitration after the upcoming 2026 season. Fangraphs<\/a> has Masyn pinned as a 3.6 WAR while ZIPS projects him with a 3.1 WAR for the 2026 season. His elite defensive skills have already been rewarded as a Gold Glove finalist in 2024<\/a> and a Gold Glove winner in 2025<\/a>. Offensively, Masyn had a solid 2024 slashing a .267 average with 15 home runs and an OPS of .730, but was hampered by nagging injuries in 2025 with his average dipping to .253, 9 home runs and an OPS of .673.<\/p>\n

What would a Masyn Winn extension look like? As I shared a few weeks ago<\/a>, it\u2019s believed that an extension at this point in his career would be somewhere in the neighborhood of 8 years for around $100 million dollars. My initial reaction to that number and those years is I would jump at the chance if I were Chaim Bloom and Masyn Winn\u2019s agent Andrew Guerra said yes. The cynical side of me says that I would wait at least one more year to see what Masyn\u2019s performance is like now that the torn meniscus in his right knee has been surgically repaired. That would be the reason for a potential \u201clater\u201d answer.<\/p>\n

The X factor for me is Masyn Winn\u2019s maturity and potential team leadership role. He addressed that during the Winter Warmup a few weeks ago. He said that he specifically wanted to help JJ Wetherholt adjust to the major leagues.<\/p>\n

Masyn Winn – \u201cAs far as\u2026leadership\u2026it\u2019s something I take pride in. I\u2019m gonna go out there and compete and play how I play\u2026I\u2019m really looking forward to playing with JJ\u2026I want him to be himself\u2026I want him to go out there and have some fun\u2026I wanna be there for JJ and let him be great.\u201d<\/p>\n

I\u2019ve seen enough of Masyn Winn to know that I want him to be a part of the new St. Louis Cardinals core, but I understand those who want to see more before they would offer an extension. What\u2019s your opinion? Now, later or never?<\/p>\n","protected":false},"excerpt":{"rendered":"I think it\u2019s safe to say that most St. Louis Cardinals fans are anxious to identify the next…\n","protected":false},"author":2,"featured_media":556821,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[2403],"tags":[5,160,4,673,67,65076,4311,4310],"class_list":{"0":"post-556820","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-st-louis-cardinals","8":"tag-baseball","9":"tag-cardinals","10":"tag-mlb","11":"tag-st-louis","12":"tag-st-louis-cardinals","13":"tag-st-louis-cardinals-analysis","14":"tag-stlouis","15":"tag-stlouiscardinals"},"share_on_mastodon":{"url":"https:\/\/channels.im\/@mlb\/116020551658820965","error":""},"_links":{"self":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts\/556820","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/comments?post=556820"}],"version-history":[{"count":0,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts\/556820\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/media\/556821"}],"wp:attachment":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/media?parent=556820"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/categories?post=556820"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/tags?post=556820"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}