The Toronto Blue Jays made big news on Monday by extending Vladimir Guerrero Jr. The 14-year, $500 million deal has fans of many other teams dreaming of long-term deals for their young stars. One of those fan bases is the Cincinnati Reds, who have a superstar in Elly De La Cruz, who will need a new contract soon. Multiple ESPN insiders say that won't be happening for one specific reason.

The answer would've been Gunnar Henderson or Elly De La Cruz — if their agent wasn't Scott Boras, who has a track record of preferring to take his star clients to free agency,” ESPN's Jorge Castillo said when asked who the next star to sign would be. Buster Olney simply said, “Elly De La Cruz.” And David Schoenfield said, “The window might be closing for a De La Cruz extension with the Reds, but I'd love to see Cincinnati lock him up like the Royals did with Bobby Witt Jr.”

The Reds have not signed a big-money contract in years, but De La Cruz is an elite talent they need to keep. While they are a small market team, this is the type of player they need to keep for a long time.

The Reds need to figure out how to pay Elly De La Cruz

Related Cincinnati Reds NewsArticle continues below
Reds OF Rece Hinds stand alone atop with huge MLB milestone
Reds OF Rece Hinds stand alone atop with huge MLB milestone
Fans wear a Pete Rose jersey at Great American Ball Park during the Cincinnati Red’s Pete Rose night at the ballpark on Wednesday, May 14, 2025 in Cincinnati. Rangers
Rangers coach gets brutally honest about why Pete Rose shouldn’t be ‘in’
Cincinnati Reds manager Pete Rose greets first baseman Terry Francona (10) at the dugout during the 1987 season.
Reds manager Terry Francona claims ‘there’s no Hall of Fame’ without Pete Rose
Cincinnati Reds shortstop Elly De La Cruz (44) celebrates at second base after hitting an RBI single during the seventh inning against the Milwaukee Brewers at American Family Field.
Jeff Hanisch-Imagn Images

Across the Queen City, the Bengals are trying to figure out how to pay all of their superstars. They have paid Joe Burrow, Ja'Marr Chase, and Tee Higgins, but can't field a competitive defense at the same time. The Reds have two players, Nick Martinez and Jeimer Candelario, making over $10 million this season. De La Cruz would likely make four times that.

Part of being a small-market team is taking advantage of every window. In the first two years of his excellent career, De La Cruz has not played in the playoffs or finished over .500. The Reds have multiple years of control left on the shortstop, but they should be trying to extend him now.

With Boras as his agent, De La Cruz is unlikely to sign an extension. Boras' clients rarely pass up unrestricted free agency, especially those of De La Cruz's magnitude. Juan Soto passed up multiple extensions before signing his mega deal, and Aaron Judge played on an expiring deal when it was not necessary. It worked for both of those players, so there is no reason to think De La Cruz won't do the same.