Elly De La Cruz and Scott Boras sat for dinner in Cincinnati last week, a sighting that means the Reds have approximately nine months to lock in their franchise cornerstone before arbitration eligibility arrives in 2026. The meeting was not accidental. De La Cruz switched representation to Boras Corporation in late 2024, and when the industry's most patient negotiator shows up in a small market during the offseason, the clock is running.

De La Cruz posted .875 OPS across 160 games in 2024, his second full season, with 25 home runs and 67 stolen bases. He led the National League in steals and ranked fourth in sprint speed at 30.2 feet per second. The Reds control him through 2028 under pre-arbitration and arbitration rules, but comparable players—Fernando Tatis Jr., Julio Rodríguez, Bobby Witt Jr.—signed eight-figure annual value extensions before reaching arbitration. Tatis signed 14 years, $340 million at age 23. Rodríguez signed 12 years, $210 million guaranteed at 21, with escalators pushing the deal past $400 million. Witt signed 11 years, $288.8 million at 23. The Reds have not signed a position player to a nine-figure extension since Joey Votto in 2012.

Cincinnati's front office has been quietly preparing for this. Team president Nick Krall extended pitcher Hunter Greene to six years, $53 million in March 2024, a below-market deal that bought out arbitration years and one free-agent season. That structure does not work here. De La Cruz has Boras, who does not discount future earnings for early certainty unless the guarantee is overwhelming. The Reds ranked 23rd in payroll at $104 million in 2024, per Cot's Baseball Contracts, but ownership approved stadium district upgrades worth $40 million and hired a new sponsorship chief from the NBA in October. The money is being positioned.

The extension window closes faster than it appears. De La Cruz will be arbitration-eligible after the 2025 season, at which point Boras gains leverage and the player's camp can test one-year deals while waiting for free agency in 2029. The Reds need the deal done before Opening Day 2026 to avoid the Witt timeline, where Kansas City waited until March of his arbitration-eligible year and paid an extra $50 million in guarantee to close. Cincinnati has not won a playoff series since 1995, and De La Cruz is the first homegrown position player since Barry Larkin to generate this much trade value and jersey revenue simultaneously. The Reds sold 2.3 million tickets in 2024, up 11% year-over-year, and De La Cruz led the team in merchandise sales by April.

Boras does not take dinner meetings for photo opportunities. He takes them when a team is ready to present a number, or when a player needs to hear the market position before arbitration filings in January. The Reds have $68 million committed for 2026, per Spotrac, with Greene, India, and Fraley the only significant multi-year obligations. De La Cruz's camp will want $300 million guaranteed over ten years, given his age and toolkit. The Reds will offer closer to $240 million over eight, structured to defer tax hit and preserve payroll flexibility for pitching. The gap is not insurmountable if ownership decides Great American Ball Park attendance can support a $150 million payroll by 2027.

Watch for two markers in the next 90 days: whether Krall meets Boras again before spring training in mid-February, and whether the Reds extend hitting coach Alan Zinter, whose contract expires after 2025. Front offices lock in coaching staff before committing nine figures to a player, because the infrastructure around the asset matters as much as the term sheet. If Zinter gets a two-year deal by Valentine's Day, the De La Cruz extension is live. If not, the Reds are waiting one more year, and Boras will pocket the arbitration raise as a down payment on 2029 leverage.

De La Cruz reports to Goodyear, Arizona for spring training on February 12. By then, the Reds will know if they are buying out free agency or renting him through arbitration.