Are Yankees, Blake Snell getting closer to striking a deal?

As Blake Snell continues to linger in free agency, speculation regarding him and the Yankees persists. The Yanks reportedly offered the lefty five years and $150M before pivoting to sign Marcus Stroman on a two-year deal last month. Since then, it’s been reported that the Yankees still have an offer out to Snell, though the shape of that offer is presumably different after signing Stroman and pushing themselves into the top tier of luxury-tax penalization in the process. Whatever is presently on the table doesn’t appear to be a “take it or leave it” type of offer, as the New York Post’s Jon Heyman writes that the Yankees and Snell talked about various contract parameters as recently as Monday.

Notably, Heyman writes that agent Scott Boras has suggested the possibility of a shorter-term deal with higher annual salaries and opt-out opportunities. That’d be a pivot from Snell seeking maximum guarantees, as has been the case throughout the winter. It’s also not a concept that works well with a team in the Yankees’ situation.

The Yankees are a third-time luxury tax payor who are in the top tier of penalization. Any additional spending at this point will be taxed at 110%. And since the luxury tax is based on a contract’s average annual value, there’s no skirting the issue by backloading a deal. In that sense, dialing up the contract’s AAV only further penalizes the Yankees. The taxes are only part of the issue. New York would also be forfeiting its second- and fifth-highest draft selections, as well as $1M from next year’s international bonus pool, in order to sign Snell, who rejected a qualifying offer from the Padres.

A longer-term pact that stretches out an agreed-upon guarantee while weighing down the AAV would be more sensible. The Yankees took that approach with DJ LeMahieu in free agency a couple years back, when he inked a six-year deal at a time when a contract around four years was widely expected. There’s no indication such an arrangement is currently being discussed, however, and going longer term on Snell would present the Yankees with its own slate of worrying factors. New York already has Gerrit Cole, Aaron Judge, Carlos Rodon and Giancarlo Stanton under contract through the 2027 season. Each of Cole, Rodon and Judge are on the books through 2028, giving the Yankees $103M in guaranteed money on the books in a season that’s still four years down the road. Add in the $10M buyout on Stanton’s 2028 option, and that’s $113M of considerations for that season.

Furthermore, they’ll very likely wind up tacking an extra year onto Cole’s contract this coming offseason. The reigning AL Cy Young winner has an opt-out in his contract after the ’24 season, but the Yankees can void that by picking up a 2029 club option at $36M. That’d give the Yanks $76M on the books as far down the line as 2029; adding Snell on a long-term deal designed to tamp down his contract’s AAV could push them close to or even north of $100M in commitments a half-decade from the current season. Not only that, but Judge will be 37 that year and Cole will be 38. Snell would be 36. It’d be plenty understandable if the Yankees have some trepidation about locking in $100M+ in guarantees to three players who’ll be 36 or older in 2029.

Heyman also notes that the Yankees have some interest in fellow lefty and fellow unsigned Boras client Jordan Montgomery, whom they of course originally drafted and developed. However, the Yankees prefer Snell, and the financial hurdles just laid out regarding Snell applies to Montgomery — but on a slightly smaller scale, as he doesn’t have quite the earning power of a two-time Cy Young winner.