Morton's The Steakhouse

Silver Oak Cabernet Sauvignon Alexander Valley — $165/bottle

At roughly 1.9x retail, this is the closest thing to a fair deal on the bottle list. Silver Oak Alexander Valley always skews more approachable and food-friendly than the Jordan-valley Napa version, and at a steakhouse with a New York strip in front of you, it genuinely earns its place. You're still spending real money, but at least you're not getting fleeced.

Louis Jadot Burgundy

Everyone at the table is ordering Cab, which means the Jadot Burgundy selections sit overlooked and under-ordered. If you want something that actually makes the kitchen work for its compliments — especially alongside the filet — a Jadot Pinot is doing more interesting things on your palate than the fourth Napa Cab of the evening. Ask what they have available; it's worth the conversation.

Rombauer Chardonnay Carneros

At $22 a glass, you're paying roughly $88 per bottle equivalent for a wine that retails for $40. Rombauer is a crowd-pleaser — big, buttery, and impossible to argue with — but this is the steepest glass-pour markup on the list and it's going to the most predictable wine in the program. Order it if you love it, but know exactly what you're paying for.

Duckhorn Cabernet Sauvignon + Prime New York Strip

Duckhorn Cab has enough structure and dark fruit to go toe-to-toe with a well-marbled New York strip without bullying the beef. It's a textbook steakhouse pairing done well — where Caymus can feel like a sugar rush next to a big cut of meat, Duckhorn keeps things grounded and lets the steak lead.