Chris Bassitt’s free agency doesn’t come with fireworks, but it does come with something far more valuable in this market: certainty.Following three seasons of being an answer for the Blue Jays from 30-start durability to pressure innings in October, the veteran right-hander heads to the winter as one of the few pitchers teams know exactly what they’re getting.Since the Jays signed him in 2022, Bassitt has remained the same pitcher he was in Oakland and New York: a durable No. 2 or 3 starter who shows up, throws six competitive innings, is adept at mixing eight different pitches while keeping his team in games.Most projections have him landing a two-year deal in the low 30-million dollar range, the same band that contenders are shopping for innings and retooling teams are looking for stability. And in that lane, a couple of clubs do stand out.#1. Baltimore OriolesIf there’s one team that fits Bassitt like a glove, it’s Baltimore. The Orioles are no longer a young, adorable story; they’re now expected to win deep into October.What they’re missing is that calming, every-fifth-day presence. Their 2025 rotation was stretched thin, inconsistent, and overloaded with arms that carried more promise than polish.Bassitt solves that instantly, and he doesn’t need to be their ace; Baltimore already has enough upside. What they need is someone who stops losing streaks, works deep into games, and gives their explosive lineup a chance every night.#2. Milwaukee BrewersThe Brewers might look steady on the surface after a 97-win season, but inside the rotation there’s far more uncertainty than the standings suggest.Brandon Woodruff is back but still returning to full form, Freddy Peralta’s name pops up in trade conversations every winter, and the Brewers lost valuable innings to injuries all year.This is exactly the kind of situation where Milwaukee historically targets a steady veteran. Bassitt checks every box: short-term commitment, dependable workload, and enough postseason experience to help if they’re back in the NL race.#3. St. Louis CardinalsSt. Louis is in the middle of a quiet rebuild, not a tear-down, but a transition. Sonny Gray could be moved, young arms need space, and the Cardinals want stability while they reshape the roster under new leadership.Bassitt is the perfect bridge. He could give them 28–30 starts, take pressure off the kids, and slot into the top half of the rotation without blocking the long-term plan.If the Cardinals unexpectedly take a leap, he becomes a key piece. If they don’t, he’s a valuable trade chip in July.