Yankees open a three-game set in Houston to kick off a pivotal September, with a potential postseason rematch looming. Judge's pursuit of history adds fantasy intrigue as he sits within reach of joining the Yankee elite, while Max Fried faces Framber Valdez in the opener. Alvarez is back for Houston, and Garcia has re-entered the rotation, tightening the Astros’ rotation. New York adds J.C. Escarra and Ryan Yarbrough to the September roster as Judge's DH status remains in flux and Stanton returns to a regular DH role for now.

The Yanks sit in a top wild-card slot, but their schedule through Sept. 14 is grittier, featuring Toronto, Detroit and Boston. With closer uncertainty and a few September callups, savvy fantasy managers will watch Judge’s defensive usage, Alvarez’s health impact, and the bullpen moves as they plan streaming options and daily lineup bets.

New York heads September in playoff contention, but a brutal late-season slate tests the Yankees as they face four AL juggernauts: Astros, Blue Jays, Red Sox and Tigers. Roster expansions and injuries shape a pivotal stretch, with Yarbrough and Slater back in action to bolster depth.

Contenders aren’t standing pat: IKF lands with the Blue Jays, Heaney with a pennant hopeful, and Mayza joins the Phillies, altering late-inning matchups across the league. Fantasy players should monitor bullpen roles, lineup shifts, and the impact of these moves as the chase nears October.

Paul Blackburn landed with the New York Yankees, stepping into a bullpen role after being designated for assignment by the Mets. He traveled through Idaho to meet New York in Tampa, aiming to contribute length and veteran savvy for the stretch run. The move came with New York also designating Allan Winans for Triple-A, signaling a shuffle to shore up bullpen depth and keep options open as injuries and inconsistencies linger.

Meanwhile, the club rolled out rehab notes on Fernando Cruz and Ryan Yarbrough, both funneling toward returns that could bolster late-inning and multi-inning leverage. Boston looms as the series opponent, and Atlanta’s prior testing of Blackburn’s tracks record was cited as context for his new chapter. The moves underscore a Yankees bullpen in flux, prioritizing length, versatility, and health ahead of September call-ups.

Week 21 in fantasy baseball centers on savvy IL stashes with upside for the stretch drive. Ryan Yarbrough returns to a Yankees rotation eager for stability after an oblique ailment, offering speculative late-season value if rehab goes clean. Landen Roupp looks poised to rejoin the Giants with strong strikeout metrics and favorable home/road splits, potentially anchoring a depth start. Colton Cowser carries power upside and outfield flexibility, but concussion issues keep him risky until late August. Jacob Wilson remains a hot target for AVG/OBP and run production as he nears activation from forearm surgery. Hyeseong Kim, a versatile Dodger with speed and middle-infield eligibility, may reclaim regular at-bats once back. Across the board, managers should consider brief IL stashes to boost stacks when playoff rosters tighten.

These five players each bring a different path to value: Roupp’s strikeout ability and pitcher-friendly home park; Yarbrough’s proven 2025 form with caveats on injury recovery; Cowser’s past power in a strong Orioles lineup; Wilson’s top-line batting average and OBP splash; Kim’s speed and multi-position eligibility in a potent Dodgers lineup. Owners in redraft leagues with IL slots will want to monitor rehab updates and activation timelines, ready to pounce as Week 21 turns into Week 22 and the playoff push accelerates.

Two Yankees bullpen pieces, Ryan Yarbrough and Fernando Cruz, are closing in on returns from oblique injuries, with rehab sessions kicking off this week. Cruz threw 19 pitches in a live Double-A Somerset session, while Yarbrough advanced to two live-ups. Both are slated to begin rehab on Thursday, with Cruz possibly joining after a sequence of rehab starts and Yarbrough's usage depending on how he is built up and rotation needs. The move would add a much-needed boost to a relief corps that has felt the pinch from bullpen depth injuries.

Around the same time, Giancarlo Stanton logged field work in right, and Aaron Judge continued progress in his throwing program, though not yet expected to return for the Twins series. Oswaldo Cabrera, sidelined by a gruesome left ankle fracture and ligament damage since May, walked the clubhouse and provided a tempered outlook; his recovery remains murky. Cabrera slashed .243/.322/.308 with one homer and 11 RBI in 34 games this season, while Cruz sits at a 3.00 ERA across 32 games with a remarkable 41.2% strikeout rate. Yarbrough has struggled to a 3.90 ERA in 16 games, a reminder that his rehab timing will shape how the Yankees handle rotation and bullpen roles as Judge and Stanton push toward field readiness.