Yankees vs. Sox
Prediction, Odds & Props
Aug 29 | MLB AI Picks

Updated: 2025-08-27T03:31:50.923562ZBy Remi at Leans.AI — AI picks for ATS, ML, OU & props

The division-leading Yankees visit a struggling White Sox squad at Guaranteed Rate Field, looking to build momentum as they enter a critical stretch of their schedule. With Carlos Rodón on the mound and a lineup featuring Juan Soto and Aaron Judge, New York seems poised for another commanding performance, while Chicago scrambles for consistency in a season that’s gone off the rails.

Get key insights, betting trends, and AI-powered predictions to help incorporate into your betting strategies.

AI Sports Betting Algorithm Remi

GAME INFO

Date: Aug 29, 2025

Start Time: 7:40 PM EST​

Venue: Rate Field​

Sox Record: (48-86)

Yankees Record: (74-60)

OPENING ODDS

NYY Moneyline: -224

CHW Moneyline: +184

NYY Spread: -1.5

CHW Spread: +1.5

Over/Under: 9

NYY
Betting Trends

  • The Yankees have covered the run line in 7 of their last 10 games, demonstrating strong form against betting expectations recently. Additionally, when favored by –221 or more, New York holds a win rate of 58.8%—a solid edge.

CHW
Betting Trends

  • The White Sox have had tough season, currently at a league-worst 48–86 record and 26–37 at home, reflecting their persistent struggles both overall and in front of their fans.

MATCHUP TRENDS

  • Despite the lopsided standings, the total line of 9 runs suggests expectation for a high-scoring battle—and history shows Yankees games frequently go over, with the last 10 set totals hitting the over 8 times.

NYY vs. CHW
Best Prop Bet

  • Remi's searched hard and found the best prop for this matchup: J. Chisholm over 6.5 Fantasy Score.

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New York vs Chicago White Prediction & Odds:
Free MLB Betting Insights for 8/29/25

The August 29, 2025 matchup between the New York Yankees and the Chicago White Sox at Guaranteed Rate Field paints the picture of two franchises on completely different tracks, one angling for October relevance and the other enduring the growing pains of a rebuild. The Yankees enter the contest at 72–60, entrenched in the thick of the AL East and wild card races, and with their recent surge against weaker opponents like the Nationals, they are firmly aware of how critical it is to dominate clubs well below .500. They turn to Carlos Rodón, a left-hander who has stabilized the rotation with a strong 3.24 ERA and a WHIP hovering just above 1.00, giving them not only quality innings but also the kind of reliability that fuels confidence across the roster. The White Sox, in contrast, sit at 48–86, a record that not only reflects the struggles of 2025 but also the broader organizational reset they are undergoing under manager Will Venable, who has spent much of the season evaluating young players and working to instill fundamentals. Chicago has labored to find offense, ranking near the bottom of the league in runs scored, and without consistent power threats, they have leaned on small ball and patience to scratch across opportunities, though these spurts have been fleeting. The matchup pits a Yankees team built around star power against a White Sox squad searching for identity, and oddsmakers reflect this disparity, placing New York as a heavy favorite with a moneyline around –221 and a run line advantage of –1.5, with an over/under set at nine runs.

That total aligns with recent trends: Yankees games have gone over the number in eight of their last ten, thanks in part to their combination of potent offense and occasional bullpen leaks that add late runs. For New York, the formula remains straightforward—get a strong outing from Rodón, apply early pressure with a lineup that features Aaron Judge and Juan Soto in the heart of the order, and then turn the game over to a bullpen that, while occasionally inconsistent, is well equipped to close out a struggling Chicago offense. For the White Sox, their best chance lies in making Rodón work deep counts early, forcing New York into middle relief innings, and then capitalizing on whatever cracks emerge. Pitching-wise, Davis Martin draws the start, and though he has shown flashes of competence, he has been plagued by low strikeout rates and susceptibility to giving up the long ball, a worrying combination against a Yankees lineup built to punish mistakes. The White Sox’s defense has been serviceable, and occasionally spectacular from younger players hungry to make their mark, but extended innings caused by miscues have been a recurring issue, often leading to blowouts against superior opponents. This game, therefore, stands as a test not only of the Yankees’ ability to maintain focus against a lesser opponent but also of the White Sox’s resilience in a season where pride and development are all that remain at stake. If Chicago can keep it close through five or six innings, the crowd may sense the possibility of an upset, but if New York strikes quickly with power and Rodón cruises, this contest could unfold as another routine victory for the visitors in their march toward the postseason.

New York Yankees MLB Preview

The New York Yankees step into their August 29 matchup against the White Sox with the urgency of a club determined to make every game count as they chase both the AL East crown and a secure Wild Card spot, and at 72–60 they know that taking care of business against a struggling Chicago team is non-negotiable. The spotlight falls on Carlos Rodón, whose return to form has steadied the rotation and given the Yankees a trusted arm capable of dominating lineups deep into games, with his 3.24 ERA and efficiency making him the clear edge in this pitching matchup. Offensively, New York wields the kind of firepower that can overwhelm lesser opponents, led by the one-two punch of Aaron Judge and Juan Soto, whose mix of power and on-base prowess creates constant traffic and run-scoring potential. Behind them, Cody Bellinger and Gleyber Torres provide additional depth, while contributions from younger bats like Anthony Volpe add balance to a lineup that rarely feels top-heavy. The Yankees’ offense has been particularly potent in recent weeks, and combined with the fact that eight of their last ten games have gone over the set total, oddsmakers and fans alike expect this group to put up crooked numbers if given opportunities.

Defensively, the Yankees remain solid, with Judge patrolling the outfield and Volpe anchoring the infield, providing support for a staff that thrives when the defense avoids miscues. The bullpen has had its shaky moments but remains strong in the late innings when managed correctly, with Clay Holmes anchoring the closer role. From a betting perspective, the Yankees have been strong against the spread recently, covering in seven of their last ten games and posting a solid record as heavy favorites, a reflection of their ability to not just win but win convincingly when facing teams like Chicago. The key for New York in this game will be maintaining focus—jumping on Davis Martin early, avoiding stranded baserunners, and ensuring that Rodón has a cushion to work with so the bullpen isn’t overextended. In a season where their margin for error in the standings is slim, the Yankees cannot afford letdowns in games like these, and their experience, star power, and depth give them the tools to control the contest from the first pitch. If they execute as expected, this matchup has all the makings of another statement win for New York as they continue their push toward October.

The division-leading Yankees visit a struggling White Sox squad at Guaranteed Rate Field, looking to build momentum as they enter a critical stretch of their schedule. With Carlos Rodón on the mound and a lineup featuring Juan Soto and Aaron Judge, New York seems poised for another commanding performance, while Chicago scrambles for consistency in a season that’s gone off the rails. New York vs Chicago White AI Prediction: Free MLB Betting Insights for Aug 29. Credit USA TODAY/IMAGN

Credit: USA TODAY/IMAGN

Chicago White Sox MLB Preview

The Chicago White Sox return to Guaranteed Rate Field for their August 29 meeting with the Yankees carrying the weight of a 48–86 season, and while the standings paint a bleak picture, the game still holds significance for a young roster trying to establish itself in the midst of a long rebuild. Manager Will Venable has leaned heavily on development in 2025, giving opportunities to younger players and looking for small building blocks rather than expecting immediate results, and though the losses have piled up, there have been flashes of promise from prospects eager to prove they belong at the big-league level. Davis Martin gets the start, and though his season has been rocky with struggles in missing bats and a tendency to give up the long ball, he represents the type of pitcher Chicago is using as a developmental test case to see if he can handle the grind of a major-league rotation spot. The matchup against Carlos Rodón and a loaded Yankees lineup will be daunting, as Martin will need pinpoint command and early run support to stand a chance against one of the most dangerous offenses in baseball. Offensively, the White Sox have lacked consistent punch, ranking near the bottom of the league in run production, and without a true anchor in the lineup they’ve relied on piecing together offense through patience, small ball, and occasional bursts from players like Luis Robert Jr. when healthy.

The absence of steady power threats has left the club leaning on situational hitting, which has not always been executed cleanly, and that inefficiency has often cost them in close games. Defensively, the White Sox have had their moments, with younger players flashing athleticism in the field, but extended innings caused by errors or missed opportunities have often turned manageable deficits into blowouts against stronger opponents. At home, Chicago has posted just a 26–37 record, and the energy at Guaranteed Rate Field has reflected the challenges of a fan base enduring a rebuild while waiting for the next wave of success. Still, this matchup offers a chance to play spoiler and test themselves against a contender, and if the White Sox can keep the game close into the middle innings, the bullpen—though overworked at times—has enough capable arms to at least give them a chance. The formula for any upset rests on Martin limiting damage early, the offense capitalizing on any rare mistakes from Rodón, and the defense playing clean baseball to avoid gifting the Yankees extra outs. For Chicago, it’s less about the standings and more about resilience, pride, and growth, and a win against New York would not only provide a temporary spark for a difficult season but also serve as a reminder to the clubhouse and fans alike that there are still foundations being built for the future.

New York vs. Chicago White Prop Picks (AI)

AI algorithm Remi is pouring through loads of datapoints on each team. In fact, anytime the Yankees and Sox play there’s always several intriguing observations to key in on. Not to mention games played at Rate Field in Aug rarely follow normal, predictable betting trends.
Remi's searched hard and found the best prop for this matchup: J. Chisholm over 6.5 Fantasy Score.

New York vs. Chicago White Prediction (AI)

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Remi, our AI sports genius, has been pouring over millions of data from every angle between the Yankees and Sox and using recursive machine learning and impressive AI to analyze the data to a single cover probability.

Remi has been most fixated on the growing weight knucklehead sportsbettors tend to put on coaching factors between a Yankees team going up against a possibly rested Sox team. We’ve found the true game analytics appear to reflect a slight lean against one Vegas line specifically.

Unlock this in-depth AI prediction and all of our MLB AI picks for FREE now.

Below is our current AI New York vs Chicago White picks, computer picks Yankees vs Sox, best bets, model edges, confidence ratings.

DATE GAME LEAN %WIN UNITS LEVEL
MLB 9/26 DET@BOS UNLOCK THIS PICK 5 EXECUTIVE Locked EXECUTIVE
MLB 9/26 BAL@NYY UNLOCK THIS PICK 4 INTEL Locked INTEL
MLB 9/26 ARI@SD UNLOCK THIS PICK 4 EXECUTIVE Locked EXECUTIVE
MLB 9/26 NYM@MIA UNLOCK THIS PICK 1 INTEL Locked INTEL
MLB 9/26 NYM@MIA GET FREE PICK NOW 1
MLB 9/26 COL@SF UNLOCK THIS PICK 0 INTEL Locked INTEL

These picks update as information changes—injury reports, weather, and market movement. Each line shows our model’s fair price, the edge versus the market, and a unit confidence rating (1–10). Odds and availability vary by sportsbook and time. Edges are computed against the listed price; value may change after line moves. Always shop for the best number. See the full MLB schedule.

Yankees Betting Trends

The Yankees have covered the run line in 7 of their last 10 games, demonstrating strong form against betting expectations recently. Additionally, when favored by –221 or more, New York holds a win rate of 58.8%—a solid edge.

Sox Betting Trends

The White Sox have had tough season, currently at a league-worst 48–86 record and 26–37 at home, reflecting their persistent struggles both overall and in front of their fans.

Yankees vs. Sox Matchup Trends

Despite the lopsided standings, the total line of 9 runs suggests expectation for a high-scoring battle—and history shows Yankees games frequently go over, with the last 10 set totals hitting the over 8 times.

New York vs. Chicago White Game Info

New York vs Chicago White starts on August 29, 2025 at 7:40 PM EST.

Spread: Chicago White +1.5
Moneyline: New York -224, Chicago White +184
Over/Under: 9

New York: (74-60)  |  Chicago White: (48-86)

Remi's searched hard and found the best prop for this matchup: J. Chisholm over 6.5 Fantasy Score.. Prices move—always shop for the best number.

Despite the lopsided standings, the total line of 9 runs suggests expectation for a high-scoring battle—and history shows Yankees games frequently go over, with the last 10 set totals hitting the over 8 times.

NYY trend: The Yankees have covered the run line in 7 of their last 10 games, demonstrating strong form against betting expectations recently. Additionally, when favored by –221 or more, New York holds a win rate of 58.8%—a solid edge.

CHW trend: The White Sox have had tough season, currently at a league-worst 48–86 record and 26–37 at home, reflecting their persistent struggles both overall and in front of their fans.

See our latest MLB picks and odds pages for 2025 to compare prices before you bet.

New York vs. Chicago White Odds

Remi is pouring through loads of stats on each team. In fact, anytime the New York vs Chicago White trends are analyzed, there’s always several intriguing trends to key in on. Not to mention games played at extreme altitude can often follow normal, predictable patterns.

New York vs Chicago White Opening Odds

NYY Moneyline: -224
CHW Moneyline: +184
NYY Spread: -1.5
CHW Spread: +1.5
Over/Under: 9

New York vs Chicago White Live Odds

Games PTS ML SPR O/U
Sep 27, 2025 1:06PM EDT
Baltimore Orioles
New York Yankees
9/27/25 1:06PM
Orioles
Yankees
+194
-235
+1.5 (-105)
-1.5 (-114)
O 8.5 (-122)
U 8.5 (+100)
Sep 27, 2025 2:21PM EDT
St Louis Cardinals
Chicago Cubs
9/27/25 2:21PM
Cardinals
Cubs
 
-168
 
-1.5 (+118)
O 9 (-122)
U 9 (+100)
Sep 27, 2025 3:09PM EDT
Tampa Bay Rays
Toronto Blue Jays
9/27/25 3:09PM
Rays
Blue Jays
+132
-156
+1.5 (-154)
-1.5 (+128)
O 8.5 (-106)
U 8.5 (-114)
Sep 27, 2025 4:06PM EDT
Chicago White Sox
Washington Nationals
9/27/25 4:06PM
White Sox
Nationals
+102
-120
-1.5 (+162)
+1.5 (-196)
O 8.5 (-110)
U 8.5 (-110)
Sep 27, 2025 4:06PM EDT
Colorado Rockies
San Francisco Giants
9/27/25 4:06PM
Rockies
Giants
+198
-240
+1.5 (-110)
-1.5 (-110)
O 8 (-108)
U 8 (-112)
Sep 27, 2025 4:11PM EDT
New York Mets
Miami Marlins
9/27/25 4:11PM
Mets
Marlins
-124
+106
-1.5 (+130)
+1.5 (-156)
O 8.5 (-112)
U 8.5 (-108)
Sep 27, 2025 6:05PM EDT
Minnesota Twins
Philadelphia Phillies
9/27/25 6:05PM
Twins
Phillies
+177
-197
+1.5 (-118)
-1.5 (-102)
O 8.5 (-118)
U 8.5 (-102)
Sep 27, 2025 7:11PM EDT
Cincinnati Reds
Milwaukee Brewers
9/27/25 7:11PM
Reds
Brewers
+128
-152
+1.5 (-178)
-1.5 (+146)
O 7.5 (-120)
U 7.5 (-102)
Sep 27, 2025 7:15PM EDT
Pittsburgh Pirates
Atlanta Braves
9/27/25 7:15PM
Pirates
Braves
+143
-158
+1.5 (-150)
-1.5 (+130)
O 8.5 (+100)
U 8.5 (-120)
Sep 27, 2025 7:16PM EDT
Texas Rangers
Cleveland Guardians
9/27/25 7:16PM
Rangers
Guardians
+132
-156
+1.5 (-172)
-1.5 (+142)
O 7 (-120)
U 7 (-102)
Sep 27, 2025 8:40PM EDT
Arizona Diamondbacks
San Diego Padres
9/27/25 8:40PM
Diamondbacks
Padres
+120
-132
+1.5 (-180)
-1.5 (+157)
O 7.5 (-115)
U 7.5 (-105)
Sep 27, 2025 9:41PM EDT
Los Angeles Dodgers
Seattle Mariners
9/27/25 9:41PM
Dodgers
Mariners
+102
-120
+1.5 (-215)
-1.5 (+180)
O 7.5 (-110)
U 7.5 (-110)
Sep 27, 2025 10:05PM EDT
Kansas City Royals
Oakland Athletics
9/27/25 10:05PM
Royals
Athletics
+104
-115
+1.5 (-185)
-1.5 (+161)
O 10 (-110)
U 10 (-110)

MLB Past Picks

Remi—our in-house AI—prices every game and prop using multi-season priors, tempo/efficiency, injury/usage signals, and market movement.
We publish fair prices, recommended “buy-to” numbers, and confidence so you can bet prices, not teams.

This preview covers New York Yankees vs. Chicago White Sox on August 29, 2025 at Rate Field.
Odds shown reflect widely available numbers and may update closer to kickoff.

Want more? Check live edges, player props, and line moves on our MLB odds pages, and compare prices before you place a bet.

    LEAN     %WIN     UNITS RESULT
NYM@CHC NYM -110 54.1% 3 WIN
HOU@ATH ATH +118 50.8% 4 WIN
NYM@CHC OVER 7 54.5% 3 WIN
STL@SF OVER 7.5 55.9% 5 LOSS
KC@LAA TYLER TOLBERT UNDER 1.5 BASES 54.4% 4 WIN
MIL@SD UNDER 9 54.7% 4 WIN
MIA@PHI KYLE SCHWARBER OVER 1.5 HITS+RUNS+RBIS 53.3% 3 WIN
WAS@NYM OVER 8.5 56.1% 6 LOSS
LAA@COL COL +108 50.5% 3 WIN
TOR@KC UNDER 9 54.7% 4 LOSS
SEA@KC KC +1.5 62.3% 5 LOSS
NYY@MIN OVER 9 55.1% 4 WIN
MIA@COL OVER 10.5 55.0% 4 WIN
MIA@COL AGUSTIN RAMIREZ OVER 1.5 HITS+RUNS+RBIS 54.3% 4 WIN
SEA@KC BOBBY WITT UNDER 0.5 SINGLES 54.4% 4 LOSS
PHI@LAD LAD -113 54.7% 4 LOSS
NYY@BOS OVER 7.5 54.3% 3 WIN
KC@PHI PHI -130 58.3% 4 WIN
LAD@SF OVER 7.5 54.7% 4 LOSS
NYM@PHI PHI -122 55.6% 4 WIN
KC@CLE KC -104 52.0% 3 WIN
CIN@SD JAKE CRONEWORTH OVER 0.5 HITS 53.1% 3 WIN
WAS@MIA MIA -123 55.2% 4 LOSS
LAA@KC UNDER 9.5 54.9% 3 WIN
TEX@ARI UNDER 9 54.2% 4 WIN
SF@COL UNDER 11.5 56.4% 6 LOSS
SF@COL RAFAEL DEVERS OVER 1.5 BASES 56.1% 6 WIN
MIA@WAS WAS -110 54.4% 4 WIN
NYM@DET OVER 8.5 54.5% 4 WIN
TEX@ARI UNDER 9.5 56.4% 6 WIN
TEX@ARI ALEJANDRO OSUNA UNDER 1.5 BASES 54.1% 4 LOSS
ATL@CHC CHC -116 55.1% 3 WIN
PHI@MIL OVER 8.5 55.0% 3 WIN
ARI@LAD SHOHEI OHTANI OVER 2.5 BASES 54.2% 4 WIN
SEA@CLE CLE +1.5 57.2% 3 WIN
CHC@SF CHC -105 54.1% 4 LOSS
NYY@CHW RYAN MCMAHON OVER 0.5 BASES 54.1% 4 WIN
PHI@NYM OVER 8.5 55.6% 4 LOSS
LAA@TEX LOGAN OHOPPE OVER 1.5 HITS+RUNS+RBIS 54.1% 4 LOSS
KC@CHW KC -109 54.2% 4 WIN
SD@SEA DYLAN CEASE OVER 16.5 OUTS 53.9% 3 LOSS
SD@SEA UNDER 8.5 54.4% 4 LOSS
MIN@TOR JOE RYAN UNDER 2.5 EARNED RUNS 54.1% 4 LOSS
SF@MIL MIL +100 54.0% 6 LOSS
TOR@MIA MIA +1.5 62.0% 6 WIN
CHC@LAA OVER 9.5 54.9% 4 LOSS
BOS@NYY CARLOS RODON UNDER 4.5 HITS ALLOWED 54.2% 4 WIN
KC@DET DET -115 56.1% 5 WIN
CHC@LAA LAA +1.5 57.6% 5 LOSS
CIN@ARI KEBRYAN HAYES STRIKEOUTS UNDER 0.5 56.2% 6 WIN
LAD@SD SD +110 50.9% 6 WIN