JD Bets backed the Cubs at –108 on the road in Milwaukee. His model sheet flagged a clear batting edge for Chicago, while dome conditions at American Family Field remove any weather volatility. Although Freddy Peralta has historically muted several key Cubs (Ian Happ just 1-for-13, Nico Hoerner 2-for-10), JD noted that none of Sunday’s starters grade out as 7-of-10 or better in his strikeout/quality-start prop filters, so he is happy to side with the deeper lineup. He trusts Shota Imanaga to keep Brewers bats quiet—Milwaukee ranks bottom-10 in hard-hit rate versus lefties—while he does not believe the Brewers’ inconsistent offense can capitalize on occasional Cubs bullpen hiccups. With batting advantage, neutral park factors, and effectively even pitching, JD declared the Cubs money line his first official wager of the day.

Razzle leaned toward Shota Imanaga instead of Freddy Peralta. While Peralta owns the slate’s second-highest K-prop (6.5), the Brewers’ offense has cooled considerably, giving Imanaga a friendlier matchup and similar strikeout upside at a lower salary. The tout expects Imanaga to capitalize on Milwaukee’s recent 27 percent K-rate versus lefties and views him as the safer yet still ceiling-laden choice between the two.

Data Skrive’s computer spits out Cubs 5-4 and advises laying the modest –115 plus taking Over 7.5. Rookie left-hander Shota Imanaga (2.77 ERA, 1.05 WHIP) has limited hitters to a .208 average and profiles well against Milwaukee’s lefty-heavy order, while Chicago’s bats rank 5th in OPS vs right-handed pitching and draw Freddy Peralta, who has surrendered 9 earned in his last 11 frames. Chicago’s 21-13 start versus Milwaukee’s 16-18 mark, combined with a forecasted right-to-left breeze inside American Family Field, nudged the model toward the hotter club in a game where both offenses still scratch out runs.

Brad Francis advised betting the Cubs money line against Milwaukee. He noted the Brewers have dropped six straight games when priced as underdogs, a trend that keeps paying. On the flip side, Francis loves the surge in Chicago’s offense since adding Kyle Tucker at the deadline, saying Tucker looks 'pissed off' and has injected serious pop into a lineup that was already outperforming projections. With the bats rolling and Milwaukee in a prolonged let-down spot, Francis believes the minus-price on Chicago is justified.

Cash Out Sports Picks backed the full-game under, predicting a low-scoring affair behind two red-hot starters. Freddy Peralta owns a microscopic 0.69 ERA at home and a 2.45 mark in day games, surrendering only 24 hits and nine runs over his last 34.1 innings. He has long flummoxed this Cubs lineup, holding current Chicago hitters to a .170 average with 42 strikeouts in 117 at-bats; Ian Happ and Dansby Swanson have barely put a ball in play against him. On the other side, Shota Imanaga has followed his All-Star rookie season with a 2.77 ERA and 1.13 WHIP, and he has been almost untouchable on the road (0.53 ERA, .206 BAA in 17 IP). Although Imanaga’s daytime ERA is a touch higher at 4.38 and he struggled in his lone 2024 appearance versus Milwaukee, the tout expects both aces to work deep enough to mute the offenses. With neither bullpen overworked and a projected 3-2 or 4-3 final, Cash Out Sports labeled the under the best total play for this matchup.

Alongside his Cubs moneyline bet, Kenny G sprinkled Over 7.5 runs, reasoning that both clubs are ‘over machines.’ Chicago is 22-10 to the over and packs the league’s No. 1 offense, while Milwaukee is 22-10 to the over as well despite a recent scoring drought. He acknowledged that Imanaga (2.77 ERA) and Peralta (2.02 ERA) are quality arms but expects each to allow at least a couple of runs before handing things to two suspect bullpens—Milwaukee’s 4.98 ERA and Chicago’s still-shaky 4.41. With both teams ranking top-10 in run production on the season, and the Cubs possessing MLB’s best road record (12-6), Kenny sees eight combined runs as a realistic baseline outcome and was surprised the total opened below 8.

Kenny G jumped on the Cubs at –109, arguing oddsmakers are underrating MLB’s most explosive lineup. Chicago leads the majors in runs, batting average and sits second in slugging, with Nico Hoerner and Kyle Tucker pacing an order that has plated 16 runs in the first two games of the series. Shota Imanaga owns a 2.77 ERA and is coming off five scoreless frames versus Pittsburgh; Kenny sees him as ‘by far the better starter’ when matched with Freddy Peralta, who allowed two homers to the lowly White Sox in his last outing. The decisive edge, though, is Milwaukee’s 4.98 bullpen ERA compared to Chicago’s improving 4.41 mark. The Brewers offense has vanished—scoring 2, 0, 0 runs their past three—and Kenny notes the club has now lost three straight and been overtaken atop the NL Central. With the Cubs 12-6 on the road (best in MLB) and the Brewers merely 9-6 at home, he priced Chicago closer to –125 and labeled the near pick’em a must-bet.

For the series finale, Cash Out Sports leaned to Milwaukee on the money line. Freddy Peralta is 6-2 with a 3.16 ERA in 18 career appearances versus Chicago and sports a microscopic 0.69 ERA at home this season, plus a 2.45 ERA in day games. Shota Imanaga has been brilliant overall (2.77 ERA) but owns a 4.38 day-game ERA and was hit hard by Milwaukee in his lone start against them last season. With the clubs splitting their last 20 meetings 10-10, Peralta’s specific dominance and the home park edge tipped the handicap toward the Brewers.

Data Skrive recommended betting Over 7.5 runs, noting several converging trends. Milwaukee games have topped their listed total in six of the last ten, fueled by a shaky 4.86 staff ERA and just 6.7 K/9. On the other side, Chicago’s offense is rolling with 15 homers and 5.9 runs per game during the same stretch, while its own bullpen has worked hard in three straight series. The projection of a 5-4 final easily clears the posted number, and both lineups feature multiple top-35 home-run threats (Jackson Chourio’s six bombs, Tucker’s 15th-ranked HR pace). With American Family Field playing power-friendly in early May, the model assigns the Over a 53% edge versus the –111 price.

Data Skrive projected a 5-4 Cubs victory despite Milwaukee being the slight favorite at –110. Their model pointed to Chicago’s superior recent form: the Cubs are 6-4 over the last ten games, averaging 5.9 runs with a stingy 2.81 ERA, while the Brewers have stumbled to 4-6 with a 4.86 ERA. Chicago has already cashed as an underdog in two of its last three such spots, and Kyle Tucker, Seiya Suzuki and Pete Crow-Armstrong collectively rank top-20 in both homers and RBI. Milwaukee’s bullpen has allowed opponents to hit the over in six of its last ten contests. With the moneyline nearly a pick’em (Brewers –110 / Cubs –109), Data Skrive sees value backing the hotter Cubs lineup and pitching staff.

Peterson also took Over 7.5, projecting 7.8 runs. The Cubs enter the weekend leading MLB at 6.1 runs per game, while both starters appear due for regression: Peralta’s strikeout rate (9.4 K/9) would be a career low and Imanaga’s ERA is more than two runs better than his FIP. With a fresh day-game roof-open forecast in Milwaukee, Peterson expects enough barrels from both sides to push the total north of eight.

Peterson laid ‑105 with Milwaukee, valuing them at ‑116. He pointed out Shota Imanaga’s sparkling 2.77 ERA hides a 4.87 FIP, soft 6.7 K/9, and 1.6 HR/9, all red flags versus a Brewers lineup that feasts on left-handed pitching. Freddy Peralta’s 2.52 ERA is inflated by a 3.77 FIP, but his underlying stuff remains nasty and he draws a Cubs team traveling after a long series in Denver. Peterson expects Imanaga’s luck to finally crack at American Family Field.

Palyo advised betting Seiya Suzuki to homer at +500. Suzuki sits on nine HRs and has gone deep three times in his last four contests. Versus southpaws in 2025 he sports a .385 ISO, .769 SLG, and only a 20% K-rate, echoing 2024 splits where he posted a .360 wOBA and 134 wRC+ against lefties. Brewer starter Jose Quintana owns a shiny 1.14 ERA, but Palyo warned the peripherals (92% zone contact, 5.9% SwStr) scream regression. With Quintana rarely missing bats and Suzuki’s plate discipline, Palyo expects aggressive swings on get-me-over fastballs, making the +500 tag an overlay for a hitter near the top of the league HR board.

Kenny G targeted the No-Run First Inning prop in Cubs-Brewers, citing two red-hot arms and a shaky Milwaukee offense. Jose Quintana is 4-0 with a microscopic 1.14 ERA and has yet to allow more than one run in any start. Opposing him, Jameson Taillon has strung together back-to-back gems (12 IP, 2 ER) while holding opponents to a .200 average his first time through the order. Although the Cubs lead MLB in overall scoring, Kenny believes Quintana’s pinpoint command (4% walk rate) and the early-inning adrenaline of Wrigley’s 10-0 win still fresh will keep them quiet in the opening frame. Milwaukee has been shut out two straight games and ranks only 23rd in slugging, making a first-inning breakthrough unlikely against Taillon’s mid-90s heater. Given both starters’ form and neither team’s desire to dip into its disastrous bullpen early, Kenny thinks the NRFI is the smartest way to attack this matchup.

Dylan Rockford took Milwaukee’s full-game moneyline at –110, citing multiple bullish trends. The Brewers are 9-4 straight-up at American Family Field and have won all four of Jose Quintana’s outings thanks to 5.3 runs of support per start. Quintana owns a microscopic 0.39 WHIP his first time through orders, while Taillon’s 1.5-plus WHIP on the road sets up early traffic. Rockford acknowledged the Brewers’ bullpen walk issues, but he still prefers a full-game ticket because Chicago’s pen isn’t much better and Taillon is averaging only five innings per start. With Milwaukee’s offense ranking top-10 in HR/FB at home, he power-rated the Brewers –125 and happily took the discounted tag. He also sprinkled a small prop on Quintana Over 2.5 walks (+120) given the lefty’s tendency to nibble late in counts.

Scott Reichel isolated Milwaukee –0.5 in the first five innings at –110, trusting Jose Quintana’s current heater far more than Jameson Taillon on the road. Quintana is 4-0 with a 1.14 ERA for the Brewers and has allowed only three earned runs in 23 innings. Milwaukee has cashed every one of his starts and generally stakes him to early leads. Reichel wants no part of the Brewers’ shaky bullpen, but he does want to fade Taillon’s mediocre 4.01 ERA that gets worse outside Wrigley. The Cubs’ comeback ability worries him in a full-game wager, so he keeps it simple: ride Quintana through five and cash out before any late-inning chaos.

Kyle Purviance loves Cubs –1.5 at +150. Jameson Taillon’s 3.08 xFIP and 54 % ground-ball rate suggest his early-season rebound is real, whereas Jose Quintana, with only two decent starts, now faces a Chicago order that ranks third in OPS (.812) against southpaws. Purviance hammered Milwaukee’s offense—25.6 % K-rate and 28th in ISO vs righties—claiming they lack the punch to come back if Taillon gets an early cushion. Chicago’s bullpen is seventh in WPA, wind is forecast to blow out to left at Wrigley, and Kyle sees the +150 as badly mis-priced.

Even with Jose Quintana’s spotless 4-0, 1.14 ERA start, the computer predicts Cubs 4-3 and advises taking Chicago -110. The Cubs’ 20-13 record and higher run-differential outweigh Jameson Taillon’s 4.01 ERA. Under 8.5 is a secondary lean given both clubs’ below-average hard-hit rates.

Cash Out Sports Picks also played the UNDER, noting both starters are in excellent form: Taillon owns a 2.76 ERA and .194 opponent average over his last five, while Quintana has yet to yield more than a single run all season. With both bullpens shaky but improving and three of the last four head-to-head meetings staying under, the tout expects another low-scoring outcome.

Cash Out Sports Picks backed the Chicago Cubs on the moneyline, citing an MLB-best .864 OPS with runners in scoring position and a bullpen that, while not elite, sports a 4.53 ERA—still markedly better than Milwaukee’s 5.14 mark. The tout acknowledged Jose Quintana’s hot start (no more than one run allowed in any of his first four outings) but questioned sustainability and highlighted that Chicago remains one of the league’s toughest offenses against left-handed pitching. With Jameson Taillon supported by a deep lineup and the Cubs carrying Friday’s momentum, the pick is Chicago.

Martin grabbed the Cubs at +100 because Jameson Taillon is trending up while the matchup favors Chicago’s bats. Taillon has posted back-to-back one-run outings and is seeing his velocity steadily climb. Chicago owns the No. 2 wRC+ versus left-handed pitching and the No. 3 lineup overall, a clear edge over a Brewers offense that has underperformed and struggles against right-handers. Milwaukee starter Jose Quintana boasts a shiny 1.11 ERA and 4-0 record but Martin believes regression looms, and the Brewers’ 9-4 home mark is masking a .500 overall club. With the better lineup and a pitcher on the upswing, Martin likes the Cubs to upset the Brew Crew.

With both starters pitching to contact and each bullpen sitting bottom-10 (Cubs 4.64 ERA, Brewers 4.90 ERA), Peterson took Over 8. His modeled total was 8.6, and neither Quintana (career-low strikeout rate) nor Taillon (1.3 HR/9) is missing bats. Extra traffic plus suspect late-inning arms create multiple paths to nine or more runs.

Peterson’s line made Milwaukee -132, so he fired Brewers -108. Jose Quintana’s 1.14 ERA and 4-0 record offset his low 5.7 K/9 because the Cubs pen sits 23rd in ERA (4.64). Chicago counters with Jameson Taillon (4.01 ERA, 1.3 HR/9) and an offense that has cooled since a hot start. Even if Quintana regresses, Peterson trusts Milwaukee’s bats against a vulnerable relief corps.

Bryan Leonard recommended betting the Chicago Cubs moneyline in Milwaukee, citing clear advantages both on the mound and at the plate. He highlighted Ben Brown’s underlying metrics—82nd-percentile extension, 81st-percentile whiff rate, and 71st-percentile fastball velocity—as evidence the rookie can neutralize the Brewers. Chicago’s offense carries a 124 WRC+ (third in MLB and 24% better than league average) despite facing winning opponents in 29 of 32 games. Leonard is eager to fade Quinn Priester, whose lifetime 5.84 ERA, 1.57 WHIP, and dreadful 1.2% strikeout-minus-walk rate are propped up by a 90th-percentile ground-ball rate but undermined by 21st-percentile chase and whiff numbers. With Milwaukee’s lineup sitting at just a 94 WRC+ (6% below league average), Leonard sees the better starter and the hotter bats on the Chicago side and is backing the Cubs as road dogs.

Collin Whitchurch backed Milwaukee’s first-five moneyline at +100 or better against Chicago. He’s a self-described Quinn Priester truther, arguing the former first-rounder’s revamped pitch mix—installed in Boston last year and refined by Milwaukee’s pitching lab—has boosted his weak-contact profile despite mediocre surface numbers. Both starters carry walk problems, but Cubs rookie Ben Brown walks hitters even more often, and Milwaukee’s lineup is one of MLB’s most patient. By isolating the first five innings, Collin removes a shaky Brewers bullpen from the equation and trusts the staff’s ability to get the most out of Priester while exploiting Brown’s command issues.

Cash Out Sports Picks took the Milwaukee Brewers moneyline against the Cubs, mainly to exploit Ben Brown’s poor form. Brown sports a 6.04 ERA and 1.89 WHIP, surrendering 34 hits and 14 walks in just over 25 innings, and was shelled for six earned in 3.2 IP by Philadelphia last start. Milwaukee has momentum with three straight wins and sends Quinn Priester, who allowed five runs last time but had given up only three over his prior 14 frames and just one in five home innings this year. Chicago’s staff ERA (4.05, 17th) and WHIP (1.36, 24th) add to the edge. With the Brewers ranking fifth in runs and enjoying home field, the tout sided with Milwaukee full-game.

Kenny G suggested grabbing the Cubs at –112 in Milwaukee, calling it a buy-low on Ben Brown and a sell-high on Quinn Priester. Brown’s ERA ballooned after a Philadelphia shellacking, but he had previously shut down the Dodgers and Diamondbacks; Kenny believes his 95-mph sinker and 29% whiff rate will play against a Brewers lineup he views as overachieving. Chicago’s offense is carrying baseball—first in runs, second in average and OBP—and just took Paul Skenes deep three times. Milwaukee counters with Priester, whose 3.79 ERA hides a .325 xBA and double-digit walk rate, backed by a shaky 4.09 bullpen. With the Cubs 10-6 on the road and Milwaukee’s home games trending under (16-13-3), Kenny is ignoring the total and riding Chicago to keep its NL Central momentum.

Kelly Kirby advised moving Pete Crow-Armstrong if anyone in your league pays full freight for the early counting stats. She loves the speed but noted that every batted-ball metric on his StackCast page sits smack in the 45-55th percentile range—"right in the center," as she put it—suggesting no elite carrying skill beyond steals. Kirby expects a batting-average slide once his .354 BABIP normalizes and pointed out that his 27% chase rate and 10% swinging-strike rate mirror the marks that produced a .259 average in Triple-A. With Chicago still platooning him against tough lefties, she sees a 10-homer, 25-steal rookie season as the ceiling and would flip him now for a sturdier bat if a rival manager is mesmerized by the highlight-reel catches.

Kirby is holding Brandon Woodruff everywhere she drafted him, yet refuses to start him until his velocity returns. Reports from his latest rehab outing peg the four-seam at 92 mph—down roughly 3 mph from his 2022 average (95.2). Because 60% of Woodruff’s arsenal is four-seam/sinker, that drop is worrisome. Kirby likened the situation to a pitcher’s personal spring training and hopes velo ticks up in the next rehab turn, but warned that shoulder-related velocity dips often linger. Her plan: stash on IL or bench, monitor radar-gun readings, and activate only after seeing at least 94 mph in back-to-back starts. She still believes Woodruff can be a fantasy difference-maker if the velocity returns.

Kirby advised patience with Tobias Myers, but only for managers who can absorb ratio pain. After two rusty rehab starts (6 IP, 4 ER, 7 BB, 5 K), she expects a walk-heavy profile to remain—citing last year’s 9.7% BB-rate and the fact he has issued at least three free passes in 7 of his last 10 MLB outings. The appeal is matchup-driven strikeout juice: whenever he faces clubs in the top third of K-percentage, Myers has flashed 10+ K upside thanks to a deceptive low-90s fastball. Kirby ranked him clearly behind Gonsolin and Giolito, framing him as a streamer you deploy only versus whiff-happy lineups and bench otherwise.

Brad Francis recommended Ben Brown under 5.5 strikeouts, noting the Cubs rookie has fallen short of that mark in four of his last five starts. He added that Milwaukee is "not a bad offense at all" and expects the Brewers’ contact-oriented approach to keep Brown below six punch-outs again.

Romanelli recommended playing the Cubs in the first five innings—either laying the half-run or taking the money-line—because Ben Brown provides a slight starting-pitching edge over Quinn Priester and Chicago’s bats crush right-handed pitching. He noted the Cubs bullpen is not playoff-caliber while Milwaukee’s relief corps projects better going forward, so isolating the opening five frames removes that late-inning liability. Priester’s 4.35 xFIP and shaky command suggest regression, and Romanelli expects the Cubs’ top-10 wRC+ versus righties to show up early before the Brewer bullpen can stabilize the game.

Welsh played Jackson Chourio over 1.5 total bases at roughly even money. Chourio has cashed in three of his last five, owns a .290 ISO versus righties, and draws rookie Sean Burke, whose fourseam/curve combo has produced a .392 xwOBA against. With the White Sox bullpen sporting a 5+ ERA, Welsh likes multiple plate appearances against shaky arms, giving Chourio plenty of chances to shoot a gap or swipe a bag to get home.

Seiya Suzuki is 2-for-3 (.667) lifetime versus Quinn Priester and has a hit in 12 of his last 16 outings. The tout flagged him as a value prop despite the tiny sample because of the current form.