Monday Best Bets: One Cross-Sport Parlay, Two NBA Props

Jaylen Brown #7 of the Boston Celtics reacts against the Miami Heat at FTX Arena on November 04, 2021 in Miami, Florida.
Image Credit: Michael Reaves/Getty Images

The wagering buffet known as March Madness is temporarily closed until Thursday. However, we managed to find a few snacks to nibble on until then. The Monday Best Bets menu includes a Boston-centric parlay that, when all is said and done, will (hopefully) warm you up like a tasty bowl of clam chowder.

Serve that with a pair of NBA props on the side, and you have yourself a full betting meal.

With that, let’s dig into the Monday Best Bets (before they get cold).

Best Bets Track Record

Friday: 1-1
Year-To-Date: 23-19-1

Bostonian vs. The Book: 7-6-1
BetPrep Prop of the Day: 6-8
NBA Props: 7-3
NHL Props: 3-2

Cross-Sport Parlay: Celtics + Bruins + Cavaliers (All Moneyline)

Brad Marchand #63 of the Boston Bruins gets ready during a face off against the Arizona Coyotes at Gila River Arena on January 28, 2022 in Glendale, Arizona.
Image Credit: Norm Hall/NHLI via Getty Images

The bet: Celtics moneyline + Bruins moneyline + Cavaliers moneyline (three-team parlay)
The odds: +127
Where to bet: BetMGM
From: Matt Perrault via The Bostonian Vs. The Book Podcast

Matt Perrault, who represents “The Bostonian” portion of The Bostonian Vs. The Book Podcast, is an unabashed fan of all things Beantown sports. So we know what you’re thinking when you see Perrault touting a three-team moneyline parlay featuring two Boston teams: Homerism overkill!

Maybe. But when you look at the matchups, this Best Bet has merit and — with a plus-money potential payout — some decent value. Here’s the three-leg parlay:

  • Boston Celtics -1200 moneyline (at Oklahoma City)
  • Boston Bruins -250 moneyline (at Montreal)
  • Cleveland Cavaliers -200 moneyline (vs. LA Lakers)

Podcast co-host Dave Sharapan co-signed on this wager, despite expressing some concern about the non-Boston leg of this bet.

“That’s a winner!” Sharapan said. “The Cavs are the [only] one to be scared of. But the Lakers on the road? That’s OK, we are good with [betting against] that.”

Said Perrault: “Frankly … I would be very surprised if the Lakers win this game tonight,” theorizing that Cleveland will be especially energized playing against former Cavs’ legend LeBron James.

If you agree with Perrault and Sharapan’s consensus best bet, BetMGM is offering +127 odds on this three-teamer.

  1. 15+ States
  2. Extensive Betting Markets
  3. Top-Rated App

Perrault listed one other bet he likes during Monday’s Bostonian vs. The Book podcast — an NBA total. You can listen to the replay on Youtube, Spotify, or Apple Podcasts.

Detroit Pistons: PG Cade Cunningham

Cade Cunningham #2 of the Detroit Pistons looks on during the second quarter of the game against the Boston Celtics at TD Garden on March 11, 2022 in Boston, Massachusetts
Image Credit: Omar Rawlings/Getty Images

The bet: Under 23.5 points (vs. Portland)
The odds: +110
Where to bet: DraftKings Sportsbook
From: Matt LaMarca via Monday NBA Props

Cunningham got off to a slow start this season, but the top pick in last year’s draft is starting to pick up steam. That said, he’s still struggling with his scoring efficiency. He’s averaged 22.1 points over his past eight games while shooting 44.3% from the field and 34.9% from 3-point range.

The scary thing is those numbers are markedly better than his full-season stats — he’s averaging just 16.9 points on 40.5% shooting for the year. So he’s actually been on a bit of a heater.

Overall, Cunningham has exceeded 23.5 points in just 10 of 55 games. If he’s struggled to hit this Over even when he’s been shooting better than usual, I have no problem riding with the Under on Monday.

NBA Prop: Chicago Bulls SF DeMar DeRozan

Chicago Bulls forward DeMar DeRozan brings the ball up court against the Philadelphia 76ers
Image Credit: Kamil Krzaczynski-USA TODAY Sports

The bet: Over 4.5 assists (vs. Toronto)
The odds: -140
Where to bet: FanDuel Sportsbook
From: BetPrep Prop of the Day via

The BetPrep crew easily cashed Friday’s Best Bets selection of Zach LaVine Over 3.5 assists. In fact, LaVine had five assists by halftime, finishing with nine total dimes. Now that’s what we like to see: a sweat-free NBA prop winner!

The folks at BetPrep are wasting no time going back to the same well, as they like another Chicago player to dish some dimes on Monday. This time, it’s DeMar DeRozan Over 4.5 assists against Toronto.

Here’s the rationale behind this BetPrep Best Bet:

  • DeRozan has recorded five-plus assists in 12 of his last 15 home games
  • DeRozan has faced the Raptors three times this season — and each time, he went Over 4.5 assists (6, 7, 7)

Worried about the Raptors’ solid defense? Well, DeRozan has handed out five-plus dimes in 10 of his last 13 games against a top 10 defense. Put it all together, and you can see why this is Bet Prop’s Prop of the Day.

You can find DeRozan Over 4.5 assists (-140) at FanDuel Sportsbook.