Kentucky Derby highlights rich Labor Day weekend of betting

The sports world continues coming out of the shutdown caused by the COVID-19 pandemic and adds the Kentucky Derby and college football. This is one man’s guide to navigating the sports betting landscape this holiday weekend.

Friday, Sept. 4

As an avowed “dog-or-pass” bettor, it pains me to say that the best bet going is MLB chalk parlays. We hope we helped readers connect the dots last weekend with our suggested plays as we’ve cashed several three-teamers this past week (which isn’t too hard when favorites go 12-2 like they did on Wednesday). The faves I’m looking to connect the dot in the weekend series are the Yankees at the Orioles, Rays vs. Marlins, Twins vs. Tigers, White Sox at Royals and Dodgers vs. Rockies (drop a team from the mix if you don’t like the pitching matchup). Beware that there are several early starting times on Friday with five (count ‘em, five!) doubleheaders for your viewing/betting pleasure.

We get at least one NHL Game 7 in the Stars-Avalanche series (4:00 p.m ET). Colorado has rallied to win the last two games and the public sees the Avs as having all the momentum, but I think there’s betting value on the Stars +120 in what amounts to a coin flip. The Golden Knights-Canucks also have a Game 7 (9:00 p.m. ET), but I would pass and let my previously posted Stanley Cup pick on the Golden Knights ride.

In the NBA I’m going to pass on the Heat in this 6:30 p.m. ET game as I expect Giannis & Co. to rebound and get back in this series. I probably won’t back the Heat until after a loss (and hopefully getting more points as we get deeper in the series). I will jump right in on the Rockets +7 in Game 1 of their second-round series with the Lakers at 9 p.m. ET as they can play with anyone and they’re actually showing they can play a little defense.

I hate sounding like a broken record with my advice to check the updated PGA odds after each round because you can find value on contenders, but Jon Rahm was available at upwards of 60-1 after last week’s opening round of the BMW Championship and 150-1 (yes, that’s right) after Friday’s second round and still 10-1 after Saturday’s third round.

Saturday, Sept. 5

The college football schedule on Labor Day Weekend pales in comparison to what we’re used to, but it’s still college football and bettors are champing at the bit. I’m on just one game with Middle Tennessee State +3.5 at Army at 1:30 p.m. ET as MTSU returns 13 starters, including QB Asher O’Hara, who had 2,616 passing yards and 20 TD passes as a sophomore, plus 1,058 yards with nine more TDs. Army might grind out some drives with its running game, but I’ll take the more balanced offense.

The Kentucky Derby goes off at 7:01 p.m. ET with the whole world on Tiz the Law, who has moved to the head of the 3-year-old class and already has one leg of the Triple Crown under his saddle. But I’ll try to beat him (and, yes, I admit I lost every time going against American Pharoah in 2015 and Justify in 2018) as I believe he’ll be compromised by the No. 17 post as he has the top speed horse, No. 18 Authentic, to his outside and several more speed horses drawn inside. I believe they’ll all have to go faster than they want early and set it up for a closer. My pick is No. 2 Max Player (30-1 on the morning line), who finished third to Tiz the Law in both the Belmont and Travers, but he just needs to improve a little more to be in contention down the Churchill stretch at a very nice price.

In the NHL, Thursday’s Game 6 of the Islanders-Flyers series went to double-overtime with Philadelphia forcing a Game 7, which will take place Saturday at 7:30 ET. I’ve been on the Islanders in this space since the playoffs started and think they’re worthy of a bet in a Game 7.

In the NBA, we were high on the Celtics in this space last week and feel good about our +135 series ticket and cashing in Game 1 (unfortunately, we passed on Game 2’s upset). The Raptors eked out a one-point victory in Game 3 Thursday, so I’m jumping back on the Celtics after a loss for Saturday’s Game 4 at 6:30 p.m. ET. I was planning to pass on the Nuggets vs. the Clippers in Thursday’s opener of their series, but couldn’t resist the +9. With a 23-point loss in Game 1, I’m not sure I’ll be betting Denver again in Game 2 at 9 p.m. ET on Saturday.

Sunday, Sept. 6

Again, Sunday’s NHL slate is up in the air, but hoping to back the Islanders and/or Golden Knights moving forward.

In the NBA, I will pass on the Heat vs. the Bucks and Rockets vs. the Lakers unless they’re coming off losses.

The NASCAR Cup Series playoffs begin at Darlington at 6:30 p.m. ET. Last week, we almost scored with our pick on Denny Hamlin at 10-1 as he led going into the final restart. His odds are shorter this week and the value looks like Chase Elliott at 10-1.

Have a happy and safe (and profitable) holiday weekend!

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