NASCAR Daytona 500 Picks & Predictions: Two Longshot Drivers Who Have a Ton of Betting Value on Monday

Editor's note: This article was published prior to Sunday's race, which was delayed due to rain. Sportsbooks have re-posted odds in the run-up to Monday's restart (4 p.m. ET on FOX), and both of the longshot bets Nick Giffen analyzes below still have betting value.

The 2020 NASCAR Cup Series regular season kicks off tomorrow with the granddaddy of them all, the Daytona 500. Sunday's race features the fourth race run under the current superspeedway rules package.

Last year's three races under this rules package each finished with between 18 and 21 drivers on the lead lap. I expect even fewer lead lap finishers for tomorrow's race. That's because the honor of being crowned the Daytona 500 champion encourages drivers to take even more risks. Between the huge draft and the intensity of pushing for the win, the “Big One" — where multiple cars sometimes numbering in the double digits — always looms.

Betting Daytona is a bit strange. Because nearly anyone competing can win, it doesn't make sense to bet favorites unless you're getting a really good price on them. Instead, see if you can find prop value on favorites, while taking a few fliers on longer shot drivers.

[Check out our Daytona 500 cheat sheet for a few last-minute bets before the race gets underway.]

Matt DiBenedetto (+3200) to Win

Yesterday, my colleagues Matthew Freedman, PJ Walsh, and I ranked each driver from 1-40. I was highest on DiBenedetto, slotting him into the 10 hole, while PJ wasn't far behind putting DiBenedetto in 12th. Even taking into account the more pessimistic 21st place ranking from Freedman, DiBenedetto averages out to our 14th place driver, but is priced with the 18th best chance to win at FanDuel Sportsbook.

Given I'm even higher on DiBenedetto, this is definitely a bet I'd recommend. Last year, DiBenedetto led twice for 49 laps on his own merit while driving for Leavine Family Racing before getting caught up in a wreck not of his making. He also pushed into the lead at the spring Talladega race before wrecking again. In the only superspeedway race he didn't wreck, he finished eighth at the Coke Zero 400.

Now DiBenedetto gets an upgrade to Wood Brothers Racing, which is affiliated with Team Penske. For context, Leavine Family Racing has never had a win in its Cup Series history. Ryan Blaney piloted the Wood Brothers car to a win in 2017 en route to a ninth place finish in the final points standings. You better believe DiBenedetto will benefit from the Team Penske alliance. The Penske drivers and cars are top of the line at Daytona, and DiBenedetto will be teaming with them all day.

If he avoids the Big One, he's a legitimate contender to win. I like DiBenedetto down to +2200.

Chris Buescher (+7500) to Win

My colleague PJ Walsh wrote about Buescher back in December, but his odds haven't budged at FanDuel where he remains a 75-1 long shot a mere 24 hours prior to the green flag.

FanDuel clearly hasn't adjusted for the fact that Buescher has upgraded from JTG Daugherty to the No. 17 car at Roush Fenway Racing (RFR) previously driven by Ricky Stenhouse Jr. Stenhouse piloted that car to two superspeedway wins. Buescher is no slouch himself at Daytona. In six races at Daytona while with JTG Daugherty, he has three top-ten finishes, including two fifth places finishes in 2018. With the upgrade, we should expect an even more competitive Buescher. I'd bet Buescher down to +5000.