Home » Derry’s Super Bowl 58 Picks: Purdy and the 49ers or Mahomes, AKA God, and the Chiefs?

Derry’s Super Bowl 58 Picks: Purdy and the 49ers or Mahomes, AKA God, and the Chiefs?

With 284 games having been played in the regular season and playoffs, it comes down to this. And, really, for the first time in 9 years, the Super Bowl will feature two teams that had preseason odds of less than 10-1 to win the Lombardi Trophy, as the San Francisco 49ers and Kansas City Chiefs will face off Sunday at Allegiant Stadium in Las Vegas.

Indeed, Super Bowl LVIII, is not necessarily what the common fan wanted way back when in September, because there are certainly no underdogs here. Rather, one could argue these were the two teams many thought would be here way back when training camps opened last July.

But what do we think? Is the best bet in this particular game the spread? The money line? Game prop bets? Player props?

Well, let’s get to it and see if we can continue our recent run of success not only in these playoffs but with correct sides in our recent Super Bowl selections.

And for those who have been with me all season (and the past 10 years!), thank you so much. See you back here in September. Good luck!

NOTES: All spreads, money lines and over/under totals (as of Wednesday morning) are provided by DraftKings. (Best bets at the bottom)


SAN FRANCISCO (-2 at -102) over KANSAS CITY / Sunday at 5:35 p.m. CBS

2023 meeting: None

I can hear it now: “Derry, you big dummy, you have been saying throughout the playoffs that you ain’t betting against Patrick Mahomes. You were right for 3 weeks, and now you’re changing your mind. What the hell is wrong with you?”

Well, I can’t answer that question, but I can explain myself and my change of heart. Simply put, since the 49ers demolished the Cowboys in Week 5, I have had them as my No. 1 team in the NFL. I am not going to change my opinion because the Chiefs have had 2 incredible weeks, while San Francisco has been underwhelming.

One top piece of advice you have heard me repeat throughout the past 9 years of doing this column is never to overreact to a short period of time throughout a season. That includes the postseason.

Beyond that, as silly as it will sound to many, I honestly think what Kansas City has done has been a bit overblown. Sure, Mahomes has been Mahomes, but where has most of the talk come from: Steve Spagnuolo’s defense. And if one were to dive deep into the numbers, he really played three teams in the playoffs that completely overthought their game plan.

First off, the Dolphins were toast heading into the week after an epic blowup vs. the Bills in the final week of the regular season. But one thing the Dolphins and Ravens last week had in common is they didn’t even really try to run the ball against the 18th-best rushing D in the NFL.

Buffalo ran it OK, but that fourth quarter might have been one of the worst-managed quarters of the season both by Josh Allen and Sean McDermott.

Meanwhile, what exactly did the Kansas City offense do in the second half of all three of these games? The answer is not much.

On the other side, Brock Purdy has been fantastic in drives he absolutely has needed to be fantastic on. (Yet, he still is taking a ton of criticism from the talking heads.)

I have already been told by my know-it-all 25-year-old son I am an idiot and that I am going to “lose my money.” But one thing I will never do is regret a pick that I didn’t believe in. I believe in the Niners.

Score: 49ers 24, Chiefs 19 (Total: Under 47.5 at -108)


1, San Francisco money line (-122)

Normally, I wouldn’t make a bet such as this my best bet, but this literally is what I have put about 60 percent of my Super Bowl allotment on this year (although I have it at -120).

I think the extra 20 cents is worth it in this case, although if it is any higher when you’re reading this, I would probably wait, as I think there will be some Kansas City money come in near game time. (It already has Wednesday morning, dropping this from -125 to -122.)

2, No 2-point conversion attempt (-140)

Think about why so many are unhappy about why these are not the two teams they wanted in the Super Bowl? NO! Forget about Taylor Swift!

Many didn’t want these teams, because Andy Reid and Kyle Shanahan don’t play the game like they are playing “Madden Football” on Playstation. They play the game like successful coaches have throughout the years, and likely will only call for the two-point conversion attempt unless it is absolutely necessary, and that means never until the fourth quarter.

In other words, you’re basically getting -140 that they won’t attempt one in the fourth quarter.

And if you need more facts to back up this bet, the Niners have not attempted a two-point conversion SINCE 2021, while the Chiefs have only tried ONE THIS SEASON.

3, Deebo Samuel over 16.5 rushing yards (-130)

In the last Super Bowl matchup between these two teams, Deebo had three carries for 53 yards, which means he only needs one good rush to get past this number. Besides, there’s no question he will be key for San Francisco to have a good day offensively.

And while he has only had five games this season in which he has surpassed that 16.5 figure (one he had 15 yards rushing), there’s little question he will be very involved here. By the way, the 49ers record this season in those five games in which Deebo rushed for more than 16.5 yards? 5-0. And in his career? 20-3.

4, Deebo Samuel to win MVP (1/10 of a unit at +2000)

Like we said, we are only doing this at a fraction of whatever your unit is. In other words, if you normally bet $20 on a game, you might only want to be $2 here. If you bet $100 on a game, bet $10, etc.

The thinking here is looking for the best value, and this to me is unquestionably the best value on a side bet across the board. We know that if Kansas City wins, there’s probably an 80-percent chance Patrick Mahomes will take the award. However, if it is San Francisco, it could be almost anyone.

Sure, it is more likely to be Brock Purdy or Christian McCaffrey, but are we getting enough value at +225 or +475, respectively? Maybe on McCaffrey, but we all know this team goes on offense as Deebo goes.



Note: TIES ARE NOT COUNTED IN MY RECORD, which could result in a different total of games in the “straight up” and “against the spread” categories, as well as with totals.


Best bets: 1-3 (but the big one hit for the third straight week); All games against the spread: 1-1; Straight up: 2-0; Over/Under totals: 0-2.


Best bets: 3-1; All games against the spread: 2-2; Straight up: 4-0; Over/Under totals: 1-3.


Best bets: 2-3; All games against the spread: 3-3; Straight up: 2-4; Over/Under totals: 3-3.



Best bets: 47-41 (.534); All games: 141-121 (.538).

STRAIGHT UP (no spread): 163-108 (.601).

OVER/UNDER TOTALS: 151-117 (.563).


Straight up: W, 9-8. Against spread: W, 9-7. Total (Under 42.5): L, 10-6.


(click on week to view)

Championship round: 1-3 best bets; 1-1 ATS; 2-0 straight up; 0-2 over/unders

Divisional round: 3-1 best bets; 2-2 ATS; 4-0 straight up; 1-3 over/unders

Wild-card round: 2-3 best bets; 3-3 ATS; 2-4 straight up; 3-3 over/unders

Week 18: 2-3 best bets; 5-11 ATS; 8-8 straight up; 8-8 over/unders

Week 17: 3-2 best bets; 12-4 ATS; 13-3 straight up; 4-12 over/unders

Week 16: 2-3 best bets; 7-9 ATS; 10-6 straight up; 11-5 over/unders

Week 15: 3-2 best bets; 8-6 ATS; 12-4 straight up; 11-5 over/unders

Week 14: 3-1 best bets; 10-4 ATS; 10-5 straight up; 7-8 over/unders

Week 13: 3-2 best bets; 9-4 ATS; 8-5 straight up; 8-5 over/unders

Week 12:1-4 best bets; 5-10 ATS; 8-8 straight up, 10-6 over/unders

Week 11: 2-3 best bets; 4-9 ATS; 8-6 straight up; 7-7 over/unders

Week 10: 1-3 best bets; 7-6 ATS; 6-8 straight up; 6-8 over/unders

Week 9: 4-1 best bets; 11-3 ATS; 9-5 straight up; 8-5 over/unders

Week 8: 3-2 best bets; 9-6 ATS; 10-6 straight up; 7-9 over/unders

Week 7: 2-3 best bets; 7-6 ATS; 5-8 straight up; 9-3 over/unders

Week 6: 4-1 best bets; 7-7 ATS; 13-2 straight up; 9-6 over/unders

Week 5: 2-3 best bets; 8-6 ATS; 7-7 straight up; 9-5 over/unders

Week 4: 2-3 best bets; 8-8 ATS; 10-6 straight up; 9-7 over/unders

Week 3: 2-3 best bets; 9-6 ATS; 7-8 straight up; 8-7 over/unders

Week 2: 4-1 best bets; 7-8 ATS; 9-7 straight up; 9-7 over/unders

Week 1: 4-1 best bets; 8-8 ATS; 10-6 straight up; 11-4 over/unders

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