Caleb Wilfinger

Deputy Editor

Caleb is a Deputy Editor at Pickswise who resides in Upper Manhattan and has spent time in Philadelphia and Washington, D.C. He has been handicapping various sports since 2018, including NFL, NCAAF, NBA, NCAAB, MLB and tennis. The futures market is his favorite to target and he has a passion for sharing his plays with the Pickswise community.

Live Picks 5

Live Parlays 0

Weekly News Articles 10

Location

New York

Favorite Sports

Favorite Teams

Greatest Betting Win

One of my favorite sports betting memories was certainly in October of 2022, when I successfully cashed a 5-team Round Robin parlay involving games I had already played as straight bets. It involved Penn State catching 16 at home against Ohio State, along with Notre Dame, UCF, Louisville and Baylor all on the money line as underdogs. The Irish and Cardinals took care of business early by crushing their opponents and Penn State hung tough to cover the inflated number against the Buckeyes. Meanwhile UCF pulled out a thriller against Cincinnati, leaving me only a Baylor victory away from a serious 50U profit. Thankfully, the Bears made quick work of Texas Tech in the second half and I was able to watch the 4th quarter with a smile on my face. This was one of three 5-leg Round Robin parlays I cashed during the 2022 college football campaign, as part of what was a terrific season on the gridiron.

Greatest Achievements

Finished with a win rate of 63% in weekly 2022 NCAAF best bets column, highlighted by an 8-0 run to close out championship week and bowl season 25-8 (76%) YRFI/NRFI run from June through August 2023.

Education

Caleb attended Penn State University, where he covered Penn State football and basketball for 3 years (along with many other sports), getting an up close and personal look at the grind of a full collegiate athletics regular season. His two bachelor's degrees were in Journalism & Political Science, with sports journalism as a primary focus. During his senior year, Caleb began moving away from betting casually and turning into a sharper bettor, including creating systems, compiling data for multiple sports, etc.

Experience

5+ years betting experience 3+ years as a sports handicapper 10+ years as a sports journalist Caleb has been betting legally since 2019 but his history with gambling predates that, as he regularly picked NFL games against the spread throughout his college tenure. In 2021, Caleb started handicapping college football games for Pickswise and turned a profit for the season. After moving into a full-time Deputy Editor role in 2022, Caleb has had plenty of success and winners for the site’s users, most notably in college football, NFL and the MLB YRFI/NRFI market.

Favorite betting market / type

Futures and Point Spreads.

Favorite bookmakers

Caleb's Picks

Game Totals Pick

Under 40.5(-110)

Reasoning

Regardless of which team comes out on top in Las Vegas, the under is my preferred way to attack the total on Sunday. Even after moving on from offensive coordinator Chip Kelly, the Raiders offense is still absolutely miserable, and I can’t imagine that changes all that much against a Broncos defense that is among the league’s best in terms of generating pressure on the quarterback. On the other side of things, Bo Nix struggled mightily against Las Vegas’ zone concepts in the first meeting between these teams, and Denver has historically had problems with starting slow all season long. Look for this game to end in the 30s, even if the Broncos go on to win and cover the number.

Under 40.5 available at time of publishing. Playable to 40.

BET u40.5 NOW WITH

Caleb Wilfinger

Game Totals Pick

Under 66.5(-110)

Reasoning

While both of these offenses have the capability to score in bunches, my lean on the total is this game is on the under. The forecast is calling for rain in this game, which could certainly lead to both sides looking to lean on their advantages in the trenches in the early going. There’s the also the fact that this is easily the biggest game in program history for both teams, and we can expect each side to start off a bit slow. Each coaching staff will be very keen on not making the first mistake, and it wouldn’t surprise me if we actually had some punts in the early going before both teams settle in and start trading scores. This is not a play for the faint of heart, but there are plenty of avenues for this game to go under this monster total.

Under 66.5 available at time of publishing. Playable at that number.

BET u66.5 NOW WITH

Caleb Wilfinger

Point Spread Pick

LV Raiders +7.5(-110)

Reasoning

We appear to have a major mismatch on our hands on Sunday in the AFC West, when the Denver Broncos head to Las Vegas for a date with the reeling Raiders. Despite the fact that Las Vegas has just two wins on the season, the Raiders played a bit better against the Chargers a week ago, and they did just cover against this same Broncos team in the previous meeting between these teams this season. Denver was a 9.5-point home favorite back on November 6 and nearly lost that game outright, as the Broncos mustered just 10 points in that matchup. When you adjust for the loss of home field (a fairly significant edge for the Broncos in the first meeting) this is a line that I make around Denver -6, so it’s hard to pass up the value we’re getting with Las Vegas as a home underdog of over a touchdown.

On one hand, the Raiders are one of the worst teams in football and shouldn’t be expected to score much on this excellent Denver defense. However, despite their gaudy record, I’m still not buying the Broncos offense, as Denver has been a pretty middling unit all season long, despite facing an easy schedule of opposing defenses. That won’t be the case against a Las Vegas defense that fared very well against Nix in the first meeting between these teams, and the Raiders’ zone looks flummoxed the young Denver quarterback throughout that contest. There’s no reason to believe that Denver should be laying over a touchdown in this spot, especially since the Broncos haven’t covered the spread in this situation (road favorite of over a touchdown) at any point this season. Denver thrives in close games, but it also finds itself in a lot of one-score games for a reason. Therefore, while the Raiders have been miserable for the majority of the campaign, I’ll back an ugly ‘dog to keep things within one possession on Sunday.

Broncos vs Raiders prediction: Raiders +7.5 (-110) available at time of publishing. Playable to +7.

Now you can bet any of our Broncos vs Raiders predictions at FanDuel Sportsbook, which has a great new-customer offer to take advantage of. If you sign up for FanDuel right now, you earn a welcome bonus worth up to $300 if your first $5 bet wins! Use this link 🔗 to join FanDuel right now and learn more.

BET +7.5 NOW WITH

Caleb Wilfinger

Money Line Pick

North Texas Win(-125)

Reasoning

Arguably the most consequential game of the weekend comes in New Orleans, where the AAC title game will take place on Friday between North Texas and Tulane. With both teams currently ranked ahead of James Madison in the most recent College Football Playoff rankings, this game essentially functions as a play-in game for the right to claim the Group of 5 slot in the playoff. Both teams are currently in the midst of excellent seasons, and these are a couple of offenses that should see success in this one, as evident by the sky-high total. However, even though Tulane is going to be an attractive home underdog for many, I can only look toward North Texas as my preferred side on Friday.

This is a difficult game to handicap given that both teams have coaches that are leaving each program for Power 4 jobs after the season. Setting that fact aside, Tulane is not a team that I’ve been overly impressed with in big spots this season, even as the Green Wave have overachieved compared to preseason expectations. Theoretically, Tulane should be able to score on this North Texas defense, but the Mean Green have a strong pass defense and the Green Wave are just 86th in rushing success rate, which is how you can have success against North Texas. On the other side, the Tulane defense is certainly not the strength of the team, and the Green Wave will have a difficult task on their hands against Drew Mestemaker (29 touchdowns to just 4 interceptions this season) and a Mean Green offense that is elite in all areas. In fact, North Texas is a top 5 unit in success rate, EPA per play, early downs EPA, quality drives created and points per drive. This is a team that can beat you on the ground and through the air, which bodes well for a matchup against a Tulane team has not fared well when stepping up in class against quality offenses this season, as we saw against the likes of Ole Miss and UTSA. And even in a win over Memphis last month, Tulane’s below average pass defense (97th in passing success rate allowed, 86th in 3rd down success rate allowed) struggled to slow down the Tigers, to the tune of 368 passing yards allowed. With that in mind, as long as Mestemaker plays a fairly clean game, there should be plenty of avenues for North Texas to put up plenty of points and force Tulane’s offense to play from behind and consistently score to keep up — a role that the Green Wave have struggled with this season. I’ll back the visitors to outscore the hosts and win the AAC, capping off a storybook season in the process.

North Texas vs Tulane prediction: North Texas ML (-125) available at time of publishing. Playable to -130.

Now you can bet any of our North Texas vs Tulane predictions at FanDuel Sportsbook, which has a great new-customer offer to take advantage of. If you sign up for FanDuel right now, you earn a welcome bonus worth up to $300 if your first $5 bet wins! Use this link 🔗 to join FanDuel right now and learn more.

BET -140 NOW WITH

Caleb Wilfinger

Heisman Trophy Winner Pick

D. Dampier to win Heisman Trophy(+6000)

Reasoning

This is a shot in the dark compared to some of the favorites on the board, but it’s an educated wager on a quarterback that I could see making a major leap this fall. Devon Dampier electrified the Mountain West at New Mexico a season ago, racking up 31 total touchdowns (including a whopping 19 touchdowns on the ground) in a season that saw him take a major step forward from his freshman campaign.

Now, the 3rd-year starter steps into a promising situation with a Utah team that handed the reins over to former New Mexico offensive coordinator Jason Beck, a respected offensive mind and a surefire upgrade from what the Utes had last season. The Utes also upgraded their weapons on the perimeter via the transfer portal and get a pretty favorable schedule compared to a few other contenders in the Big 12. I’ve got Utah favored in 11 games and if the Utes are able to navigate their way through a couple of tricky conference games, they should certainly find themselves in the Big 12 title game come Championship Weekend. That alone gives this 60-1 ticket a ton of value, so Dampier is worth a sprinkle at this number.

BET +6000 NOW WITH