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 6

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

Over 39.0(-110)

Reasoning

The Texans have been a team that has traditionally played to the under all season long, but this game has the makings of a rare Houston game that actually goes over the total. Despite the fact that they no longer have the services of their starting quarterback, the Colts are still a team that operates at a pretty fast pace under head coach Shane Steichen. Typically, that bodes well for an over game script, especially since the Texans offense has also been trending up in recent weeks. On the other side of the ball, the Colts defense is not healthy and if Leonard ends up struggling and turning the ball over, that could easily set Houston up with some short fields that could lead to quick scores on Sunday.

Over 39 available at time of publishing. Playable to 39.5

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Caleb Wilfinger

Game Totals Pick

Under 37.5(-110)

Reasoning

Regardless of if Denver is able to cover the spread on Sunday, we can expect the Broncos to run the ball effectively and play a simple and efficient game in a spot where Sean Payton’s team just needs to get out of dodge with a comfortable victory over a depleted division rival. Given the fact that the Broncos’ defense in a position where it should hold a few massive advantages over the Chargers’ anemic offense without Herbert under center, it’s hard to see Los Angeles scoring more than 10 or 13 points, which should be enough for Denver to secure a comfortable win while ensuring that this game stays under the posted total.

Under 37.5 available at time of publishing. Playable to 37.

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Caleb Wilfinger

Money Line Pick

Arizona Win(-105)

Reasoning

One of the best games of the entire bowl season slate will take place on Friday, as the Arizona Wildcats are set to take on the SMU Mustangs in the Holiday Bowl. This is an instance where both teams should be motivated to be here, and each side expects to have minimal opt-outs and/or injuries in this game, which bodes well for a very competitive matchup on Friday. Arizona is a team that I have consistently backed throughout the season, and I don’t intend on stopping now, especially since the Wildcats are being priced like a team that is undeserving of being in the favorite role.

Not only is Brett Brennan’s team is one of the more underrated units in the entire country, I also have to think they’ll have the mental edge against an SMU team that was just one victory away from playing for the ACC Championship for a second consecutive season, before a loss to lowly Cal derailed the Mustangs’ season. It would be fair to question if Rhett Lashlee’s team is fully locked in for what is essentially a meaningless game. Yes, Kevin Jennings is expected to play for the Mustangs, but the veteran quarterback is going up against an Arizona defense that is top 10 in the nation in success rate allowed and 17th in points per drive allowed. SMU’s rush defense is the strength of its unit, but Arizona is not exactly a team that wants to keep the ball on the ground with its pass-centric offense. There are some clear edges for the Wildcats in this matchup and when I also factor in the possible motivation angle, so I’ll back Arizona to finish the season on a high note.

Arizona vs SMU prediction: Arizona ML (-105) available at time of publishing. Playable to -120.

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Point Spread Pick

IND Colts +10.5(-110)

Reasoning

We have an intriguing AFC South showdown on our hands on Sunday, as the shorthanded Indianapolis Colts are set to square off against the playoff-bound Houston Texans in a battle of division rivals in Houston. This isn’t the most scintillating game on paper, but it wouldn’t shock me if the Colts put up more of a fight in this game than what the market and betting public are expected. After a few weeks of somewhat competitive football, the Philip Rivers experience appears to be over in Indianapolis, as the wily veteran quarterback is not getting the start this week under center. Instead, it will be rookie quarterback Riley Leonard who gets the ball for the Colts against a Texans defense that is among the most ferocious units in football. However, this could be a game where Indianapolis keeps things within single digits against a team that is undoubtedly going to be looking ahead to the following week.

To my eyes, Leonard was perfectly serviceable against the Jaguars last week, as he went 18-for-29 for 145 yards and was also able to pick up some key first downs with his legs. With that in mind, as long as he and the Colts offense can generate a decent amount of success on early downs, Indianapolis should be able to score enough points to at least make things competitive. It’s also worth mentioning that Houston has struggled in this role as a double-digit favorite in recent weeks, as the Texans knocked off the lowly Raiders by just 2 points a few weeks ago. Even in their depleted state, the Colts are still a better team than Las Vegas, and I’ll bank on Leonard and company to keep this respectable on Sunday.

Colts vs Texans prediction: Colts +10.5 available at time of publishing. Playable to +10.

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Point Spread Pick

DEN Broncos -12.5(-110)

Reasoning

It’s not the flashiest game on the NFL Week 18 slate, but Sunday’s matchup between the Chargers and Broncos has the potential to be a pivotal game within the AFC playoff picture. After all, Denver is chasing after the top seed in the conference heading into the postseason, while the Chargers are projected to be the #7 seed in the AFC is all of the favorites take care of business this weekend. Despite the fact that this is a game where I should be looking to back the underdog given how Los Angeles likes to play, and the fact that this total is well below 40, I just can’t get there with the Chargers when considering their injuries and availability report this week.

The spot certainly favors Denver on paper, as the Broncos defense will be able to pint its ears back and get after the quarterback in front of a raucous home crowd. Most importantly, Los Angeles has elected to sit the banged-up Justin Herbert in this game, which immediately puts the Chargers offense at a massive disadvantage against one of the best defenses in the sport. Without Herbert, it’s hard to see the Chargers moving the ball at all through the air on Sunday. With that in mind, Jim Harbaugh’s team should look to keep the ball on the ground and try to grind this one out in a game that should be played in the mid-to-high 30s. However, even when taking the low total into consideration, it’s hard to see Los Angeles staying relatively close to Denver for all four quarters in this one. I’ll lay the points with Bo Nix and the Broncos.

Chargers vs Broncos prediction: Broncos -12.5 available at time of publishing. Playable to 13.

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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.

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