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 1

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

Anytime Touchdown Scorer Pick

JC French (GASO) to score a TD(-150)

Reasoning

To close out our Georgia Southern vs App State Parlay, we’ll take JC French to find the end zone on Monday. The Georgia Southern quarterback has had a pretty inconsistent season through the air to this point, but French has seen plenty of success on the ground in 2025. With 6 rushing touchdowns to his name and 5 of them coming in Sun Belt play, French should be in a position to succeed against a below-average App State run defense. The veteran found the end zone with his legs against the Mountaineers in the previous meeting between these sides, so let’s go back to the well with this angle in Birmingham.

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Caleb Wilfinger

Point Spread Pick

Appalachian State +8.5(-110)

Reasoning

This is an instance of an unstoppable force meeting an immovable object, which points us in the direction of the underdog on Monday. While Appalachian State is going to be down to its 3rd-string quarterback in this game and a number of other pieces for the Mountaineers are expected to be out of the lineup, there is still plenty that they can draw from the previous meeting against Georgia Southern this season, which was just a 2-point victory for the Eagles.

Additionally, Clay Helton has been abysmal as a coach in bowl games in his career. In fact, he’s a whopping 0-5 against the spread with a trio of outright losses as a favorite since 2017. Given his history and the fact that not all that much separates these teams on paper, let’s take the points with the ‘dog.

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Caleb Wilfinger

Game Totals Pick

Under 59.5(-110)

Reasoning

As previously mentioned, App State is likely going to be without multiple quarterbacks in this game, along with a few other key contributors at wide receiver and on the offensive line. That likely puts a cap on the amount of scoring we’ll see from the Mountaineers, and the Georgia Southern offense has also produced some rather sporadic results of late. Conversely, the defense has stepped up in that span, allowing 24 or fewer points in 3 of the past 6 outings, including the aforementioned 25-23 win at App State last month. On the other side, starting running back OJ Arnold was injured late in the season, and he is unlikely to play for the Eagles in this one, along with a couple of other pieces on offense. Let’s side with the under in the Birmingham Bowl.

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Caleb Wilfinger

Game Totals Pick

Under 55.5(-110)

Reasoning

Bowl season keeps rolling along on Tuesday, and arguably the most fascinating game on the card comes in the form of the Alamo Bowl between the USC Trojans and TCU Horned Frogs. Both of these teams are going to be missing a ton of players heading into this game, which makes this a pretty difficult handicap on paper. On the TCU side of things, quarterback Josh Hoover is out, along with wide receiver Jordan Dwyer and running back Kevorian Barnes. That eliminates a lot of the potential for offense for the Horned Frogs, even against a USC defense that is going to be down a considerable number of pieces of its own. Furthermore, offensive coordinator Kendal Briles is not going to be on the sidelines for this game, so it’s hard to see TCU mustering up a ton of offense in this one.

On the other side of the ball, USC is going to have quarterback Jayden Maiava in this game, as the veteran has re-signed with the Trojans for another season. However, Lincoln Riley’s team is dealing with a ton of roster turnover and will be without some of their best players on Tuesday, including the wide receiver duo of Makai Lemon and Ja’Kobi Lane. With that in mind, we can expect Riley to lean on his ground game against a TCU defense that hasn’t exactly put up stellar metrics in that department this season. Given the fact that USC’s offense should be a bit more limited than usual and the TCU offense is down multiple key pieces in this game, the under is the only way I can look on Tuesday.

USC vs TCU prediction: Under 55.5 (-110) available at time of publishing. Playable at that number.

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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.

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Caleb Wilfinger

Caleb's Parlays

Georgia Southern vs App State Same Game Parlay

2:00 PM ETToday

2:00 PM ET

Georgia Southern @ Appalachian State · Point Spread

Appalachian State +8.5

Reasoning

Our Analysis

This is an instance of an unstoppable force meeting an immovable object, which points us in the direction of the underdog on Monday. While Appalachian State is going to be down to its 3rd-string quarterback in this game and a number of other pieces for the Mountaineers are expected to be out of the lineup, there is still plenty that they can draw from the previous meeting against Georgia Southern this season, which was just a 2-point victory for the Eagles.

Additionally, Clay Helton has been abysmal as a coach in bowl games in his career. In fact, he’s a whopping 0-5 against the spread with a trio of outright losses as a favorite since 2017. Given his history and the fact that not all that much separates these teams on paper, let’s take the points with the ‘dog.

2:00 PM ET

Georgia Southern @ Appalachian State · Game Totals

Under 59.5

Reasoning

Our Analysis

As previously mentioned, App State is likely going to be without multiple quarterbacks in this game, along with a few other key contributors at wide receiver and on the offensive line. That likely puts a cap on the amount of scoring we’ll see from the Mountaineers, and the Georgia Southern offense has also produced some rather sporadic results of late. Conversely, the defense has stepped up in that span, allowing 24 or fewer points in 3 of the past 6 outings, including the aforementioned 25-23 win at App State last month. On the other side, starting running back OJ Arnold was injured late in the season, and he is unlikely to play for the Eagles in this one, along with a couple of other pieces on offense. Let’s side with the under in the Birmingham Bowl.

2:00 PM ET

Georgia Southern @ Appalachian State · Anytime Touchdown Scorer

JC French (GASO) to score a TD

Reasoning

Our Analysis

To close out our Georgia Southern vs App State Parlay, we’ll take JC French to find the end zone on Monday. The Georgia Southern quarterback has had a pretty inconsistent season through the air to this point, but French has seen plenty of success on the ground in 2025. With 6 rushing touchdowns to his name and 5 of them coming in Sun Belt play, French should be in a position to succeed against a below-average App State run defense. The veteran found the end zone with his legs against the Mountaineers in the previous meeting between these sides, so let’s go back to the well with this angle in Birmingham.

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Caleb Wilfinger