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 3

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 46.5(-110)

Reasoning

At first glance, I thought I was going to be targeting the under in this game, much like I did for both teams in their quarterfinal matchups. However, I’m actually more inclined to look at the over in this game now that the total has come down a bit from the opening number. While both defenses are among the best in the nation, these offenses should be able to implement some schematic adjustments from the first game and improve on their respective performances. While neither offense played all that well back in that October meeting, the game still finished with 50 total points, and that was with each side squandering a few scoring chances. Now, the Ducks will get to showcase their speed on a fast track against an Indiana defense that loves to play its safeties deep, giving the opponent plenty of room to move the ball with the short and intermediate passing game — a mainstay in Will Stein’s offense.

On the other side, the Hoosiers offense was able to generate consistent success on the ground in the previous matchup, and that should continue into this game given how well Indiana’s offense line has played all year. The Oregon secondary is excellent, but this is the best wide receiver duo the Ducks have played, so it’s reasonable to assume that they’ll give up a few big plays here and there as well. Let’s roll with the over now that we’re under a key number.

Oregon vs Indiana pick: Over 46.5 (-110) available at time of publishing. Playable at that number.

If you’re looking for a new sportsbook for the football season, we recommend checking out Fanatics Sportsbook. New users can get $250 in FanCash INSTANTLY when they make their first $50 wager! Join Fanatics Sportsbook, where you can bet on our Oregon vs Indiana predictions.

BET o46.5 NOW WITH

Caleb Wilfinger

Point Spread Pick

Oregon +4.5(-118)

Reasoning

The 2nd round of the College Football Playoff is behind us, and there are now just 4 teams remaining in the pursuit of a National Championship. Back on New Year’s Day, the 5th-seeded Oregon Ducks defeated Texas Tech to advance to this semifinal round, while the top-seeded Indiana Hoosiers rolled through Alabama in impressive fashion just a few hours later. Which of these teams will come out on top in the Peach Bowl on Friday and advance to the National Championship game? It’s almost time to find out.

You could convincingly make the case that these are the 2 best teams in the country at the moment, and while it’s hard to ignore what we’ve seen from the Hoosiers over their last few contests, the basic market fundamentals clearly point to Oregon as the side in this game at the current number. For starters, it’s clear that a wager on Indiana in this game is buying the Hoosiers at the peak of their market value, while the Ducks are still being priced like a lesser team than they were a few months ago, which I just don’t believe is the case. After all, Oregon was a 7-point favorite against Indiana at Autzen Stadium back on October 11, which would roughly make this a line move of over 8 points since the first meeting between these teams. While Indiana deserves to be priced as the best team in the field, I’ve certainly upgraded Oregon following its dominant showing against Texas Tech, a team that is significantly better than an Alabama team that essentially quit after Indiana took an early double-digit lead in the Rose Bowl.

There’s no doubt that the Ducks played their worst game of the season by some distance in that first meeting, and they still were tied midway through the 4th quarter. Now, Dan Lanning’s group appears to be playing its best football of the season on defense, and the offense can hone in on making the necessary schematic adjustments to fix what went wrong in the previous meeting. It certainly won’t be easy against Heisman Trophy-winning quarterback Fernando Mendoza and the Hoosiers’ extremely balanced offense (2nd in success rate, 2nd in EPA per play, 3rd in points per drive) and the Indiana defense has also been a top-5 unit in the sport over the course of the season. However, given the fact that Oregon’s offense just had to face the best defensive front in the nation, I’m expecting a much better effort from the Ducks on the ground in this one, which was something they were able to do successfully for a decent chunk of the first meeting against Curt Cignetti’s defense.

Will Stein’s offense should also finally be getting Evan Stewart back for this game, which makes this the healthiest that Oregon’s deep group of pass-catchers (Dakorien Moore, Kenyon Sadiq, Malik Benson, Gary Bryant Jr., etc.) has been all season. With that in mind, as long as Dante Moore is able to play to his strengths and avoid making some of the mistakes he made in the first meeting, the Ducks should be able to grind out scoring drives and potentially even strike for some explosive plays downfield. Look for Oregon to empty the tank and pull out all the stops schematically on both sides of the ball in a game that could come down to the final possession.

Oregon vs Indiana prediction: Oregon +4.5 (-118) available at time of publishing. Playable to 3.5.

You can bet on our Oregon vs Indiana pick with BetMGM, where right now new users can activate your new BetMGM account ⚡ and receive $150 in bonus bets INSTANTLY if your first $10+ wager is a winner!

BET +3.5 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