Caleb Wilfinger

Deputy Editor
Google News
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 7
Live Parlays 0
Weekly News Articles 10
Location
New York
Favorite Sports
Favorite Teams
Kansas Jayhawks
Los Angeles Dodgers
New York Giants
New York Knicks
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
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Caleb's Picks

Money Line Pick
Arizona Win(-105)

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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Game Totals Pick
Under 48.5(-110)

Despite the fact that both offenses have the capability of putting up points, I actually believe that we’re getting a point or two of value on the under in a game where both defenses should have their say by the time the game ends. On one side, the Indiana defense is one of the best units in the nation, as we saw against the likes of Oregon and Ohio State this season. Time and again, the Hoosiers have proven that their success up front is no flue, and they should be able to dominate the matchup against a middling Alabama offensive line and put pressure on Ty Simpson as a result.

As for the Crimson Tide, this is not a vintage Nick Saban era defense, but Kane Womack is still one of the better defensive minds in the country, and I expect his unit to respond to the challenge against an Indiana offense that has largely done what its wanted to against any opponent all season long. Let’s roll with the under on Thursday.

Alabama vs Indiana prediction: Under 48.5 (-110) available at time of publishing. Playable to 48.

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Game Totals Pick
Under 52.5(-110)

While both offenses certainly have the capability to put up points in a game that should be played in relatively favorable weather conditions on Thursday, I’m projecting that scoring should be tougher than most would expect in this matchup. For starters, both teams are anchored by their stout defenses, as each unit ranks inside the top 15 nationally in success rate and points per drive allowed on the season. It’s also worth mentioning that each defense has been able to step up in their biggest games of the season to this point, and there’s no real reason to shy away from that trend in this one.

As previously mentioned, it’s hard for any offense to move the ball on this elite Texas Tech defense, as the Red Raiders are 1st in the nation in opponent EPA per play and tops in the country in both Early Downs EPA and quality drive rate allowed. On the other side, I can imagine that some will point to Oregon’s lackluster performance in the 4th quarter against James Madison as a sign of what a better offense could do to the Ducks defense, but it’s important to remember that most of the players on the field in that fourth quarter were backups in a game that was already well out of hand early in the second half. Both defenses should be locked in for a game where red zone success rate could prove to be the difference. I’ll grab the under while it’s still above a key number.

Oregon vs Texas Tech prediction: Under 52.5 (-110) available at time of publishing. Playable to 51.5.

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Point Spread Pick
CHI Bears -3.0(-105)

Last season, the Lions captured the NFC North crown and the Bears finished in last place. How things have changed in one season as Chicago is the 2025 NFC North champion and Detroit is a loss away from closing in fourth place. Bears head coach Ben Johnson helped the Detroit offense dominate in 2024 as their offensive coordinator, but with his shift to the Windy City has flipped the division. Chicago (11-5) is coming off a tough 42-38 defeat at San Francisco last Sunday night in spite of 330 passing yards and a pair of TDs from QB Caleb Williams.

The Lions (8-8) buried the Bears in Week 2 at Ford Field, 52-21 as 6.5-point favorites in Johnson’s return to the Motor City. That began a four-game winning streak for Dan Campbell’s team, but the Lions alternated wins and losses in the next nine games. Detroit is looking to snap a three-game slide after falling to the Rams, Steelers, and Vikings. On Christmas, the Lions dropped a 23-10 decision at Minnesota as 7-point road favorites, falling to 1-4 in division play. Coincidentally, the only win against an NFC North opponent for Detroit was in Week 2 against Chicago, as the Lions seek their first road victory since Week 10 at Washington.

Chicago is playing for playoff seeding at this point, as the Bears are out of the running for the top seed and will begin the first round at Soldier Field. There is no confirmation on which starters may potentially sit for Detroit with them being eliminated. The Lions stumbled to a 1-4 SU/ATS mark as an underdog, with the lone victory coming at Baltimore in Week 3. The Bears have won five consecutive home games since dropping the opener to Minnesota. It’s hard to back an unmotivated team in Detroit, even as an underdog after being favored in the last 2 weeks.

Lions vs Bears prediction: Bears -3 available at time of publishing. Playable at that number. 

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Point Spread Pick
Indiana -6.5(-110)

The opening round of the College Football Playoff is behind us, and there are now just 8 teams remaining in the pursuit of a National Championship. Earlier this month, the 9th-seeded Alabama Crimson Tide rallied from a 17-0 deficit against Oklahoma to knock off the Sooners and advance to the quarterfinal round, while the top-seeded Indiana Hoosiers had a bye in the opening round following an undefeated regular season and a victory in the Big Ten title game. Which of these teams will come out on top in the Rose Bowl on New Year’s Day and advance to the semifinals? It’s almost time to find out. 

Heading into the season, I was very high on Alabama’s chances of capturing a national championship given all of the talent on the roster and the upside of what this team could be. However, the Crimson Tide have not exactly been the team I thought they would be prior to the campaign. With that in mind, it’s hard to ignore the value that we’re getting on Indiana to win Thursday’s contest by only a touchdown in a game where the Hoosiers should hold plenty of advantages. Not only do the Hoosiers have Heisman Trophy-winning quarterback Fernando Mendoza on their side, but Indiana’s extremely balanced offense (2nd in success rate, 2nd in EPA per play, 3rd in points per drive) should see consistent success against an Alabama defense that has struggled at points against teams with strong passing attacks. The Crimson Tide are also operating at a significant disadvantage on special teams in this game, and that is certainly a factor that could rear its ugly head on Thursday. 

While the Alabama defense can be inconsistent, it’s still a solid unit across the board all things considered. However, the Crimson Tide have more questions on offense, if you can believe that. After all, Kalen DeBoer’s team has not been able to effectively run the ball all season long, and those struggles continued into their matchup with Oklahoma a few weeks ago. Jam Miller has been banged up, and even if he does end up playing in this one, it’s far from a guarantee that Alabama will suddenly see success on the ground against an Indiana defense that is 3rd in rushing success rate allowed and 2nd in opponent EPA per rush. Ty Simpson has struggled when pressured this season and the Hoosiers secondary just performed well against Ohio State’s outstanding trio of wide receivers, so I wouldn’t expect them to be intimidated by the Crimson Tide wideouts. Ultimately, I can only look toward laying the points with the top-ranked team in the nation.

Alabama vs Indiana prediction: Indiana -6.5 (-120) available at time of publishing. Playable to Indiana -7

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Money Line Pick
Oregon Win(-110)

The opening round of the College Football Playoff is behind us, and there are now just 8 teams remaining in the pursuit of a National Championship. Earlier this month, the 5th-seeded Oregon Ducks made quick work of James Madison to advance to this round, while the 4th-seeded Texas Tech Red Raiders had a bye in the opening round following a 12-1 season and a routine victory in the Big 12 title game. Which of these teams will come out on top in the Orange Bowl on New Year’s Day and advance to the semifinals? It’s almost time to find out. 

Given that this is the shortest spread on the board for the CFP quarterfinal round, this has the feeling of a game that should come down to the wire. Therefore, it’s hard to find a ton of clear advantages for either side in Thursday’s game. However, Oregon has a few edges that it should be able to exploit in this matchup. For starters, the Ducks have the better quarterback in the game, and Dante Moore should also be getting back 2 of his top 3 wide receivers in Dakorien Moore and Gary Bryant Jr. for this matchup. The jury is still out on if Evan Stewart is going to suit up on Thursday, but considering that Stewart hasn’t played for the entire season to this point, his absence isn’t anything new for Will Stein’s offense. With Moore and Bryant Jr. joining the dynamic and explosive Malik Benson in the lineup, this gives the Ducks a formidable trio of targets on the outside, to go along with All-American tight end Kenyon Sadiq at the tight end spot. Oregon is expected to have its top 3 running backs available for this matchup as well, so it’s hard not to be confident in the Ducks’ ability to manufacture offense in this one, even against an excellent Red Raiders defense. 

While Joey McGuire’s defense has been one of the top 5 units in the sport this season, Texas Tech’s issue in this game could be its offense. The Red Raiders certainly have a good offense — albeit one that has been the beneficiary of a somewhat weak schedule of opposing defenses — but there have been clear limitations for this group both on the ground and inside the red zone this season. After all, Texas Tech is just 50th in rushing success rate and 28th in points per drive on offense. In a game that is projected to be close throughout, just one or two failed red zone trips could decide the outcome. With that in mind, I can only side with Oregon to knock off the Red Raiders and advance to the College Football Playoff semifinals.

Oregon vs Texas Tech prediction: Oregon ML (-110) available at time of publishing. Playable to -130.

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Heisman Trophy Winner Pick
D. Dampier to win Heisman Trophy(+6000)

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.

Caleb's Analysis