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 6
Live Parlays 1
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
Read More

Caleb's Picks

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.

If you’re looking for a new sportsbook, check out Bet365, the world’s #1 sportsbook. They have an amazing sign-up offer where you can INSTANTLY receive $150 in bonus bets from a $5 wager, regardless of whether that bet wins or loses! There’s no catch, it’s really that simple. Join Bet365 right now ⏰ in time to fade or follow our experts’ Alabama vs Indiana predictions.

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.

You can bet on our Oregon vs Texas Tech 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!

Game Totals Pick
Under 55.5(-110)

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.

Bet like a Caesar with this AMAZING new customer offer from Caesars Sportsbook. If you bet just $1, you’ll receive DOUBLE YOUR WINNINGS on your next 20 bets! 👥 using the Caesars promo code PWCONTENT20X, where you can bet on our USC vs TCU picks.

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

You can bet on our Alabama vs Indiana pick at DraftKings Sportsbook, which has thousands of betting options available and a great new customer offer where you can get $200 in bonus bets INSTANTLY when you make a first bet of just $5! Click here 👈🏼 to sign up for a DraftKings account now.

Money Line Pick
Oregon Win(-135)

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 (-125) available at time of publishing. Playable to -135.

You can bet on our Oregon vs Texas Tech pick at DraftKings Sportsbook, which has thousands of betting options available and a great new customer offer where you can get $200 in bonus bets INSTANTLY when you make a first bet of just $5! Click here 👈🏼 to sign up for a DraftKings account now.

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 Parlays

Tuesday's NHL Parlay
Yesterday
New Jersey Devils
Toronto Maple Leafs
NJ Devils @ TOR Maple Leafs · Money Line
TOR Maple Leafs Win
Our Analysis

The New Jersey Devils will be looking to put an end to their 3-game losing streak as they travel to Toronto to take on the Maple Leafs. The Leafs come into this game as winners of two of their last three games and their overall game appears to be trending in the right direction. Most notably has been the play of superstar Auston Matthews. In his last 2 games, he has 4 points and an impressive 14 shots on goal. He is starting to look like the 69-goal scorer that we saw from a few seasons ago. The powerplay that was the worst in the league seems to have figured some things out, they have scored three powerplay goals in their last two games. They may be without forward William Nylander which will be a big part of their offense missing, but I like their chances to get it done without him.

The Devils can’t seem to figure things out, even with the return of Jack Hughes. Their offense has been sluggish as they have only scored 5 goals in their last 3 games. On the year, they are averaging only 2.71 goals per game. The Leafs have been a very good home team this year with a record of 12-5-5 on home ice. Give me the home team in this one.

Devils vs Maple Leafs prediction: Leafs ML (-105) 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 Devils vs Maple Leafs predictions.

New York Islanders
Chicago Blackhawks
NY Islanders @ CHI Blackhawks · Money Line
NY Islanders Win
Our Analysis

The New York Islanders and Chicago Blackhawks clash for some Tuesday night action in the NHL. This is the first of two matchups this season, and both will be looking to return to the win column after coming off a multi-goal loss. To get you set for this matchup, here is our Islanders vs. Blackhawks prediction.

I expect Chicago to enter this game on home ice extremely hungry after an embarrassing 7-3 loss in their most recent game, but I don’t think it will be enough. New York has shown far more strength and consistency this year, led by first overall pick Matthew Schaefer and a great mix of young and old talent. There is a reason the Islanders have won seven more games than Chicago, and that is the major difference in roster capabilities. Blackhawks star Connor Bedard also remains out with injury, which has complicated things for Chicago who has just one win in seven games without him. For our Islanders vs. Blackhawks prediction, take New York on the money line on the road.

Islanders vs Blackhawks prediction: Islanders ML (-150) available at time of publishing. Playable to -175.

You can bet on our Islanders vs Blackhawks 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!

Philadelphia Flyers
Vancouver Canucks
PHI Flyers @ VAN Canucks · Game Totals
Under 5.5
Our Analysis

The Philadelphia Flyers are Vancouver Canucks are set for a Tuesday night matchup at Rogers Arena. These teams met last week on December 22, with Philadelphia prevailing by a score of 5-2. While 7 total goals were scored to take that game over the total, Tuesday’s meeting could be a bit lower-scoring. Vancouver’s offense ceiling took a significant dive by trading away Quinn Hughes. While Zeev Buium and Marco Rossi are playing significant minutes, it’s tough to replace the production that Hughes would bring night-in and night-out. The Canucks rank 26th in the NHL in goals per game with 2.76, and could have some trouble getting things going offensively playing on back-to-back nights.

On the other side, the Flyers also rank in the bottom-third of the NHL in scoring, as their 2.89 goals per game ranks 21st in the league. Trevor Zegras paces Philadelphia with 37 points in 37 games, but finding consistent offense has still been a bit of an uphill battle for the Flyers. The power play hasn’t been effective, ranking 25th in the NHL with a conversion rate of 16.3%. Given the offensive question marks on each side, look to the under in this one.

Flyers vs Canucks prediction: Under 5.5 (-115) available at time of publishing. Playable at that number.

You can bet on our Flyers vs Canucks pick at DraftKings Sportsbook, which has thousands of betting options available and a great new customer offer where you can get $200 in bonus bets INSTANTLY when you make a first bet of just $5! Click here 👈🏼 to sign up for a DraftKings account now.

BET +521 NOW WITH

Caleb's Analysis