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 5

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

Point Spread Pick

Santa Clara +3.5(-105)

Reasoning

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The WCC Tournament is into the semifinal round on Monday, and this matchup between Santa Clara and Saint Mary’s is arguably the most important contest of the entire day of college hoops action. After all, the Broncos are squarely on the NCAA Tournament bubble and this game against a Quad 1 opponent presents Santa Clara with a massive opportunity to make a statement on a national stage and essentially lock itself into the field of 68. The Broncos have split the season series against Saint Mary’s, and given that they were clearly the better team in the first meeting, there is a clear path to success for Santa Clara to at least keep this game within one possession, if not win it outright. With that in mind, I can only look toward backing Santa Clara in a situation where the Broncos are live to spring the outright upset.

These teams are fairly evenly matched on paper, which is part of why I gravitate toward taking the points with the underdog. We know that this is going to be a clash of styles, with Saint Mary’s sitting at 257th in adjusted tempo, while Santa Clara is 57th in pace of play. However, while the Gaels offense has been inconsistent against high-level competition, the Broncos have the capability to score on any defense. Herb Sendek’s offense is among the best at the mid-major level, as Santa Clara ranks 23rd in adjusted efficiency (BartTorvik) while tallying 80 or more points in 8 of its last 11 games played. Santa Clara is extremely efficient around the rim as a unit, and the Broncos also do a great job of attacking the offensive glass (19th in offensive rebounding rate). Furthermore, Saint Mary’s also really struggles at getting to the free-throw line, so manufacturing points could be a little more difficult to come by for an offense that is 163rd in free-throw rate on the season. I’ll take the points in this crucial matchup on Monday.

Santa Clara vs Saint Mary’s prediction: Santa Clara +3.5 available at time of publishing. Playable to Santa Clara +3.

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Point Spread Pick

Santa Clara -9.0(-110)

Reasoning

The WCC Tournament keeps on rolling along on Sunday, and this matchup between Pacific and Santa Clara is arguably the most important contest of the quarterfinal round. After all, the Broncos are squarely on the NCAA Tournament bubble and after a Saturday in which not a single bubble team did anything to improve their stock, Santa Clara has a massive opportunity to make a statement on a national stage and take another step toward solidifying its tournament resume. The Broncos have not lost to any team in WCC play outside of Gonzaga and Saint Mary’s, and this matchup shouldn’t be one that gives them much trouble. With that in mind, while Pacific is coming off a solid victory over Seattle and has generally played above expectations this season, I can only look toward backing Santa Clara in a situation where it should win by margin.

A common refrain you’ll hear during conference tournament time is “it’s hard to beat a team 3 times”. However, the historical data has shown that this line of thinking is incorrect more often than not. In this particular instance, we’ve seen Santa Clara dominate Pacific over the first 2 meetings — winning each game by at least 15 points — and that should continue on Sunday. The Broncos offense is among the best at the mid-major level, as Santa Clara ranks 23rd in adjusted efficiency (BartTorvik) while tallying 80 or more points in 8 of its last 10 games played. Herb Sendek’s group is extremely efficient around the rim and also does a great job of attacking the offensive glass (19th in offensive rebounding rate). On the other side of the ball, the Broncos defense is excellent at forcing turnovers, which happens to be a major issue for a Pacific offense that ranks 349th in turnover percentage. The Tigers also really struggle at getting to the free-throw line, so manufacturing points could be a little more difficult to come by for an offense that is 151st in adjusted efficiency on the season. I’ll lay the points with the considerably better side on Sunday.

Pacific vs Santa Clara prediction: Santa Clara -9 available at time of publishing. Playable to Santa Clara -10.

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Caleb Wilfinger

Game Totals Pick

Under 125.5(-110)

Reasoning

The Missouri Valley Conference is one of the best mid-major tournaments on the Championship Week calendar every year, and this season’s installment has been no exception. Top-seeded Belmont was upset in the quarterfinal round, which has led to a couple of the lower seeds playing for an NCAA Tournament berth on Sunday. On one side, UIC has dispatched of both opponents its played thus far, winning both of its games in this tournament by double digits. On the other end, Northern Iowa has rattled off 3 wins in as many days to advance to this game, including wins over Illinois State and Bradley. The Panthers have been no stranger to success in “Arch Madness”, and while I do lean toward backing Northern Iowa as the side in this one, I have more conviction with targeting the total on Sunday.

Historically, this tournament has been one that features plenty of low-scoring contests, particularly in the title game. In fact, we just saw Drake knock off Bradley in a championship game that featured just 111 total points a season ago. While I don’t expect this game to be as low-scoring as last year’s installment, we should still see a game dictated by both defenses on Sunday. Northern Iowa is a top 25 defense in the nation per KenPom and BartTorvik, and the Panthers are especially elite at cleaning the glass (ranked 20th in defensive rebounding percentage) and defending the arc (3rd in 3-point percentage allowed). On the other side, UIC boasts a strong defense of its own, as the Flames are excellent on the glass and adept at forcing turnovers. Lastly, both teams play at an extremely slow pace, with Northern Iowa sitting at 364th in adjusted tempo and UIC checking in at 235th in that same metric. We should see a slow, grind-it-out affair in St. Louis on Sunday.

UIC vs Northern Iowa prediction: Under 125.5 available at time of publishing. Playable to Under 124.5

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Caleb Wilfinger