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 4

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 PickBest Bet

Northern Iowa +10.5(-110)

Reasoning

After a long and eventful regular season and the chaos of Championship Week, the best time of year is finally here. March Madness has arrived and with it comes a plethora of games for us to dig into over the course of a couple of action-packed days. For my money, Friday’s slate has some of the most intriguing matchups of the Round of 64, and that includes a game between Northern Iowa and St. John’s from San Diego, California. The Panthers are the champions of the Missouri Valley — a conference that typically acquits itself very well in March — while St. John’s emerged as the champions of a very weak Big East conference. Both teams have played well entering this week, but which side will survive and advance to the weekend?

Northern Iowa has been in this spot before, and this program is no stranger to springing upsets in March. This year’s version of the Panthers is a veteran bunch that is led by its defense, which is ranked 24th nationally in adjusted efficiency per KenPom. While they did have some growing pains earlier in the season, Ben Jacobson’s group has won 10 of its last 13 games dating back to January 31. Not only are the Panthers playing at a top 40 level nationally over the last 6 weeks, but they’ve been able to do that while opponents are still making a higher than average number of threes against them. With that in mind, a bit of positive regression is still in order for what has been an elite perimeter defense this season (3rd in 3-point percentage allowed per BartTorvik). On offense, Northern Iowa is extremely comfortable playing at a deliberate pace, as the Panthers are ranked 364th in adjusted tempo and consistently look to grind out quality shots late in the clock. That bodes well for an underdog in a tournament setting, as teams that shorten the game and put a massive emphasis on each possession generally keep their games close against higher-seeded opponents. A year ago, a Drake team that played at a slow pace was able to knock off Missouri, so there’s certainly precedent for a Missouri Valley team to spring an upset over a power conference opponent by following a similar script.

As for the higher seed, St. John’s has been playing some of its best basketball over the last few weeks, but it’s worth mentioning that most of those performances have come against pretty poor competition in what was a lousy Big East this season. Furthermore, the Red Storm have struggled mightily on offense all season long, with Rick Pitino’s team sitting at 191st in effective field goal percentage, 187th in 2-point percentage and a whopping 214th in 3-point percentage (BartTorvik). That doesn’t bode well against an excellent Panthers defense that is fundamentally sound and won’t commit fouls to bail St. John’s out of bad possessions. If the Red Storm are not able to get out in transition and generate easy buckets, it could be a long day for this extremely inconsistent offense. All things considered, this has all the makings of a defensive struggle, so I’ll grab the points with Northern Iowa now that the Panthers are catching double digits.

Northern Iowa vs St. John’s prediction: Northern Iowa +10.5 (-110) available at time of publishing. Playable to +9

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Caleb Wilfinger

Point Spread Pick

Akron +8.5(-110)

Reasoning

After a long and eventful regular season and the beautiful chaos of Championship Week, the best time of year is finally here. March Madness has arrived and with it comes a plethora of games for us to dig into over the course of a couple of action-packed days. One of the first games on Friday’s slate features a team that profiles as a March sleeper in the Akron Zips, and there is an opportunity for the champions of the MAC to make a splash against a Big 12 opponent.

Akron has been in this spot before, as this is the third straight year that John Groce’s side has made the Big Dance, and they should be able to learn from their previous experiences in this setting. Led by Tavari Johnson and Shammah Scott in the backcourt, the Zips have veteran leaders all over the floor and an offense that has the capability to do major damage both from the perimeter and in the paint. Akron boasts one of the most efficient mid-major offenses inside of 15 feet, and the Zips can also knock down outside shots at nearly a 40% clip. Furthermore, Akron should be able to create second-chance opportunities with its prowess on the glass, while Texas Tech has taken a massive hit in the rebounding department over the last month (288th in defensive rebounding rate). On the other side, it’s also worth mentioning that while Texas Tech has played admirably without the services of JT Toppin (out for the season with a torn ACL), the Red Raiders have now become incredibly reliant on their backcourt play and outside shooters. To their credit, Grant McCasland’s team has shot the lights out from beyond the arc in recent weeks, but that just signals to me that regression is certainly coming due for a team that is top 10 in both 3-point rate and 3-point percentage over the last month. If Texas Tech has a less-than-stellar day from deep, that creates a real opportunity for Akron to keep things very close and potentially spring the upset.

Akron vs Texas Tech prediction: Akron +8.5 (-110) available at time of publishing. Playable to +7.5.

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Caleb Wilfinger

Point Spread Pick

Santa Clara +3.5(-110)

Reasoning

After a long and eventful regular season and the chaos of Championship Week, the best time of year is finally here. March Madness has arrived, and with it comes a plethora of games for us to dig into over the course of a couple of action-packed days. The opening game on Friday’s slate features an intriguing matchup between the Santa Clara Broncos and Kentucky Wildcats in a battle between a couple of teams that are trending in opposite directions. While Kentucky is likely to be a popular choice in this game, there is certainly an opportunity for the WCC finalists to compete in this game, and potentially win outright against an overvalued SEC opponent.

Santa Clara is a team that I’ve been high on all season long, and the Broncos not only showed their prowess in WCC play, but they also played really well in the non-conference portion of the schedule. In fact, Herb Sendek’s team knocked off the likes of Minnesota, Xavier, Nevada and McNeese State, while losing to St. Louis by just 1 point in a neutral site game. The Broncos consistently played up to their competition level this season, and if they had managed to upset St. Louis or Arizona State (a game they lost by just 3 points), they likely would be sitting on the #9 seed line, instead of a bubble team on the #10 seed line. Santa Clara boasts one of the best offenses at the mid-major level, with the Broncos ranking inside the top 15 in adjusted efficiency and top 40 in 2-point percentage (BartTorvik). This is a team that also generates offensive rebounds at an elite level (ranked 19th nationally) and should be able to thrive against a Kentucky defense that is outside the top 150 in rebounding rate and is an abysmal 233rd in free-throw rate allowed on the season.

On the other side, it’s fair to expect the Wildcats to have the majority of the crown for this one, seeing as the game is being played in St. Louis. However, this still doesn’t profile as a good matchup for Mark Pope’s team. For starters, Santa Clara’s pressure defense should be able to force the Kentucky offense into some turnovers, which is an issue the Wildcats have struggled with all season. If the pace of this game starts to increase, that also favors a Santa Clara team that likes to get out and run in order to generate early offense. I do have some concerns with the Broncos’ high foul rate, and Kentucky should be able to generate success against the Santa Clara interior defense. However, the Broncos do a pretty decent job of defending the 3-point line, and Kentucky has not shot the ball well from beyond the arc this season (167th in 3-point percentage). In a game that should come down to the final minutes, I’ll side with the underdog Broncos catching over a possession.

Santa Clara vs Kentucky prediction: Santa Clara +3.5 (-110) available at time of publishing. Playable to +3.

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Caleb Wilfinger

Point Spread PickBest Bet

South Florida +6.5(-120)

Reasoning

After a long and eventful regular season and the beautiful chaos of Championship Week, the best time of year is finally here. March Madness has arrived, and with it comes a plethora of games for us to dig into over the course of a couple of action-packed days. One of the first games on Thursday’s slate comes in the East Region between Louisville and South Florida in what should be a battle of teams that mirror each other a bit in certain areas. The Bulls are a side that I’ve enjoyed backing down the stretch. South Florida heads into this contest having won 11 straight games, with most of those victories coming by double-digits. Conversely, Louisville is on the opposite end of the spectrum, having dropped 4 of its last 8 games after bowing out in the quarterfinals of the ACC tournament. There are some serious warning signs that suggest the Cardinals should be on upset alert, and this is a solid spot to take a shot on USF in a matchup where they should hold some crucial edges.

The Bulls are unlike some of the other popular mid-major picks that you’ll see in many brackets this time of year, and it’s largely due to the fact that their roster is littered with high-major transfers and veteran players who are not new to this sort of high-pressure situation. Bryan Hodgson’s team starts a trio of excellent seniors, including Izaiyah Nelson — the AAC Player of the Year. The Bulls typically employ a 7-man rotation, and 5 of those players are upperclassmen who have played dozens of games at this level. There won’t be an intimidation factor in this game, and given the fact that South Florida has been a top-35 team since February 1 per BartTorvik, the Bulls are certainly trending in a better direction compared to their opponent.

It all starts on defense, with South Florida sitting inside the top 40 in adjusted efficiency and 24th in two-point percentage defense on the year. On offense, the Bulls are a dominant unit in transition in league play, and we saw them use that comfort of playing at a very fast tempo to great advantage during the conference tournament. Furthermore, South Florida should be very competitive in the shot volume battle in this matchup, seeing as it is ranked sixth in offensive rebounding percentage on the season, while Louisville sits at 168th over the last 2 months in that same statistic (BartTorvik). On the other side, Louisville has struggled away from home all season long, and the Cardinals are also at the mercy of a nagging lower-back injury that has caused Mikel Brown Jr. to miss 10 games this season. If Brown Jr. is unable to play or is limited in this game, the Louisville offense would certainly take a major hit. Even if Brown is a full-go, I like the matchup for South Florida and think the Bulls can spring the upset. With that in mind, I’ll back USF with the points on Thursday.

South Florida vs Louisville prediction: USF +6.5 (-120) available at time of publishing. Playable to +4.5

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Caleb Wilfinger