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 1
Live Parlays 0
Weekly News Articles 9
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

Point Spread Pick
Connecticut +5.5(-115)

This matchup between blue bloods in the East Region is the highlight of Sunday’s Elite 8 action, as the UConn Huskies will take on the Duke Blue Devils. The Huskies struggled down the stretch to close the regular season, but UConn has raised their level in March, as they typically have under Danny Hurley in recent seasons. To his credit, Hurley might be the best postseason coach in the sport at the moment, and he is now 16-1 against the spread over his last 17 NCAA Tournament games. Furthermore, the Huskies are in much better shape than Duke heading into this game, as it took an all-out effort from the Blue Devils to rally from a double-digit deficit in the second half to knock off St. John’s on Friday. Duke is undoubtedly an extremely talented team, but it remains to be seen if we’ll see another heroic effort from Caleb Foster just 48 hours after logging significant minutes while playing with an injured foot. Foster is the engine of this team on both sides of the floor, so anything less than a solid effort from him would spell trouble for Duke.

UConn has a blend of experienced veterans (Alex Karaban, Taris Reed Jr.) and younger players, and this mixture has proven to be very effective through its first 3 games played in this tournament. In fact, while the Huskies have played well of late, you could certainly argue that they’re still due for some positive shooting regression from beyond the arc — especially against a Duke team that just allowed plenty of 3-point looks against St. John’s. UConn has also been excellent on the glass in this tournament, which could go a long way to staying close against a Duke team that boasts an elite first-shot defense. If the Huskies are able to generate second-chance looks and impose their will in the paint, they are certainly capable of keeping this one close down the stretch.

There’s also the matter of UConn’s offense being incredibly difficult to prepare for on a short turnaround, which is certainly a major factor as to why Hurley is such an effective NCAA Tournament coach. It’s a massive credit to this coaching staff that teams consistently fall behind against UConn, and we saw that on Friday as Michigan State trailed by as many as 19 in the first half and looked totally out of sorts for the first 20 minutes. Jon Scheyer’s team has trailed in the second half in every game of this tournament, but the Duke staff has been excellent with their halftime adjustments. With that in mind, it wouldn’t shock me at all if UConn jumps out to an early lead and holds an edge at the break, before the talent of Cam Boozer and the Blue Devils’ ultimately wins out in a tight, physical battle down the stretch. I’ll be taking a plus-money shot on the 1st half money line with the Huskies in this game, but my favorite bet focuses on UConn to cover the full-game spread.

UConn vs Duke prediction: UConn +5.5 available at time of publishing. Playable to UConn +5

Caleb's Analysis