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 19
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

Ole Miss Rebels
College Football
Sat Nov 23
Florida Gators
Point Spread Pick
Ole Miss -6.5(-110)Ole Miss @ Florida
BET -6.5 NOW WITH
Caleb Wilfinger
USC Trojans
College Football
Sat Sep 21
Michigan Wolverines
Point Spread Pick
USC +8.5(-110)USC @ Michigan
BET +8.5 NOW WITH
Caleb Wilfinger

Caleb's Parlays

2024 NFL season parlay
Sun Sep 8
New Orleans Saints
Kansas City Chiefs
NO Saints @ KC Chiefs · Point Spread
KC Chiefs -7.5
Our Analysis

The Saints are in no man’s land, which is arguably the worst position you can be in as an NFL franchise. That’s what having Derek Carr gets you in today’s day and age, but at least New Orleans gets the benefit of having one of the easiest schedules in the league this season based on opponent win totals. However, one of the worst spots on this schedule comes in Week 5 when the Saints will head to Kansas City to take on the Chiefs on Monday Night Football, and we have our Saints vs Chiefs prediction.

This will not only be the second straight road game for New Orleans, but the Saints will also be playing their fourth straight game against a team projected to make the postseason. Throw in the fact that Kansas City has a bye week on deck, so there will be no overlook for Andy Reid’s team in this spot. Look for Patrick Mahomes and company to put on a show under the lights with the nation watching and for KC to prevail as our Saints vs Chiefs best bet.

Saints vs Chiefs prediction: Chiefs -7.5 (-110) available at time of publishing.

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Minnesota Vikings
Chicago Bears
MIN Vikings @ CHI Bears · Point Spread
CHI Bears -3.0
Our Analysis

I’m not exactly a long-term believer in the Chicago Bears this season, but we’re getting a fantastic scheduling spot to back Caleb Williams and company against the Minnesota Vikings in Week 12 as our Vikings vs Bears prediction. The Vikings have one of the toughest schedules in football and they’ll head into this game after having already played two consecutive road games against Jacksonville and Tennessee. Now, Minnesota will head to Soldier Field for a matchup against a divisional foe in the cold after a couple of warmer weather encounters against much different offenses.

Despite my trepidation with the market love for the Bears heading into this season, Williams should be much more equipped to handle business as a favorite by this point in the campaign. Furthermore, the Vikings quarterback situation could be a real issue by this stage in the season, so I’ll grab the field goal with Chicago for my Vikings vs Bears pick before any possible movement down the road.

Vikings vs Bears prediction: Bears -3 (-110) available at time of publishing.

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Caleb's Analysis