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 5
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
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Caleb's Picks

Caleb's Parlays

Bears vs Commanders MNF Same Game Parlay
Yesterday
Chicago Bears
Washington Commanders
CHI Bears @ WAS Commanders · Game Totals
Over 49.5
Our Analysis

Neither team in this matchup is setting the world on fire on the defensive side of the ball, and both offenses should be in good position to take advantage of this on Monday. On one side, Caleb Williams and the Bears have tallied at least 24 points in three of their four games this season, and the Commanders are just 18th in EPA per pass defense while Washington is also below average at defending the run. As for the visitors, the Bears have been a mess defensively, with Chicago sitting at 30th in success rate allowed and 26th in sack rate for the season. With that in mind, I can’t see Daniels being disrupted all that much when he drops back, so I’ll lean to the over on Monday.

Chicago Bears
Washington Commanders
CHI Bears @ WAS Commanders · Player Rushing Yards
J. Daniels (WSH) - Under 46.5 rush yds
Our Analysis

Our second leg of this SGP pairs nicely with the first leg in that if there a high-scorer affair on Monday, it will likely featuring a lot more passing than running, especially if the Commanders’ injury history at the moment on offense. In steps Jayden Daniels, who is in just his second game back from injury, and he should look to remain healthy as the seasons draws on and a spot in the NFC playoffs grows closer. The LSU product has gone under this number in two of his three games played this season, which gives us confidence that he’ll come up short one again in this one.

Chicago Bears
Washington Commanders
CHI Bears @ WAS Commanders · Anytime Touchdown Scorer
R. Odunze (CHI) to score a TD
Our Analysis

To close out our SGP, let’s target Rome Odunze to find the end zone for a fifth consecutive week. Odunze has been the clear best wideout on the team in his second season in Chicago, and it’s quickly taken him no time to build up a good rapport with Caleb Williams, which has already paid dividends. With five receiving touchdowns in just four weeks to this point, let’s bank on the Washington Huskies product to remain slept on and pick up another touchdown in this revamped artist.

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Caleb Wilfinger

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