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 7
Live Parlays 2
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

Player Receiving Yards Pick
A. St. Brown (DET) - Over 76.5 rec yds(-114)

To close out our Vikings vs Lions SGP, we’re going to take Amon-Ra St. Brown to clear his receiving yards prop on Thursday. While the Detroit offense has been inconsistent in recent weeks, one constant has been the production of St. Brown in the leading role. St. Brown and Jared Goff have established a great rapport with each other over the last few seasons, and the top Lions wideout should be able to see plenty of success in an indoor, pass-friendly environment on Thursday. St. Brown has cleared this number in 3 of the last 4 games and in 9 games this season, so let’s bank on that trend to continue in this one.

Point Spread Pick
MIN Vikings +7.5(-105)

For the first leg of our Lions vs Vikings Same Game Parlay, we’re going to be backing the hosts with the points. This is a terrible situational spot for the Lions, as Detroit is coming off a brutal loss in the final seconds at the hands of the Pittsburgh Steelers at home. Now, the Lions playoff aspirations are on life support and it doesn’t appear that Detroit is going to be able to come back from this crushing defeat. Therefore, while the Vikings are dealing with a number of key injuries on the offensive line and at quarterback, our expert is just fine fading a sputtering Lions team that is just 4-6 over their last 10 contests. Look for this matchup to be decided by one possession on Thursday. 

Game Totals Pick
Under 51.0(-110)

This is an instance where I’m bullish on a lower-scoring game than what the market is projecting, and it all starts with Washington’s situation on offense. Even though the Cowboys defense has struggled, the secondary is catching a major break by facing a Commanders passing attack that likely won’t have much juice with Johnson under center. Conversely, the Cowboys offense is still potent, but Dallas has leaned on its ground attack moreso in recent weeks compared what we saw earlier in the season. This number is just under the key of 51, but we’ll rely on Dallas to sit on the ball late in the game and grind this game out on the road.

Game Totals Pick
Under 43.5(-110)

As previously mentioned, this is a difficult game to handicap, given the injuries and lack of motivation for both sides. With that in mind, the Under is the only way our expert can look in this game, especially now factoring in the quarterback situation for the Vikings. Ultimately, regardless of the motivation angle at play here, Detroit shouldn’t need to score much to outpace a Minnesota offense led by Max Brosmer — who was dreadful against the Seahawks a few weeks ago — and the Lions should look to keep the ball on the ground and grind out scoring drives in a matchup that shouldn’t produce many explosive plays.

Anytime Touchdown Scorer Pick
J. Williams (DAL) to score a TD(-180)

The Dallas run game has been a lot better than what most were expecting heading into this season, and Javonte Williams has found himself within this Cowboys offense. The lead running back has racked up 10 touchdowns on the season, and his previous matchup against the Commanders could certainly be instructive for how Thursday’s meeting could shake out. Williams tallied 19 carries for 116 yards and a touchdown in the first meeting back on October 19, and it would be hard to see Williams not getting at least a handful of carries around the goal line in this one.

Point Spread Pick
DAL Cowboys -7.0(-110)

For the first leg of our Cowboys vs Commanders Same Game Parlay, we’re going to be backing the visitors by laying the points. Each of these teams has struggled for consistency on a week-to-week basis, as the Dallas defense has proven to be a massive weakness, while the Commanders have struggled on both sides of the ball due to injuries and poor play. However, even though it’s hard to trust the Cowboys on the road, the Commanders are clearly handicapped with third-string quarterback Josh Johnson at the controls of an offense that is already struggling. On the other side, the Cowboys offense is one of the better units in the NFC, and Dallas should see plenty of success against this porous Washington pass defense.

Heisman Trophy Winner Pick
D. Dampier to win Heisman Trophy(+6000)

This is a shot in the dark compared to some of the favorites on the board, but it’s an educated wager on a quarterback that I could see making a major leap this fall. Devon Dampier electrified the Mountain West at New Mexico a season ago, racking up 31 total touchdowns (including a whopping 19 touchdowns on the ground) in a season that saw him take a major step forward from his freshman campaign.

Now, the 3rd-year starter steps into a promising situation with a Utah team that handed the reins over to former New Mexico offensive coordinator Jason Beck, a respected offensive mind and a surefire upgrade from what the Utes had last season. The Utes also upgraded their weapons on the perimeter via the transfer portal and get a pretty favorable schedule compared to a few other contenders in the Big 12. I’ve got Utah favored in 11 games and if the Utes are able to navigate their way through a couple of tricky conference games, they should certainly find themselves in the Big 12 title game come Championship Weekend. That alone gives this 60-1 ticket a ton of value, so Dampier is worth a sprinkle at this number.

Caleb's Parlays

Lions vs Vikings Same Game Parlay
Today
Detroit Lions
Minnesota Vikings
DET Lions @ MIN Vikings · Point Spread
MIN Vikings +7.5
Our Analysis

For the first leg of our Lions vs Vikings Same Game Parlay, we’re going to be backing the hosts with the points. This is a terrible situational spot for the Lions, as Detroit is coming off a brutal loss in the final seconds at the hands of the Pittsburgh Steelers at home. Now, the Lions playoff aspirations are on life support and it doesn’t appear that Detroit is going to be able to come back from this crushing defeat. Therefore, while the Vikings are dealing with a number of key injuries on the offensive line and at quarterback, our expert is just fine fading a sputtering Lions team that is just 4-6 over their last 10 contests. Look for this matchup to be decided by one possession on Thursday. 

Detroit Lions
Minnesota Vikings
DET Lions @ MIN Vikings · Game Totals
Under 43.5
Our Analysis

As previously mentioned, this is a difficult game to handicap, given the injuries and lack of motivation for both sides. With that in mind, the Under is the only way our expert can look in this game, especially now factoring in the quarterback situation for the Vikings. Ultimately, regardless of the motivation angle at play here, Detroit shouldn’t need to score much to outpace a Minnesota offense led by Max Brosmer — who was dreadful against the Seahawks a few weeks ago — and the Lions should look to keep the ball on the ground and grind out scoring drives in a matchup that shouldn’t produce many explosive plays.

Detroit Lions
Minnesota Vikings
DET Lions @ MIN Vikings · Player Receiving Yards
A. St. Brown (DET) - Over 76.5 rec yds
Our Analysis

To close out our Vikings vs Lions SGP, we’re going to take Amon-Ra St. Brown to clear his receiving yards prop on Thursday. While the Detroit offense has been inconsistent in recent weeks, one constant has been the production of St. Brown in the leading role. St. Brown and Jared Goff have established a great rapport with each other over the last few seasons, and the top Lions wideout should be able to see plenty of success in an indoor, pass-friendly environment on Thursday. St. Brown has cleared this number in 3 of the last 4 games and in 9 games this season, so let’s bank on that trend to continue in this one.

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Cowboys vs Commanders Same Game Parlay
Today
Dallas Cowboys
Washington Commanders
DAL Cowboys @ WAS Commanders · Point Spread
DAL Cowboys -7.0
Our Analysis

For the first leg of our Cowboys vs Commanders Same Game Parlay, we’re going to be backing the visitors by laying the points. Each of these teams has struggled for consistency on a week-to-week basis, as the Dallas defense has proven to be a massive weakness, while the Commanders have struggled on both sides of the ball due to injuries and poor play. However, even though it’s hard to trust the Cowboys on the road, the Commanders are clearly handicapped with third-string quarterback Josh Johnson at the controls of an offense that is already struggling. On the other side, the Cowboys offense is one of the better units in the NFC, and Dallas should see plenty of success against this porous Washington pass defense.

Dallas Cowboys
Washington Commanders
DAL Cowboys @ WAS Commanders · Game Totals
Under 51.0
Our Analysis

This is an instance where I’m bullish on a lower-scoring game than what the market is projecting, and it all starts with Washington’s situation on offense. Even though the Cowboys defense has struggled, the secondary is catching a major break by facing a Commanders passing attack that likely won’t have much juice with Johnson under center. Conversely, the Cowboys offense is still potent, but Dallas has leaned on its ground attack moreso in recent weeks compared what we saw earlier in the season. This number is just under the key of 51, but we’ll rely on Dallas to sit on the ball late in the game and grind this game out on the road.

Dallas Cowboys
Washington Commanders
DAL Cowboys @ WAS Commanders · Anytime Touchdown Scorer
J. Williams (DAL) to score a TD
Our Analysis

The Dallas run game has been a lot better than what most were expecting heading into this season, and Javonte Williams has found himself within this Cowboys offense. The lead running back has racked up 10 touchdowns on the season, and his previous matchup against the Commanders could certainly be instructive for how Thursday’s meeting could shake out. Williams tallied 19 carries for 116 yards and a touchdown in the first meeting back on October 19, and it would be hard to see Williams not getting at least a handful of carries around the goal line in this one.

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Caleb's Analysis